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).
Belitsky, Jason M. 2010. "Aryl Boronic Acid Inhibition Of Synthetic Melanin Polymerization." Bioorganic & Medicinal Chemistry Letters 20(15): 4475-4478.
Bioorganic & Medicinal Chemistry Letters
Chemistry and Biochemistry
Melanin, Boronic acid, Catechol, Hammett correlation