Inhibitory effect of synthetic aromatic heterocycle thiosemicarbazone derivatives on mushroom tyrosinase: Insights from fluorescence, 1H NMR titration and molecular docking studies. (1st January 2016)

• Record Type: Journal Article
• Authors: Xie, Juan; Dong, Huanhuan; Yu, Yanying; Cao, Shuwen
• Is Part Of: Food chemistry. Volume 190(2016)
• Page Start: 709
• Page End: 716
• Publication Date: 2016-01-01
• Subjects: Aromatic heterocyclic thiosemicarbazone derivatives -- Tyrosinase inhibitors -- Fluorescence spectrum -- 1H NMR titration -- Molecular docking; Food -- Analysis -- Periodicals; Food -- Composition -- Periodicals; 664
• DOI: 10.1016/j.foodchem.2015.05.124
• Languages: English
• ISSNs: 0308-8146

Abstract

Highlights: Complex formation between the S atom and enzymic Cu 2+ was a main route of inhibition. Fluorescence spectrum and 1 H NMR firm and direct methods for inhibitor and enzyme. Aromatic heterocyclic thiosemicarbazone maybe a potential novel tyrosinase inhibitor. The molecular docking has certain predictability. Abstract: Three structurally similar aromatic heterocyclic compounds 2-thiophenecarboxaldehyde (a ), 2-furaldehyde (b ), 2-pyrrolecarboxaldehyde (c ) were chosen and a series of their thiosemicarbazone derivatives(1a –3a, 1b –3b and1c –3c ) were synthesized to evaluate their biological activities as mushroom tyrosinase inhibitors. The inhibitory effects of these compounds on tyrosinase were investigated by using spectrofluorimetry, 1 H NMR titration and molecular docking techniques. From the results of fluorescence spectrum and 1 H NMR titration, it was found that forming complexes between the sulfur atom from thiourea and copper ion of enzyme center may play a key role for inhibition activity. Moreover, investigation of 1 H NMR spectra further revealed that formation of hydrogen bond between inhibitor and enzyme may be helpful to above complexes formation. The results were well coincident with the suggestion of molecular docking and obviously showed that 2-thiophone N(4)-thiosemicarbazone (1a ), 2-furfuran N(4)-thiosemicarbazone (1b ) and 2-pyrrole N(4)-thiosemicarbazone (1c ) are potential inhibitors which deserves further investigation.