Quantitative structure-activity relationship of hydroxyl-substituent Schiff bases in radical-induced hemolysis of human erythrocytes.
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.
Tang
You-Zhi
YZ
Department of Organic Chemistry, College of Chemistry, Jilin University, Changchun, China.
Liu
Zai-Qun
ZQ
D000578:Amidines / Q000494:pharmacology; D004305:Dose-Response Relationship, Drug; D004912:Erythrocytes / Q000187:drug effects* / Q000378:metabolism / Q000528:radiation effects; D016166:Free Radical Scavengers / Q000737:chemistry / Q000494:pharmacology*; D006461:Hemolysis / Q000187:drug effects* / Q000528:radiation effects; D006801:Humans; D015394:Molecular Structure; D021281:Quantitative Structure-Activity Relationship; D012545:Schiff Bases / Q000737:chemistry / Q000494:pharmacology*; D013237:Stereoisomerism; D013997:Time Factors
D000578:Amidines; D016166:Free Radical Scavengers; D012545:Schiff Bases; C046728:2,2'-azobis(2-amidinopropane)