TY  - CONF
AU  - Simić, Milena
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Žižak, Željko
AU  - Tasić, Gordana
AU  - Jovanović, Miloš
AU  - Savić, Vladimir
PY  - 2021
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5391
AB  - Kumarini su heterociklična jedinjenja veoma rasprostranjen u prirodi. Kao privilegovana struktura,
ovaj molekul se nalazi i u velikom broju sintetskih derivata sa značajnom biološkom aktivnošću.
Posebno su interesantni hibridi koji sadrže dve farmakofore, od kojih je jedna kumarin. Cilj ovog
istraživanja bio je sinteza serije jednostavnih novih 4-azolil kumarina i evaluacija njihove in vitro
citotoksičnosti prema humanim kancerskim ćelijskim linijama HeLa, K562, MCF-7 i MDA-MB-
453.
AB  - Coumarins are heterocyclic compounds widely distributed in nature. As a privileged structure,
coumarin is also found in a large number of synthetic molecules with important biological activity.
Particularly interesting compounds are coumarin-containing hybrids, compounds with two or more
pharmacophores. The aim of this work was preparation of simple novel azolyl-coumarin hybrids
and evaluation of their cytotoxic effect on human cancer cells, HeLa, K562, MDA-MB-453 and
MCF-7.
PB  - Srpsko hemijsko društvo, Beograd
C3  - 57. Savetovanje Srpskog hemijskog društva. Kratki izvodi, Juni 18 i 19, 2021, Kragujevac, Srbija
T1  - Sinteza i antikancerski potencijal 4-azolilkumarina
T1  - Synthesis and anticancer potential of 4-azolylcoumarins
SP  - 88
EP  - 88
UR  - https://hdl.handle.net/21.15107/rcub_farfar_5391
ER  - 

@conference{
author = "Simić, Milena and Jovanović, Predrag and Petković, Miloš and Žižak, Željko and Tasić, Gordana and Jovanović, Miloš and Savić, Vladimir",
year = "2021",
abstract = "Kumarini su heterociklična jedinjenja veoma rasprostranjen u prirodi. Kao privilegovana struktura,
ovaj molekul se nalazi i u velikom broju sintetskih derivata sa značajnom biološkom aktivnošću.
Posebno su interesantni hibridi koji sadrže dve farmakofore, od kojih je jedna kumarin. Cilj ovog
istraživanja bio je sinteza serije jednostavnih novih 4-azolil kumarina i evaluacija njihove in vitro
citotoksičnosti prema humanim kancerskim ćelijskim linijama HeLa, K562, MCF-7 i MDA-MB-
453., Coumarins are heterocyclic compounds widely distributed in nature. As a privileged structure,
coumarin is also found in a large number of synthetic molecules with important biological activity.
Particularly interesting compounds are coumarin-containing hybrids, compounds with two or more
pharmacophores. The aim of this work was preparation of simple novel azolyl-coumarin hybrids
and evaluation of their cytotoxic effect on human cancer cells, HeLa, K562, MDA-MB-453 and
MCF-7.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "57. Savetovanje Srpskog hemijskog društva. Kratki izvodi, Juni 18 i 19, 2021, Kragujevac, Srbija",
title = "Sinteza i antikancerski potencijal 4-azolilkumarina, Synthesis and anticancer potential of 4-azolylcoumarins",
pages = "88-88",
url = "https://hdl.handle.net/21.15107/rcub_farfar_5391"
}

Simić, M., Jovanović, P., Petković, M., Žižak, Ž., Tasić, G., Jovanović, M.,& Savić, V.. (2021). Sinteza i antikancerski potencijal 4-azolilkumarina. in 57. Savetovanje Srpskog hemijskog društva. Kratki izvodi, Juni 18 i 19, 2021, Kragujevac, Srbija
Srpsko hemijsko društvo, Beograd., 88-88.
https://hdl.handle.net/21.15107/rcub_farfar_5391

Simić M, Jovanović P, Petković M, Žižak Ž, Tasić G, Jovanović M, Savić V. Sinteza i antikancerski potencijal 4-azolilkumarina. in 57. Savetovanje Srpskog hemijskog društva. Kratki izvodi, Juni 18 i 19, 2021, Kragujevac, Srbija. 2021;:88-88.
https://hdl.handle.net/21.15107/rcub_farfar_5391 .

