TY  - JOUR
AU  - Simić, Milena
AU  - Erić, Slavica
AU  - Borić, Ivan
AU  - Lubelska, Annamaria
AU  - Latacz, Gneiwomir
AU  - Kiec-Kononowicz, Katarzyna
AU  - Vojnović, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Savić, Vladimir
PY  - 2021
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/4985
AB  - In the continuation of our study of substituted isocoumarins a series of novel 3-azolyl isocoumarin and their thio derivatives, including some related lactone compounds was prepared and biologically profiled against C. albicans showing moderate activity with MIC values in range of 4-60 μg mL-1, in general. The additional characterisation of selected compounds was carried out by exploring their activity on CYP3A4 and CYP2D6 enzymes, while experiments on mutagenicity were performed by AMES test. The representative isocoumarins 3b, 4a and 4b showed lower inhibitory activity on CYP enzymes, when compared to the reference inhibitors, ketoconazole and quinidine. Compound 4a showed a higher mutagenic potential than the other two compounds. Further characterization included cytotoxicity profiling against normal MRC5 cells.
AB  - Синтетисана је серија нових 3-азолил-изокумарина и сличних лактонских деривата и евалуирана је њихова антифунгална активност на Candida albicans, где су показали умерену активност (MIC 4–60 μg mL -1 ). Испитана је и интеракција одабраних изокума- ринских деривата са хуманим CYP3A4 и CYP2D6 ензимима помоћу луминисцентног теста, док им је мутагени потенцијал одређен AMES тестом. Испитивани изокумарини 3b, 4a и 4b не показују значајну интеракцију са наведеним CYP ензимима у поређењу сареферентним инхибиторима. Једињењe 4a показује већи мутагени потенцијал у односу на друга два. Додатна биолошка карактеризација је укључила одређивање цитотоксич- ности према нормалним MRC5 ћелијама.
PB  - Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and biological profiling of novel isocoumarin derivatives
and related compounds
T1  - СИНТЕЗА И БИОЛОШКО ПРОФИЛИСАЊЕ НОВИХ ИЗОКУМАРИНСКИХ ДЕРИВАТА И СЛИЧНИХ ЈЕДИЊЕЊА
VL  - 86
IS  - 7-8
SP  - 639
EP  - 649
DO  - 10.2298/JSC201201025S
ER  - 

@article{
author = "Simić, Milena and Erić, Slavica and Borić, Ivan and Lubelska, Annamaria and Latacz, Gneiwomir and Kiec-Kononowicz, Katarzyna and Vojnović, Sandra and Nikodinović-Runić, Jasmina and Savić, Vladimir",
year = "2021",
abstract = "In the continuation of our study of substituted isocoumarins a series of novel 3-azolyl isocoumarin and their thio derivatives, including some related lactone compounds was prepared and biologically profiled against C. albicans showing moderate activity with MIC values in range of 4-60 μg mL-1, in general. The additional characterisation of selected compounds was carried out by exploring their activity on CYP3A4 and CYP2D6 enzymes, while experiments on mutagenicity were performed by AMES test. The representative isocoumarins 3b, 4a and 4b showed lower inhibitory activity on CYP enzymes, when compared to the reference inhibitors, ketoconazole and quinidine. Compound 4a showed a higher mutagenic potential than the other two compounds. Further characterization included cytotoxicity profiling against normal MRC5 cells., Синтетисана је серија нових 3-азолил-изокумарина и сличних лактонских деривата и евалуирана је њихова антифунгална активност на Candida albicans, где су показали умерену активност (MIC 4–60 μg mL -1 ). Испитана је и интеракција одабраних изокума- ринских деривата са хуманим CYP3A4 и CYP2D6 ензимима помоћу луминисцентног теста, док им је мутагени потенцијал одређен AMES тестом. Испитивани изокумарини 3b, 4a и 4b не показују значајну интеракцију са наведеним CYP ензимима у поређењу сареферентним инхибиторима. Једињењe 4a показује већи мутагени потенцијал у односу на друга два. Додатна биолошка карактеризација је укључила одређивање цитотоксич- ности према нормалним MRC5 ћелијама.",
publisher = "Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and biological profiling of novel isocoumarin derivatives
and related compounds, СИНТЕЗА И БИОЛОШКО ПРОФИЛИСАЊЕ НОВИХ ИЗОКУМАРИНСКИХ ДЕРИВАТА И СЛИЧНИХ ЈЕДИЊЕЊА",
volume = "86",
number = "7-8",
pages = "639-649",
doi = "10.2298/JSC201201025S"
}

Simić, M., Erić, S., Borić, I., Lubelska, A., Latacz, G., Kiec-Kononowicz, K., Vojnović, S., Nikodinović-Runić, J.,& Savić, V.. (2021). Synthesis and biological profiling of novel isocoumarin derivatives
and related compounds. in Journal of the Serbian Chemical Society
Serbian Chemical Society., 86(7-8), 639-649.
https://doi.org/10.2298/JSC201201025S

Simić M, Erić S, Borić I, Lubelska A, Latacz G, Kiec-Kononowicz K, Vojnović S, Nikodinović-Runić J, Savić V. Synthesis and biological profiling of novel isocoumarin derivatives
and related compounds. in Journal of the Serbian Chemical Society. 2021;86(7-8):639-649.
doi:10.2298/JSC201201025S .

Simić, Milena, Erić, Slavica, Borić, Ivan, Lubelska, Annamaria, Latacz, Gneiwomir, Kiec-Kononowicz, Katarzyna, Vojnović, Sandra, Nikodinović-Runić, Jasmina, Savić, Vladimir, "Synthesis and biological profiling of novel isocoumarin derivatives
and related compounds" in Journal of the Serbian Chemical Society, 86, no. 7-8 (2021):639-649,
https://doi.org/10.2298/JSC201201025S . .

TY  - JOUR
AU  - Simić, Milena
AU  - Petković, Miloš
AU  - Jovanović, Predrag
AU  - Jovanović, Miloš
AU  - Tasić, Gordana
AU  - Besu, Irina
AU  - Žižak, Željko
AU  - Aleksić, Ivana
AU  - Nikodinović-Runić, Jasmina
AU  - Savić, Vladimir
PY  - 2021
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3935
AB  - Several coumarin derivatives with a directly attached azole substituent at C‐4 were synthesized and biologically studied for their anticancer properties. The cell lines used for this investigation (HeLa, K‐562, MDA‐MB‐53, and MCF‐7) demonstrated different sensitivities. The best response in the MTT (3‐(4,5‐dimethyl‐2‐thiazolyl)‐ 2,5‐diphenyl‐2H‐tetrazolium bromide) assay was shown by K‐562 cells, with compounds displaying activity (3c, IC50 3.06 μM; 4a, IC50 5.24 μM; 4c, IC50 4.7 μM) similar to that of cisplatin (IC50 ~6 μM), which was used as the standard. The studied azole‐substituted coumarins demonstrated weaker activity toward other cell lines, except for compound 4c, which was equally potent in the case of MCF‐7 cells. Additional biological evaluations supported interference with the cell cycle as a potential mechanism of action and confirmed the absence of toxicity in zebrafish embryos. On the basis of these initial results, 4‐azole coumarins should be explored further. Although their activity would need additional optimization, the fact that these compounds are fragment‐like structures with MW <300 and clog P <3 offers enough flexibility to fine‐tune their drug‐like properties.
PB  - John Wiley and Sons Inc
T2  - Archiv der Pharmazie
T1  - Fragment-type 4-azolylcoumarin derivatives with anticancer properties
DO  - 10.1002/ardp.202100238
ER  - 

