Structural insight into the active site of mushroom tyrosinase using phenylbenzoic acid derivatives

Bioorganic & Medicinal Chemistry Letters
Takahiro OyamaSei-Ichi Tanuma

Abstract

So far, many inhibitors of tyrosinase have been discovered for cosmetic and clinical agents. However, the molecular mechanisms underlying the inhibition in the active site of tyrosinase have not been well understood. To explore this problem, we examined here the inhibitory effects of 4'-hydroxylation and methoxylation of phenylbenzoic acid (PBA) isomers, which have a unique scaffold to inhibit mushroom tyrosinase. The inhibitory effect of 3-PBA, which has the most potent inhibitory activity among the isomers, was slightly decreased by 4'-hydroxylation and further decreased by 4'-methoxylation against mushroom tyrosinase. Surprisingly, 4'-hydroxylation but not methoxylation of 2-PBA appeared inhibitory activity. On the other hand, both 4'-hydroxylation and methoxylation of 4-PBA increased the inhibitory activity against mushroom tyrosinase. In silico docking analyses using the crystallographic structure of mushroom tyrosinase indicated that the carboxylic acid or 4'-hydroxyl group of PBA derivatives could chelate with cupric ions in the active site of mushroom tyrosinase, and that the interactions of Asn260 and Phe264 in the active site with the adequate-angled biphenyl group are involved in the inhibitory activities of the modi...Continue Reading

Citations

Sep 10, 2019·Journal of Enzyme Inhibition and Medicinal Chemistry·Zhiwei ShenYi Zhang
Jul 31, 2019·Journal of Biological Inorganic Chemistry : JBIC : a Publication of the Society of Biological Inorganic Chemistry·Kourosh AbdollahiReza Panahi
Feb 9, 2019·Journal of Enzyme Inhibition and Medicinal Chemistry·Samaneh ZolghadriAli Akbar Saboury
Aug 9, 2021·European Journal of Medicinal Chemistry·Jin LiGuan Wang
May 16, 2018·Journal of Medicinal Chemistry·Thanigaimalai PillaiyarSang-Hun Jung

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