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

2017; Elsevier BV; Volume: 98; Linguagem: Inglês

10.1016/j.ijbiomac.2017.02.032

1879-0003

Antonio Garcia-Jimenez, José A. Teruel, Pedro Antonio Garcı́a-Ruiz, José Berná, José Neptuno Rodríguez‐López, José Tudela, Francisco Garcı́a-Cánovas,

Skin Protection and Aging

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 ± 0.09 mM and IC50 = 3.82 ± 0.39 mM 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.