Thin-layer chromatography on reversed phase in the characterization of retention behaviour, lipophilicity, and pharmacokinetics of cyanoacetamide derivatives
Само за регистроване кориснике
2020
Аутори
Apostolov, SuzanaVastag, Gyongyi
Matijević, Borko M.
Đaković-Sekulić, Tatjana
Marinković, Aleksandar
Чланак у часопису (Објављена верзија)
Метаподаци
Приказ свих података о документуАпстракт
Biological activity of a molecule is closely related to its lipophilicity. This significant parameter was determined for a group of potentially bioactive N-(4-phenylmonosubstituted)-2-cyanoacetamides applying thin-layer chromatography on reversed phase (RP-TLC) in mixtures of water and two organic modifiers separately, i-propanol and dioxane. The effect of the chemical structure of derivatives and the influence of the applied organic modifier on their retention were studied. The determined chromatographic retention constants, R-M(0), and the chromatographic parameter, m, of compounds were correlated with software calculated partition coefficients, log P as the standard measure of lipophilicity and with different pharmacokinetic predictors applying classical linear and multiple regression analysis. By classical linear regression analysis in both water-modifier systems only R-M(0)-log P and m-log P correlations were established (average r, 0.909 and 0.826). All studied relationships were... enhanced by molecular descriptors that fulfilled the modified Lipinski's rule of five. Thereby, the performed multiple regression analysis gave better correlations (for R-M(0)-log P and m-log P average r(2), 0.994 and 0.993; for R-M(0)-pharmacokinetic parameters and m-pharmacokinetic parameters average r(2) 0.978 and 0.980). The obtained results indicate that the chromatographic parameters, R-M(0) and m determined by RP-TLC at given conditions could be used successfully for the description of lipophilicity and the evaluation of pharmacokinetic properties of N-(4-phenylmonosubstituted)-2-cyanoacetamides as potential bioactive molecules.
Кључне речи:
N-(4-phenylmonosubstituted)-2-cyanoacetamides / RP-TLC / lipophilicity / Lipinski's molecular descriptors / pharmacokinetic predictorsИзвор:
Journal of the Chilean Chemical Society, 2020, 65, 1, 4654-4660Финансирање / пројекти:
- Проучавање синтезе, структуре и активности органских једињења природног и синтетског порекла (RS-MESTD-Basic Research (BR or ON)-172013)
DOI: 10.4067/S0717-97072020000104654
ISSN: 0717-9324
WoS: 000528017500001
Scopus: 2-s2.0-85083848551
Институција/група
Tehnološko-metalurški fakultetTY - JOUR AU - Apostolov, Suzana AU - Vastag, Gyongyi AU - Matijević, Borko M. AU - Đaković-Sekulić, Tatjana AU - Marinković, Aleksandar PY - 2020 UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/4576 AB - Biological activity of a molecule is closely related to its lipophilicity. This significant parameter was determined for a group of potentially bioactive N-(4-phenylmonosubstituted)-2-cyanoacetamides applying thin-layer chromatography on reversed phase (RP-TLC) in mixtures of water and two organic modifiers separately, i-propanol and dioxane. The effect of the chemical structure of derivatives and the influence of the applied organic modifier on their retention were studied. The determined chromatographic retention constants, R-M(0), and the chromatographic parameter, m, of compounds were correlated with software calculated partition coefficients, log P as the standard measure of lipophilicity and with different pharmacokinetic predictors applying classical linear and multiple regression analysis. By classical linear regression analysis in both water-modifier systems only R-M(0)-log P and m-log P correlations were established (average r, 0.909 and 0.826). All studied relationships were enhanced by molecular descriptors that fulfilled the modified Lipinski's rule of five. Thereby, the performed multiple regression analysis gave better correlations (for R-M(0)-log