@article{
author = "Simić, Milena and Petković, Miloš and Jovanović, Predrag and Jovanović, Miloš and Tasić, Gordana and Besu, Irina and Žižak, Željko and Aleksić, Ivana and Nikodinović-Runić, Jasmina and Savić, Vladimir",
year = "2021",
abstract = "Several coumarin derivatives with a directly attached azole substituent at C‐4 were synthesized and biologically studied for their anticancer properties. The cell lines used for this investigation (HeLa, K‐562, MDA‐MB‐53, and MCF‐7) demonstrated different sensitivities. The best response in the MTT (3‐(4,5‐dimethyl‐2‐thiazolyl)‐ 2,5‐diphenyl‐2H‐tetrazolium bromide) assay was shown by K‐562 cells, with compounds displaying activity (3c, IC50 3.06 μM; 4a, IC50 5.24 μM; 4c, IC50 4.7 μM) similar to that of cisplatin (IC50 ~6 μM), which was used as the standard. The studied azole‐substituted coumarins demonstrated weaker activity toward other cell lines, except for compound 4c, which was equally potent in the case of MCF‐7 cells. Additional biological evaluations supported interference with the cell cycle as a potential mechanism of action and confirmed the absence of toxicity in zebrafish embryos. On the basis of these initial results, 4‐azole coumarins should be explored further. Although their activity would need additional optimization, the fact that these compounds are fragment‐like structures with MW <300 and clog P <3 offers enough flexibility to fine‐tune their drug‐like properties.",
publisher = "John Wiley and Sons Inc",
journal = "Archiv der Pharmazie",
title = "Fragment-type 4-azolylcoumarin derivatives with anticancer properties",
doi = "10.1002/ardp.202100238"
}

Simić, M., Petković, M., Jovanović, P., Jovanović, M., Tasić, G., Besu, I., Žižak, Ž., Aleksić, I., Nikodinović-Runić, J.,& Savić, V.. (2021). Fragment-type 4-azolylcoumarin derivatives with anticancer properties. in Archiv der Pharmazie
John Wiley and Sons Inc..
https://doi.org/10.1002/ardp.202100238

Simić M, Petković M, Jovanović P, Jovanović M, Tasić G, Besu I, Žižak Ž, Aleksić I, Nikodinović-Runić J, Savić V. Fragment-type 4-azolylcoumarin derivatives with anticancer properties. in Archiv der Pharmazie. 2021;.
doi:10.1002/ardp.202100238 .

Simić, Milena, Petković, Miloš, Jovanović, Predrag, Jovanović, Miloš, Tasić, Gordana, Besu, Irina, Žižak, Željko, Aleksić, Ivana, Nikodinović-Runić, Jasmina, Savić, Vladimir, "Fragment-type 4-azolylcoumarin derivatives with anticancer properties" in Archiv der Pharmazie (2021),
https://doi.org/10.1002/ardp.202100238 . .

TY  - JOUR
AU  - Milovanović, Jelena
AU  - Gözde Gündüz, Miyase
AU  - Zerva, Anastasia
AU  - Petković, Miloš
AU  - Beskoski, Vladimir
AU  - Thomaidis, Nikolaos
AU  - Topakas, Evangelos
AU  - Nikodinović-Runić, Jasmina
PY  - 2021
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3917
AB  - We describe herein the synthesis and laccasemediated oxidation of six novel 1,4-dihydropyridine (DHP)-based hexahydroquinolines (DHP1-DHP3) and decahydroacridines (DHP4-DHP6). We employed different laccase enzymes with varying redox potential to convert DHP1-DHP3 and DHP4- DHP6 to the corresponding pyridine-containing tetrahydroquinoline and octahydroacridine derivatives, respectively. Intensively coloured products were detected in all biocatalytic reactions using laccase from Trametes versicolor (TvLacc), possibly due to the presence of conjugated chromophores formed in products after oxidation. The NMR assessment confirmed that the oxidation product of DHP1 was its corresponding pyridine-bearing tetrahydroquinoline derivative. Laccase from Bacillus subtillis (BacillusLacc) was the most efficient enzyme for this group of substrates using HPLC assessment. Overall, it could be concluded that DHP2 and DHP5, bearing catecholic structures, were easily oxidized by all tested laccases, while DHP3 and DHP6 containing electron-withdrawing nitro-groups are not readily oxidized by laccases. DHP4 with decahydroacridine moiety consisting of three condensed six-membered rings that contribute not only to the volume but also to the higher redox potential of the substrate rendered this compound not to be biotransformed with any of the mentioned enzymes. Overall, we showed that multiple analytical approaches are needed in order to assess biocatalytical reactions.
PB  - MDPI
T2  - Catalysts
T1  - Synthesis and laccase-mediated oxidation of new condensed 1,4-dihydropyridine derivatives
VL  - 11
IS  - 6
DO  - 10.3390/catal11060727
ER  - 

@article{
author = "Milovanović, Jelena and Gözde Gündüz, Miyase and Zerva, Anastasia and Petković, Miloš and Beskoski, Vladimir and Thomaidis, Nikolaos and Topakas, Evangelos and Nikodinović-Runić, Jasmina",
year = "2021",
abstract = "We describe herein the synthesis and laccasemediated oxidation of six novel 1,4-dihydropyridine (DHP)-based hexahydroquinolines (DHP1-DHP3) and decahydroacridines (DHP4-DHP6). We employed different laccase enzymes with varying redox potential to convert DHP1-DHP3 and DHP4- DHP6 to the corresponding pyridine-containing tetrahydroquinoline and octahydroacridine derivatives, respectively. Intensively coloured products were detected in all biocatalytic reactions using laccase from Trametes versicolor (TvLacc), possibly due to the presence of conjugated chromophores formed in products after oxidation. The NMR assessment confirmed that the oxidation product of DHP1 was its corresponding pyridine-bearing tetrahydroquinoline derivative. Laccase from Bacillus subtillis (BacillusLacc) was the most efficient enzyme for this group of substrates using HPLC assessment. Overall, it could be concluded that DHP2 and DHP5, bearing catecholic structures, were easily oxidized by all tested laccases, while DHP3 and DHP6 containing electron-withdrawing nitro-groups are not readily oxidized by laccases. DHP4 with decahydroacridine moiety consisting of three condensed six-membered rings that contribute not only to the volume but also to the higher redox potential of the substrate rendered this compound not to be biotransformed with any of the mentioned enzymes. Overall, we showed that multiple analytical approaches are needed in order to assess biocatalytical reactions.",
publisher = "MDPI",
journal = "Catalysts",
title = "Synthesis and laccase-mediated oxidation of new condensed 1,4-dihydropyridine derivatives",
volume = "11",
number = "6",
doi = "10.3390/catal11060727"
}

Milovanović, J., Gözde Gündüz, M., Zerva, A., Petković, M., Beskoski, V., Thomaidis, N., Topakas, E.,& Nikodinović-Runić, J.. (2021). Synthesis and laccase-mediated oxidation of new condensed 1,4-dihydropyridine derivatives. in Catalysts
MDPI., 11(6).
https://doi.org/10.3390/catal11060727

Milovanović J, Gözde Gündüz M, Zerva A, Petković M, Beskoski V, Thomaidis N, Topakas E, Nikodinović-Runić J. Synthesis and laccase-mediated oxidation of new condensed 1,4-dihydropyridine derivatives. in Catalysts. 2021;11(6).
doi:10.3390/catal11060727 .

Milovanović, Jelena, Gözde Gündüz, Miyase, Zerva, Anastasia, Petković, Miloš, Beskoski, Vladimir, Thomaidis, Nikolaos, Topakas, Evangelos, Nikodinović-Runić, Jasmina, "Synthesis and laccase-mediated oxidation of new condensed 1,4-dihydropyridine derivatives" in Catalysts, 11, no. 6 (2021),
https://doi.org/10.3390/catal11060727 . .

TY  - JOUR
AU  - Jakšić, Jovana
AU  - Ostojić, Sanja
AU  - Micić, Darko
AU  - Tokić-Vujošević, Zorana
AU  - Milovanović, Jelena
AU  - Karkalić, Radovan
AU  - O'Connor, Kevin E.
AU  - Kenny, Shane T.
AU  - Casey, William
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
PY  - 2020
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3534
AB  - In the present work, we describe the chemical synthesis of 3-HFAs as prominent derivatives of fatty acids and assess if they could be applied as phase change materials (PCM). In addition, 3-HFAs were obtained by depolymerization of a bacterial biopolymeric material, polyhydroxyalkanoate. Thermal properties of 3-hydoxyoctanoic, decanoic, and dodecanoic acids are reported for the first time. These materials showed the potential to be applied as PCM in temperature range from 33°C to 66°C. In order to expand the temperature range for application of 3-HFAs as PCM, eutectic mass ratios of three kinds of binary mixtures of 3-HFAs were calculated, and their properties were predicted using the Schröder-van Laar equation. Thermal properties of these mixtures were validated by differential scanning calorimetry (DSC) analysis. These results showed that eutectics considerably expanded the scope of applications of 3-HFAs as PCMs. 3-HFAs originating from biotechnologically obtained polyhydroxyalkanoates also showed potential to be applied in development of PCMs.
PB  - John Wiley & Sons, Ltd.
T2  - International Journal of Energy Research
T1  - Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials
VL  - 44
IS  - 2
SP  - 1294
EP  - 1302
DO  - 10.1002/er.4934
ER  - 

