Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (2): 500-506.DOI: 10.6023/cjoc201805014 Previous Articles     Next Articles

ARTICLE

8-氨基喹啉类铜离子螯合剂的合成及螯合选择性研究

黄达涯a, 李佑智a, 刘艳a, Bernard Meuniera,b   

  1. a 广东工业大学轻工化工学院 广州 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
  • 收稿日期:2018-05-04 修回日期:2018-07-31 出版日期:2019-02-25 发布日期:2018-09-05
  • 通讯作者: 刘艳, Bernard Meunier E-mail:yanliu@gdut.edu.cn;bmeunier@lcc-toulouse.fr
  • 基金资助:

    国家自然科学基金(No.21502023)、广东省新药筛选重点实验室开放课题(No.GDKLNDS-2018OF004)、广东省领军人才(No.2050205)、广东工业大学(No.220418037)资助项目.

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

Huang Dayaa, Li Youzhia, Liu Yana, Meunier Bernarda,b   

  1. 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
  • Received:2018-05-04 Revised:2018-07-31 Online:2019-02-25 Published:2018-09-05
  • Contact: 10.6023/cjoc201805014 E-mail:yanliu@gdut.edu.cn;bmeunier@lcc-toulouse.fr
  • Supported by:

    Project 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 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 Kapp[Cu-TDMQ29] to be 15.7 and log Kapp[Zn-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.

Key words: Alzheimer disease (AD), 8-aminoquinoline, copper chelation, selectivity