Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode

In this study, a series of sulfonamide chalcones derivatives was synthesized and its chemical structures were confirmed by spectral characteristics. The synthesized compounds were evaluated for their tyrosinase inhibitory activities along with molecular docking study. The tyrosinase inhibitory resul...

Full description

Bibliographic Details
Main Authors: Thawanrat Kobkeatthawin (Author), Suchada Chantrapromma (Author), Thitipone Suwunwong (Author), Lydia Rhyman (Author), Choong, Yee Siew (Author), Ponnadurai Ramasami (Author)
Format: Article
Language:English
Published: Penerbit Universiti Kebangsaan Malaysia, 2021-09.
Online Access:Get fulltext
LEADER 02024 am a22001813u 4500
001 18058
042 |a dc 
100 1 0 |a Thawanrat Kobkeatthawin,   |e author 
700 1 0 |a Suchada Chantrapromma,   |e author 
700 1 0 |a Thitipone Suwunwong,   |e author 
700 1 0 |a Lydia Rhyman,   |e author 
700 1 0 |a Choong, Yee Siew  |e author 
700 1 0 |a Ponnadurai Ramasami,   |e author 
245 0 0 |a Synthesis, molecular docking and tyrosinase inhibitory activity of the decorated methoxy sulfonamide chalcones : in vitro inhibitory effects and the possible binding mode 
260 |b Penerbit Universiti Kebangsaan Malaysia,   |c 2021-09. 
856 |z Get fulltext  |u http://journalarticle.ukm.my/18058/1/9.pdf 
520 |a In this study, a series of sulfonamide chalcones derivatives was synthesized and its chemical structures were confirmed by spectral characteristics. The synthesized compounds were evaluated for their tyrosinase inhibitory activities along with molecular docking study. The tyrosinase inhibitory results indicated that compounds 5b, 5c, 5f, 5g and 5h displayed the significant tyrosinase inhibitory activity and comparable to the standard drug (kojic acid). Compound 5c exhibits the most potent tyrosinase inhibition among the synthesized compounds with IC50 = 0.43±0.07 mM, L-DOPA as the substrate, and better than that of the standard kojic acid (IC50 = 0.60±0.20 mM). Molecular docking studies showed that the binding mode of some compounds is in the tyrosinase binding pocket surrounding the copper in the active site. The correlation between the docking results with IC50 values showed that the binding mode prediction of the test compounds would also be convincing. This comprehensive study allows for a possible mechanism for the antityrosinase activity of the sulfonamide chalcones. These sulfonamide chalcones bind to copper atoms of tyrosinase which responsible for the catalytic activity of tyrosinase. These compounds may be used as a lead for rational drug designing for the multi-functional tyrosinase inhibitor. 
546 |a en