Evidence for a 2,3-epoxide as an intermediate in the microsomal metabolism of benzo[a]pyrene to 3-hydroxybenzo[a]pyrene.
Evidence for a 2,3-epoxide as an intermediate in the microsomal metabolism of benzo[a]pyrene to 3-hydroxybenzo[a]pyrene.
复制标题
2,3-环氧化物作为苯并[a]芘微粒体代谢为3-羟基苯并[a]芘的中间体的证据。
DOI：
10.1016/s0006-291x(77)80103-4
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发表时间：
1977
影响因子：
3.1
通讯作者：
H. Gelboin
中科院分区：
文献类型：
--
作者：
Shen K. Yang;P. Roller;P. Fu;Ronald G. Harvey;H. Gelboin
在NADPH和氧存在下，将氘标记的苯并[a]芘（BP）与大鼠肝微粒体孵育。通过高压液相色谱法分离的代谢物的质谱分析表明，3-羟基苯并[a]芘（3-OH-BP）和BP-3，6-醌分别保留29%和15%的氘标记，而BP 4，5-、7，8-和9，10-二醇、9-OH-BP、BP-1，6-醌和BP-6，12-醌基本上保留所有氘标记。结果表明，至少29%的检测到的3-OH-BP代谢产物是通过2，3-环氧化物中间体形成的，该中间体将NIH自发转换机制重排为3-OH-BP。至少15%作为代谢产物检测的BP-3，6-醌衍生自酶促形成的3-OH-BP。
A synthetic benzo[a]pyrene (BP) specifically labeled with deuterium at the 3-position was incubated with rat liver microsomes in the presence of NADPH and oxygen. Mass spectral analysis of the metabolites isolated by high pressure liquid chromatography indicated that the 3-hydroxybenzo[a]pyrene (3-OH-BP) and BP-3,6-quinone retained 29% and 15% of the deuterium label respectively, whereas the BP 4,5-, 7,8-, and 9,10- diols, 9-OH-BP, BP-1,6-quinone, and BP-6,12-quinone retained essentially all the deuterium label. The results indicate that at least 29% of the 3-OH-BP detected as metabolite is formed through a 2,3-epoxide intermediate which rearranges spontaneouslyviaan NIH shift mechanism to 3-OH-BP. At least 15% of the BP-3,6-quinone detected as a metabolite is derived from the enzymatically formed 3-OH-BP.