Metabolic studies on polychlorinated biphenyls. 3. Complete structure and acute toxicity of the metabolites of 2,4,3',4'-tetrachlorobiphenyl.
Metabolic studies on polychlorinated biphenyls. 3. Complete structure and acute toxicity of the metabolites of 2,4,3',4'-tetrachlorobiphenyl.
复制标题
多氯联苯的代谢研究。
DOI：
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发表时间：
1973
影响因子：
1.7
通讯作者：
H. Yoshimura
中科院分区：
文献类型：
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作者：
H. Yamamoto;H. Yoshimura
本研究的目的是确定两种代谢物的结构，这些代谢物是从服用 2,4,3',4'-四氯联苯 (2,4,3',4'-TCB) 的大鼠粪便中分离出来的，2,4,3',4'-TCB 是商业多氯联苯制剂的主要成分。为此目的，通过适当的重氮化二氯苯胺和二氯酚之间的缩合反应合成了单羟基-2,4,3',4'-TCB的六种可能的异构体。在这些异构体中，5-羟基-和3-羟基-2,4,3',4'-TCB分别与主要代谢物（M-A2）（熔点155-156°）和次要代谢物（M-A1）（熔点92-98°）相同。通过腹腔注射进一步研究了2,4,3',4'-TCB及其主要代谢物5-羟基-2,4,3',4'-TCB的急性致死剂量。使用CF-1品系的雄性小鼠进行注射。结果表明，2,4,3',4'-TCB和5-羟基-2,4,3',4'-TCB的LD50分别为2.15 g/kg和0.43 g/kg，表明2,4,3',4'-TCB的急性毒性可能归因于体内产生的酚类代谢产物。
The present investigation was undertaken to establish the structures of two metabolites which were isolated from the feces of rats administered with 2, 4, 3', 4'-tetrachlorobiphenyl (2, 4, 3', 4'-TCB), a major component of commercial preparation of polychlorinated biphenyls. For this purpose six possible isomers of monohydroxy-2, 4, 3', 4'-TCB were synthesized by condensation reactions between appropriate diazotized dichloroanilines and dichlorophenols. Among these isomers, 5-hydroxy-and 3-hydroxy-2, 4, 3', 4'-TCB were shown to be identical with a major metabolite (M-A2), mp 155-156°, and a minor metabolite (M-A1), mp 92-98°, respectively. Further study was made to know the acute lethal dose of 2, 4, 3', 4'-TCB and its major metabolite, 5-hydroxy-2, 4, 3', 4'-TCB, by i.p. injection using male mice of CF-1 strain. The results showed that LD50 of 2, 4, 3', 4'-TCB and 5-hydroxy-2, 4, 3', 4'-TCB were 2.15 g/kg and 0.43 g/kg, respectively, suggesting that acute toxicity of 2, 4, 3', 4'-TCB might be attributable to phenolic metabolites produced in vivo.