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Synthesis, Characterization and Antiproliferative Activity of 1,2-Naphthoquinone and Its Derivatives

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Abstract

In the present study substituted 1,2-naphthoquinones were synthesized, purified and characterized by spectroscopic studies (UV, FT-IR, 1H NMR, 13 C NMR and elemental analysis). These compounds were evaluated for cytotoxicity against a panel of human cancer cell lines (Hep-G2 for liver sarcoma, MG-63 for osteosarcoma and MCF-7 for human breast cancer). The cells were dosed with these ortho-naphthoquinone derivatives at varying concentrations, and cell viability was measured by a 3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay with doxorubicin as positive control. Significant anticancer activities were observed in vitro for some members of the series, and compounds 1,2-naphthoquinone 2-thiosemicarbazone (3), 1,2-naphthoquinone-2-semicarbazone (4), 4-amino-1,2-naphthoquinone 2-thiosemicarbazone (7) and 4-amino-1,2-naphthoquinone-2-semicarbazone (8) are active cytotoxic agents against different cancer cell lines with IC50 values in the range of 5.73–17.67 μM. The obtained data suggested that better anticancer activity was linked with introduction of thiosemicarbazone and semicarbazone moiety in 1,2-naphthoquinone ring system. Outcomes of experimentation also reveal that incorporation of amino group in 1,2-naphthoquinone moiety contributes positively for cytotoxic action of compounds. Docking experiments showed a good correlation between their calculated interaction energies with the topoisomerase-II and the observed IC50 values of all these compounds.

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Acknowledgements

The authors are grateful to the head of the Department of Chemistry, Faculty of Science, Banaras Hindu University (BHU), and Varanasi, India, for 1H NMR and 13 C NMR spectroscopy. One of the authors, Shubhanjali Shukla, thanks the Jawahar Lal Nehru Memorial Fund, New Delhi, for providing financial assistance to continue the research.

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Authors and Affiliations

  1. Department of Pharmaceutics, I.T., Banaras Hindu University, Varanasi, 221005, India

    S. Shukla, R. S. Srivastava & S. K. Shrivastava

  2. School of Biotechnology, Faculty of Science, Banaras Hindu University, Varanasi, 221005, India

    A. Sodhi

  3. School of Pharmaceutical science, S.O.A., Bhubneshwar, India

    Pankaj Kumar

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  1. S. Shukla
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  2. R. S. Srivastava
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  3. S. K. Shrivastava
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  4. A. Sodhi
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  5. Pankaj Kumar
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Correspondence to R. S. Srivastava.

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Shukla, S., Srivastava, R.S., Shrivastava, S.K. et al. Synthesis, Characterization and Antiproliferative Activity of 1,2-Naphthoquinone and Its Derivatives. Appl Biochem Biotechnol 167, 1430–1445 (2012). https://doi.org/10.1007/s12010-012-9551-9

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  • DOI: https://doi.org/10.1007/s12010-012-9551-9

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