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Design, synthesis, and anti-melanogenic effects of (E)-2-benzoyl-3-(substituted phenyl)acrylonitriles

Authors Yun HY, Kim DH, Son S, Ullah S, Kim SJ, Kim Y, Yoo J, Jung Y, Chun P, Moon HR

Received 6 June 2015

Accepted for publication 10 July 2015

Published 4 August 2015 Volume 2015:9 Pages 4259—4268

DOI https://doi.org/10.2147/DDDT.S89976

Checked for plagiarism Yes

Review by Single anonymous peer review

Peer reviewer comments 3

Editor who approved publication: Prof. Dr. Wei Duan


Hwi Young Yun,1 Do Hyun Kim,1 Sujin Son,1 Sultan Ullah,1 Seong Jin Kim,1 Yeon-Jeong Kim,2 Jin-Wook Yoo,1 Yunjin Jung,1 Pusoon Chun,2 Hyung Ryong Moon1

1College of Pharmacy, Pusan National University, Busan, 2College of Pharmacy, Inje University, Gimhae, Republic of Korea

Background: Tyrosinase is the most prominent target for inhibitors of hyperpigmentation because it plays a critical role in melaninogenesis. Although many tyrosinase inhibitors have been identified, from both natural and synthetic sources, there remains a considerable demand for novel tyrosinase inhibitors that are safer and more effective.
Methods: (E)-2-Benzoyl-3-(substituted phenyl)acrylonitriles (BPA analogs) with a linear β-phenyl-α,β-unsaturated carbonyl scaffold were designed and synthesized as potential tyrosinase inhibitors. We evaluated their effects on cellular tyrosinase activity and melanin biosynthesis in murine B16F10 melanoma cells and their ability to inhibit mushroom tyrosinase activity.
Results: BPA analogs exhibited inhibitory activity against mushroom tyrosinase. In particular, BPA13 significantly suppressed melanin biosynthesis and inhibited cellular tyrosinase activity in B16F10 cells in a dose-dependent manner. A docking study revealed that BPA13 had higher binding affinity for tyrosinase than kojic acid.
Conclusion: BPA13, which possesses a linear β-phenyl-α,β-unsaturated carbonyl scaffold, is a potential candidate skin-whitening agent and treatment for diseases associated with hyperpigmentation.

Keywords: (E)-2-benzoyl-3-(substituted phenyl)acrylonitriles, melanogenesis, tyrosinase inhibitor

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