TY  - JOUR
AU  - Drakulić, Branko
AU  - Juranić, Ivan O.
AU  - Erić, Slavica
AU  - Zloh, Mire
PY  - 2008
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1029
AB  - The use of chemical penetration enhancers (CPE) is growing due to their ability to improve drug delivery through the skin. A possible mechanism of penetration enhancement could involve the complex formation between drug and components in the pharmaceutical formulation, thus altering the physicochemical properties of the active substance. Here, modelling studies indicate that hydrocarbon and oxygen-containing terpenes (penetration enhancers) could form complexes with drugs. Satisfactory correlations have been obtained between the predicted molecular properties of enhancers and their enhancement effects. Crown Copyright
PB  - Elsevier Science BV, Amsterdam
T2  - International Journal of Pharmaceutics
T1  - Role of complexes formation between drugs and penetration enhancers in transdermal delivery
VL  - 363
IS  - 1-2
SP  - 40
EP  - 49
DO  - 10.1016/j.ijpharm.2008.06.032
ER  - 

@article{
author = "Drakulić, Branko and Juranić, Ivan O. and Erić, Slavica and Zloh, Mire",
year = "2008",
abstract = "The use of chemical penetration enhancers (CPE) is growing due to their ability to improve drug delivery through the skin. A possible mechanism of penetration enhancement could involve the complex formation between drug and components in the pharmaceutical formulation, thus altering the physicochemical properties of the active substance. Here, modelling studies indicate that hydrocarbon and oxygen-containing terpenes (penetration enhancers) could form complexes with drugs. Satisfactory correlations have been obtained between the predicted molecular properties of enhancers and their enhancement effects. Crown Copyright",
publisher = "Elsevier Science BV, Amsterdam",
journal = "International Journal of Pharmaceutics",
title = "Role of complexes formation between drugs and penetration enhancers in transdermal delivery",
volume = "363",
number = "1-2",
pages = "40-49",
doi = "10.1016/j.ijpharm.2008.06.032"
}

Drakulić, B., Juranić, I. O., Erić, S.,& Zloh, M.. (2008). Role of complexes formation between drugs and penetration enhancers in transdermal delivery. in International Journal of Pharmaceutics
Elsevier Science BV, Amsterdam., 363(1-2), 40-49.
https://doi.org/10.1016/j.ijpharm.2008.06.032

Drakulić B, Juranić IO, Erić S, Zloh M. Role of complexes formation between drugs and penetration enhancers in transdermal delivery. in International Journal of Pharmaceutics. 2008;363(1-2):40-49.
doi:10.1016/j.ijpharm.2008.06.032 .

Drakulić, Branko, Juranić, Ivan O., Erić, Slavica, Zloh, Mire, "Role of complexes formation between drugs and penetration enhancers in transdermal delivery" in International Journal of Pharmaceutics, 363, no. 1-2 (2008):40-49,
https://doi.org/10.1016/j.ijpharm.2008.06.032 . .

TY  - JOUR
AU  - Dilber, Sanda
AU  - Dobrić, Silva
AU  - Juranić, Zorica
AU  - Marković, Bojan
AU  - Vladimirov, Sote
AU  - Juranić, Ivan O.
PY  - 2008
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1101
AB  - The article describes a two-step synthesis of diastereomeric 3-hydroxy-2methyl-3-( 4-biphenylyl) butanoic acids. In the first step an intermediate alpha-bromo propanoic acid 1-ethoxyethyl ester was synthesized. The second step is a new modified Reformatsky reaction in presence of Zn in tetrahydrofuran (THF) at -5 to 10 C between the previously synthesized intermediate and 4-acetylbiphenyl. Synthesis of the other studied beta-hydroxy- beta-arylpropanoic acids has already been reported. These beta-hydroxy-beta-arylpropanoic acids belong to the arylpropanoic acid class of compounds, structurally similar to the NSAIDs such as ibuprofen. The anti-inflammatory activity and gastric tolerability of the synthesized compounds were evaluated. Molecular docking experiments were carried out to identify potential COX-2 inhibitors among the beta-hydroxy- beta-aryl-alkanoic acids class. The results indicate that all compounds possess significant anti-inflammatory activity after oral administration and that the compounds 2-(9-( 9-hydroxy-fluorenyl))-2-methylpropanoic acid ( 5) and 3-hydroxy-3,3-diphenyl- propanoic acid (3) possess the strongest anti-inflammatory activity, comparable to that of ibuprofen, a standard NSAID, and that none of tested substances or ibuprofen produced any significant gastric lesions.
PB  - Molecular Diversity Preservation Int, Basel
T2  - Molecules
T1  - Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids
VL  - 13
IS  - 3
SP  - 603
EP  - 615
DO  - 10.3390/molecules13030603
ER  - 

