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Synthesis and antiproliferative studies of curcumin pyrazole derivatives

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Abstract

A series of curcumin pyrazole derivatives (3a–e) were synthesized. The chemical structures were determined by 1H and 13C NMR spectroscopic techniques and their purity was confirmed by LC–MS and melting point determination. The compounds were screened for anticancer effects on different cancer cell lines by MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-Diphenyltetrazolium Bromide) assay. The analogs demonstrated growth inhibitory effect on MCF-7, HeLa, and K562 cell lines with significant IC50 values. Compound 3b exhibited a high degree of cytotoxicity against cancer cells and minimum growth inhibitory effects against normal cells HEK293T and hence further, cell cycle analysis and mitochondrial membrane potential studies (JC-1 assay) were conducted by utilizing flow cytometry against K562 cells. This compound effectively arrested cell cycle progression at SubG1 phase and cells exhibited decreased membrane potential in a concentration-dependent manner with fluorescence shifting from red to green. Our findings suggest that compound 3b could be a promising anticancer agent since it effectively inhibited cell proliferation and can be selected for further in vitro and in vivo investigations.

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Acknowledgments

The authors express sincere gratitude to Dr. S Nagendra, Managing Director and Chief executive officer, Scintilla BIO-MARC pvt. Ltd, Bangalore, India for providing technical assistance regarding cell culture facilities for the work.

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Authors and Affiliations

  1. Department of Biochemistry, Yuvaraja’s College, University of Mysore, Mysuru, 570005, Karnataka, India

    Honnalagere Ramesh Puneeth & Angatahally Chandrashekariah Sharada

  2. Department of Studies in Chemistry, Manasagangotri, University of Mysore, Mysuru, 570006, Karnataka, India

    Hanumappa Ananda, Kothanahally S. Sharath Kumar & Kanchugarakoppal S. Rangappa

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  1. Honnalagere Ramesh Puneeth
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  2. Hanumappa Ananda
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  3. Kothanahally S. Sharath Kumar
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  4. Kanchugarakoppal S. Rangappa
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  5. Angatahally Chandrashekariah Sharada
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Correspondence to Angatahally Chandrashekariah Sharada.

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Puneeth, H.R., Ananda, H., Kumar, K.S.S. et al. Synthesis and antiproliferative studies of curcumin pyrazole derivatives. Med Chem Res 25, 1842–1851 (2016). https://doi.org/10.1007/s00044-016-1628-5

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  • DOI: https://doi.org/10.1007/s00044-016-1628-5

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