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Action of 2,2',4,4'-tetrahydroxybenzophenone in the biosynthesis pathway of melanin.

Abstract：

:2,2',4,4'-tetrahydroxybenzophenone (Uvinul D50), a sunscreen used in cosmetics, has two effects in the melanin biosynthesis pathway. On the one hand, it acts a weak inhibitor of tyrosinase and on the other, it accelerates the conversion of dopachrome to melanin. Uvinul D50 was seen to behave as a weak competitive inhibitor: apparent constant inhibition=2.02±0.09mM and IC50=3.82±0.39mM established in this work. These values are higher than those in the bibliography, which tend to be undersetimated. This discrepancy could be explained by the reaction of Uvinul D50 with the dopachrome produced from l-tyrosine or l-dopa, which would interfere in the measurement. Based on studies of its docking to tyrosinase, it seems that Uvinul D50 interacts with the active site of the enzyme (oxytyrosinase) both in its protonated and deprotonated forms (pKa=7). However, it cannot be hydroxylated, meaning that it acts as a weak inhibitor, not as an alternative substrate, despite its resorcinol structure. Uvinul D50 can be used as sunscreen, in low concentrations without significant adverse effects on melanogenesis.

journal_name

Int J Biol Macromol

journal_title

International journal of biological macromolecules

authors

Garcia-Jimenez A,Teruel-Puche JA,Garcia-Ruiz PA,Berna J,Rodríguez-López JN,Tudela J,Garcia-Canovas F

doi

10.1016/j.ijbiomac.2017.02.032

subject

Has Abstract

pub_date

2017-05-01 00:00:00

pages

622-629

eissn

0141-8130

issn

1879-0003

pii

S0141-8130(16)32325-X

journal_volume

98

pub_type

杂志文章

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