@article{
author = "Dilber, Sanda and Dobrić, Silva and Juranić, Zorica and Marković, Bojan and Vladimirov, Sote and Juranić, Ivan O.",
year = "2008",
abstract = "The article describes a two-step synthesis of diastereomeric 3-hydroxy-2methyl-3-( 4-biphenylyl) butanoic acids. In the first step an intermediate alpha-bromo propanoic acid 1-ethoxyethyl ester was synthesized. The second step is a new modified Reformatsky reaction in presence of Zn in tetrahydrofuran (THF) at -5 to 10 C between the previously synthesized intermediate and 4-acetylbiphenyl. Synthesis of the other studied beta-hydroxy- beta-arylpropanoic acids has already been reported. These beta-hydroxy-beta-arylpropanoic acids belong to the arylpropanoic acid class of compounds, structurally similar to the NSAIDs such as ibuprofen. The anti-inflammatory activity and gastric tolerability of the synthesized compounds were evaluated. Molecular docking experiments were carried out to identify potential COX-2 inhibitors among the beta-hydroxy- beta-aryl-alkanoic acids class. The results indicate that all compounds possess significant anti-inflammatory activity after oral administration and that the compounds 2-(9-( 9-hydroxy-fluorenyl))-2-methylpropanoic acid ( 5) and 3-hydroxy-3,3-diphenyl- propanoic acid (3) possess the strongest anti-inflammatory activity, comparable to that of ibuprofen, a standard NSAID, and that none of tested substances or ibuprofen produced any significant gastric lesions.",
publisher = "Molecular Diversity Preservation Int, Basel",
journal = "Molecules",
title = "Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids",
volume = "13",
number = "3",
pages = "603-615",
doi = "10.3390/molecules13030603"
}

Dilber, S., Dobrić, S., Juranić, Z., Marković, B., Vladimirov, S.,& Juranić, I. O.. (2008). Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids. in Molecules
Molecular Diversity Preservation Int, Basel., 13(3), 603-615.
https://doi.org/10.3390/molecules13030603

Dilber S, Dobrić S, Juranić Z, Marković B, Vladimirov S, Juranić IO. Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids. in Molecules. 2008;13(3):603-615.
doi:10.3390/molecules13030603 .

Dilber, Sanda, Dobrić, Silva, Juranić, Zorica, Marković, Bojan, Vladimirov, Sote, Juranić, Ivan O., "Docking studies and anti-inflammatory activity of ss-Hydroxy-ss-arylpropanoic acids" in Molecules, 13, no. 3 (2008):603-615,
https://doi.org/10.3390/molecules13030603 . .

TY  - JOUR
AU  - Verbić, Tatjana Ž.
AU  - Drakulić, Branko
AU  - Zloh, Mire
AU  - Pecelj, Jovana R.
AU  - Popović, Gordana
AU  - Juranić, Ivan O.
PY  - 2007
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/997
AB  - The protolytic equilibria of 13 4-aryl-2,4-dioxobutanoic acids (ADKs) were spectrophotometrically studied in aqueous solutions in the pH range 1-9 at 25±1 °C and an ionic strength of 0.1 mol l-1 (NaCl), with the exception of the 4-OH-derivative which was also potentiometrically studied in the pH range 7-10 at 25±1 °C and an ionic strength of 0.1 mol l-1 (NaCl). In solution, the compounds simultaneously exist in one diketo and two enolic forms; therefore, the determined acidity constants (pKa1 1.87-2.29, pKa2 6.63-8.13 and pKa3(4-OH-) 9.52) represent system macro constants. The 1H-NMR spectrum of the parent compound (4-phenyl- -2,4-dioxobutanoic acid) (25 °C, pD 5.0) proved the existence of all tautomeric forms. Using the extended Hammett relation, the determined pKa values were correlated with literature σ values. The predicted pKa values were in fair accordance with the experimentally observed ones. Molecular, monoanionic and dianionic forms of the parent compound were optimized by the semi-empirical molecular orbital PM6 method using the implicit water solvation model (COSMO). The obtained geometries were used to explain the quality of the LFER models.
AB  - Protolitičke ravnoteže 13 jedinjenja iz klase 4-aril-2,4-dioksobutanskih kiselina (ADK) spektrofotometrijski su proučavane u vodenim rastvorima u pH intervalu 1-9 pri temperaturi 25±1 °C i jonskoj jačini rastvora 0.1 mol l-1 (NaCl), sa izuzetkom 4-OH-derivata koji je proučavan i potenciometrijski u pH intervalu 7-10 pri istim uslovima. Kako ADK u vodenom rastvoru podležu keto-enolnoj tautomeriji i istovremeno postoje u diketo i dva enolna oblika, to određene kiselinske konstante (pKa1 1.87-2.29, pKa2 6.63-8.13 i pKa3(4-OH-) 9.52) predstavljaju makro konstante za dati sistem. 1H-NMR spektar osnovne supstance (4-fenil-2,4-dioksobutanska kiselina) (25 °C, pD 5.0) potvrđuje prisustvo svih tautomernih oblika. Upotrebom proširene Hametove korelacije, određene pKa vrednosti korelisane su sa literaturnim σ vrednostima. Predviđene pKa vrednosti dobro se slažu sa eksperimentalno dobijenim. Molekulski, monoanjonski i dianjonski oblici osnovne supstance su optimizovani semiempirijskom molekulsko-orbitalnom PM6 metodom sa implicitnim modelom solvatacije u vodi (COSMO). Dobijene geometrije su upotrebljene za objašnjenje kvaliteta LFER modela.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - An LFER study of the protolytic equilibria of 4-aryl-2,4-dioxobutanoic acids in aqueous solutions
T1  - Linearne korelacije slobodne energije (LFER) protolitičkih ravnoteža 4-aril-2,4-dioksobutanskih kiselina u vodenim rastvorima
VL  - 72
IS  - 12
SP  - 1201
EP  - 1216
DO  - 10.2298/JSC0712201V
ER  - 

