title: Inhibitory effect of synthetic aromatic heterocycle thiosemicarbazone derivatives on mushroom tyrosinase: Insights from fluorescence, (1)H NMR titration and molecular docking studies.
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 and 1c-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.
authors.affiliation: State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, PR China; Department of Chemistry, Nanchang University, Nanchang 330031, PR China. Electronic address: 15870622557@163.com.
authors.forename: Juan
authors.initials: J
authors.lastname: Xie
authors.affiliation: State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, PR China. Electronic address: donghuanhuan@outlook.com.
authors.forename: Huanhuan
authors.initials: H
authors.lastname: Dong
authors.affiliation: Department of Chemistry, Nanchang University, Nanchang 330031, PR China. Electronic address: yuyanying@ncu.edu.cn.
authors.forename: Yanying
authors.initials: Y
authors.lastname: Yu
authors.affiliation: State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, PR China; Department of Chemistry, Nanchang University, Nanchang 330031, PR China. Electronic address: caosw@ncu.edu.cn.
authors.forename: Shuwen
authors.initials: S
authors.lastname: Cao
mesh_terms: D000363:Agaricales / Q000737:chemistry*; D005453:Fluorescence; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D062105:Molecular Docking Simulation / Q000379:methods*; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D013882:Thiosemicarbazones
keywords: (1)H NMR titration; Aromatic heterocyclic thiosemicarbazone derivatives; Fluorescence spectrum; Molecular docking; Tyrosinase inhibitors