Simić, Milena, Jovanović, Predrag, Petković, Miloš, Žižak, Željko, Tasić, Gordana, Jovanović, Miloš, Savić, Vladimir, "Sinteza i antikancerski potencijal 4-azolilkumarina" in 57. Savetovanje Srpskog hemijskog društva. Kratki izvodi, Juni 18 i 19, 2021, Kragujevac, Srbija (2021):88-88,
https://hdl.handle.net/21.15107/rcub_farfar_5391 .

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  - Dražić, Branka
AU  - Antonijević-Nikolić, Mirjana
AU  - Žižak, Željko
AU  - Tanasković, Slađana
PY  - 2020
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3650
AB  - Two   new   complexes   with   the   general   formula [Cu2(L)tpmc](ClO4)3·nH2O  (tpmc  = N,N′,N′′,N′′′-tetrakis(2-pyridylmethyl)- -1,4,8,11-tetraazacyclotetradecane,  L  = N-methylglycine, n =  3;  L  = N,N- -dimethylglycine, n = 2) were isolated and their composition, some physical and  chemical  properties  and  geometries  were  proposed  based  on  elemental analysis (C, H, N), conductometric and magnetic measurements and spectro-scopic data (UV–Vis, FTIR). It is evident that the complexes are binuclear and an exo coordination mode of the macrocyclic ligand in the boat conformation was proposed. The co-ligands are coordinated as a bridge using both oxygen atoms of the OCO- group. The cytotoxic activity of Cu(II) complexes as well as  their  Co(II)  analogs,  the  starting  ligands  and  the  free  salts  were  tested against human cervix adenocarcinoma cell line (HeLa), human chronic myelo-genous leukemia cells (K562), human breast cancer cell line (MDA-MB-453), and a non-cancerous cell line, human embryonic lung fibroblast (MRC-5). The IC50 values for the Cu(II) complexes were from 21.6±0.04 to 66.1±0.8, and for the Co(II) analogs were within the range from 8.8±0.74 to 15.40±1.52. All four complexes were tested for their antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and the yeast Candida albicans.
PB  - Belgrade : Serbian Chemical Society
T2  - Journal of the Serbian Chemical Society
T1  - Synthesis and characterization of copper(II) octaazamacrocyclic complexes with glycine derivatives. In vitro antiproliferative and antimicrobial evaluation of the Cu(II) and Co(II) analogous
VL  - 85
IS  - 5
SP  - 637
EP  - 649
DO  - 10.2298/JSC190710088D
ER  - 

@article{
author = "Dražić, Branka and Antonijević-Nikolić, Mirjana and Žižak, Željko and Tanasković, Slađana",
year = "2020",
abstract = "Two   new   complexes   with   the   general   formula [Cu2(L)tpmc](ClO4)3·nH2O  (tpmc  = N,N′,N′′,N′′′-tetrakis(2-pyridylmethyl)- -1,4,8,11-tetraazacyclotetradecane,  L  = N-methylglycine, n =  3;  L  = N,N- -dimethylglycine, n = 2) were isolated and their composition, some physical and  chemical  properties  and  geometries  were  proposed  based  on  elemental analysis (C, H, N), conductometric and magnetic measurements and spectro-scopic data (UV–Vis, FTIR). It is evident that the complexes are binuclear and an exo coordination mode of the macrocyclic ligand in the boat conformation was proposed. The co-ligands are coordinated as a bridge using both oxygen atoms of the OCO- group. The cytotoxic activity of Cu(II) complexes as well as  their  Co(II)  analogs,  the  starting  ligands  and  the  free  salts  were  tested against human cervix adenocarcinoma cell line (HeLa), human chronic myelo-genous leukemia cells (K562), human breast cancer cell line (MDA-MB-453), and a non-cancerous cell line, human embryonic lung fibroblast (MRC-5). The IC50 values for the Cu(II) complexes were from 21.6±0.04 to 66.1±0.8, and for the Co(II) analogs were within the range from 8.8±0.74 to 15.40±1.52. All four complexes were tested for their antimicrobial activity against Staphylococcus aureus, Bacillus subtilis, Escherichia coli and the yeast Candida albicans.",
publisher = "Belgrade : Serbian Chemical Society",
journal = "Journal of the Serbian Chemical Society",
title = "Synthesis and characterization of copper(II) octaazamacrocyclic complexes with glycine derivatives. In vitro antiproliferative and antimicrobial evaluation of the Cu(II) and Co(II) analogous",
volume = "85",
number = "5",
pages = "637-649",
doi = "10.2298/JSC190710088D"
}

