Synthesis of thiazolidine-2,4-dione derivatives: anticancer, antimicrobial and DNA cleavage studies

• Published in: Journal of chemical biology Vol. 9; no. 4; pp. 97 - 106
• Main Authors: Laxmi, S. Vijaya, Anil, P., Rajitha, G., Rao, Asha Jyothi, Crooks, Peter A., Rajitha, B.
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01.10.2016; Springer Nature B.V
• Subjects: Anticancer properties; Antiinfectives and antibacterials; Antineoplastic drugs; Antitumor activity; Antitumor agents; Biochemistry; Biological and Medical Physics; Biophysics; Biotechnology; Breast cancer; Cancer; Cell Biology; Chemistry; Chemistry and Materials Science; Cleavage; Colon; Colon cancer; Deoxyribonucleic acid; Derivatives; Digestion; DNA; Kidney cancer; Leukemia; Lung cancer; Melanoma; Microorganisms; Non-small cell lung carcinoma; Original; Original Article; Ovarian cancer; Pharmacology/Toxicology; Physical Chemistry; Prostate cancer; Synthesis; Tumor cell lines; 4-dione; Antimicrobial activity; DNA cleavages studies; 4-hydroxybenzyledenethiazolidine-2; Anticancer activity; Cancer
• ISSN: 1864-6158; 1864-6166
• DOI: 10.1007/s12154-016-0154-8

In the search of efficient anticancer agents, here, new 5-(4-alkylbenzyledene)thiazolidine-2,4-dione derivatives ( 5a–g ) have been successfully synthesized and characterized and are evaluated for anticancer and antimicrobial activities using DNA cleavage studies. In vitro studies on anticancer activity of compound 5d (NSC: 768619/1) was done against the full panel of 60 human tumor cell lines. The five-level dose activity results revealed that, the compound 5d was active against all the cell lines, it has shown potential activity against leukemia SR (GI 50 : 2.04 μM), non-small cell lung cancer NCI-H522 (GI 50 : 1.36 μM), colon cancer COLO 205 (GI 50 : 1.64 μM), CNS cancer SF-539 (GI 50 : 1.87 μM), melanoma SK-MEL-2 (GI 50 : 1.64 μM), ovarian cancer OVCAR-3 (GI 50 : 1.87 μM), renal cancer RXF 393 (GI 50 : 1.15 μM), prostate cancer PC-3 (GI 50 : 1.90 μM), and breast cancer MDA-MB-468(GI 50 : 1.11 μM). DNA cleavage studies revealed that at 50 μg/mL concentration, partial DNA digestion was observed and when the concentration is increasing to threefold (150 μg/mL), complete linear DNA digestion and partial supercoiled DNA digestion was observed. Further antimicrobial studies indicate that all the synthesized compounds except compound 5a possess prominent activity against all the screened microbial species. This study throws a ray of light in the field of anticancer drugs.