Bechara E J, Catalani L H
Departamento de Bioquímica, Universidade de São Paulo, Brazil.
Free Radic Biol Med. 1995 Apr;18(4):731-8. doi: 10.1016/0891-5849(94)00194-o.
The oxidation of chlorpromazine (CPZ) by tetramethyldioxetane (TMD) and isobutanal (IBAL)/O2/horseradish peroxidase (HRP) system was investigated. The reaction with TMD proved to be of the oxygen transfer type, generating chlorpromazine-5-oxide (CPZO) and tetramethylethylene-oxide, and not by single-electron transfer, as previously reported. In contrast, the reaction of CPZ with IBAL/O2/HRP leads to formation of chlorpromazine cation radical, through reaction with active intermediates Compound I and II, following its dismutation and hydrolysis to CPZO. For comparison, 10-methylphenothiazine was also tested. Despite the fact that both systems are known to generate oxidizing triplet acetone, this species does not participate in the oxidation path in either case.
研究了氯丙嗪（CPZ）在四甲基二氧杂环丁烷（TMD）以及异丁醛（IBAL）/O₂/辣根过氧化物酶（HRP）体系中的氧化反应。事实证明，CPZ与TMD的反应属于氧转移类型，生成氯丙嗪-5-氧化物（CPZO）和四甲基环氧乙烷，并非如先前报道的那样通过单电子转移。相比之下，CPZ与IBAL/O₂/HRP的反应会生成氯丙嗪阳离子自由基，这是通过与活性中间体化合物I和II反应，随后经歧化和水解生成CPZO实现的。为作比较，还测试了10-甲基吩噻嗪。尽管已知这两种体系都会产生氧化态的三线态丙酮，但该物种在这两种情况下均不参与氧化途径。
