TY  - JOUR
AU  - Tubić, Biljana
AU  - Dobričić, Vladimir
AU  - Poljarević, Jelena
AU  - Savić, Aleksandar
AU  - Sabo, Tibor
AU  - Marković, Bojan
PY  - 2020
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3553
AB  - Passive gastrointestinal absorption and membrane retention of twelve esters of (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (EDCP) and (S,S)-1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (PDCP), as well as of these two non-esterified acids were estimated using PAMPA test. Artificial PAMPA membrane used in this study for the simulation of gastrointestinal barrier was solution of egg lecithin in dodecane (1 % w/v). All tested compounds belong to class III (high membrane retention and low permeation), whereas EDCP, dipentyl ester of PDCP (DPE-PDCP) and diisopentyl ester of PDCP (DIPE-PDCP) belong to class I (negligible membrane retention and low permeation). Finally, quantitative structure – permeability and structure – retention relationships models were created in order to find quantitative relationships between physico-chemical properties of tested compounds and PAMPA membrane permeability/membrane retention parameters. Statistically the most reliable models were analysed and used for the design of new compounds for which favourable membrane permeability and retention can be expected.
PB  - Elsevier B.V.
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives
VL  - 184
DO  - 10.1016/j.jpba.2020.113213
ER  - 

@article{
author = "Tubić, Biljana and Dobričić, Vladimir and Poljarević, Jelena and Savić, Aleksandar and Sabo, Tibor and Marković, Bojan",
year = "2020",
abstract = "Passive gastrointestinal absorption and membrane retention of twelve esters of (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (EDCP) and (S,S)-1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (PDCP), as well as of these two non-esterified acids were estimated using PAMPA test. Artificial PAMPA membrane used in this study for the simulation of gastrointestinal barrier was solution of egg lecithin in dodecane (1 % w/v). All tested compounds belong to class III (high membrane retention and low permeation), whereas EDCP, dipentyl ester of PDCP (DPE-PDCP) and diisopentyl ester of PDCP (DIPE-PDCP) belong to class I (negligible membrane retention and low permeation). Finally, quantitative structure – permeability and structure – retention relationships models were created in order to find quantitative relationships between physico-chemical properties of tested compounds and PAMPA membrane permeability/membrane retention parameters. Statistically the most reliable models were analysed and used for the design of new compounds for which favourable membrane permeability and retention can be expected.",
publisher = "Elsevier B.V.",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives",
volume = "184",
doi = "10.1016/j.jpba.2020.113213"
}

Tubić, B., Dobričić, V., Poljarević, J., Savić, A., Sabo, T.,& Marković, B.. (2020). Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier B.V.., 184.
https://doi.org/10.1016/j.jpba.2020.113213

Tubić B, Dobričić V, Poljarević J, Savić A, Sabo T, Marković B. Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives. in Journal of Pharmaceutical and Biomedical Analysis. 2020;184.
doi:10.1016/j.jpba.2020.113213 .

Tubić, Biljana, Dobričić, Vladimir, Poljarević, Jelena, Savić, Aleksandar, Sabo, Tibor, Marković, Bojan, "Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives" in Journal of Pharmaceutical and Biomedical Analysis, 184 (2020),
https://doi.org/10.1016/j.jpba.2020.113213 . .

TY  - JOUR
AU  - Tubić, Biljana
AU  - Dobričić, Vladimir
AU  - Poljarević, Jelena
AU  - Savić, Aleksandar
AU  - Sabo, Tibor
AU  - Marković, Bojan
PY  - 2020
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3550
AB  - Passive gastrointestinal absorption and membrane retention of twelve esters of (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (EDCP) and (S,S)-1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (PDCP), as well as of these two non-esterified acids were estimated using PAMPA test. Artificial PAMPA membrane used in this study for the simulation of gastrointestinal barrier was solution of egg lecithin in dodecane (1 % w/v). All tested compounds belong to class III (high membrane retention and low permeation), whereas EDCP, dipentyl ester of PDCP (DPE-PDCP) and diisopentyl ester of PDCP (DIPE-PDCP) belong to class I (negligible membrane retention and low permeation). Finally, quantitative structure – permeability and structure – retention relationships models were created in order to find quantitative relationships between physico-chemical properties of tested compounds and PAMPA membrane permeability/membrane retention parameters. Statistically the most reliable models were analysed and used for the design of new compounds for which favourable membrane permeability and retention can be expected.
PB  - Elsevier B.V.
T2  - Journal of Pharmaceutical and Biomedical Analysis
T1  - Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives
VL  - 184
DO  - 10.1016/j.jpba.2020.113213
ER  - 

