New insights into highly potent tyrosinase inhibitors based on 3-heteroarylcoumarins: Anti-melanogenesis and antioxidant activities, and computational molecular modeling studies

• Type: Article in International Scientific Journal
• Date: 2017

Authors

Varela, C (Author) Other; Uriarte, E (Author) Other; Santana, L (Author) Other; Fernanda Borges (Author) FCUP; Medda, R (Author) Other; Di Petrillo, A (Author) Other; Era, B (Author) Other; Fais, A (Author) Other; Pintus, F (Author) Other; Matos, MJ (Author) Other; Vilar, S (Author) Other; Hripcsak, G (Author) Other

Journal

Title: Bioorganic and Medicinal Chemistry

Vol. 25

Pages: 1687-1695

ISSN: 0968-0896

Publisher: Elsevier

Indexing

ISI Web of Knowledge - 52 Citations

Scopus - 51 Citations

Other information

Authenticus ID: P-00M-K4F

DOI: 10.1016/j.bmc.2017.01.037

Abstract (EN): Melanogenesis is a physiological pathway for the formation of melanin. Tyrosinase catalyzes the first step of this process and down-regulation of its activity is responsible for the inhibition of melanogenesis. The search for molecules capable of controlling hyperpigmentation is a trend topic in health and cosmetics. A series of heteroarylcoumarins have been synthesized and evaluated. Compounds 4 and 8 exhibited higher tyrosinase inhibitory activities (IC50 = 0.15 and 0.38 mu M, respectively), than the reference compound, kojic acid (IC50 = 17.9 mu M). Compound 4 acts as competitive, while compound 8 as uncompetitive inhibitor of mushroom tyrosinase. Furthermore, compounds 2 and 8 inhibited tyrosinase activity and melanin production in B16F10 cells. In addition, compounds 2-4 and 8 proved to have an interesting antioxidant profile in both ABTS and DPPH radicals scavenging assays. Docking experiments were carried out in order to study the interactions between these heteroarylcoumarins and mushroom tyrosinase.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 9