THIN-LAYER CHROMATOGRAPHY ON REVERSED PHASE IN THE CHARACTERIZATION OF RETENTION BEHAVIOUR, LIPOPHILICITY, AND PHARMACOKINETICS OF CYANOACETAMIDE DERIVATIVES

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...

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Autores principales:	Apostolov,Suzana, Vastag,Gyöngyi, Matijević,Borko, Đaković-Sekulić,Tatjana, Marinković,Aleksandar
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2020
Materias:	N-(4-phenylmonosubstituted)-2-cyanoacetamides RP-TLC lipophilicity Lipinski's molecular descriptors pharmacokinetic predictors
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072020000104654
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spelling	oai:scielo:S0717-970720200001046542020-04-16THIN-LAYER CHROMATOGRAPHY ON REVERSED PHASE IN THE CHARACTERIZATION OF RETENTION BEHAVIOUR, LIPOPHILICITY, AND PHARMACOKINETICS OF CYANOACETAMIDE DERIVATIVESApostolov,SuzanaVastag,GyöngyiMatijević,BorkoĐaković-Sekulić,TatjanaMarinković,Aleksandar N-(4-phenylmonosubstituted)-2-cyanoacetamides RP-TLC lipophilicity Lipinski's molecular descriptors pharmacokinetic predictors 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, RM0, 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 RM0-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 RM0-log P and m-log P average r2, 0.994 and 0.993; for RM0-pharmacokinetic parameters and m-pharmacokinetic parameters average r2 0.978 and 0.980). The obtained results indicate that the chromatographic parameters, RM0 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.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.65 n.1 20202020-03-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072020000104654en10.4067/S0717-97072020000104654
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	N-(4-phenylmonosubstituted)-2-cyanoacetamides RP-TLC lipophilicity Lipinski's molecular descriptors pharmacokinetic predictors
spellingShingle	N-(4-phenylmonosubstituted)-2-cyanoacetamides RP-TLC lipophilicity Lipinski's molecular descriptors pharmacokinetic predictors Apostolov,Suzana Vastag,Gyöngyi Matijević,Borko Đaković-Sekulić,Tatjana Marinković,Aleksandar THIN-LAYER CHROMATOGRAPHY ON REVERSED PHASE IN THE CHARACTERIZATION OF RETENTION BEHAVIOUR, LIPOPHILICITY, AND PHARMACOKINETICS OF CYANOACETAMIDE DERIVATIVES
description	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, RM0, 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 RM0-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 RM0-log P and m-log P average r2, 0.994 and 0.993; for RM0-pharmacokinetic parameters and m-pharmacokinetic parameters average r2 0.978 and 0.980). The obtained results indicate that the chromatographic parameters, RM0 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.
author	Apostolov,Suzana Vastag,Gyöngyi Matijević,Borko Đaković-Sekulić,Tatjana Marinković,Aleksandar
author_facet	Apostolov,Suzana Vastag,Gyöngyi Matijević,Borko Đaković-Sekulić,Tatjana Marinković,Aleksandar
author_sort	Apostolov,Suzana
title	THIN-LAYER CHROMATOGRAPHY ON REVERSED PHASE IN THE CHARACTERIZATION OF RETENTION BEHAVIOUR, LIPOPHILICITY, AND PHARMACOKINETICS OF CYANOACETAMIDE DERIVATIVES
title_short	THIN-LAYER CHROMATOGRAPHY ON REVERSED PHASE IN THE CHARACTERIZATION OF RETENTION BEHAVIOUR, LIPOPHILICITY, AND PHARMACOKINETICS OF CYANOACETAMIDE DERIVATIVES
title_full	THIN-LAYER CHROMATOGRAPHY ON REVERSED PHASE IN THE CHARACTERIZATION OF RETENTION BEHAVIOUR, LIPOPHILICITY, AND PHARMACOKINETICS OF CYANOACETAMIDE DERIVATIVES
title_fullStr	THIN-LAYER CHROMATOGRAPHY ON REVERSED PHASE IN THE CHARACTERIZATION OF RETENTION BEHAVIOUR, LIPOPHILICITY, AND PHARMACOKINETICS OF CYANOACETAMIDE DERIVATIVES
title_full_unstemmed	THIN-LAYER CHROMATOGRAPHY ON REVERSED PHASE IN THE CHARACTERIZATION OF RETENTION BEHAVIOUR, LIPOPHILICITY, AND PHARMACOKINETICS OF CYANOACETAMIDE DERIVATIVES
title_sort	thin-layer chromatography on reversed phase in the characterization of retention behaviour, lipophilicity, and pharmacokinetics of cyanoacetamide derivatives
publisher	Sociedad Chilena de Química
publishDate	2020
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072020000104654
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_version_	1714200944225288192

THIN-LAYER CHROMATOGRAPHY ON REVERSED PHASE IN THE CHARACTERIZATION OF RETENTION BEHAVIOUR, LIPOPHILICITY, AND PHARMACOKINETICS OF CYANOACETAMIDE DERIVATIVES

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