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

  • Original Article
  • Published:
Journal of Chemical Biology

Abstract

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 (GI50: 2.04 μM), non-small cell lung cancer NCI-H522 (GI50: 1.36 μM), colon cancer COLO 205 (GI50: 1.64 μM), CNS cancer SF-539 (GI50: 1.87 μM), melanoma SK-MEL-2 (GI50: 1.64 μM), ovarian cancer OVCAR-3 (GI50: 1.87 μM), renal cancer RXF 393 (GI50: 1.15 μM), prostate cancer PC-3 (GI50: 1.90 μM), and breast cancer MDA-MB-468(GI50: 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.

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Acknowledgments

The authors wish to thank NCI/NIH, Bethesda, USA, for performing the antitumor testing of the synthesized compounds, and one of the authors (RG) is thankful to the Ministry of Human Resource Development, New Delhi for providing the fellowship.

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Authors and Affiliations

  1. Department of Chemistry, K L University, Guntur, 522502, India

    S. Vijaya Laxmi & P. Anil

  2. Department of Chemistry, National Institute of Technology, Warangal, 506004, India

    G. Rajitha & B. Rajitha

  3. Department of Zoology, Bhavan’s College, Andheri(W), Mumbai, 400058, India

    Asha Jyothi Rao

  4. Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for medical Sciences, Little Rock, AR, 72205, USA

    Peter A. Crooks

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  1. S. Vijaya Laxmi
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  2. P. Anil
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Correspondence to S. Vijaya Laxmi.

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Laxmi, S.V., Anil, P., Rajitha, G. et al. Synthesis of thiazolidine-2,4-dione derivatives: anticancer, antimicrobial and DNA cleavage studies. J Chem Biol 9, 97–106 (2016). https://doi.org/10.1007/s12154-016-0154-8

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  • DOI: https://doi.org/10.1007/s12154-016-0154-8

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