@article{
author = "Tubić, Biljana and Dobričić, Vladimir and Poljarević, Jelena and Savić, Aleksandar and Sabo, Tibor and Marković, Bojan",
year = "2020",
abstract = "Passive gastrointestinal absorption and membrane retention of twelve esters of (S,S)-ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (EDCP) and (S,S)-1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid (PDCP), as well as of these two non-esterified acids were estimated using PAMPA test. Artificial PAMPA membrane used in this study for the simulation of gastrointestinal barrier was solution of egg lecithin in dodecane (1 % w/v). All tested compounds belong to class III (high membrane retention and low permeation), whereas EDCP, dipentyl ester of PDCP (DPE-PDCP) and diisopentyl ester of PDCP (DIPE-PDCP) belong to class I (negligible membrane retention and low permeation). Finally, quantitative structure – permeability and structure – retention relationships models were created in order to find quantitative relationships between physico-chemical properties of tested compounds and PAMPA membrane permeability/membrane retention parameters. Statistically the most reliable models were analysed and used for the design of new compounds for which favourable membrane permeability and retention can be expected.",
publisher = "Elsevier B.V.",
journal = "Journal of Pharmaceutical and Biomedical Analysis",
title = "Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives",
volume = "184",
doi = "10.1016/j.jpba.2020.113213"
}

Tubić, B., Dobričić, V., Poljarević, J., Savić, A., Sabo, T.,& Marković, B.. (2020). Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives. in Journal of Pharmaceutical and Biomedical Analysis
Elsevier B.V.., 184.
https://doi.org/10.1016/j.jpba.2020.113213

Tubić B, Dobričić V, Poljarević J, Savić A, Sabo T, Marković B. Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives. in Journal of Pharmaceutical and Biomedical Analysis. 2020;184.
doi:10.1016/j.jpba.2020.113213 .

Tubić, Biljana, Dobričić, Vladimir, Poljarević, Jelena, Savić, Aleksandar, Sabo, Tibor, Marković, Bojan, "Estimation of passive gastrointestinal absorption and membrane retention using PAMPA test, quantitative structure-permeability and quantitative structure-retention relationship analyses of ethylenediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid and 1,3-propanediamine-N,N'-di-2-(3-cyclohexyl)propanoic acid derivatives" in Journal of Pharmaceutical and Biomedical Analysis, 184 (2020),
https://doi.org/10.1016/j.jpba.2020.113213 . .

TY  - JOUR
AU  - Francuski, Bojana M.
AU  - Ivković, Branka
AU  - Stojanović, I
AU  - Vladimirov, S
AU  - Francuski, Đorđe
PY  - 2012
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1800
AB  - In the title compound, C16H11F3O 2, the -pyran-one ring adopts an envelope conformation with the chiral C atom standing out of the ring plane. In the crystal, molecules are linked by C - H⋯O and C - H⋯F inter-actions.
PB  - International Union of Crystallography
T2  - Acta Crystallographica Section E: Structure Reports Online
T1  - 2-[2-(Trifluoromethyl)phenyl]-2H-1-benzopyran-4(3H)-one
VL  - 68
IS  - 5
DO  - 10.1107/S160053681201687X
ER  - 

@article{
author = "Francuski, Bojana M. and Ivković, Branka and Stojanović, I and Vladimirov, S and Francuski, Đorđe",
year = "2012",
abstract = "In the title compound, C16H11F3O 2, the -pyran-one ring adopts an envelope conformation with the chiral C atom standing out of the ring plane. In the crystal, molecules are linked by C - H⋯O and C - H⋯F inter-actions.",
publisher = "International Union of Crystallography",
journal = "Acta Crystallographica Section E: Structure Reports Online",
title = "2-[2-(Trifluoromethyl)phenyl]-2H-1-benzopyran-4(3H)-one",
volume = "68",
number = "5",
doi = "10.1107/S160053681201687X"
}

Francuski, B. M., Ivković, B., Stojanović, I., Vladimirov, S.,& Francuski, Đ.. (2012). 2-[2-(Trifluoromethyl)phenyl]-2H-1-benzopyran-4(3H)-one. in Acta Crystallographica Section E: Structure Reports Online
International Union of Crystallography., 68(5).
https://doi.org/10.1107/S160053681201687X

Francuski BM, Ivković B, Stojanović I, Vladimirov S, Francuski Đ. 2-[2-(Trifluoromethyl)phenyl]-2H-1-benzopyran-4(3H)-one. in Acta Crystallographica Section E: Structure Reports Online. 2012;68(5).
doi:10.1107/S160053681201687X .