P and m-log P average r(2), 0.994 and 0.993; for R-M(0)-pharmacokinetic parameters and m-pharmacokinetic parameters average r(2) 0.978 and 0.980). The obtained results indicate that the chromatographic parameters, R-M(0) and m determined by RP-TLC at given conditions could be used successfully for the description of lipophilicity and the evaluation of pharmacokinetic properties of N-(4-phenylmonosubstituted)-2-cyanoacetamides as potential bioactive molecules. T2 - Journal of the Chilean Chemical Society T1 - Thin-layer chromatography on reversed phase in the characterization of retention behaviour, lipophilicity, and pharmacokinetics of cyanoacetamide derivatives EP - 4660 IS - 1 SP - 4654 VL - 65 DO - 10.4067/S0717-97072020000104654 ER -
@article{ author = "Apostolov, Suzana and Vastag, Gyongyi and Matijević, Borko M. and Đaković-Sekulić, Tatjana and Marinković, Aleksandar", year = "2020", abstract = "Biological activity of a molecule is closely related to its lipophilicity. This significant parameter was determined for a group of potentially bioactive N-(4-phenylmonosubstituted)-2-cyanoacetamides applying thin-layer chromatography on reversed phase (RP-TLC) in mixtures of water and two organic modifiers separately, i-propanol and dioxane. The effect of the chemical structure of derivatives and the influence of the applied organic modifier on their retention were studied. The determined chromatographic retention constants, R-M(0), and the chromatographic parameter, m, of compounds were correlated with software calculated partition coefficients, log P as the standard measure of lipophilicity and with different pharmacokinetic predictors applying classical linear and multiple regression analysis. By classical linear regression analysis in both water-modifier systems only R-M(0)-log P and m-log P correlations were established (average r, 0.909 and 0.826). All studied relationships were enhanced by molecular descriptors that fulfilled the modified Lipinski's rule of five. Thereby, the performed multiple regression analysis gave better correlations (for R-M(0)-log P and m-log P average r(2), 0.994 and 0.993; for R-M(0)-pharmacokinetic parameters and m-pharmacokinetic parameters average r(2) 0.978 and 0.980). The obtained results indicate that the chromatographic parameters, R-M(0) and m determined by RP-TLC at given conditions could be used successfully for the description of lipophilicity and the evaluation of pharmacokinetic properties of N-(4-phenylmonosubstituted)-2-cyanoacetamides as potential bioactive molecules.", journal = "Journal of the Chilean Chemical Society", title = "Thin-layer chromatography on reversed phase in the characterization of retention behaviour, lipophilicity, and pharmacokinetics of cyanoacetamide derivatives", pages = "4660-4654", number = "1", volume = "65", doi = "10.4067/S0717-97072020000104654" }
Apostolov, S., Vastag, G., Matijević, B. M., Đaković-Sekulić, T.,& Marinković, A.. (2020). Thin-layer chromatography on reversed phase in the characterization of retention behaviour, lipophilicity, and pharmacokinetics of cyanoacetamide derivatives. in Journal of the Chilean Chemical Society, 65(1), 4654-4660. https://doi.org/10.4067/S0717-97072020000104654
Apostolov S, Vastag G, Matijević BM, Đaković-Sekulić T, Marinković A. Thin-layer chromatography on reversed phase in the characterization of retention behaviour, lipophilicity, and pharmacokinetics of cyanoacetamide derivatives. in Journal of the Chilean Chemical Society. 2020;65(1):4654-4660. doi:10.4067/S0717-97072020000104654 .
Apostolov, Suzana, Vastag, Gyongyi, Matijević, Borko M., Đaković-Sekulić, Tatjana, Marinković, Aleksandar, "Thin-layer chromatography on reversed phase in the characterization of retention behaviour, lipophilicity, and pharmacokinetics of cyanoacetamide derivatives" in Journal of the Chilean Chemical Society, 65, no. 1 (2020):4654-4660, https://doi.org/10.4067/S0717-97072020000104654 . .