TY  - JOUR
AU  - Rabtti, El Hadi M. A.
AU  - Natić, Maja
AU  - Milojković-Opsenica, Dušanka
AU  - Trifković, Jelena
AU  - Tosti, Tomislav
AU  - Vučković, Ivan
AU  - Vajs, Vlatka
AU  - Tešić, Živoslav
PY  - 2012
UR  - http://cherry.chem.bg.ac.rs/handle/123456789/1554
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2721
AB  - Four lipophilicity descriptors (R-M(0), b, C-0 and PCl) for twelve coumarin derivatives were determined by reversed-phase thin-layer chromatography in order to analyze the descriptor which best describes the lipophilicity of the investigated coumarins. Moreover, possible chemical toxicity of coumarins, expressed as the probability of a compound to cause organ-specific health effects, was calculated using ACD/Tox Suite program. The quantitative relationships between toxicity and molecular descriptors, including experimentally determined lipophilicity descriptors obtained in current study were investigated using partial least square regression. The best models were obtained for kidney and liver health effects. Quantitative structure-toxicity relationship models revealed the importance of electric polarization descriptors, size descriptors and lipophilicity descriptors. The obtained models were used for the selection of the structural features of the compounds that are significantly affecting their absorption, distribution, metabolism, excretion and toxicity.
AB  - Primenom reverzno-fazne tankoslojne hromatografije na dvanaest derivata kumarina određena su četiri parametara lipofilnosti (RM0, b, C0 i PC1). Korelacijom dobijenih rezultata sa izračunatim log P vrednostima utvrđen je deskriptor koji na najbolji način opisuje lipofilnost ispitivanih kumarina. Pored toga izračunata je moguća hemijska toksičnost kumarina, izražena kao verovatnoća uticaja pomenutih jedinjenja na specifične organe (krv, kardiovaskularni sistem, gastrointestinalni sistem, bubrege, jetru i pluća) a koja je izračunata primenom ACD/Tox Suite programa. Dobijene vrednosti toksičnosti korelisane su sa molekulskim deskriptorima i eksperimentalno određenim parametrima lipofilnosti, primenom metode parcijalne regresije najmanjih kvadrata (partial least square regression). Uzimajući u obzir parametre koji opisuju kvalitet modela zavisnosti strukture i toksičnosti, utvrđeno je da su najbolji modeli dobijeni za uticaj kumarina na bubrege i jetru. Svi dobijeni modeli ukazuju na značaj električno polarizacionih deskriptora, kao i deskriptora koji opisuju veličinu i lipofilnost jedinjenja, a upotrebljeni su za utvrđivanje strukturnih karakteristika koje značajno utiču na njihovu apsorpciju, distribuciju, metabolizam, izlučivanje i toksičnost.
PB  - Serbian Chemical Soc, Belgrade
T2  - Journal of the Serbian Chemical Society
T1  - Quantitative structure-toxicity relationship study of some natural and synthetic coumarins using retention parameters
T1  - Analiza zavisnosti strukture i toksičnosti nekih prirodnih i sintetičkih kumarina korišćenjem retencionih parametara
VL  - 77
IS  - 10
SP  - 1443
EP  - 1456
DO  - 10.2298/JSC120716091R
ER  - 