Dražić, B., Antonijević-Nikolić, M., Žižak, Ž.,& Tanasković, S.. (2020). Synthesis and characterization of copper(II) octaazamacrocyclic complexes with glycine derivatives. In vitro antiproliferative and antimicrobial evaluation of the Cu(II) and Co(II) analogous. in Journal of the Serbian Chemical Society
Belgrade : Serbian Chemical Society., 85(5), 637-649.
https://doi.org/10.2298/JSC190710088D

Dražić B, Antonijević-Nikolić M, Žižak Ž, Tanasković S. Synthesis and characterization of copper(II) octaazamacrocyclic complexes with glycine derivatives. In vitro antiproliferative and antimicrobial evaluation of the Cu(II) and Co(II) analogous. in Journal of the Serbian Chemical Society. 2020;85(5):637-649.
doi:10.2298/JSC190710088D .

Dražić, Branka, Antonijević-Nikolić, Mirjana, Žižak, Željko, Tanasković, Slađana, "Synthesis and characterization of copper(II) octaazamacrocyclic complexes with glycine derivatives. In vitro antiproliferative and antimicrobial evaluation of the Cu(II) and Co(II) analogous" in Journal of the Serbian Chemical Society, 85, no. 5 (2020):637-649,
https://doi.org/10.2298/JSC190710088D . .

TY  - JOUR
AU  - Jovanović, Predrag
AU  - Petković, Miloš
AU  - Simić, Milena
AU  - Jovanović, Miloš
AU  - Tasić, Gordana
AU  - Crnogorac, Marija Dj.
AU  - Žižak, Željko
AU  - Savić, Vladimir
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/5329
AB  - A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.
PB  - Wiley-VCH Verlag
T2  - European Journal of Organic Chemistry
T1  - Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals
VL  - 2019
IS  - 29
SP  - 4701
EP  - 4709
DO  - 10.1002/ejoc.201900672
ER  - 

@article{
author = "Jovanović, Predrag and Petković, Miloš and Simić, Milena and Jovanović, Miloš and Tasić, Gordana and Crnogorac, Marija Dj. and Žižak, Željko and Savić, Vladimir",
year = "2019",
abstract = "A novel synthetic route for highly substituted conjugated ketones has been developed utilizing glycals as starting materials. The two-step process combined the Heck reaction/Lewis acid promoted ring opening to afford the products in 33–80 % overall yields and with a high level of trans stereoselectivity. Since the products are essentially the aldols, this methodology may be employed in some cases as an alternative synthetic route to the typical aldol condensation. Densely substituted, selectively protected conjugated ketones are synthetically attractive structures which, in our case, proved to be biologically equally appealing. Namely, they showed activity against several cancer cell lines, such as HeLa, K562, MDA-MB-453, in some instances overperforming cisplatin used as a standard.",
publisher = "Wiley-VCH Verlag",
journal = "European Journal of Organic Chemistry",
title = "Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals",
volume = "2019",
number = "29",
pages = "4701-4709",
doi = "10.1002/ejoc.201900672"
}

Jovanović, P., Petković, M., Simić, M., Jovanović, M., Tasić, G., Crnogorac, M. Dj., Žižak, Ž.,& Savić, V.. (2019). Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals. in European Journal of Organic Chemistry
Wiley-VCH Verlag., 2019(29), 4701-4709.
https://doi.org/10.1002/ejoc.201900672

Jovanović P, Petković M, Simić M, Jovanović M, Tasić G, Crnogorac MD, Žižak Ž, Savić V. Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals. in European Journal of Organic Chemistry. 2019;2019(29):4701-4709.
doi:10.1002/ejoc.201900672 .

Jovanović, Predrag, Petković, Miloš, Simić, Milena, Jovanović, Miloš, Tasić, Gordana, Crnogorac, Marija Dj., Žižak, Željko, Savić, Vladimir, "Stereocontrolled Synthesis of Highly Substituted trans α,β-Unsaturated Ketones with Potent Anticancer Properties from Glycals" in European Journal of Organic Chemistry, 2019, no. 29 (2019):4701-4709,
https://doi.org/10.1002/ejoc.201900672 . .