@article{
author = "Jakšić, Jovana and Ostojić, Sanja and Micić, Darko and Tokić-Vujošević, Zorana and Milovanović, Jelena and Karkalić, Radovan and O'Connor, Kevin E. and Kenny, Shane T. and Casey, William and Nikodinović-Runić, Jasmina and Maslak, Veselin",
year = "2020",
abstract = "In the present work, we describe the chemical synthesis of 3-HFAs as prominent derivatives of fatty acids and assess if they could be applied as phase change materials (PCM). In addition, 3-HFAs were obtained by depolymerization of a bacterial biopolymeric material, polyhydroxyalkanoate. Thermal properties of 3-hydoxyoctanoic, decanoic, and dodecanoic acids are reported for the first time. These materials showed the potential to be applied as PCM in temperature range from 33°C to 66°C. In order to expand the temperature range for application of 3-HFAs as PCM, eutectic mass ratios of three kinds of binary mixtures of 3-HFAs were calculated, and their properties were predicted using the Schröder-van Laar equation. Thermal properties of these mixtures were validated by differential scanning calorimetry (DSC) analysis. These results showed that eutectics considerably expanded the scope of applications of 3-HFAs as PCMs. 3-HFAs originating from biotechnologically obtained polyhydroxyalkanoates also showed potential to be applied in development of PCMs.",
publisher = "John Wiley & Sons, Ltd.",
journal = "International Journal of Energy Research",
title = "Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials",
volume = "44",
number = "2",
pages = "1294-1302",
doi = "10.1002/er.4934"
}

Jakšić, J., Ostojić, S., Micić, D., Tokić-Vujošević, Z., Milovanović, J., Karkalić, R., O'Connor, K. E., Kenny, S. T., Casey, W., Nikodinović-Runić, J.,& Maslak, V.. (2020). Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials. in International Journal of Energy Research
John Wiley & Sons, Ltd.., 44(2), 1294-1302.
https://doi.org/10.1002/er.4934

Jakšić J, Ostojić S, Micić D, Tokić-Vujošević Z, Milovanović J, Karkalić R, O'Connor KE, Kenny ST, Casey W, Nikodinović-Runić J, Maslak V. Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials. in International Journal of Energy Research. 2020;44(2):1294-1302.
doi:10.1002/er.4934 .

Jakšić, Jovana, Ostojić, Sanja, Micić, Darko, Tokić-Vujošević, Zorana, Milovanović, Jelena, Karkalić, Radovan, O'Connor, Kevin E., Kenny, Shane T., Casey, William, Nikodinović-Runić, Jasmina, Maslak, Veselin, "Thermal properties of 3-hydroxy fatty acids and their binary mixtures as phase change energy storage materials" in International Journal of Energy Research, 44, no. 2 (2020):1294-1302,
https://doi.org/10.1002/er.4934 . .

TY  - JOUR
AU  - Jovanović, Miloš
AU  - Radivojević, Jelena
AU  - O'Connor, Kevin
AU  - Blagojević, Stevan
AU  - Begović, Biljana
AU  - Lukić, Vera
AU  - Nikodinović-Runić, Jasmina
AU  - Savić, Vladimir
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3335
AB  - Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 mu g/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.
PB  - Academic Press Inc Elsevier Science, San Diego
T2  - Bioorganic Chemistry
T1  - Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans
VL  - 87
SP  - 209
EP  - 217
DO  - 10.1016/j.bioorg.2019.03.023
ER  - 

@article{
author = "Jovanović, Miloš and Radivojević, Jelena and O'Connor, Kevin and Blagojević, Stevan and Begović, Biljana and Lukić, Vera and Nikodinović-Runić, Jasmina and Savić, Vladimir",
year = "2019",
abstract = "Rhamnolipids are biodegradable low toxic biosurfactants which exert antimicrobial and anti-biofilm properties. They have attracted much attention recently due to potential applications in areas of bioremediation, therapeutics, cosmetics and agriculture, however, the full potential of these versatile molecules is yet to be explored. Based on the facts that many naturally occurring lipopeptides are potent antimicrobials, our study aimed to explore the potential of replacing rhamnose in rhamnolipids with amino acids thus creating lipopeptides that would mimic or enhance properties of the parent molecule. This would allow not only for more economical and greener production but also, due to the availability of structurally different amino acids, facile manipulation of physico-chemical and biological properties. Our synthetic efforts produced a library of 43 lipopeptides revealing biologically more potent molecules. The structural changes significantly increased, in particular, anti-biofilm properties against Candida albicans, although surface activity of the parent molecule was almost completely abolished. Our findings show that the most active compounds are leucine derivatives of 3-hydroxy acids containing benzylic ester functionality. The SAR study demonstrated a further increase in activity with aliphatic chain elongation. The most promising lipopeptides 15, 23 and 36 at 12.5 mu g/mL concentration allowed only 14.3%, 5.1% and 11.2% of biofilm formation, respectively after 24 h. These compounds inhibit biofilm formation by preventing adhesion of C. albicans to abiotic and biotic surfaces.",
publisher = "Academic Press Inc Elsevier Science, San Diego",
journal = "Bioorganic Chemistry",
title = "Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans",
volume = "87",
pages = "209-217",
doi = "10.1016/j.bioorg.2019.03.023"
}

Jovanović, M., Radivojević, J., O'Connor, K., Blagojević, S., Begović, B., Lukić, V., Nikodinović-Runić, J.,& Savić, V.. (2019). Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans. in Bioorganic Chemistry
Academic Press Inc Elsevier Science, San Diego., 87, 209-217.
https://doi.org/10.1016/j.bioorg.2019.03.023

Jovanović M, Radivojević J, O'Connor K, Blagojević S, Begović B, Lukić V, Nikodinović-Runić J, Savić V. Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans. in Bioorganic Chemistry. 2019;87:209-217.
doi:10.1016/j.bioorg.2019.03.023 .

Jovanović, Miloš, Radivojević, Jelena, O'Connor, Kevin, Blagojević, Stevan, Begović, Biljana, Lukić, Vera, Nikodinović-Runić, Jasmina, Savić, Vladimir, "Rhamnolipid inspired lipopeptides effective in preventing adhesion and biofilm formation of Candida albicans" in Bioorganic Chemistry, 87 (2019):209-217,
https://doi.org/10.1016/j.bioorg.2019.03.023 . .

TY  - JOUR
AU  - Andrejević, Tina P.
AU  - Nikolić, Andrea M.
AU  - Glisić, Biljana D.
AU  - Wadepohl, Hubert
AU  - Vojnović, Sandra
AU  - Zlatović, Mario
AU  - Petković, Miloš
AU  - Nikodinović-Runić, Jasmina
AU  - Opsenica, Igor M.
AU  - Đuran, Miloš, I
PY  - 2018
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3086
AB  - Herein, we report the synthesis and structural characteristics of three tetrazole-containing compounds, 1-benzyl-1H-tetrazole (bntz), 1-benzyl-1H-tetrazol-5-amine (bntza) and 1-(4-methoxybenzyl)-1H-tetrazol-5-amine (mbntza) and the corresponding silver(I) complexes of the general formula [Ag(NO3-O)(L-N4)(2)](n), L = bntz (1), bntza (2) and mbntza (3). Silver(I) complexes 1-3 and 1-benzyl-1H-tetrazoles have been studied in detail by NMR, IR and UV-Vis spectroscopic methods and the structures of 1 and 2 have been determined by single-crystal X-ray diffraction analysis. The results of these analyses revealed a monodentate coordination of the ligands to Ag(I) ion via the N4 tetrazole nitrogen. The antimicrobial potential of silver(I) complexes 1-3 was evaluated against the broad panel of Gram-positive and Gram-negative bacteria and fungi, displaying their remarkable inhibiting activity with MIC (minimal inhibitory concentration) values in the range 2-8 and 0.16-1.25 mu g/mL (3.8-16.3 and 0.31-2.15 mu M), respectively. On the other hand, 1-benzyl-1H-tetrazoles used for the synthesis of the silver(I) complexes were not active against the investigated strains, suggesting that the activity of the complexes originates from the Ag(I) ion exclusively. Moreover, silver(I) complexes 1-3 have good therapeutic potential, which can be deduced from their moderate cytotoxicity on the human fibroblast cell line MRC5, with IC50 values falling in the range 30-60 mu g/mL (57.7-103.4 mu M).
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Polyhedron
T1  - Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles
VL  - 154
SP  - 325
EP  - 333
DO  - 10.1016/j.poly.2018.08.001
ER  - 

