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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| Format: | Article |
| Language: | English |
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MDPI AG
2022-06-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/13/3965 |
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| author | Monika Pastewska Beata Żołnowska Strahinja Kovačević Hanna Kapica Maciej Gromelski Filip Stoliński Jarosław Sławiński Wiesław Sawicki Krzesimir Ciura |
| author_facet | Monika Pastewska Beata Żołnowska Strahinja Kovačević Hanna Kapica Maciej Gromelski Filip Stoliński Jarosław Sławiński Wiesław Sawicki Krzesimir Ciura |
| author_sort | Monika Pastewska |
| collection | DOAJ |
| 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 log<i>P</i>, employing various computational approaches. Similarities and dissimilarities between experimental and computational log<i>P</i> 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. |
| first_indexed | 2024-03-09T12:46:17Z |
| format | Article |
| id | doaj.art-e80ded7d0fcf4212a75d42b975af059c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T12:46:17Z |
| publishDate | 2022-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e80ded7d0fcf4212a75d42b975af059c2023-11-30T22:12:32ZengMDPI AGMolecules1420-30492022-06-012713396510.3390/molecules27133965Modeling of Anticancer Sulfonamide Derivatives Lipophilicity by Chemometric and Quantitative Structure-Retention Relationships ApproachesMonika Pastewska0Beata Żołnowska1Strahinja Kovačević2Hanna Kapica3Maciej Gromelski4Filip Stoliński5Jarosław Sławiński6Wiesław Sawicki7Krzesimir Ciura8Department of Physical Chemistry, Medical University of Gdańsk, Al. Gen. Hallera 107, 80-416 Gdańsk, PolandDepartment of Organic Chemistry, Medical University of Gdańsk, Al. Gen. Hallera 107, 80-416 Gdańsk, PolandDepartment of Applied and Engineering Chemistry, Faculty of Technology Novi Sad, University of Novi Sad, Bulevar Cara Lazara 1, 21000 Novi Sad, SerbiaDepartment of Physical Chemistry, Medical University of Gdańsk, Al. Gen. Hallera 107, 80-416 Gdańsk, PolandQSAR Lab Ltd., Trzy Lipy 3 St., 80-172 Gdańsk, PolandQSAR Lab Ltd., Trzy Lipy 3 St., 80-172 Gdańsk, PolandDepartment of Organic Chemistry, Medical University of Gdańsk, Al. Gen. Hallera 107, 80-416 Gdańsk, PolandDepartment of Physical Chemistry, Medical University of Gdańsk, Al. Gen. Hallera 107, 80-416 Gdańsk, PolandDepartment of Physical Chemistry, Medical University of Gdańsk, Al. Gen. Hallera 107, 80-416 Gdańsk, PolandSulfonamides 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 log<i>P</i>, employing various computational approaches. Similarities and dissimilarities between experimental and computational log<i>P</i> 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.https://www.mdpi.com/1420-3049/27/13/3965sulfonamide derivativesquantitative structure-retention relationshipslipophilicity |
| spellingShingle | Monika Pastewska Beata Żołnowska Strahinja Kovačević Hanna Kapica Maciej Gromelski Filip Stoliński Jarosław Sławiński Wiesław Sawicki Krzesimir Ciura Modeling of Anticancer Sulfonamide Derivatives Lipophilicity by Chemometric and Quantitative Structure-Retention Relationships Approaches Molecules sulfonamide derivatives quantitative structure-retention relationships lipophilicity |
| 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 | sulfonamide derivatives quantitative structure-retention relationships lipophilicity |
| url | https://www.mdpi.com/1420-3049/27/13/3965 |
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