TY  - JOUR
AU  - Petrović, Predrag
AU  - Vunduk, J.
AU  - Klaus, A.
AU  - Carević, Momir
AU  - Petković, Miloš
AU  - Vuković, N.
AU  - Cvetković, A.
AU  - Žižak, Željko
AU  - Bugarski, Branko
PY  - 2019
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3357
AB  - Methanol extracts of mosaic puffball (Handkea utriformis, Bovistella utriformis, Lycoperdon utriforme, Calvatia utriformis - current name is a subject of debate), from three different stages - mycelium (HUMIC), immature (HUI) and mature fruiting bodies (HUM) were characterized and tested for antioxidant, antimicrobial and inhibitory activity on tyrosinase, acetyholinesterase (AChE), butyrylcholinesterase (BuChE) and 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA-R). Immature, edible, fruiting bodies were shown to be a good source of antioxidants (11.5 mg/g of extract) and cholesterol-lowering agent, lovastatin (234 mu g/g of extract), and exhibited significant antimicrobial activity. In addition, HUI showed good and selective AChE (4.48 mg/mL) and non-lovastatin related HMG-CoA-R inhibition (1.16 mg/mL), which all together suggests that regular consumption of it may have health benefits. Mature fruiting bodies, inedible due to powdery consistence, have been used in traditional medicine for wound treatment; their extract was relatively rich in free ergosterol (31.65 mg/g of extract), N-acetylglucosamine (24 mg/g of extract), alpha-tocopherol (4 mg/g of extract) and had best overall antioxidant activity, which was in correlation with its highest phenolic content (19.4 mg GAE/mL). It also exhibited significant tyrosinase inhibitory activity (0.22 mg/mL) and thus could be used in medicinal and cosmetic products for wound healing and bleaching. Mycelium, which can be easily grown in laboratory conditions did not have the same properties as, neither immature or mature fruiting bodies, although it showed prominent antimicrobial activity, notably against Pseudomonas aeruginosa (MIC = 0.0625 mg/mL) and could be a source of antimicrobial compounds.
PB  - Elsevier Science BV, Amsterdam
T2  - Southern Medical Journal
T1  - From mycelium to spores: A whole circle of biological potency of mosaic puffball
VL  - 123
SP  - 152
EP  - 160
DO  - 10.1016/j.sajb.2019.03.016
ER  - 

@article{
author = "Petrović, Predrag and Vunduk, J. and Klaus, A. and Carević, Momir and Petković, Miloš and Vuković, N. and Cvetković, A. and Žižak, Željko and Bugarski, Branko",
year = "2019",
abstract = "Methanol extracts of mosaic puffball (Handkea utriformis, Bovistella utriformis, Lycoperdon utriforme, Calvatia utriformis - current name is a subject of debate), from three different stages - mycelium (HUMIC), immature (HUI) and mature fruiting bodies (HUM) were characterized and tested for antioxidant, antimicrobial and inhibitory activity on tyrosinase, acetyholinesterase (AChE), butyrylcholinesterase (BuChE) and 3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMG-CoA-R). Immature, edible, fruiting bodies were shown to be a good source of antioxidants (11.5 mg/g of extract) and cholesterol-lowering agent, lovastatin (234 mu g/g of extract), and exhibited significant antimicrobial activity. In addition, HUI showed good and selective AChE (4.48 mg/mL) and non-lovastatin related HMG-CoA-R inhibition (1.16 mg/mL), which all together suggests that regular consumption of it may have health benefits. Mature fruiting bodies, inedible due to powdery consistence, have been used in traditional medicine for wound treatment; their extract was relatively rich in free ergosterol (31.65 mg/g of extract), N-acetylglucosamine (24 mg/g of extract), alpha-tocopherol (4 mg/g of extract) and had best overall antioxidant activity, which was in correlation with its highest phenolic content (19.4 mg GAE/mL). It also exhibited significant tyrosinase inhibitory activity (0.22 mg/mL) and thus could be used in medicinal and cosmetic products for wound healing and bleaching. Mycelium, which can be easily grown in laboratory conditions did not have the same properties as, neither immature or mature fruiting bodies, although it showed prominent antimicrobial activity, notably against Pseudomonas aeruginosa (MIC = 0.0625 mg/mL) and could be a source of antimicrobial compounds.",
publisher = "Elsevier Science BV, Amsterdam",
journal = "Southern Medical Journal",
title = "From mycelium to spores: A whole circle of biological potency of mosaic puffball",
volume = "123",
pages = "152-160",
doi = "10.1016/j.sajb.2019.03.016"
}