@article{
author = "Andrejević, Tina P. and Nikolić, Andrea M. and Glisić, Biljana D. and Wadepohl, Hubert and Vojnović, Sandra and Zlatović, Mario and Petković, Miloš and Nikodinović-Runić, Jasmina and Opsenica, Igor M. and Đuran, Miloš, I",
year = "2018",
abstract = "Herein, we report the synthesis and structural characteristics of three tetrazole-containing compounds, 1-benzyl-1H-tetrazole (bntz), 1-benzyl-1H-tetrazol-5-amine (bntza) and 1-(4-methoxybenzyl)-1H-tetrazol-5-amine (mbntza) and the corresponding silver(I) complexes of the general formula [Ag(NO3-O)(L-N4)(2)](n), L = bntz (1), bntza (2) and mbntza (3). Silver(I) complexes 1-3 and 1-benzyl-1H-tetrazoles have been studied in detail by NMR, IR and UV-Vis spectroscopic methods and the structures of 1 and 2 have been determined by single-crystal X-ray diffraction analysis. The results of these analyses revealed a monodentate coordination of the ligands to Ag(I) ion via the N4 tetrazole nitrogen. The antimicrobial potential of silver(I) complexes 1-3 was evaluated against the broad panel of Gram-positive and Gram-negative bacteria and fungi, displaying their remarkable inhibiting activity with MIC (minimal inhibitory concentration) values in the range 2-8 and 0.16-1.25 mu g/mL (3.8-16.3 and 0.31-2.15 mu M), respectively. On the other hand, 1-benzyl-1H-tetrazoles used for the synthesis of the silver(I) complexes were not active against the investigated strains, suggesting that the activity of the complexes originates from the Ag(I) ion exclusively. Moreover, silver(I) complexes 1-3 have good therapeutic potential, which can be deduced from their moderate cytotoxicity on the human fibroblast cell line MRC5, with IC50 values falling in the range 30-60 mu g/mL (57.7-103.4 mu M).",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Polyhedron",
title = "Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles",
volume = "154",
pages = "325-333",
doi = "10.1016/j.poly.2018.08.001"
}

Andrejević, T. P., Nikolić, A. M., Glisić, B. D., Wadepohl, H., Vojnović, S., Zlatović, M., Petković, M., Nikodinović-Runić, J., Opsenica, I. M.,& Đuran, M. I.. (2018). Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles. in Polyhedron
Pergamon-Elsevier Science Ltd, Oxford., 154, 325-333.
https://doi.org/10.1016/j.poly.2018.08.001

Andrejević TP, Nikolić AM, Glisić BD, Wadepohl H, Vojnović S, Zlatović M, Petković M, Nikodinović-Runić J, Opsenica IM, Đuran MI. Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles. in Polyhedron. 2018;154:325-333.
doi:10.1016/j.poly.2018.08.001 .

Andrejević, Tina P., Nikolić, Andrea M., Glisić, Biljana D., Wadepohl, Hubert, Vojnović, Sandra, Zlatović, Mario, Petković, Miloš, Nikodinović-Runić, Jasmina, Opsenica, Igor M., Đuran, Miloš, I, "Synthesis, structural characterization and antimicrobial activity of silver(I) complexes with 1-benzyl-1H-tetrazoles" in Polyhedron, 154 (2018):325-333,
https://doi.org/10.1016/j.poly.2018.08.001 . .

TY  - JOUR
AU  - Aleksić, Ivana
AU  - Petković, Miloš
AU  - Jovanović, Miloš
AU  - Milivojević, Dušan
AU  - Vasiljević, Branka
AU  - Nikodinović-Runić, Jasmina
AU  - Senerović, Lidija
PY  - 2017
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2858
AB  - A new strain, namely Lysinibacillus sp. BV152.1 was isolated from the rhizosphere of ground ivy (Glechoma hederacea L.) producing metabolites with potent ability to inhibit biofilm formation of an important human pathogens Pseudomonas aeruginosa PAO1, Staphylococcus aureus, and Serratia marcescens. Structural characterization revealed di-rhamnolipids mixture containing rhamnose (Rha)-Rha-C10-C10, Rha-Rha-C8-C10, and Rha-Rha-C10-C12 in the ratio 7: 2: 1 as the active principle. Purified di-rhamnolipids, as well as commercially available di-rhamnolipids (Rha-Rha-C10-C10, 93%) were used as the substrate for the chemical derivatization for the first time, yielding three semisynthetic amide derivatives, benzyl-, piperidine-, and morpholine. A comparative study of the anti-biofilm, antibacterial and cytotoxic properties revealed that di-Rha from Lysinibacillus sp. BV152.1 were more potent in biofilm inhibition, both cell adhesion and biofilm maturation, than commercial di-rhamnolipids inhibiting 50% of P. aeruginosa PAO1 biofilm formation at 50 mu g mL(-1) and 75 mu g mL(-1), respectively. None of the dirhamnolipids exhibited antimicrobial properties at concentrations of up to 500 mu g mL(-1). Amide derivatization improved inhibition of biofilm formation and dispersion activities of di-rhamnolipids from both sources, with morpholine derivative being the most active causing more than 80% biofilm inhibition at concentrations 100 mu g mL(-1). Semisynthetic amide derivatives showed increased antibacterial activity against S. aureus, and also showed higher cytotoxicity. Therefore, described di-rhamnolipids are potent anti-biofilm agents and the described approach can be seen as viable approach in reaching new rhamnolipid based derivatives with tailored biological properties.
PB  - Frontiers Media Sa, Lausanne
T2  - Frontiers in Microbiology
T1  - Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives
VL  - 8
DO  - 10.3389/fmicb.2017.02454
ER  - 

@article{
author = "Aleksić, Ivana and Petković, Miloš and Jovanović, Miloš and Milivojević, Dušan and Vasiljević, Branka and Nikodinović-Runić, Jasmina and Senerović, Lidija",
year = "2017",
abstract = "A new strain, namely Lysinibacillus sp. BV152.1 was isolated from the rhizosphere of ground ivy (Glechoma hederacea L.) producing metabolites with potent ability to inhibit biofilm formation of an important human pathogens Pseudomonas aeruginosa PAO1, Staphylococcus aureus, and Serratia marcescens. Structural characterization revealed di-rhamnolipids mixture containing rhamnose (Rha)-Rha-C10-C10, Rha-Rha-C8-C10, and Rha-Rha-C10-C12 in the ratio 7: 2: 1 as the active principle. Purified di-rhamnolipids, as well as commercially available di-rhamnolipids (Rha-Rha-C10-C10, 93%) were used as the substrate for the chemical derivatization for the first time, yielding three semisynthetic amide derivatives, benzyl-, piperidine-, and morpholine. A comparative study of the anti-biofilm, antibacterial and cytotoxic properties revealed that di-Rha from Lysinibacillus sp. BV152.1 were more potent in biofilm inhibition, both cell adhesion and biofilm maturation, than commercial di-rhamnolipids inhibiting 50% of P. aeruginosa PAO1 biofilm formation at 50 mu g mL(-1) and 75 mu g mL(-1), respectively. None of the dirhamnolipids exhibited antimicrobial properties at concentrations of up to 500 mu g mL(-1). Amide derivatization improved inhibition of biofilm formation and dispersion activities of di-rhamnolipids from both sources, with morpholine derivative being the most active causing more than 80% biofilm inhibition at concentrations 100 mu g mL(-1). Semisynthetic amide derivatives showed increased antibacterial activity against S. aureus, and also showed higher cytotoxicity. Therefore, described di-rhamnolipids are potent anti-biofilm agents and the described approach can be seen as viable approach in reaching new rhamnolipid based derivatives with tailored biological properties.",
publisher = "Frontiers Media Sa, Lausanne",
journal = "Frontiers in Microbiology",
title = "Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives",
volume = "8",
doi = "10.3389/fmicb.2017.02454"
}

Aleksić, I., Petković, M., Jovanović, M., Milivojević, D., Vasiljević, B., Nikodinović-Runić, J.,& Senerović, L.. (2017). Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives. in Frontiers in Microbiology
Frontiers Media Sa, Lausanne., 8.
https://doi.org/10.3389/fmicb.2017.02454

Aleksić I, Petković M, Jovanović M, Milivojević D, Vasiljević B, Nikodinović-Runić J, Senerović L. Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives. in Frontiers in Microbiology. 2017;8.
doi:10.3389/fmicb.2017.02454 .

