苯并(a)芘和苯并(e)芘的三种芘并呋喃类似物与DNA的反应活性。
Reactivity with DNA of three pyrenofuran analogues of benzo(a)pyrene and benzo(e)pyrene.
作者信息
Jolles B, Demerseman P, Chalvet O, Strapelias H, Herning T, Royer R, Duquesne M
机构信息
Institut Curie, UA 198 CNRS, Paris, France.
出版信息
Nucleic Acids Res. 1987 Nov 25;15(22):9487-97. doi: 10.1093/nar/15.22.9487.
Three pyrenofurans, the pyreno[1,2-b]furan (FP1), the pyreno[2,1-b] furan (FP2) and the pyreno[4,5-b]furan (FP3) have been synthesized as analogues of the mutagenic and carcinogenic benzo(a)pyrene (FP1 and FP2) and of its non-carcinogenic isomer benzo(e)pyrene (FP3). For each of the pyrenofurans, the reactivity with DNA has been tested in presence of liver microsomes of rats induced with 3-methylcholanthrene. Fluorescence spectroscopy showed that only FP2 and FP3 which possess a "bay region" react with DNA. In both cases, metabolites bound to DNA have a fluorescence emission comparable to that of the "bay region" dihydrodiols obtained after the "in vitro" metabolism of initial molecules. FP2 is shown to react similarly to benzo(a)pyrene whereas the reactivity of FP3 is different from that of benzo(e)pyrene, in spite of their structural similarities. This is probably due to reasons of three-dimensional space configuration. The peculiar reactivity of FP3 is predicted by calculations of the bond order values.
三种芘并呋喃，即芘并[1,2 - b]呋喃（FP1）、芘并[2,1 - b]呋喃（FP2）和芘并[4,5 - b]呋喃（FP3）已被合成，作为致突变和致癌的苯并(a)芘（FP1和FP2）及其非致癌异构体苯并(e)芘（FP3）的类似物。对于每种芘并呋喃，在经3 - 甲基胆蒽诱导的大鼠肝脏微粒体存在的情况下，测试了其与DNA的反应活性。荧光光谱表明，只有具有“湾区”的FP2和FP3与DNA发生反应。在这两种情况下，与DNA结合的代谢产物的荧光发射与初始分子“体外”代谢后得到的“湾区”二氢二醇的荧光发射相当。结果表明，FP2与苯并(a)芘的反应相似，而尽管FP3与苯并(e)芘结构相似，但其反应活性却与之不同。这可能是由于三维空间构型的原因。通过键序值的计算预测了FP3的特殊反应活性。
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