Abstract

Inhibitors of melanin formation are sought after for a range of applications. Boronophenylalanine is known to inhibit melanogenesis via boronic acid-catechol interactions. A spectroscopic assay was developed to study the polymerization of L-dopa to synthetic melanin in the presence of para-substituted aryl boronic acids. The best inhibition was observed for aryl boronic acids with electron-withdrawing substituents. The IC50 values exhibit a correlation with the Hammett sigma(p) parameter (rho = 0.97, r(2) = 0.92).

Publisher

Pergamon Press

Publication Date

8-1-2010

Publication Title

Bioorganic & Medicinal Chemistry Letters

Department

Chemistry and Biochemistry

Document Type

Article

DOI

10.1016/j.bmcl.2010.06.039

Keywords

Melanin, Boronic acid, Catechol, Hammett correlation

Document Version

post-print

Language

English

Format

text

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