Petrović, P., Vunduk, J., Klaus, A., Carević, M., Petković, M., Vuković, N., Cvetković, A., Žižak, Ž.,& Bugarski, B.. (2019). From mycelium to spores: A whole circle of biological potency of mosaic puffball. in Southern Medical Journal
Elsevier Science BV, Amsterdam., 123, 152-160.
https://doi.org/10.1016/j.sajb.2019.03.016

Petrović P, Vunduk J, Klaus A, Carević M, Petković M, Vuković N, Cvetković A, Žižak Ž, Bugarski B. From mycelium to spores: A whole circle of biological potency of mosaic puffball. in Southern Medical Journal. 2019;123:152-160.
doi:10.1016/j.sajb.2019.03.016 .

Petrović, Predrag, Vunduk, J., Klaus, A., Carević, Momir, Petković, Miloš, Vuković, N., Cvetković, A., Žižak, Željko, Bugarski, Branko, "From mycelium to spores: A whole circle of biological potency of mosaic puffball" in Southern Medical Journal, 123 (2019):152-160,
https://doi.org/10.1016/j.sajb.2019.03.016 . .

TY  - JOUR
AU  - Sova, Matej
AU  - Žižak, Željko
AU  - Antić-Stanković, Jelena
AU  - Prijatelj, Matevz
AU  - Turk, Samo
AU  - Juranić, Zorica
AU  - Mlinarić-Rascan, Irena
AU  - Gobec, Stanislav
PY  - 2013
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1962
AB  - Cinnamic acid derivatives can be found in plant material, and they possess a remarkable variety of biological effects. In the present study, we have investigated the cytotoxic effects of representative cinnamic acid esters and amides. The cytotoxicity was determined by MTT test on human cervix adenocarcinoma (HeLa), myelogenous leukemia (K562), malignant melanoma (Fem-x), and estrogen-receptor-positive breast cancer (MCF-7) cells, versus peripheral blood mononuclear cells (PBMCs) without or with the addition of the plant lectin phytohemaglutinin (PHA). The compounds tested showed significant cytotoxicity (IC(50)s between 42 and 166 mu M) and furthermore selectivity of these cytotoxic effects on the malignant cell lines versus the PBMCs was also seen, especially when electron-withdrawing groups, such as a cyano group (compound 5), were present on the aromatic rings of the alcohol or amine parts of the cinnamic acid derivatives. The additional study on cell cycle phase distribution indicated that novel cinnamic acid derivatives inhibit cell growth by induction of cell death. Thus, cinnamic acids derivatives represent important lead compounds for further development of antineoplastic agents.
PB  - Bentham Science Publ Ltd, Sharjah
T2  - Medicinal Chemistry
T1  - Cinnamic Acid Derivatives Induce Cell Cycle Arrest in Carcinoma Cell Lines
VL  - 9
IS  - 5
SP  - 633
EP  - 641
DO  - 10.2174/1573406411309050002
ER  - 

@article{
author = "Sova, Matej and Žižak, Željko and Antić-Stanković, Jelena and Prijatelj, Matevz and Turk, Samo and Juranić, Zorica and Mlinarić-Rascan, Irena and Gobec, Stanislav",
year = "2013",
abstract = "Cinnamic acid derivatives can be found in plant material, and they possess a remarkable variety of biological effects. In the present study, we have investigated the cytotoxic effects of representative cinnamic acid esters and amides. The cytotoxicity was determined by MTT test on human cervix adenocarcinoma (HeLa), myelogenous leukemia (K562), malignant melanoma (Fem-x), and estrogen-receptor-positive breast cancer (MCF-7) cells, versus peripheral blood mononuclear cells (PBMCs) without or with the addition of the plant lectin phytohemaglutinin (PHA). The compounds tested showed significant cytotoxicity (IC(50)s between 42 and 166 mu M) and furthermore selectivity of these cytotoxic effects on the malignant cell lines versus the PBMCs was also seen, especially when electron-withdrawing groups, such as a cyano group (compound 5), were present on the aromatic rings of the alcohol or amine parts of the cinnamic acid derivatives. The additional study on cell cycle phase distribution indicated that novel cinnamic acid derivatives inhibit cell growth by induction of cell death. Thus, cinnamic acids derivatives represent important lead compounds for further development of antineoplastic agents.",
publisher = "Bentham Science Publ Ltd, Sharjah",
journal = "Medicinal Chemistry",
title = "Cinnamic Acid Derivatives Induce Cell Cycle Arrest in Carcinoma Cell Lines",
volume = "9",
number = "5",
pages = "633-641",
doi = "10.2174/1573406411309050002"
}