Aleksić, Ivana, Petković, Miloš, Jovanović, Miloš, Milivojević, Dušan, Vasiljević, Branka, Nikodinović-Runić, Jasmina, Senerović, Lidija, "Anti-biofilm Properties of Bacterial Di-Rhamnolipids and Their Semi-Synthetic Amide Derivatives" in Frontiers in Microbiology, 8 (2017),
https://doi.org/10.3389/fmicb.2017.02454 . .

TY  - JOUR
AU  - Simić, Milena
AU  - Paunović, Nikola
AU  - Borić, Ivan
AU  - Ranđelović, Jelena
AU  - Vojnović, Sandra
AU  - Nikodinović-Runić, Jasmina
AU  - Pekmezović, Marina
AU  - Savić, Vladimir
PY  - 2016
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2580
AB  - A series of novel 3-substituted isocoumarins was prepared via Pd-catalysed coupling processes and screened in vitro for antifungal activity against Candida species. The study revealed antifungal potential of isocoumarins possessing the azole substituents, which, in some cases, showed biological properties equal to those of clinically used voriconazole. Selected compounds were also screened against voriconazole resistant Candida krusei 6258 and a clinical isolate Candida parapsilosis CA-27. Although the activity against these targets needs to be improved further, the results emphasise additional potential of this new class of antifungal compounds.
PB  - Pergamon-Elsevier Science Ltd, Oxford
T2  - Bioorganic & Medicinal Chemistry Letters
T1  - Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies
VL  - 26
IS  - 1
SP  - 235
EP  - 239
DO  - 10.1016/j.bmcl.2015.08.086
ER  - 

@article{
author = "Simić, Milena and Paunović, Nikola and Borić, Ivan and Ranđelović, Jelena and Vojnović, Sandra and Nikodinović-Runić, Jasmina and Pekmezović, Marina and Savić, Vladimir",
year = "2016",
abstract = "A series of novel 3-substituted isocoumarins was prepared via Pd-catalysed coupling processes and screened in vitro for antifungal activity against Candida species. The study revealed antifungal potential of isocoumarins possessing the azole substituents, which, in some cases, showed biological properties equal to those of clinically used voriconazole. Selected compounds were also screened against voriconazole resistant Candida krusei 6258 and a clinical isolate Candida parapsilosis CA-27. Although the activity against these targets needs to be improved further, the results emphasise additional potential of this new class of antifungal compounds.",
publisher = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Bioorganic & Medicinal Chemistry Letters",
title = "Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies",
volume = "26",
number = "1",
pages = "235-239",
doi = "10.1016/j.bmcl.2015.08.086"
}

Simić, M., Paunović, N., Borić, I., Ranđelović, J., Vojnović, S., Nikodinović-Runić, J., Pekmezović, M.,& Savić, V.. (2016). Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies. in Bioorganic & Medicinal Chemistry Letters
Pergamon-Elsevier Science Ltd, Oxford., 26(1), 235-239.
https://doi.org/10.1016/j.bmcl.2015.08.086

Simić M, Paunović N, Borić I, Ranđelović J, Vojnović S, Nikodinović-Runić J, Pekmezović M, Savić V. Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies. in Bioorganic & Medicinal Chemistry Letters. 2016;26(1):235-239.
doi:10.1016/j.bmcl.2015.08.086 .

Simić, Milena, Paunović, Nikola, Borić, Ivan, Ranđelović, Jelena, Vojnović, Sandra, Nikodinović-Runić, Jasmina, Pekmezović, Marina, Savić, Vladimir, "Functionalised isocoumarins as antifungal compounds: Synthesis and biological studies" in Bioorganic & Medicinal Chemistry Letters, 26, no. 1 (2016):235-239,
https://doi.org/10.1016/j.bmcl.2015.08.086 . .

TY  - JOUR
AU  - Lazić, Jelena
AU  - Spasić, Jelena
AU  - Francuski, Đorđe
AU  - Tokić-Vujošević, Zorana
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
AU  - Đokić, Lidija
PY  - 2016
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2690
AB  - Michael addition of aldehydes to nitro-olefins is an effective method to obtain useful chiral gamma-nitroaldehydes. gamma-Nitroaldehydes are precursors for chiral gamma-aminobutyric acid analogues, which have numerous pharmacological activities and are used for the treatment of neurological disorders. A whole-cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the Michael addition of branched aldehydes to beta-nitrostyrenes. The aim of this study was to investigate the influence of the substitution of the N-terminal proline with lysine and arginine, both containing a reactive epsilon-amino group, on the Michael addition catalyzed by 4-OT. First, the effects of these mutations were examined by in silico analysis, followed by the generation of three terminal lysine mutants. The generated mutants, 4-OT_K, 4-OT_PK and 4-OT_KK were tested for their ability to utilise beta-nitrostyrene (1), (E)-1-nitro-2-(2-thienyl)ethene (2) and trans-p-chloro-beta-nitrostyrene (3) as Michael acceptors with isobutanal (2-methylpropanal) as the donor. For comparison, the lithium salt of lysine was used in the same organocatalytic reactions. In general, the introduction of lysine had a negative effect on Michael additions based on overall product yields. However, additional lysine residues at the N-terminus of the protein resulted in structural changes that enhanced the activity towards 2 and 3. Therefore, the N-terminal proline is important for 4-OT-catalysed Michael-additions, but it is not essential.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)
VL  - 81
IS  - 8
SP  - 871
EP  - 881
DO  - 10.2298/JSC160222053L
ER  - 

@article{
author = "Lazić, Jelena and Spasić, Jelena and Francuski, Đorđe and Tokić-Vujošević, Zorana and Nikodinović-Runić, Jasmina and Maslak, Veselin and Đokić, Lidija",
year = "2016",
abstract = "Michael addition of aldehydes to nitro-olefins is an effective method to obtain useful chiral gamma-nitroaldehydes. gamma-Nitroaldehydes are precursors for chiral gamma-aminobutyric acid analogues, which have numerous pharmacological activities and are used for the treatment of neurological disorders. A whole-cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the Michael addition of branched aldehydes to beta-nitrostyrenes. The aim of this study was to investigate the influence of the substitution of the N-terminal proline with lysine and arginine, both containing a reactive epsilon-amino group, on the Michael addition catalyzed by 4-OT. First, the effects of these mutations were examined by in silico analysis, followed by the generation of three terminal lysine mutants. The generated mutants, 4-OT_K, 4-OT_PK and 4-OT_KK were tested for their ability to utilise beta-nitrostyrene (1), (E)-1-nitro-2-(2-thienyl)ethene (2) and trans-p-chloro-beta-nitrostyrene (3) as Michael acceptors with isobutanal (2-methylpropanal) as the donor. For comparison, the lithium salt of lysine was used in the same organocatalytic reactions. In general, the introduction of lysine had a negative effect on Michael additions based on overall product yields. However, additional lysine residues at the N-terminus of the protein resulted in structural changes that enhanced the activity towards 2 and 3. Therefore, the N-terminal proline is important for 4-OT-catalysed Michael-additions, but it is not essential.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)",
volume = "81",
number = "8",
pages = "871-881",
doi = "10.2298/JSC160222053L"
}

Lazić, J., Spasić, J., Francuski, Đ., Tokić-Vujošević, Z., Nikodinović-Runić, J., Maslak, V.,& Đokić, L.. (2016). Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT). in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 81(8), 871-881.
https://doi.org/10.2298/JSC160222053L

Lazić J, Spasić J, Francuski Đ, Tokić-Vujošević Z, Nikodinović-Runić J, Maslak V, Đokić L. Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT). in Journal of the Serbian Chemical Society. 2016;81(8):871-881.
doi:10.2298/JSC160222053L .

