title: Synthesis, structures and Helicobacter pylori urease inhibitory activity of copper(II) complexes with tridentate aroylhydrazone ligands.
abstract: A series of new copper(II) complexes were prepared. They are [CuL(1)(NCS)] (1), [CuClL(1)]·CH3OH (2), [CuClL(2)]·CH3OH (3), [CuL(3)(NCS)]·CH3OH (4), [CuL(4)(NCS)]·0.4H2O (5), and [CuL(5)(bipy)] (6), where L(1), L(2), L(3) and L(4) are the deprotonated form of N'-(2-hydroxybenzylidene)-3-methylbenzohydrazide, 4-bromo-N'-(2-hydroxy-5-methoxybenzylidene)benzohydrazide, N'-(2-hydroxy-5-methoxybenzylidene)-3-methylbenzohydrazide and 2-chloro-N'-(2-hydroxy-5-methoxybenzylidene)benzohydrazide, respectively, L(5) is the dianionic form of N'-(2-hydroxybenzylidene)-3-methylbenzohydrazide, and bipy is 2,2'-bipyridine. The complexes were characterized by infrared and UV-Vis spectra and single crystal X-ray diffraction. The Cu atoms in complexes 1, 2, 3, 4 and 5 are coordinated by the NOO donor set of the aroylhydrazone ligands, and one Cl or thiocyanate N atom, forming square planar coordination. The Cu atom in complex 6 is in a square pyramidal coordination, with the NOO donor set of L(1), and one N atom of bipy defining the basal plane, and with the other N atom of bipy occupying the apical position. Complexes 1, 2, 3, 4 and 5 show effective urease inhibitory activities, with IC50 values of 5.14, 0.20, 4.06, 5.52 and 0.26μM, respectively. Complex 6 has very weak activity against urease, with IC50 value over 100μM. Molecular docking study of the complexes with the Helicobacter pylori urease was performed. The relationship between structures and urease inhibitory activities indicated that copper complexes with square planar coordination are better models for urease inhibition.
authors.affiliation: Department of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, PR China.
authors.forename: Lin
authors.initials: L
authors.lastname: Pan
authors.affiliation: School of Life Sciences, Shandong University of Technology, Zibo 255049, PR China.
authors.forename: Cunfang
authors.initials: C
authors.lastname: Wang
authors.affiliation: School of Life Sciences, Shandong University of Technology, Zibo 255049, PR China.
authors.forename: Kai
authors.initials: K
authors.lastname: Yan
authors.affiliation: School of Life Sciences, Shandong University of Technology, Zibo 255049, PR China.
authors.forename: Kedong
authors.initials: K
authors.lastname: Zhao
authors.affiliation: School of Life Sciences, Shandong University of Technology, Zibo 255049, PR China.
authors.forename: Guihua
authors.initials: G
authors.lastname: Sheng
authors.affiliation: School of Life Sciences, Shandong University of Technology, Zibo 255049, PR China.
authors.forename: Hailiang
authors.initials: H
authors.lastname: Zhu
authors.affiliation: Department of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, PR China.
authors.forename: Xinlu
authors.initials: X
authors.lastname: Zhao
authors.affiliation: Department of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, PR China.
authors.forename: Dan
authors.initials: D
authors.lastname: Qu
authors.affiliation: Department of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, PR China.
authors.forename: Fang
authors.initials: F
authors.lastname: Niu
authors.affiliation: Department of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, PR China. Electronic address: youzhonglu@163.com.
authors.forename: Zhonglu
authors.initials: Z
authors.lastname: You
mesh_terms: D001426:Bacterial Proteins / Q000037:antagonists & inhibitors / Q000737:chemistry; D003300:Copper / Q000737:chemistry*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry; D016480:Helicobacter pylori / Q000201:enzymology*; D006835:Hydrazones / Q000138:chemical synthesis / Q000737:chemistry; D008024:Ligands; D014510:Urease / Q000037:antagonists & inhibitors / Q000737:chemistry
chemical_list: D001426:Bacterial Proteins; D004791:Enzyme Inhibitors; D006835:Hydrazones; D008024:Ligands; D003300:Copper; D014510:Urease
keywords: Aroylhydrazone; Copper complex; Crystal structure; Molecular docking; Urease inhibition