Sova, M., Žižak, Ž., Antić-Stanković, J., Prijatelj, M., Turk, S., Juranić, Z., Mlinarić-Rascan, I.,& Gobec, S.. (2013). Cinnamic Acid Derivatives Induce Cell Cycle Arrest in Carcinoma Cell Lines. in Medicinal Chemistry
Bentham Science Publ Ltd, Sharjah., 9(5), 633-641.
https://doi.org/10.2174/1573406411309050002

Sova M, Žižak Ž, Antić-Stanković J, Prijatelj M, Turk S, Juranić Z, Mlinarić-Rascan I, Gobec S. Cinnamic Acid Derivatives Induce Cell Cycle Arrest in Carcinoma Cell Lines. in Medicinal Chemistry. 2013;9(5):633-641.
doi:10.2174/1573406411309050002 .

Sova, Matej, Žižak, Željko, Antić-Stanković, Jelena, Prijatelj, Matevz, Turk, Samo, Juranić, Zorica, Mlinarić-Rascan, Irena, Gobec, Stanislav, "Cinnamic Acid Derivatives Induce Cell Cycle Arrest in Carcinoma Cell Lines" in Medicinal Chemistry, 9, no. 5 (2013):633-641,
https://doi.org/10.2174/1573406411309050002 . .

TY  - JOUR
AU  - Ivković, Branka
AU  - Nikolić, Katarina
AU  - Ilić, Bojana B.
AU  - Žižak, Željko
AU  - Novaković, Radmila
AU  - Čudina, Olivera
AU  - Vladimirov, Sote
PY  - 2013
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1977
AB  - Series of twelve chalcone and propafenone derivatives has been synthesized and evaluated for anticancer activities against Hela, Fem-X, PC-3, MCF-7, LS174 and K562 cell lines. The 2D-QSAR and 3D-QSAR studies were performed for all compounds with cytotoxic activities against each cancer cell line. Partial least squares (PLS) regression has been applied for selection of the most relevant molecular descriptors and QSAR models building. Predictive potentials of the created 2D-QSAR and 3D-QSAR models for each cell line were compared, by use of leave-one-out cross-validation and external validation, and optimal QSAR models for each cancer cell line were selected. The QSAR studies have selected the most significant molecular descriptors and pharmacophores of the chalcone and propafenone derivatives and proposed structures of novel chalcone and propafenone derivatives with enhanced anticancer activity on the HeLa, Fem-X, PC-3, MCF-7, LS174 and K562 cells.
PB  - Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux
T2  - European Journal of Medicinal Chemistry
T1  - Phenylpropiophenone derivatives as potential anticancer agents: Synthesis, biological evaluation and quantitative structure-activity relationship study
VL  - 63
SP  - 239
EP  - 255
DO  - 10.1016/j.ejmech.2013.02.013
ER  - 

@article{
author = "Ivković, Branka and Nikolić, Katarina and Ilić, Bojana B. and Žižak, Željko and Novaković, Radmila and Čudina, Olivera and Vladimirov, Sote",
year = "2013",
abstract = "Series of twelve chalcone and propafenone derivatives has been synthesized and evaluated for anticancer activities against Hela, Fem-X, PC-3, MCF-7, LS174 and K562 cell lines. The 2D-QSAR and 3D-QSAR studies were performed for all compounds with cytotoxic activities against each cancer cell line. Partial least squares (PLS) regression has been applied for selection of the most relevant molecular descriptors and QSAR models building. Predictive potentials of the created 2D-QSAR and 3D-QSAR models for each cell line were compared, by use of leave-one-out cross-validation and external validation, and optimal QSAR models for each cancer cell line were selected. The QSAR studies have selected the most significant molecular descriptors and pharmacophores of the chalcone and propafenone derivatives and proposed structures of novel chalcone and propafenone derivatives with enhanced anticancer activity on the HeLa, Fem-X, PC-3, MCF-7, LS174 and K562 cells.",
publisher = "Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux",
journal = "European Journal of Medicinal Chemistry",
title = "Phenylpropiophenone derivatives as potential anticancer agents: Synthesis, biological evaluation and quantitative structure-activity relationship study",
volume = "63",
pages = "239-255",
doi = "10.1016/j.ejmech.2013.02.013"
}

