(+)-和(-)-苯并[a]芘4,5-氧化物的致突变性和细胞毒性差异：对映体的协同相互作用
Differences in mutagenicity and cytotoxicity of (+)- and (-)-benzo[a]pyrene 4,5-oxide: a synergistic interaction of enantiomers.
作者信息
Chang R L, Wood A W, Levin W, Mah H D, Thakker D R, Jerina D M, Conney A H
出版信息
Proc Natl Acad Sci U S A. 1979 Sep;76(9):4280-4. doi: 10.1073/pnas.76.9.4280.
In order to study the biological effects of (+)- and (-)-benzo[a]pyrene 4,5-oxide, a synthesis of these molecules has been developed based on the resolution of (+/-)-cis-4,5-dihydroxy-4,5-dihydrobenzo[a]pyrene. The (-) enantiomer of benzo[a]pyrene 4,5-oxide was 1.5- to 5.5-fold more mutagenic than the (+) enantiomer in strains TA 98, TA 100, TA 1537, and TA 1538 of Salmonella typhimurium and in Chinese hamster V79 cells. In studies with V79 Cells, the (-) enantiomer of benzo[a]pyrene 4,5-oxide was also more cytotoxic than the (+) enantiomer. When mixtures of the enantiomers were studied in V79 cells, synergistic cytotoxic and mutagenic responses were observed. The greatest cytotoxic and mutagenic effects occurred with a 3:1 mixture of the (-) and (+) enantiomers of benzo[a]pyrene 4,5-oxide, respectively.
为了研究（+）-和（-）-苯并[a]芘4,5-氧化物的生物学效应，基于（±）-顺式-4,5-二羟基-4,5-二氢苯并[a]芘的拆分开发了这些分子的合成方法。在鼠伤寒沙门氏菌的TA 98、TA 100、TA 1537和TA 1538菌株以及中国仓鼠V79细胞中，苯并[a]芘4,5-氧化物的（-）对映体的诱变性比（+）对映体高1.5至5.5倍。在用V79细胞进行的研究中，苯并[a]芘4,5-氧化物的（-）对映体的细胞毒性也比（+）对映体更强。当在V79细胞中研究对映体混合物时，观察到了协同的细胞毒性和诱变性反应。苯并[a]芘4,5-氧化物的（-）和（+）对映体以3:1的混合物分别产生了最大的细胞毒性和诱变性作用。
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