@article{
author = "Rabtti, El Hadi M. A. and Natić, Maja and Milojković-Opsenica, Dušanka and Trifković, Jelena and Tosti, Tomislav and Vučković, Ivan and Vajs, Vlatka and Tešić, Živoslav",
year = "2012",
abstract = "Four lipophilicity descriptors (R-M(0), b, C-0 and PCl) for twelve coumarin derivatives were determined by reversed-phase thin-layer chromatography in order to analyze the descriptor which best describes the lipophilicity of the investigated coumarins. Moreover, possible chemical toxicity of coumarins, expressed as the probability of a compound to cause organ-specific health effects, was calculated using ACD/Tox Suite program. The quantitative relationships between toxicity and molecular descriptors, including experimentally determined lipophilicity descriptors obtained in current study were investigated using partial least square regression. The best models were obtained for kidney and liver health effects. Quantitative structure-toxicity relationship models revealed the importance of electric polarization descriptors, size descriptors and lipophilicity descriptors. The obtained models were used for the selection of the structural features of the compounds that are significantly affecting their absorption, distribution, metabolism, excretion and toxicity., Primenom reverzno-fazne tankoslojne hromatografije na dvanaest derivata kumarina određena su četiri parametara lipofilnosti (RM0, b, C0 i PC1). Korelacijom dobijenih rezultata sa izračunatim log P vrednostima utvrđen je deskriptor koji na najbolji način opisuje lipofilnost ispitivanih kumarina. Pored toga izračunata je moguća hemijska toksičnost kumarina, izražena kao verovatnoća uticaja pomenutih jedinjenja na specifične organe (krv, kardiovaskularni sistem, gastrointestinalni sistem, bubrege, jetru i pluća) a koja je izračunata primenom ACD/Tox Suite programa. Dobijene vrednosti toksičnosti korelisane su sa molekulskim deskriptorima i eksperimentalno određenim parametrima lipofilnosti, primenom metode parcijalne regresije najmanjih kvadrata (partial least square regression). Uzimajući u obzir parametre koji opisuju kvalitet modela zavisnosti strukture i toksičnosti, utvrđeno je da su najbolji modeli dobijeni za uticaj kumarina na bubrege i jetru. Svi dobijeni modeli ukazuju na značaj električno polarizacionih deskriptora, kao i deskriptora koji opisuju veličinu i lipofilnost jedinjenja, a upotrebljeni su za utvrđivanje strukturnih karakteristika koje značajno utiču na njihovu apsorpciju, distribuciju, metabolizam, izlučivanje i toksičnost.",
publisher = "Serbian Chemical Soc, Belgrade",
journal = "Journal of the Serbian Chemical Society",
title = "Quantitative structure-toxicity relationship study of some natural and synthetic coumarins using retention parameters, Analiza zavisnosti strukture i toksičnosti nekih prirodnih i sintetičkih kumarina korišćenjem retencionih parametara",
volume = "77",
number = "10",
pages = "1443-1456",
doi = "10.2298/JSC120716091R"
}

Rabtti, E. H. M. A., Natić, M., Milojković-Opsenica, D., Trifković, J., Tosti, T., Vučković, I., Vajs, V.,& Tešić, Ž.. (2012). Quantitative structure-toxicity relationship study of some natural and synthetic coumarins using retention parameters. in Journal of the Serbian Chemical Society
Serbian Chemical Soc, Belgrade., 77(10), 1443-1456.
https://doi.org/10.2298/JSC120716091R

Rabtti EHMA, Natić M, Milojković-Opsenica D, Trifković J, Tosti T, Vučković I, Vajs V, Tešić Ž. Quantitative structure-toxicity relationship study of some natural and synthetic coumarins using retention parameters. in Journal of the Serbian Chemical Society. 2012;77(10):1443-1456.
doi:10.2298/JSC120716091R .

Rabtti, El Hadi M. A., Natić, Maja, Milojković-Opsenica, Dušanka, Trifković, Jelena, Tosti, Tomislav, Vučković, Ivan, Vajs, Vlatka, Tešić, Živoslav, "Quantitative structure-toxicity relationship study of some natural and synthetic coumarins using retention parameters" in Journal of the Serbian Chemical Society, 77, no. 10 (2012):1443-1456,
https://doi.org/10.2298/JSC120716091R . .

