Citation: Huang Daya, Li Youzhi, Liu Yan, Meunier Bernard. Synthesis and Chelation Selectivity Evaluation of 8-Aminoquinoline Derivatives as Copper Chelator[J]. Chinese Journal of Organic Chemistry, ;2019, 39(2): 500-506. doi: 10.6023/cjoc201805014 shu

Synthesis and Chelation Selectivity Evaluation of 8-Aminoquinoline Derivatives as Copper Chelator

Huang Daya ^a ,
Li Youzhi ^a ,
Liu Yan ^a,, ,
Meunier Bernard ^a,b,,

a.
School of Chemical Engineering and Light Industry, Guangdong University of Technology, Guangzhou 510006
b.
Laboratoire de Chimie de Coordination du CNRS, Centre National de la Recherche Scientifique, 205 Route de Narbonne, BP 44099, 31077 Toulouse Cedex 4, France

Corresponding author: Liu Yan, yanliu@gdut.edu.cn Meunier Bernard, bmeunier@lcc-toulouse.fr
Received Date: 4 May 2018
Revised Date: 31 July 2018
Available Online: 5 February 2018
Fund Project: the Program for Innovative Research Teams and Leading Talents Introduction of Guangdong Province 2050205Project supported by the National Natural Science Foundation of China (No. 21502023), the Open Project of Guangdong Provincial Key Laboratory of New Drug Screening (No. GDKLNDS-2018OF004), the Program for Innovative Research Teams and Leading Talents Introduction of Guangdong Province (No. 2050205), and the Guangdong University of Technology (No. 220418037)the National Natural Science Foundation of China 21502023the Open Project of Guangdong Provincial Key Laboratory of New Drug Screening GDKLNDS-2018OF004the Guangdong University of Technology 220418037

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The non-controlled redox-active metal ions, especially copper, in the brain of patients with Alzheimer disease (AD) should be considered at the origin of the intense oxidative damage in AD brain. In this paper, we designed and synthesized new compounds based on 8-aminoquinoline motif with a lateral chain at the C2 position of the aromatic ring. The affinities for Cu(Ⅱ) and Zn(Ⅱ) of these ligands are reported in the present article. Among these chelators, TDMQ29 is specific for copper chelation with log K_app[Cu^Ⅱ-TDMQ29] to be 15.7 and log K_app[Zn^Ⅱ-TDMQ29] to be 5.8. Such metal ligands can be consi-dered as potential ligands, which are able to regulate the homeostasis of copper in brains.
- Alzheimer disease (AD),
- 8-aminoquinoline,
- copper chelation,
- selectivity
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