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Lipophilicity and Pharmacokinetic Properties of New Anticancer Dipyridothiazine with 1,2,3-Triazole Substituents

The lipophilicity parameters (logP(calcd), R(M)(0) and logP(TLC)) of 10 new active anticancer dipirydothiazines with a 1,2,3-triazole ring were determined theoretically using computational methods and experimentally by reversed-phase TLC. Experimental lipophilicity was assessed using mobile phases (...

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Autores principales: Morak-Młodawska, Beata, Jeleń, Małgorzata
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8878114/
https://www.ncbi.nlm.nih.gov/pubmed/35209047
http://dx.doi.org/10.3390/molecules27041253
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author Morak-Młodawska, Beata
Jeleń, Małgorzata
author_facet Morak-Młodawska, Beata
Jeleń, Małgorzata
author_sort Morak-Młodawska, Beata
collection PubMed
description The lipophilicity parameters (logP(calcd), R(M)(0) and logP(TLC)) of 10 new active anticancer dipirydothiazines with a 1,2,3-triazole ring were determined theoretically using computational methods and experimentally by reversed-phase TLC. Experimental lipophilicity was assessed using mobile phases (a mixture of TRIS buffer and acetone) using a linear correlation between the R(M) retention parameter and the volume of acetone. The R(M)(0) parameter was correlated with the specific hydrophobic surface b, revealing two congenerative subgroups: 1,2,3-triazole-1,6-diazaphenothiazines and 1,2,3-triazole-1,8-diazaphenothiazines hybrids. The R(M)(0) parameter was converted into the logP(TLC) lipophilicity parameter using a calibration curve. The investigated compounds appeared to be moderately lipophilic. Lipophilicity has been compared with molecular descriptors and ADME properties. The new derivatives followed Lipinski’s, Ghose’s and Veber’s rules.
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spelling pubmed-88781142022-02-26 Lipophilicity and Pharmacokinetic Properties of New Anticancer Dipyridothiazine with 1,2,3-Triazole Substituents Morak-Młodawska, Beata Jeleń, Małgorzata Molecules Article The lipophilicity parameters (logP(calcd), R(M)(0) and logP(TLC)) of 10 new active anticancer dipirydothiazines with a 1,2,3-triazole ring were determined theoretically using computational methods and experimentally by reversed-phase TLC. Experimental lipophilicity was assessed using mobile phases (a mixture of TRIS buffer and acetone) using a linear correlation between the R(M) retention parameter and the volume of acetone. The R(M)(0) parameter was correlated with the specific hydrophobic surface b, revealing two congenerative subgroups: 1,2,3-triazole-1,6-diazaphenothiazines and 1,2,3-triazole-1,8-diazaphenothiazines hybrids. The R(M)(0) parameter was converted into the logP(TLC) lipophilicity parameter using a calibration curve. The investigated compounds appeared to be moderately lipophilic. Lipophilicity has been compared with molecular descriptors and ADME properties. The new derivatives followed Lipinski’s, Ghose’s and Veber’s rules. MDPI 2022-02-13 /pmc/articles/PMC8878114/ /pubmed/35209047 http://dx.doi.org/10.3390/molecules27041253 Text en © 2022 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Morak-Młodawska, Beata
Jeleń, Małgorzata
Lipophilicity and Pharmacokinetic Properties of New Anticancer Dipyridothiazine with 1,2,3-Triazole Substituents
title Lipophilicity and Pharmacokinetic Properties of New Anticancer Dipyridothiazine with 1,2,3-Triazole Substituents
title_full Lipophilicity and Pharmacokinetic Properties of New Anticancer Dipyridothiazine with 1,2,3-Triazole Substituents
title_fullStr Lipophilicity and Pharmacokinetic Properties of New Anticancer Dipyridothiazine with 1,2,3-Triazole Substituents
title_full_unstemmed Lipophilicity and Pharmacokinetic Properties of New Anticancer Dipyridothiazine with 1,2,3-Triazole Substituents
title_short Lipophilicity and Pharmacokinetic Properties of New Anticancer Dipyridothiazine with 1,2,3-Triazole Substituents
title_sort lipophilicity and pharmacokinetic properties of new anticancer dipyridothiazine with 1,2,3-triazole substituents
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8878114/
https://www.ncbi.nlm.nih.gov/pubmed/35209047
http://dx.doi.org/10.3390/molecules27041253
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