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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

Structure-based Drug Design of New Cinnamic Acid Derivatives as Tyrosinase Inhibitors

Author(s): Fayezeh Yousefnejad, Mohammad Hossein Sayahi, Ali Moazzam, Fatemeh Gholami, Nader Tanideh, Cambyz Irajie, Helia Tayebi, Fatemeh Rasekh, Bagher Larijani, Maliheh Barazandeh Tehrani, Mohammad Mahdavi* and Aida Iraji*

Volume 21, Issue 8, 2024

Published on: 25 January, 2024

Page: [647 - 654] Pages: 8

DOI: 10.2174/0115701786263337231227113513

Price: $65

Abstract

Tyrosinase is a critical enzyme responsible for pigmentation disorders, and tyrosinase inhibition is an established strategy to treat hyperpigmentation. In the current study, cinnamic acidbased derivatives were designed and synthesized. All synthesized compounds were confirmed using IR, 1HNMR, 13CNMR, and CNH analysis. The inhibitory potencies of all derivatives against tyrosinase were determined, and it was shown that 5m bearing para-chloro moiety exhibits an IC50 value of 77.62 μmol/L. Analysis of enzyme kinetic studies revealed that 5m is an uncompetitive inhibitor. In silico studies against tyrosinase predicted possible binding mode in the pocket such that 5m formed critical interactions with both Cu co-factors within the binding site. This study presents the potential of aryl-substituted cinnamic acids that can benefit various cosmetic formulations as depigmentation agents.

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