@article{
author = "Verbić, Tatjana Ž. and Drakulić, Branko and Zloh, Mire and Pecelj, Jovana R. and Popović, Gordana and Juranić, Ivan O.",
year = "2007",
abstract = "The protolytic equilibria of 13 4-aryl-2,4-dioxobutanoic acids (ADKs) were spectrophotometrically studied in aqueous solutions in the pH range 1-9 at 25±1 °C and an ionic strength of 0.1 mol l-1 (NaCl), with the exception of the 4-OH-derivative which was also potentiometrically studied in the pH range 7-10 at 25±1 °C and an ionic strength of 0.1 mol l-1 (NaCl). In solution, the compounds simultaneously exist in one diketo and two enolic forms; therefore, the determined acidity constants (pKa1 1.87-2.29, pKa2 6.63-8.13 and pKa3(4-OH-) 9.52) represent system macro constants. The 1H-NMR spectrum of the parent compound (4-phenyl- -2,4-dioxobutanoic acid) (25 °C, pD 5.0) proved the existence of all tautomeric forms. Using the extended Hammett relation, the determined pKa values were correlated with literature σ values. The predicted pKa values were in fair accordance with the experimentally observed ones. Molecular, monoanionic and dianionic forms of the parent compound were optimized by the semi-empirical molecular orbital PM6 method using the implicit water solvation model (COSMO). The obtained geometries were used to explain the quality of the LFER models., Protolitičke ravnoteže 13 jedinjenja iz klase 4-aril-2,4-dioksobutanskih kiselina (ADK) spektrofotometrijski su proučavane u vodenim rastvorima u pH intervalu 1-9 pri temperaturi 25±1 °C i jonskoj jačini rastvora 0.1 mol l-1 (NaCl), sa izuzetkom 4-OH-derivata koji je proučavan i potenciometrijski u pH intervalu 7-10 pri istim uslovima. Kako ADK u vodenom rastvoru podležu keto-enolnoj tautomeriji i istovremeno postoje u diketo i dva enolna oblika, to određene kiselinske konstante (pKa1 1.87-2.29, pKa2 6.63-8.13 i pKa3(4-OH-) 9.52) predstavljaju makro konstante za dati sistem. 1H-NMR spektar osnovne supstance (4-fenil-2,4-dioksobutanska kiselina) (25 °C, pD 5.0) potvrđuje prisustvo svih tautomernih oblika. Upotrebom proširene Hametove korelacije, određene pKa vrednosti korelisane su sa literaturnim σ vrednostima. Predviđene pKa vrednosti dobro se slažu sa eksperimentalno dobijenim. Molekulski, monoanjonski i dianjonski oblici osnovne supstance su optimizovani semiempirijskom molekulsko-orbitalnom PM6 metodom sa implicitnim modelom solvatacije u vodi (COSMO). Dobijene geometrije su upotrebljene za objašnjenje kvaliteta LFER modela.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "An LFER study of the protolytic equilibria of 4-aryl-2,4-dioxobutanoic acids in aqueous solutions, Linearne korelacije slobodne energije (LFER) protolitičkih ravnoteža 4-aril-2,4-dioksobutanskih kiselina u vodenim rastvorima",
volume = "72",
number = "12",
pages = "1201-1216",
doi = "10.2298/JSC0712201V"
}

Verbić, T. Ž., Drakulić, B., Zloh, M., Pecelj, J. R., Popović, G.,& Juranić, I. O.. (2007). An LFER study of the protolytic equilibria of 4-aryl-2,4-dioxobutanoic acids in aqueous solutions. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 72(12), 1201-1216.
https://doi.org/10.2298/JSC0712201V

Verbić TŽ, Drakulić B, Zloh M, Pecelj JR, Popović G, Juranić IO. An LFER study of the protolytic equilibria of 4-aryl-2,4-dioxobutanoic acids in aqueous solutions. in Journal of the Serbian Chemical Society. 2007;72(12):1201-1216.
doi:10.2298/JSC0712201V .

Verbić, Tatjana Ž., Drakulić, Branko, Zloh, Mire, Pecelj, Jovana R., Popović, Gordana, Juranić, Ivan O., "An LFER study of the protolytic equilibria of 4-aryl-2,4-dioxobutanoic acids in aqueous solutions" in Journal of the Serbian Chemical Society, 72, no. 12 (2007):1201-1216,
https://doi.org/10.2298/JSC0712201V . .