Ivković, B., Nikolić, K., Ilić, B. B., Žižak, Ž., Novaković, R., Čudina, O.,& Vladimirov, S.. (2013). Phenylpropiophenone derivatives as potential anticancer agents: Synthesis, biological evaluation and quantitative structure-activity relationship study. in European Journal of Medicinal Chemistry
Elsevier France-Editions Scientifiques Medicales Elsevier, Issy-Les-Moulineaux., 63, 239-255.
https://doi.org/10.1016/j.ejmech.2013.02.013

Ivković B, Nikolić K, Ilić BB, Žižak Ž, Novaković R, Čudina O, Vladimirov S. Phenylpropiophenone derivatives as potential anticancer agents: Synthesis, biological evaluation and quantitative structure-activity relationship study. in European Journal of Medicinal Chemistry. 2013;63:239-255.
doi:10.1016/j.ejmech.2013.02.013 .

Ivković, Branka, Nikolić, Katarina, Ilić, Bojana B., Žižak, Željko, Novaković, Radmila, Čudina, Olivera, Vladimirov, Sote, "Phenylpropiophenone derivatives as potential anticancer agents: Synthesis, biological evaluation and quantitative structure-activity relationship study" in European Journal of Medicinal Chemistry, 63 (2013):239-255,
https://doi.org/10.1016/j.ejmech.2013.02.013 . .

TY  - JOUR
AU  - Holclajtner-Antunović, Ivanka
AU  - Kuntić, Vesna
AU  - Juranić, Zorica
AU  - Filipović, Ivana M.
AU  - Mioč, Ubavka B.
AU  - Stanojković, Tatjana
AU  - Žižak, Željko
PY  - 2004
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/556
AB  - The antitumour action of three polyoxometallate compounds of Keggin's type: 12-molibdophosphoric acid (MoPA), 12-tungstophosphoric acid (WPA) and Mg salt of WPA (MgHWPA) was studied in vitro. For human cervix carcinoma (HeLa) cells survival, as well as for nonstimulated and stimulated peripheral blood mononuclear cells (PBMC), MTT test was applied and IC50 values of POMs were determinated. Index selectivity for WPA and MgHWPA are 1.9 and 1.8, calculated for nonstimulated, as well as 2.5 and 2.0, calculated for stimulated PBMS. Combination of studied POMs do not contribute to their lower IC50 values. Apoptosis detection implies mild cytotoxic effect of WPA and more cytostatical effect of MgHWPA. Combination of each of the studied POMs with caffeine decreases HeLa survival in dose dependent way. None of the studied POMs in the used concentrations (up to 100 mmol/L) damages blood cells and/or decreases their number.
AB  - Ispitivano je in vitro antitumorsko dejstvo tri jedinjenja iz grupe polioksometalata (POM-a) Keginovog tipa: 12-fosformolibdenska kiselina (MoPA), 12-fosforvolframova kiselina (WPA) i Mg so 12-fosforvolframove kiseline (MgHWPA). Primenom MTT testa na ćelije karcinoma cerviksa (HeLa ćelije), kao i na nestimulisane i stimulisane mononuklearne ćelije iz periferne krvi (PBMC), određene su IC50 vrednosti ispitivanih POM-a. Indeksi selektivnosti za WPA i MgHWPA su 1,9 i 1,8 računati za nestimulisane, odnosno 2,5 i 2,0 za stimulisane PBMC. Kombinacijom ispitivanih POMa ne postiže se smanjenje njihovih IC50 vrednosti. Detekcijom apoptoze utvrđeno je da WPA pokazuje blagi citotoksični efekat, dok MgHWPA ima blagi citotostatski efekat. U kombinaciji sa kofeinom, POM jedinjenja još više smanjuju preživljavanje HeLa ćelija. U ispitivanim koncentracijama (do 100 mmol/L), nijedno od POM jedinjenja ne utiče na broj i izgled krvnih ćelija pune krvi zdravih davalaca.
PB  - Društvo medicinskih biohemičara Srbije i Crne Gore, Beograd i Univerzitet u Beogradu - Farmaceutski fakultet, Beograd
T2  - Jugoslovenska medicinska biohemija
T1  - Study of some polyoxometallates of Keggin's type as potential antitumour agents
T1  - Ispitivanje nekih polioksalometalata Keginovog tipa kao potencijalnih antitumorskih agenasa
VL  - 23
IS  - 1
SP  - 25
EP  - 30
DO  - 10.2298/JMH0401025H
ER  - 