TY  - JOUR
AU  - Rabtti, El Hadi M. A.
AU  - Natić, Maja
AU  - Milojković-Opsenica, Dušanka
AU  - Trifković, Jelena
AU  - Vučković, Ivan
AU  - Vajs, Vlatka
AU  - Tešić, Živoslav
PY  - 2012
UR  - https://cer.ihtm.bg.ac.rs/handle/123456789/2726
AB  - The lipophilic character of twelve coumarins was investigated by reversed-phase thin-layer chromatography (RP TLC) on RP-18 silica. The three different binary solvent systems composed of water and organic modifier (methanol, tetrahydrofuran or acetonitrile) were used in order to determine retention parameter (R-M(0)) and octanol-water partition coefficient (log P-OW) as a measure of the lipophilicity of the tested compounds. Lipophilicity parameter (log P-OW) was experimentally determined using eight standard solutes with known log P-OW values which were analyzed under the same chromatographic conditions as the target substances. Lipophilicity parameters together with 2D molecular descriptors were subjected to the multivariate statistical analysis (principal component analysis (PCA) and partial least square (PLS) regression) in order to reveal the most influential factors governing the retention, i.e., lipophilicity of the investigated compounds. The quantitative structure-retention relationship models reveal the importance of descriptors which describe the size and the shape of the molecule as well as their polar properties.
PB  - Soc Brasileira Quimica, Sao Paulo
T2  - Journal of the Brazilian Chemical Society
T1  - RP TLC-Based Lipophilicity Assessment of Some Natural and Synthetic Coumarins
VL  - 23
IS  - 3
SP  - 522
UR  - https://hdl.handle.net/21.15107/rcub_cherry_1274
ER  - 

@article{
author = "Rabtti, El Hadi M. A. and Natić, Maja and Milojković-Opsenica, Dušanka and Trifković, Jelena and Vučković, Ivan and Vajs, Vlatka and Tešić, Živoslav",
year = "2012",
abstract = "The lipophilic character of twelve coumarins was investigated by reversed-phase thin-layer chromatography (RP TLC) on RP-18 silica. The three different binary solvent systems composed of water and organic modifier (methanol, tetrahydrofuran or acetonitrile) were used in order to determine retention parameter (R-M(0)) and octanol-water partition coefficient (log P-OW) as a measure of the lipophilicity of the tested compounds. Lipophilicity parameter (log P-OW) was experimentally determined using eight standard solutes with known log P-OW values which were analyzed under the same chromatographic conditions as the target substances. Lipophilicity parameters together with 2D molecular descriptors were subjected to the multivariate statistical analysis (principal component analysis (PCA) and partial least square (PLS) regression) in order to reveal the most influential factors governing the retention, i.e., lipophilicity of the investigated compounds. The quantitative structure-retention relationship models reveal the importance of descriptors which describe the size and the shape of the molecule as well as their polar properties.",
publisher = "Soc Brasileira Quimica, Sao Paulo",
journal = "Journal of the Brazilian Chemical Society",
title = "RP TLC-Based Lipophilicity Assessment of Some Natural and Synthetic Coumarins",
volume = "23",
number = "3",
pages = "522",
url = "https://hdl.handle.net/21.15107/rcub_cherry_1274"
}

Rabtti, E. H. M. A., Natić, M., Milojković-Opsenica, D., Trifković, J., Vučković, I., Vajs, V.,& Tešić, Ž.. (2012). RP TLC-Based Lipophilicity Assessment of Some Natural and Synthetic Coumarins. in Journal of the Brazilian Chemical Society
Soc Brasileira Quimica, Sao Paulo., 23(3), 522.
https://hdl.handle.net/21.15107/rcub_cherry_1274

Rabtti EHMA, Natić M, Milojković-Opsenica D, Trifković J, Vučković I, Vajs V, Tešić Ž. RP TLC-Based Lipophilicity Assessment of Some Natural and Synthetic Coumarins. in Journal of the Brazilian Chemical Society. 2012;23(3):522.
https://hdl.handle.net/21.15107/rcub_cherry_1274 .

Rabtti, El Hadi M. A., Natić, Maja, Milojković-Opsenica, Dušanka, Trifković, Jelena, Vučković, Ivan, Vajs, Vlatka, Tešić, Živoslav, "RP TLC-Based Lipophilicity Assessment of Some Natural and Synthetic Coumarins" in Journal of the Brazilian Chemical Society, 23, no. 3 (2012):522,
https://hdl.handle.net/21.15107/rcub_cherry_1274 .