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RP TLC-Based Lipophilicity Assessment of Some Natural and Synthetic Coumarins

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2012
1272.pdf (486.6Kb)
Authors
Rabtti, El Hadi M. A.
Natić, Maja
Milojković-Opsenica, Dušanka
Trifković, Jelena
Vučković, Ivan M.
Vajs, Vlatka
Tešić, Živoslav Lj.
Article (Published version)
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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 re...lationship models reveal the importance of descriptors which describe the size and the shape of the molecule as well as their polar properties.

Keywords:
coumarins / lipophilicity / quantitative structure-retention relationships / principal component analysis / partial least square
Source:
Journal of the Brazilian Chemical Society, 2012, 23, 3, 522-
Publisher:
  • Soc Brasileira Quimica, Sao Paulo
Funding / projects:
  • Structure-properties relationships of natural and synthetic molecules and their metal complexes (RS-172017)

ISSN: 0103-5053

WoS: 000302461200020

Scopus: 2-s2.0-84859045039
[ Google Scholar ]
17
15
Handle
https://hdl.handle.net/21.15107/rcub_cherry_1274
URI
https://cherry.chem.bg.ac.rs/handle/123456789/1274
Collections
  • Publikacije
Institution/Community
Hemijski fakultet
TY  - JOUR
AU  - Rabtti, El Hadi M. A.
AU  - Natić, Maja
AU  - Milojković-Opsenica, Dušanka
AU  - Trifković, Jelena
AU  - Vučković, Ivan M.
AU  - Vajs, Vlatka
AU  - Tešić, Živoslav Lj.
PY  - 2012
UR  - https://cherry.chem.bg.ac.rs/handle/123456789/1274
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  - Kon_2297
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 M. and Vajs, Vlatka and Tešić, Živoslav Lj.",
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 = "Kon_2297, https://hdl.handle.net/21.15107/rcub_cherry_1274"
}
Rabtti, E. H. M. A., Natić, M., Milojković-Opsenica, D., Trifković, J., Vučković, I. M., Vajs, V.,& Tešić, Ž. Lj.. (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.
Kon_2297
Rabtti EHMA, Natić M, Milojković-Opsenica D, Trifković J, Vučković IM, Vajs V, Tešić ŽL. RP TLC-Based Lipophilicity Assessment of Some Natural and Synthetic Coumarins. in Journal of the Brazilian Chemical Society. 2012;23(3):522.
Kon_2297 .
Rabtti, El Hadi M. A., Natić, Maja, Milojković-Opsenica, Dušanka, Trifković, Jelena, Vučković, Ivan M., Vajs, Vlatka, Tešić, Živoslav Lj., "RP TLC-Based Lipophilicity Assessment of Some Natural and Synthetic Coumarins" in Journal of the Brazilian Chemical Society, 23, no. 3 (2012):522,
Kon_2297 .

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