Lazić, Jelena, Spasić, Jelena, Francuski, Đorđe, Tokić-Vujošević, Zorana, Nikodinović-Runić, Jasmina, Maslak, Veselin, Đokić, Lidija, "Importance of N-terminal proline for the promiscuous activity of 4-oxalocrotonate tautomerase (4-OT)" in Journal of the Serbian Chemical Society, 81, no. 8 (2016):871-881,
https://doi.org/10.2298/JSC160222053L . .

TY  - JOUR
AU  - Kramar, Ana
AU  - Ilić-Tomić, Tatjana
AU  - Petković, Miloš
AU  - Radulović, Niko
AU  - Kostić, Mirjana
AU  - Jocić, Dragan
AU  - Nikodinović-Runić, Jasmina
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2214
AB  - Renewed demand for incorporation of natural dyes (bio-colorants) in textile industry could be met through biotechnological production of bacterial pigments. Two new Streptomyces strains (NP2 and NP4) were isolated for the remarkable ability to produce diffusible deep blue and deep red pigment into fermentation medium. Crude mycelial extracts of both strains were used as bio-colorants in conventional textile dyeing procedures avoiding downstream purification procedures. The yields of bio-colorants obtained in this way were 62 and 84 mg per g of mycelia for Streptomyces sp. NP2 and Streptomyces sp. NP4, respectively. Through nuclear magnetic resonance analysis of crude extracts before and after dyeing procedures, it was shown that both extracts contained prodigiosin-like family of compounds that exhibited different dyeing capabilities towards different textile fibers. Polyamide and acrylic fibers were colored to the deepest shade, polyester and triacetate fibers to a noticeable, but much lower shade depth, while cotton and cellulosic fibers stained weakly. These results confirmed that crude bacterial extracts had the characteristics similar to those of ionic and disperse dyes, which was consistent with the identified polypyrrolic prodigiosin-like structures.
PB  - Springer, New York
T2  - Yakugaku Zasshi - Journal of the Pharmaceutical Society of Japan
T1  - Crude bacterial extracts of two new Streptomyces sp isolates as bio-colorants for textile dyeing
VL  - 30
IS  - 8
SP  - 2231
EP  - 2240
DO  - 10.1007/s11274-014-1644-x
ER  - 

@article{
author = "Kramar, Ana and Ilić-Tomić, Tatjana and Petković, Miloš and Radulović, Niko and Kostić, Mirjana and Jocić, Dragan and Nikodinović-Runić, Jasmina",
year = "2014",
abstract = "Renewed demand for incorporation of natural dyes (bio-colorants) in textile industry could be met through biotechnological production of bacterial pigments. Two new Streptomyces strains (NP2 and NP4) were isolated for the remarkable ability to produce diffusible deep blue and deep red pigment into fermentation medium. Crude mycelial extracts of both strains were used as bio-colorants in conventional textile dyeing procedures avoiding downstream purification procedures. The yields of bio-colorants obtained in this way were 62 and 84 mg per g of mycelia for Streptomyces sp. NP2 and Streptomyces sp. NP4, respectively. Through nuclear magnetic resonance analysis of crude extracts before and after dyeing procedures, it was shown that both extracts contained prodigiosin-like family of compounds that exhibited different dyeing capabilities towards different textile fibers. Polyamide and acrylic fibers were colored to the deepest shade, polyester and triacetate fibers to a noticeable, but much lower shade depth, while cotton and cellulosic fibers stained weakly. These results confirmed that crude bacterial extracts had the characteristics similar to those of ionic and disperse dyes, which was consistent with the identified polypyrrolic prodigiosin-like structures.",
publisher = "Springer, New York",
journal = "Yakugaku Zasshi - Journal of the Pharmaceutical Society of Japan",
title = "Crude bacterial extracts of two new Streptomyces sp isolates as bio-colorants for textile dyeing",
volume = "30",
number = "8",
pages = "2231-2240",
doi = "10.1007/s11274-014-1644-x"
}

Kramar, A., Ilić-Tomić, T., Petković, M., Radulović, N., Kostić, M., Jocić, D.,& Nikodinović-Runić, J.. (2014). Crude bacterial extracts of two new Streptomyces sp isolates as bio-colorants for textile dyeing. in Yakugaku Zasshi - Journal of the Pharmaceutical Society of Japan
Springer, New York., 30(8), 2231-2240.
https://doi.org/10.1007/s11274-014-1644-x

Kramar A, Ilić-Tomić T, Petković M, Radulović N, Kostić M, Jocić D, Nikodinović-Runić J. Crude bacterial extracts of two new Streptomyces sp isolates as bio-colorants for textile dyeing. in Yakugaku Zasshi - Journal of the Pharmaceutical Society of Japan. 2014;30(8):2231-2240.
doi:10.1007/s11274-014-1644-x .

Kramar, Ana, Ilić-Tomić, Tatjana, Petković, Miloš, Radulović, Niko, Kostić, Mirjana, Jocić, Dragan, Nikodinović-Runić, Jasmina, "Crude bacterial extracts of two new Streptomyces sp isolates as bio-colorants for textile dyeing" in Yakugaku Zasshi - Journal of the Pharmaceutical Society of Japan, 30, no. 8 (2014):2231-2240,
https://doi.org/10.1007/s11274-014-1644-x . .

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Jeremić, Sanja
AU  - Đokić, Lidija
AU  - Savić, Vladimir
AU  - Radivojević, Jelena
AU  - Maslak, Veselin
AU  - Ivković, Branka
AU  - Vasiljević, Branka
AU  - Nikodinović-Runić, Jasmina
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2202
AB  - Chemoselective reduction of activated carbon-carbon double bond in conjugated nitroalkenes was achieved using Escherichia coli BL21(DE3) whole cells. Nine different substrates have been used furnishing the reduced products in moderate to good yields. 1-Nitro-4-phenyl-1,3-butadiene and (2-nitro-1-propenyl)benzene were successfully biotransformed with corresponding product yields of 54% and 45% respectively. Using this simple and environmentally friendly system 2-(2-nitropropyl)pyridine and 2-(2-nitropropyl)naphthalene were synthesized and characterized for the first time. High substrate conversion efficiency was coupled with low enantioselectivity, however 29% enantiomeric excess was detected in the case of 2-(2-nitropropyl)pyridine. It was shown that electronic properties of the aromatic ring, which affected polarity of the double bond, were not highly influential factors in the reduction process, but the presence of the nitro functionality was essential for the reaction to proceed. 1-Phenyl-4-nitro-1,3-butadiene could not be biotransformed by whole cells of Pseudomonas putida KT2440 or Bacillus subtilis 168 while it was successfully reduced by E. coli DH5 alpha but with lower efficiency in comparison to E. coli BL21(DE3). Knockout mutant affected in nemA gene coding for N-ethylmaleimide reductase (BL21 Delta nemA) could still catalyze bioreductions suggesting multiple active reductases within E. coli BL21(DE3) biocatalyst. The described biocatalytic reduction of substituted nitroalkenes provides an efficient route for the preparation of the corresponding nitroalkanes and introduces the new application of the strain traditionally utilized for recombinant protein expression.
PB  - Elsevier Science Inc, New York
T2  - Enzyme and Microbial Technology
T1  - Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain
VL  - 60
SP  - 16
EP  - 23
DO  - 10.1016/j.enzmictec.2014.03.010
ER  - 

@article{
author = "Jovanović, Predrag and Jeremić, Sanja and Đokić, Lidija and Savić, Vladimir and Radivojević, Jelena and Maslak, Veselin and Ivković, Branka and Vasiljević, Branka and Nikodinović-Runić, Jasmina",
year = "2014",
abstract = "Chemoselective reduction of activated carbon-carbon double bond in conjugated nitroalkenes was achieved using Escherichia coli BL21(DE3) whole cells. Nine different substrates have been used furnishing the reduced products in moderate to good yields. 1-Nitro-4-phenyl-1,3-butadiene and (2-nitro-1-propenyl)benzene were successfully biotransformed with corresponding product yields of 54% and 45% respectively. Using this simple and environmentally friendly system 2-(2-nitropropyl)pyridine and 2-(2-nitropropyl)naphthalene were synthesized and characterized for the first time. High substrate conversion efficiency was coupled with low enantioselectivity, however 29% enantiomeric excess was detected in the case of 2-(2-nitropropyl)pyridine. It was shown that electronic properties of the aromatic ring, which affected polarity of the double bond, were not highly influential factors in the reduction process, but the presence of the nitro functionality was essential for the reaction to proceed. 1-Phenyl-4-nitro-1,3-butadiene could not be biotransformed by whole cells of Pseudomonas putida KT2440 or Bacillus subtilis 168 while it was successfully reduced by E. coli DH5 alpha but with lower efficiency in comparison to E. coli BL21(DE3). Knockout mutant affected in nemA gene coding for N-ethylmaleimide reductase (BL21 Delta nemA) could still catalyze bioreductions suggesting multiple active reductases within E. coli BL21(DE3) biocatalyst. The described biocatalytic reduction of substituted nitroalkenes provides an efficient route for the preparation of the corresponding nitroalkanes and introduces the new application of the strain traditionally utilized for recombinant protein expression.",
publisher = "Elsevier Science Inc, New York",
journal = "Enzyme and Microbial Technology",
title = "Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain",
volume = "60",
pages = "16-23",
doi = "10.1016/j.enzmictec.2014.03.010"
}

