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Dimeric cinnamoylamide analogues for regulation of tyrosinase activity in melanoma cells: A role of diamide-link chain length.

Abstract：

:Dimeric cynnamoyl analogues (DCAs) with depigmenting activity have been developed. In this study, a role of diamide linkage chain length of DCAs as a tyrosinase inhibitor was investigated on tyrosinase inhibitory activity, antioxidative activity, hydrophobicity and anti-melanogenesis as well as structural characteristics and dipole moments based on density functional theory. DCAs with different diamide-link chain lengths (n = 2, 3, and 4) and various functional groups (m-coumaroyl, p-coumaroyl, isoferuloyl and feruloyl groups) were synthesized. DCAs with a diamide-link chain length of three indicated high inhibitory effect of melanin production on α-melanocyte stimulating hormone (α-MSH) stimulated B16F1 cells. Approach of p-hydroxyl group of DCAs to active site of tyrosinase, an important melanogenic enzyme, is interfered by addition of m-methoxy group. In structural modeling based on density functional theory, DCAs with a diamide-link chain length of three showed folded shapes, and they had lower dipole moment than with a diamide-link chain length of two or four. Thus, for the enhancement of the depigmenting activities of dimeric compounds, the diamide-link chain length is important. Our results provide an important index for the design of dimeric compounds with physiological activities.

journal_name

Bioorg Med Chem

journal_title

Bioorganic & medicinal chemistry

authors

Ha JH,Park SN

doi

10.1016/j.bmc.2018.10.036

subject

Has Abstract

pub_date

2018-12-15 00:00:00

pages

6015-6022

issue

23-24

eissn

0968-0896

issn

1464-3391

pii

S0968-0896(18)31492-5

journal_volume

26

pub_type

杂志文章

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