Open AccessThe mono(catecholamine) derivatives as iron chelators: synthesis, solution thermodynamic stability and antioxidant properties research
Author(s) -
Qingchun Zhang,
Bo Jin,
Xiaofang Wang,
Lei Shan,
ZhaoTao Shi,
Jia Zhao,
Qiangqiang Liu,
Rufang Peng
Publication year - 2018
Publication title -
royal society open science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.84
H-Index - 51
ISSN - 2054-5703
DOI - 10.1098/rsos.171492
Subject(s) - chemistry , chelation , catecholamine , metal ions in aqueous solution , chemical stability , fourier transform infrared spectroscopy , metal , antioxidant , benzamide , ion , nuclear chemistry , inorganic chemistry , stereochemistry , organic chemistry , chemical engineering , medicine , engineering
There is a growing interest in the development of new iron chelators as novel promising therapeutic strategies for neurodegenerative disorders. In this article, a series of mono(catecholamine) derivatives, 2,3-bis(hydroxy)- N -(hydroxyacyl)benzamide, containing a pendant hydroxy, have been synthesized and fully characterized by nuclear magnetic resonance, Fourier transform infrared spectroscopy and mass spectrum. The thermodynamic stability of the chelators with Fe III , Mg II and Zn II ions was then investigated. The chelators enable formation of (3 : 1) Fe III complexes with high thermodynamic stability and exhibited improved selectivity to Fe III ion. Meanwhile, the results of 1,1-diphenyl-2-picryl-hydrazyl assays of mono(catecholamine) derivatives indicated that they all possess excellent antioxidant properties. These results support the hypothesis that the mono(catecholamine) derivatives be used as high-affinity chelator for iron overload situations without depleting essential metal ions, such as Mg II and Zn II ions.