Aryl boronic acid inhibition of synthetic melanin polymerization.
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 IC(50) values exhibit a correlation with the Hammett sigma(p) parameter (rho=0.97, r(2)=0.92).
Belitsky
Jason M
JM
Department of Chemistry and Biochemistry, Oberlin College, Oberlin, OH, USA. Jason.Belitsky@Oberlin.edu
D001897:Boronic Acids / Q000737:chemistry* / Q000494:pharmacology; D002396:Catechols / Q000737:chemistry; D007980:Levodopa / Q000737:chemistry; D008543:Melanins / Q000037:antagonists & inhibitors / Q000378:metabolism*; D013329:Structure-Activity Relationship
D001897:Boronic Acids; D002396:Catechols; D008543:Melanins; D007980:Levodopa; C034221:catechol