Azachalcones: a new class of potent polyphenol oxidase inhibitors

Sini Karanayil Radhakrishnan; Ronald Gibrial Shimmon; Costa Conn; Anthony T Baker

doi:10.1016/j.bmcl.2015.02.060

Azachalcones: a new class of potent polyphenol oxidase inhibitors

Bioorg Med Chem Lett. 2015 Apr 15;25(8):1753-1756. doi: 10.1016/j.bmcl.2015.02.060. Epub 2015 Mar 2.

Authors

Sini Karanayil Radhakrishnan¹, Ronald Gibrial Shimmon², Costa Conn², Anthony T Baker²

Affiliations

¹ School of Chemistry and Forensic Science, University of Technology Sydney, 15 Broadway, Ultimo, NSW 2007, Australia. Electronic address: Sini.KaranayilRadhakrishnan@student.uts.edu.au.
² School of Chemistry and Forensic Science, University of Technology Sydney, 15 Broadway, Ultimo, NSW 2007, Australia.

PMID: 25782744
DOI: 10.1016/j.bmcl.2015.02.060

Abstract

A library of potent inhibitors of polyphenol oxidase and their structure activity relationships are described. Azachalcone derivatives were synthesized and tested for their tyrosinase inhibitory activity. Their inhibitory activities on mushroom tyrosinase using l-DOPA as a substrate were investigated. Two compounds that are the reduction congeners of the pyridinyl azachalcones strongly inhibited the enzyme activity and were more potent than the positive control kojic acid.

Keywords: Azachalcone; Competitive inhibitor; PPO; Tyrosinase.

MeSH terms

Agaricales / enzymology
Aza Compounds / chemistry*
Catechol Oxidase / antagonists & inhibitors*
Catechol Oxidase / metabolism
Chalcones / chemical synthesis
Chalcones / chemistry*
Chalcones / metabolism
Enzyme Inhibitors / chemical synthesis
Enzyme Inhibitors / chemistry*
Enzyme Inhibitors / metabolism
Kinetics
Levodopa / chemistry
Levodopa / metabolism
Monophenol Monooxygenase / antagonists & inhibitors
Monophenol Monooxygenase / metabolism
Protein Binding
Structure-Activity Relationship

Substances

Aza Compounds
Chalcones
Enzyme Inhibitors
Levodopa
Catechol Oxidase
Monophenol Monooxygenase