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Modeling of Anticancer Sulfonamide Derivatives Lipophilicity by Chemometric and Quantitative Structure-Retention Relationships Approaches

Sulfonamides are a classic group of chemotherapeutic drugs with a broad spectrum of pharmacological action, including anticancer activity. In this work, reversed-phase high-performance liquid chromatography and biomimetic chromatography were applied to characterize the lipophilicity of sulfonamide d...

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Autores principales: Pastewska, Monika, Żołnowska, Beata, Kovačević, Strahinja, Kapica, Hanna, Gromelski, Maciej, Stoliński, Filip, Sławiński, Jarosław, Sawicki, Wiesław, Ciura, Krzesimir
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2022
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9268166/
https://www.ncbi.nlm.nih.gov/pubmed/35807212
http://dx.doi.org/10.3390/molecules27133965
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author Pastewska, Monika
Żołnowska, Beata
Kovačević, Strahinja
Kapica, Hanna
Gromelski, Maciej
Stoliński, Filip
Sławiński, Jarosław
Sawicki, Wiesław
Ciura, Krzesimir
author_facet Pastewska, Monika
Żołnowska, Beata
Kovačević, Strahinja
Kapica, Hanna
Gromelski, Maciej
Stoliński, Filip
Sławiński, Jarosław
Sawicki, Wiesław
Ciura, Krzesimir
author_sort Pastewska, Monika
collection PubMed
description Sulfonamides are a classic group of chemotherapeutic drugs with a broad spectrum of pharmacological action, including anticancer activity. In this work, reversed-phase high-performance liquid chromatography and biomimetic chromatography were applied to characterize the lipophilicity of sulfonamide derivatives with proven anticancer activities against human colon cancer. Chromatographically determined lipophilicity parameters were compared with obtained logP, employing various computational approaches. Similarities and dissimilarities between experimental and computational logP were studied using principal component analysis, cluster analysis, and the sum of ranking differences. Furthermore, quantitative structure–retention relationship modeling was applied to understand the influences of sulfonamide’s molecular properties on lipophilicity and affinity to phospholipids.
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spelling pubmed-92681662022-07-09 Modeling of Anticancer Sulfonamide Derivatives Lipophilicity by Chemometric and Quantitative Structure-Retention Relationships Approaches Pastewska, Monika Żołnowska, Beata Kovačević, Strahinja Kapica, Hanna Gromelski, Maciej Stoliński, Filip Sławiński, Jarosław Sawicki, Wiesław Ciura, Krzesimir Molecules Article Sulfonamides are a classic group of chemotherapeutic drugs with a broad spectrum of pharmacological action, including anticancer activity. In this work, reversed-phase high-performance liquid chromatography and biomimetic chromatography were applied to characterize the lipophilicity of sulfonamide derivatives with proven anticancer activities against human colon cancer. Chromatographically determined lipophilicity parameters were compared with obtained logP, employing various computational approaches. Similarities and dissimilarities between experimental and computational logP were studied using principal component analysis, cluster analysis, and the sum of ranking differences. Furthermore, quantitative structure–retention relationship modeling was applied to understand the influences of sulfonamide’s molecular properties on lipophilicity and affinity to phospholipids. MDPI 2022-06-21 /pmc/articles/PMC9268166/ /pubmed/35807212 http://dx.doi.org/10.3390/molecules27133965 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
Pastewska, Monika
Żołnowska, Beata
Kovačević, Strahinja
Kapica, Hanna
Gromelski, Maciej
Stoliński, Filip
Sławiński, Jarosław
Sawicki, Wiesław
Ciura, Krzesimir
Modeling of Anticancer Sulfonamide Derivatives Lipophilicity by Chemometric and Quantitative Structure-Retention Relationships Approaches
title Modeling of Anticancer Sulfonamide Derivatives Lipophilicity by Chemometric and Quantitative Structure-Retention Relationships Approaches
title_full Modeling of Anticancer Sulfonamide Derivatives Lipophilicity by Chemometric and Quantitative Structure-Retention Relationships Approaches
title_fullStr Modeling of Anticancer Sulfonamide Derivatives Lipophilicity by Chemometric and Quantitative Structure-Retention Relationships Approaches
title_full_unstemmed Modeling of Anticancer Sulfonamide Derivatives Lipophilicity by Chemometric and Quantitative Structure-Retention Relationships Approaches
title_short Modeling of Anticancer Sulfonamide Derivatives Lipophilicity by Chemometric and Quantitative Structure-Retention Relationships Approaches
title_sort modeling of anticancer sulfonamide derivatives lipophilicity by chemometric and quantitative structure-retention relationships approaches
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9268166/
https://www.ncbi.nlm.nih.gov/pubmed/35807212
http://dx.doi.org/10.3390/molecules27133965
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