Synthesis, cytotoxic evaluation, and in silico studies of novel benzenesulfonamide-thiazolidinone derivatives against colorectal carcinoma

•Thirteen novel benzenesulfonamide bearing 4-thiazolidinone derivatives were designed and synthesized.•The effects on colorectal cell line were evaluated.•Molecular docking studies, molecular dynamics simulations and ADME properties investigated. Thirteen new benzenesulfonamide derivatives containin...

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Bibliographic Details
Published in:	Journal of molecular structure Vol. 1321; p. 140153
Main Authors:	Zengin Kurt, Belma, Gökçe, Mustafa, Şenol, Halil, Öztürk Civelek, Dilek, Dandin, Gülnur, Gazioglu, Isil
Format:	Journal Article
Language:	English
Published:	Elsevier B.V 05-02-2025
Subjects:	4-Thiazolidinone ADME properties Apoptosis Benzenesulfonamide Cytotoxcity Molecular docking Cytotoxcity 4-Thiazolidinone ADME properties Benzenesulfonamide Molecular docking Apoptosis
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Summary:	•Thirteen novel benzenesulfonamide bearing 4-thiazolidinone derivatives were designed and synthesized.•The effects on colorectal cell line were evaluated.•Molecular docking studies, molecular dynamics simulations and ADME properties investigated. Thirteen new benzenesulfonamide derivatives containing 4-thiazolidinone were synthesized. Their cytotoxic properties were tested on colorectal carcinoma (HT-29, DLD-1, COLO-205) and normal colon fibroblast (CCD-986Sk) cell lines. Compounds 3l (IC50=114.62 µM), 3a (IC50=25.82 µM), 3k (IC50=30.99 µM), and 3i (IC50=62.94 µM) showed the highest cytotoxicity on HT-29, DLD-1, COLO-205, and CCD-986Sk cell lines, respectively. Compound 3e (IC50=1075.4 µM) exhibited the least cytotoxicity against CCD-986Sk. The apoptosis profile of 5-FU at 5 µM was similar to that of compound 3e at 30 µM. Molecular docking and MD simulations showed stable interactions for compounds 3i and 3e. Molecular docking and MD simulations revealed that compounds 3i and 3e exhibit stable interactions with key cancer-related protein targets, particularly TGFβ2. These interactions suggest their potential as therapeutic agents. The predicted ADME parameters further highlighted compounds 3e and 3i for their favorable lipophilicity, solubility, permeability, and oral absorption profiles, supporting their promise as candidates for future drug development. [Display omitted]
ISSN:	0022-2860
DOI:	10.1016/j.molstruc.2024.140153