Design, synthesis and biological evaluation of oxindole-based chalcones as small-molecule inhibitors of melanogenic tyrosinase

Suthar, Sharad Kumar and Bansal, Sumit and Narkhede, Niteen and Alex, Angel Treasa and Joseph, Alex (2017) Design, synthesis and biological evaluation of oxindole-based chalcones as small-molecule inhibitors of melanogenic tyrosinase. Chemical and Pharmaceutical Bulletin, 65 (9). pp. 833-839. ISSN 0009-2363

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Abstract

The enzyme tyrosinase regulates melanogenesis and skin hyperpigmentation by converting L-3,4-dihydroxyphenylalanine (L-DOPA) into dopaquinone, a key step in the melanin biosynthesis. The present work deals with design and synthesis of various oxindole-based chalcones as monophenolase and diphenolase activity inhibitors of tyrosinase. Among the screened compounds, 4-hydroxy-3-methoxybenzylidene moiety bearing chalcone (7) prepared by one pot reaction of oxindole and vanillin displayed the highest activity against tyrosinase with IC50s of 63.37 and 59.71 μM in monophenolase and diphenolase activity assays, respectively. In molecular docking studies, chalcone 7 also showed the highest binding affinity towards the enzyme tyrosinase while exhibiting the lowest estimated free energy of binding, among all the ligands docked.

Item Type: Article
Uncontrolled Keywords: Tyrosinase inhibitor; oxindole-based chalcone; melanogenesis; molecular docking.
Subjects: Pharmacy > MCOPS Manipal > Pharmaceutical Biotechnology
Pharmacy > MCOPS Manipal > Pharmaceutical Chemistry
Depositing User: KMC Library
Date Deposited: 20 Nov 2017 05:52
Last Modified: 20 Nov 2017 05:52
URI: http://eprints.manipal.edu/id/eprint/149987

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