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Dimeric Cinnamoylamide Analogues for Regulation of Tyrosinase Activity in Melanoma Cells: A Role of Diamide-Link Chain Length

Dimeric Cinnamoylamide Analogues for Regulation of Tyrosinase Activity in Melanoma Cells: A Role of Diamide-Link Chain Length

Ji Hoon Ha, Soo Nam Park

Bioorg Med Chem. 2018 Dec 15;26(23-24):6015-6022.

PMID: 30446440

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP10465788	Diamide		10465-78-8	Price

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