Francuski, Bojana M., Ivković, Branka, Stojanović, I, Vladimirov, S, Francuski, Đorđe, "2-[2-(Trifluoromethyl)phenyl]-2H-1-benzopyran-4(3H)-one" in Acta Crystallographica Section E: Structure Reports Online, 68, no. 5 (2012),
https://doi.org/10.1107/S160053681201687X . .

TY  - JOUR
AU  - Marjanović, Budimir
AU  - Juranić, Ivan O.
AU  - Ćirić-Marjanović, Gordana
AU  - Mojović, M
AU  - Pasti, Igor
AU  - Janošević, Aleksandra
AU  - Trchova, Miroslava
AU  - Holler, P
AU  - Horský, J
PY  - 2012
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1806
AB  - Novel electroactive paramagnetic ethacridine oligomers were synthesized by the oxidation of ethacridine lactate with ammonium peroxydisulfate in acidic aqueous solution. The oxidative coupling of ethacridine was proved by gel permeation chromatography and MALDI-TOF mass spectrometry demonstrating the presence of oligomeric chains. Theoretical study of the mechanism of oxidation of ethacridine has been based on the semi-empirical quantum chemical computations of heat of formation and ionization energy of ethacridine, protonated ethacridine, generated reactive species and reaction intermediates, taking into account influence of pH and solvation effects. It was revealed that the prevalent ethacridine dimers are N(C6)C5 coupled. The influence of oxidant to monomer mole ratio on the molecular structure and the morphology of ethacridine oligomers has been studied by elemental analysis, FTIR, Raman, EPR and UV-Visible spectroscopies, MALDI-TOF mass spectrometry and scanning electron microscopy. Besides unoxidized monomeric units as prevalent, oligoethacridines contain the iminoquinonoid and newly formed fused phenazine units. The electroactivity of ethacridine oligomers was investigated by cyclic voltammetry.
T2  - Reactive and Functional Polymers
T1  - Chemical oxidative polymerization of ethacridine
VL  - 72
IS  - 1
SP  - 25
EP  - 35
DO  - 10.1016/j.reactfunctpolym.2011.10.002
ER  - 

@article{
author = "Marjanović, Budimir and Juranić, Ivan O. and Ćirić-Marjanović, Gordana and Mojović, M and Pasti, Igor and Janošević, Aleksandra and Trchova, Miroslava and Holler, P and Horský, J",
year = "2012",
abstract = "Novel electroactive paramagnetic ethacridine oligomers were synthesized by the oxidation of ethacridine lactate with ammonium peroxydisulfate in acidic aqueous solution. The oxidative coupling of ethacridine was proved by gel permeation chromatography and MALDI-TOF mass spectrometry demonstrating the presence of oligomeric chains. Theoretical study of the mechanism of oxidation of ethacridine has been based on the semi-empirical quantum chemical computations of heat of formation and ionization energy of ethacridine, protonated ethacridine, generated reactive species and reaction intermediates, taking into account influence of pH and solvation effects. It was revealed that the prevalent ethacridine dimers are N(C6)C5 coupled. The influence of oxidant to monomer mole ratio on the molecular structure and the morphology of ethacridine oligomers has been studied by elemental analysis, FTIR, Raman, EPR and UV-Visible spectroscopies, MALDI-TOF mass spectrometry and scanning electron microscopy. Besides unoxidized monomeric units as prevalent, oligoethacridines contain the iminoquinonoid and newly formed fused phenazine units. The electroactivity of ethacridine oligomers was investigated by cyclic voltammetry.",
journal = "Reactive and Functional Polymers",
title = "Chemical oxidative polymerization of ethacridine",
volume = "72",
number = "1",
pages = "25-35",
doi = "10.1016/j.reactfunctpolym.2011.10.002"
}

Marjanović, B., Juranić, I. O., Ćirić-Marjanović, G., Mojović, M., Pasti, I., Janošević, A., Trchova, M., Holler, P.,& Horský, J.. (2012). Chemical oxidative polymerization of ethacridine. in Reactive and Functional Polymers, 72(1), 25-35.
https://doi.org/10.1016/j.reactfunctpolym.2011.10.002

Marjanović B, Juranić IO, Ćirić-Marjanović G, Mojović M, Pasti I, Janošević A, Trchova M, Holler P, Horský J. Chemical oxidative polymerization of ethacridine. in Reactive and Functional Polymers. 2012;72(1):25-35.
doi:10.1016/j.reactfunctpolym.2011.10.002 .