Jovanović, P., Jeremić, S., Đokić, L., Savić, V., Radivojević, J., Maslak, V., Ivković, B., Vasiljević, B.,& Nikodinović-Runić, J.. (2014). Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain. in Enzyme and Microbial Technology
Elsevier Science Inc, New York., 60, 16-23.
https://doi.org/10.1016/j.enzmictec.2014.03.010

Jovanović P, Jeremić S, Đokić L, Savić V, Radivojević J, Maslak V, Ivković B, Vasiljević B, Nikodinović-Runić J. Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain. in Enzyme and Microbial Technology. 2014;60:16-23.
doi:10.1016/j.enzmictec.2014.03.010 .

Jovanović, Predrag, Jeremić, Sanja, Đokić, Lidija, Savić, Vladimir, Radivojević, Jelena, Maslak, Veselin, Ivković, Branka, Vasiljević, Branka, Nikodinović-Runić, Jasmina, "Chemoselective biocatalytic reduction of conjugated nitroalkenes: New application for an Escherichia coli BL21(DE3) expression strain" in Enzyme and Microbial Technology, 60 (2014):16-23,
https://doi.org/10.1016/j.enzmictec.2014.03.010 . .

TY  - JOUR
AU  - Radivojević, Jelena
AU  - Minovska, Gordana
AU  - Senerović, Lidija
AU  - O'Connor, Kevin
AU  - Jovanović, Predrag
AU  - Savić, Vladimir
AU  - Tokić-Vujošević, Zorana
AU  - Nikodinović-Runić, Jasmina
AU  - Maslak, Veselin
PY  - 2014
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/2107
AB  - Synthesis of gamma-nitroaldehydes from branched chain aldehydes and a range of alpha,beta-unsaturated nitroalkenes was achieved by a whole-cell biocatalytic reaction using 4-oxalocrotonate tautomerase as catalyst. Under mild conditions, cyclic and acyclic branched aldehydes were converted into synthetically valuable quaternary carbon containing gamma-nitroaldehydes. The yields of the desired products were influenced by reaction condition parameters such as organic solvent, temperature and pH. The whole-cell biocatalytic approach to the generation of alpha,alpha-substituted gamma-nitroaldehydes was compared to the organocatalytic approach involving the lithium salt of phenylalanine as a catalyst. As the resulting gamma-nitroaldehydes exhibited moderate antifungal activity and mild in vitro cytotoxicity against human fibroblasts (0.2-0.4 mM) they could further be examined as potentially useful pharmaceutical synthons.
PB  - Royal Soc Chemistry, Cambridge
T2  - Russian Journal of Genetics
T1  - Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst
VL  - 4
IS  - 105
SP  - 60502
EP  - 60510
DO  - 10.1039/c4ra05517a
ER  - 

@article{
author = "Radivojević, Jelena and Minovska, Gordana and Senerović, Lidija and O'Connor, Kevin and Jovanović, Predrag and Savić, Vladimir and Tokić-Vujošević, Zorana and Nikodinović-Runić, Jasmina and Maslak, Veselin",
year = "2014",
abstract = "Synthesis of gamma-nitroaldehydes from branched chain aldehydes and a range of alpha,beta-unsaturated nitroalkenes was achieved by a whole-cell biocatalytic reaction using 4-oxalocrotonate tautomerase as catalyst. Under mild conditions, cyclic and acyclic branched aldehydes were converted into synthetically valuable quaternary carbon containing gamma-nitroaldehydes. The yields of the desired products were influenced by reaction condition parameters such as organic solvent, temperature and pH. The whole-cell biocatalytic approach to the generation of alpha,alpha-substituted gamma-nitroaldehydes was compared to the organocatalytic approach involving the lithium salt of phenylalanine as a catalyst. As the resulting gamma-nitroaldehydes exhibited moderate antifungal activity and mild in vitro cytotoxicity against human fibroblasts (0.2-0.4 mM) they could further be examined as potentially useful pharmaceutical synthons.",
publisher = "Royal Soc Chemistry, Cambridge",
journal = "Russian Journal of Genetics",
title = "Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst",
volume = "4",
number = "105",
pages = "60502-60510",
doi = "10.1039/c4ra05517a"
}

Radivojević, J., Minovska, G., Senerović, L., O'Connor, K., Jovanović, P., Savić, V., Tokić-Vujošević, Z., Nikodinović-Runić, J.,& Maslak, V.. (2014). Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst. in Russian Journal of Genetics
Royal Soc Chemistry, Cambridge., 4(105), 60502-60510.
https://doi.org/10.1039/c4ra05517a

Radivojević J, Minovska G, Senerović L, O'Connor K, Jovanović P, Savić V, Tokić-Vujošević Z, Nikodinović-Runić J, Maslak V. Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst. in Russian Journal of Genetics. 2014;4(105):60502-60510.
doi:10.1039/c4ra05517a .

Radivojević, Jelena, Minovska, Gordana, Senerović, Lidija, O'Connor, Kevin, Jovanović, Predrag, Savić, Vladimir, Tokić-Vujošević, Zorana, Nikodinović-Runić, Jasmina, Maslak, Veselin, "Synthesis of gamma-nitroaldehydes containing quaternary carbon in the alpha-position using a 4-oxalocrotonate tautomerase whole-cell biocatalyst" in Russian Journal of Genetics, 4, no. 105 (2014):60502-60510,
https://doi.org/10.1039/c4ra05517a . .

TY  - JOUR
AU  - Narancić, Tanja
AU  - Kadivojević, Jelena
AU  - Jovanović, Predrag
AU  - Francuski, Đorđe
AU  - Bigović, Miljan
AU  - Maslak, Veselin
AU  - Savić, Vladimir
AU  - Vasiljević, Branka
AU  - O'Connor, Kevin
AU  - Nikodinović-Runić, Jasmina
PY  - 2013
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1960
AB  - A novel whole cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the asymmetric Michael addition of acetaldehyde to beta-nitrostyrenes. Optimal ratio of substrates (2 mM beta-nitrostyrenes and 20 mM acetaldehyde) and biocatalyst of 5 g of cell dry weight of biocatalyst per liter was determined. Through further bioprocess improvement by sequential addition of substrate 10 mM nitrostyrene biotransformation was achieved within 150 min. Excellent enantioselectivity (>99% ee) and product yields of up to 60% were obtained with beta-nitrostyrene substrate. The biotransformation product, 4-nitro-3-phenyl-butanal, was isolated from aqueous media and further transformed into the corresponding amino alcohol. The biocatalyst exhibited lower reaction rates with p-Cl-, o-Cl- and p-F-beta-nitrostyrenes with product yields of 38%, 51%, 31% and ee values of 84%, 88% and 94% respectively. The importance of the terminal,proline of 4-UT was confirmed by two proline enriched variants and homology modeling.
PB  - Elsevier Sci Ltd, Oxford
T2  - Bioresource Technology
T1  - Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase
VL  - 142
SP  - 462
EP  - 468
DO  - 10.1016/j.biortech.2013.05.074
ER  - 

