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Quantitative structure–activity relationship of hydroxyl‐substituent Schiff bases in radical‐induced hemolysis of human erythrocytes
Author(s) -
Tang YouZhi,
Liu ZaiQun
Publication year - 2008
Publication title -
cell biochemistry and function
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.933
H-Index - 61
eISSN - 1099-0844
pISSN - 0263-6484
DOI - 10.1002/cbf.1426
Subject(s) - chemistry , substituent , schiff base , phenol , hydroxyl radical , radical , medicinal chemistry , steric effects , methylene , hemolysis , stereochemistry , organic chemistry , immunology , biology
The major objective of this work was to explore the quantitative structure–activity relationship (QSAR) of hydroxyl‐substituent Schiff bases in protecting human erythrocytes against 2,2′‐azobis(2‐amidinopropane hydrochloride) (AAPH)‐ induced hemolysis, in which 10 Schiff bases including 4‐phenyliminomethylphenol (PIH); 4‐((4‐hydroxybenzylidene) amino)phenol (PAH); 2‐methoxy‐4‐((4‐hydroxyphenylimino)methyl)phenol (PMH); 4‐((furan‐2‐ylmethylene)amino) phenol (FAH); 4‐((4‐ N,N ‐dimethylaminobenzylidene)amino)phenol (PDH); 2‐((4‐ N,N ‐dimethylaminobenzylidene)amino) phenol (ODH); 2‐(naphthalene‐1‐yliminomethyl)phenol (NAH); 2‐(benzyliminomethyl)phenol (BPH); 1,4‐di((2‐hydroxyphenylimino) methyl)benzene (DOH); 1,4‐di((4‐hydroxyphenylimino)methyl)benzene DPH, were available for this in vitro experimental system. The results revealed that the radical‐scavenging activity of the OH attached to the para position of methylene in Schiff base was much lower than that attached to the ortho position of the N atom. The large conjugate system and low steric hindrance in the framework of Schiff base benefit the Schiff base to trap radicals. Meanwhile, since a Schiff base, even without any substituent, can also play an antioxidative role in this experimental system, the QSAR results suggest that hydroxyl‐substituent Schiff bases are potential drugs in the treatment of radical‐related diseases, and provide more information for designing novel drugs. Copyright © 2007 John Wiley & Sons, Ltd.