Marjanović, Budimir, Juranić, Ivan O., Ćirić-Marjanović, Gordana, Mojović, M, Pasti, Igor, Janošević, Aleksandra, Trchova, Miroslava, Holler, P, Horský, J, "Chemical oxidative polymerization of ethacridine" in Reactive and Functional Polymers, 72, no. 1 (2012):25-35,
https://doi.org/10.1016/j.reactfunctpolym.2011.10.002 . .

TY  - JOUR
AU  - Vitnik, Vesna
AU  - Milenković, Marina
AU  - Dilber, Sanda
AU  - Vitnik, Željko J.
AU  - Juranić, Ivan O.
PY  - 2012
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1832
AB  - A series of α,β-unsaturated and α-bromo carboxylic acids were identified as potent antimicrobial agents. The antimicrobial activity was evaluated using the broth microdilution method. All acids 1-12 exhibited a significant activity against nine laboratory control strains of bacteria and two strains of yeast Candida albicans. The tested acids were efficiently prepared by optimized phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent with triethylbenzyl ammonium chloride (TEBA) as catalyst.
AB  - U ovom radu je prikazano in vitro ispitivanje antimikrobnog dejstva serije α,β-nezasićenih i α-bromkarboksilnih kiselina i pokazano je da su one potencijalno dobri antimikrobni agensi. Sve kiseline 1-12 pokazale su značajnu aktivnost prema devet sojeva bakterija i dva soja gljivica Candida albicans. Ispitivane kiseline sintetisane su u optimizovanoj reakciji ketona sa bromoformom i litijum-hidroksidom u smesi rastvarača (terc-butanol/voda). Kao katalizator za prenos između faza upotrebljen je trietilbenzilamonijum-hlorid (TEBA).
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids
T1  - Optimizacija sinteze i in vitro proučavanje antimikrobnog dejstva α,β-nezasićenih i α-bromkarboksilnih kiselina
VL  - 77
IS  - 6
SP  - 741
EP  - 750
DO  - 10.2298/JSC111104016V
ER  - 

@article{
author = "Vitnik, Vesna and Milenković, Marina and Dilber, Sanda and Vitnik, Željko J. and Juranić, Ivan O.",
year = "2012",
abstract = "A series of α,β-unsaturated and α-bromo carboxylic acids were identified as potent antimicrobial agents. The antimicrobial activity was evaluated using the broth microdilution method. All acids 1-12 exhibited a significant activity against nine laboratory control strains of bacteria and two strains of yeast Candida albicans. The tested acids were efficiently prepared by optimized phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent with triethylbenzyl ammonium chloride (TEBA) as catalyst., U ovom radu je prikazano in vitro ispitivanje antimikrobnog dejstva serije α,β-nezasićenih i α-bromkarboksilnih kiselina i pokazano je da su one potencijalno dobri antimikrobni agensi. Sve kiseline 1-12 pokazale su značajnu aktivnost prema devet sojeva bakterija i dva soja gljivica Candida albicans. Ispitivane kiseline sintetisane su u optimizovanoj reakciji ketona sa bromoformom i litijum-hidroksidom u smesi rastvarača (terc-butanol/voda). Kao katalizator za prenos između faza upotrebljen je trietilbenzilamonijum-hlorid (TEBA).",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids, Optimizacija sinteze i in vitro proučavanje antimikrobnog dejstva α,β-nezasićenih i α-bromkarboksilnih kiselina",
volume = "77",
number = "6",
pages = "741-750",
doi = "10.2298/JSC111104016V"
}

Vitnik, V., Milenković, M., Dilber, S., Vitnik, Ž. J.,& Juranić, I. O.. (2012). Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 77(6), 741-750.
https://doi.org/10.2298/JSC111104016V

Vitnik V, Milenković M, Dilber S, Vitnik ŽJ, Juranić IO. Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids. in Journal of the Serbian Chemical Society. 2012;77(6):741-750.
doi:10.2298/JSC111104016V .

Vitnik, Vesna, Milenković, Marina, Dilber, Sanda, Vitnik, Željko J., Juranić, Ivan O., "Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids" in Journal of the Serbian Chemical Society, 77, no. 6 (2012):741-750,
https://doi.org/10.2298/JSC111104016V . .