@article{
author = "Narancić, Tanja and Kadivojević, Jelena and Jovanović, Predrag and Francuski, Đorđe and Bigović, Miljan and Maslak, Veselin and Savić, Vladimir and Vasiljević, Branka and O'Connor, Kevin and Nikodinović-Runić, Jasmina",
year = "2013",
abstract = "A novel whole cell system based on recombinantly expressed 4-oxalocrotonate tautomerase (4-OT) was developed and shown to be an effective biocatalyst for the asymmetric Michael addition of acetaldehyde to beta-nitrostyrenes. Optimal ratio of substrates (2 mM beta-nitrostyrenes and 20 mM acetaldehyde) and biocatalyst of 5 g of cell dry weight of biocatalyst per liter was determined. Through further bioprocess improvement by sequential addition of substrate 10 mM nitrostyrene biotransformation was achieved within 150 min. Excellent enantioselectivity (>99% ee) and product yields of up to 60% were obtained with beta-nitrostyrene substrate. The biotransformation product, 4-nitro-3-phenyl-butanal, was isolated from aqueous media and further transformed into the corresponding amino alcohol. The biocatalyst exhibited lower reaction rates with p-Cl-, o-Cl- and p-F-beta-nitrostyrenes with product yields of 38%, 51%, 31% and ee values of 84%, 88% and 94% respectively. The importance of the terminal,proline of 4-UT was confirmed by two proline enriched variants and homology modeling.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Bioresource Technology",
title = "Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase",
volume = "142",
pages = "462-468",
doi = "10.1016/j.biortech.2013.05.074"
}

Narancić, T., Kadivojević, J., Jovanović, P., Francuski, Đ., Bigović, M., Maslak, V., Savić, V., Vasiljević, B., O'Connor, K.,& Nikodinović-Runić, J.. (2013). Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase. in Bioresource Technology
Elsevier Sci Ltd, Oxford., 142, 462-468.
https://doi.org/10.1016/j.biortech.2013.05.074

Narancić T, Kadivojević J, Jovanović P, Francuski Đ, Bigović M, Maslak V, Savić V, Vasiljević B, O'Connor K, Nikodinović-Runić J. Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase. in Bioresource Technology. 2013;142:462-468.
doi:10.1016/j.biortech.2013.05.074 .

Narancić, Tanja, Kadivojević, Jelena, Jovanović, Predrag, Francuski, Đorđe, Bigović, Miljan, Maslak, Veselin, Savić, Vladimir, Vasiljević, Branka, O'Connor, Kevin, Nikodinović-Runić, Jasmina, "Highly efficient Michael-type addition of acetaldehyde to beta-nitrostyrenes by whole resting cells of Escherichia coli expressing 4-oxalocrotonate tautomerase" in Bioresource Technology, 142 (2013):462-468,
https://doi.org/10.1016/j.biortech.2013.05.074 . .

TY  - JOUR
AU  - Stanković, Nada
AU  - Radulović, Vanja
AU  - Petković, Miloš
AU  - Vucković, Ivan M.
AU  - Jadranin, Milka
AU  - Vasiljević, Branka
AU  - Nikodinović-Runić, Jasmina
PY  - 2012
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1683
AB  - A Gram-positive, red-pigment-producing bacterial strain, designated JS520 was isolated from the pristine sediment from the cave on mountain Miroc in Serbia. Strain was confirmed to belong to Streptomyces genus based on phenotypic and genetic analysis. Streptomyces sp. JS520 has the ability to produce exceptionally high amounts of deep red pigment into both solid and liquid media. Liquid chromatography and mass spectroscopy of the purified pigments revealed the major component to be undecylprodigiosin (93 %) with minor component being oxidatively cyclized derivative. The pigment production was affected by medium composition, temperature, pH, and the aeration rate. By medium optimization, yields of undecylprodigiosin of 138 mg l(-1) were achieved, what is the highest level of undecylprodigiosin production reported for the members of Gram-positive Streptomyces genus. Purified pigment had antimicrobial properties against bacterial Bacillus and Micrococcus species (50 mu g ml(-1)) and against Candida albicans species (100-200 mu g ml(-1) range). The ability to affect auto-oxidation of the linoleic acid was demonstrated for the purified undecylprodigiosin, suggesting antioxidative properties of this pigment. Multiple ecophysiological roles of the pigment were revealed by comparing cultures grown under pigment-producing and pigment-nonproducing conditions. Cells grown under undecylprodigiosin-producing conditions could tolerate presence of hydrogen peroxide exhibiting three times smaller zones of inhibition at 100 mM H2O2. Undecylprodigiosin-producing cells were also less susceptible to tetracycline, kanamycin, chloramphenicol, and 8-hydroxyquinoline. While the growth of the cells not producing pigment was completely inhibited by 15 min of exposure to ultraviolet light (254 nm), cells producing undecylprodigiosin and cells supplied with purified pigment in vitro showed survival rates at 22 and 8 %, respectively.
PB  - Springer, New York
T2  - Applied Microbiology and Biotechnology
T1  - Streptomyces sp JS520 produces exceptionally high quantities of undecylprodigiosin with antibacterial, antioxidative, and UV-protective properties
VL  - 96
IS  - 5
SP  - 1217
EP  - 1231
DO  - 10.1007/s00253-012-4237-3
ER  - 

@article{
author = "Stanković, Nada and Radulović, Vanja and Petković, Miloš and Vucković, Ivan M. and Jadranin, Milka and Vasiljević, Branka and Nikodinović-Runić, Jasmina",
year = "2012",
abstract = "A Gram-positive, red-pigment-producing bacterial strain, designated JS520 was isolated from the pristine sediment from the cave on mountain Miroc in Serbia. Strain was confirmed to belong to Streptomyces genus based on phenotypic and genetic analysis. Streptomyces sp. JS520 has the ability to produce exceptionally high amounts of deep red pigment into both solid and liquid media. Liquid chromatography and mass spectroscopy of the purified pigments revealed the major component to be undecylprodigiosin (93 %) with minor component being oxidatively cyclized derivative. The pigment production was affected by medium composition, temperature, pH, and the aeration rate. By medium optimization, yields of undecylprodigiosin of 138 mg l(-1) were achieved, what is the highest level of undecylprodigiosin production reported for the members of Gram-positive Streptomyces genus. Purified pigment had antimicrobial properties against bacterial Bacillus and Micrococcus species (50 mu g ml(-1)) and against Candida albicans species (100-200 mu g ml(-1) range). The ability to affect auto-oxidation of the linoleic acid was demonstrated for the purified undecylprodigiosin, suggesting antioxidative properties of this pigment. Multiple ecophysiological roles of the pigment were revealed by comparing cultures grown under pigment-producing and pigment-nonproducing conditions. Cells grown under undecylprodigiosin-producing conditions could tolerate presence of hydrogen peroxide exhibiting three times smaller zones of inhibition at 100 mM H2O2. Undecylprodigiosin-producing cells were also less susceptible to tetracycline, kanamycin, chloramphenicol, and 8-hydroxyquinoline. While the growth of the cells not producing pigment was completely inhibited by 15 min of exposure to ultraviolet light (254 nm), cells producing undecylprodigiosin and cells supplied with purified pigment in vitro showed survival rates at 22 and 8 %, respectively.",
publisher = "Springer, New York",
journal = "Applied Microbiology and Biotechnology",
title = "Streptomyces sp JS520 produces exceptionally high quantities of undecylprodigiosin with antibacterial, antioxidative, and UV-protective properties",
volume = "96",
number = "5",
pages = "1217-1231",
doi = "10.1007/s00253-012-4237-3"
}

Stanković, N., Radulović, V., Petković, M., Vucković, I. M., Jadranin, M., Vasiljević, B.,& Nikodinović-Runić, J.. (2012). Streptomyces sp JS520 produces exceptionally high quantities of undecylprodigiosin with antibacterial, antioxidative, and UV-protective properties. in Applied Microbiology and Biotechnology
Springer, New York., 96(5), 1217-1231.
https://doi.org/10.1007/s00253-012-4237-3

Stanković N, Radulović V, Petković M, Vucković IM, Jadranin M, Vasiljević B, Nikodinović-Runić J. Streptomyces sp JS520 produces exceptionally high quantities of undecylprodigiosin with antibacterial, antioxidative, and UV-protective properties. in Applied Microbiology and Biotechnology. 2012;96(5):1217-1231.
doi:10.1007/s00253-012-4237-3 .

Stanković, Nada, Radulović, Vanja, Petković, Miloš, Vucković, Ivan M., Jadranin, Milka, Vasiljević, Branka, Nikodinović-Runić, Jasmina, "Streptomyces sp JS520 produces exceptionally high quantities of undecylprodigiosin with antibacterial, antioxidative, and UV-protective properties" in Applied Microbiology and Biotechnology, 96, no. 5 (2012):1217-1231,
https://doi.org/10.1007/s00253-012-4237-3 . .