Design, synthesis and biological evaluation of hydroxy substituted amino chalcone compounds for antityrosinase activity in B16 cells.
A series of hydroxy substituted amino chalcone compounds have been synthesized. These compounds were then evaluated for their inhibitory activities on tyrosinase and melanogenesis in murine B16F10 melanoma cell lines. The structures of the compounds synthesized were confirmed by (1)H NMR, (13)C NMR, FTIR and HRMS. Two novel amino chalcone compounds exhibited higher tyrosinase inhibitory activities (IC50 values of 9.75μM and 7.82μM respectively) than the control kojic acid (IC50: 22.83μM). Kinetic studies revealed them to act as competitive tyrosinase inhibitors with their Ki values of 4.82μM and 1.89μM respectively. Both the compounds inhibited melanin production and tyrosinase activity in B16 cells. Docking results confirm that the active inhibitors strongly interact with mushroom tyrosinase residues. This study suggests that the depigmenting effect of novel amino chalcone compounds might be attributable to inhibition of tyrosinase activity, suggesting amino chalcones to be a promising candidate for use as depigmentation agents or as anti-browning food additives.
School of Chemistry and Forensic Science, University of Technology Sydney, 15 Broadway, Ultimo, NSW 2007, Australia. Electronic address: Sini.KaranayilRadhakrishnan@student.uts.edu.au.
Sini
S
Radhakrishnan
School of Chemistry and Forensic Science, University of Technology Sydney, 15 Broadway, Ultimo, NSW 2007, Australia.
Ronald
R
Shimmon
School of Chemistry and Forensic Science, University of Technology Sydney, 15 Broadway, Ultimo, NSW 2007, Australia.
Costa
C
Conn
School of Chemistry and Forensic Science, University of Technology Sydney, 15 Broadway, Ultimo, NSW 2007, Australia.
Anthony
A
Baker
D000818:Animals; D045744:Cell Line, Tumor; D047188:Chalcones / Q000138:chemical synthesis* / Q000494:pharmacology*; D004791:Enzyme Inhibitors / Q000494:pharmacology*; D008543:Melanins / Q000037:antagonists & inhibitors; D051379:Mice; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D010636:Phenols / Q000138:chemical synthesis* / Q000494:pharmacology*; D011407:Propane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D062327:Skin Lightening Preparations / Q000494:pharmacology
C000607301:3-(3-amino-4-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one; C000607303:3-(4-amino-2-methoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-1-one; D047188:Chalcones; D004791:Enzyme Inhibitors; D008543:Melanins; D010636:Phenols; D062327:Skin Lightening Preparations; D014442:Monophenol Monooxygenase; D011407:Propane
Cytotoxic; Docking; Hyperpigmentation; Melanin; Tyrosinase inhibitor