@article{
author = "Holclajtner-Antunović, Ivanka and Kuntić, Vesna and Juranić, Zorica and Filipović, Ivana M. and Mioč, Ubavka B. and Stanojković, Tatjana and Žižak, Željko",
year = "2004",
abstract = "The antitumour action of three polyoxometallate compounds of Keggin's type: 12-molibdophosphoric acid (MoPA), 12-tungstophosphoric acid (WPA) and Mg salt of WPA (MgHWPA) was studied in vitro. For human cervix carcinoma (HeLa) cells survival, as well as for nonstimulated and stimulated peripheral blood mononuclear cells (PBMC), MTT test was applied and IC50 values of POMs were determinated. Index selectivity for WPA and MgHWPA are 1.9 and 1.8, calculated for nonstimulated, as well as 2.5 and 2.0, calculated for stimulated PBMS. Combination of studied POMs do not contribute to their lower IC50 values. Apoptosis detection implies mild cytotoxic effect of WPA and more cytostatical effect of MgHWPA. Combination of each of the studied POMs with caffeine decreases HeLa survival in dose dependent way. None of the studied POMs in the used concentrations (up to 100 mmol/L) damages blood cells and/or decreases their number., Ispitivano je in vitro antitumorsko dejstvo tri jedinjenja iz grupe polioksometalata (POM-a) Keginovog tipa: 12-fosformolibdenska kiselina (MoPA), 12-fosforvolframova kiselina (WPA) i Mg so 12-fosforvolframove kiseline (MgHWPA). Primenom MTT testa na ćelije karcinoma cerviksa (HeLa ćelije), kao i na nestimulisane i stimulisane mononuklearne ćelije iz periferne krvi (PBMC), određene su IC50 vrednosti ispitivanih POM-a. Indeksi selektivnosti za WPA i MgHWPA su 1,9 i 1,8 računati za nestimulisane, odnosno 2,5 i 2,0 za stimulisane PBMC. Kombinacijom ispitivanih POMa ne postiže se smanjenje njihovih IC50 vrednosti. Detekcijom apoptoze utvrđeno je da WPA pokazuje blagi citotoksični efekat, dok MgHWPA ima blagi citotostatski efekat. U kombinaciji sa kofeinom, POM jedinjenja još više smanjuju preživljavanje HeLa ćelija. U ispitivanim koncentracijama (do 100 mmol/L), nijedno od POM jedinjenja ne utiče na broj i izgled krvnih ćelija pune krvi zdravih davalaca.",
publisher = "Društvo medicinskih biohemičara Srbije i Crne Gore, Beograd i Univerzitet u Beogradu - Farmaceutski fakultet, Beograd",
journal = "Jugoslovenska medicinska biohemija",
title = "Study of some polyoxometallates of Keggin's type as potential antitumour agents, Ispitivanje nekih polioksalometalata Keginovog tipa kao potencijalnih antitumorskih agenasa",
volume = "23",
number = "1",
pages = "25-30",
doi = "10.2298/JMH0401025H"
}

Holclajtner-Antunović, I., Kuntić, V., Juranić, Z., Filipović, I. M., Mioč, U. B., Stanojković, T.,& Žižak, Ž.. (2004). Study of some polyoxometallates of Keggin's type as potential antitumour agents. in Jugoslovenska medicinska biohemija
Društvo medicinskih biohemičara Srbije i Crne Gore, Beograd i Univerzitet u Beogradu - Farmaceutski fakultet, Beograd., 23(1), 25-30.
https://doi.org/10.2298/JMH0401025H

Holclajtner-Antunović I, Kuntić V, Juranić Z, Filipović IM, Mioč UB, Stanojković T, Žižak Ž. Study of some polyoxometallates of Keggin's type as potential antitumour agents. in Jugoslovenska medicinska biohemija. 2004;23(1):25-30.
doi:10.2298/JMH0401025H .

Holclajtner-Antunović, Ivanka, Kuntić, Vesna, Juranić, Zorica, Filipović, Ivana M., Mioč, Ubavka B., Stanojković, Tatjana, Žižak, Željko, "Study of some polyoxometallates of Keggin's type as potential antitumour agents" in Jugoslovenska medicinska biohemija, 23, no. 1 (2004):25-30,
https://doi.org/10.2298/JMH0401025H . .