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1
Reactivity with DNA of three pyrenofuran analogues of benzo(a)pyrene and benzo(e)pyrene.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。
Nucleic Acids Res. 1987 Nov 25;15(22):9487-97. doi: 10.1093/nar/15.22.9487.
2
Genotoxic activity of two furan analogues of benzo[a]pyrene and their 2-nitro derivatives.苯并[a]芘的两种呋喃类似物及其2-硝基衍生物的遗传毒性活性。
Mutat Res. 1986 Dec;172(3):223-30. doi: 10.1016/0165-1218(86)90059-5.
3
Species-specific enhancement by 7,8-benzoflavone of hepatic microsomal metabolism of benzo[e]pyrene 9,10-dihydrodiol to bay-region diol epoxides.7,8-苯并黄酮对苯并[e]芘9,10-二氢二醇向湾区二醇环氧化物的肝微粒体代谢的种属特异性增强作用。
Cancer Res. 1981 Apr;41(4):1389-96.
4
Kinetic determinants of benzo[a]pyrene metabolism to dihydrodiol epoxides by 3-methylcholanthrene-induced rat liver microsomes.3-甲基胆蒽诱导的大鼠肝微粒体将苯并[a]芘代谢为二氢二醇环氧化物的动力学决定因素。
Mol Pharmacol. 1982 Sep;22(2):451-8.
5
Specificity of chemiluminescence in the metabolism of benzo[a]pyrene to its carcinogenic diol epoxide.苯并[a]芘代谢为其致癌二醇环氧化物过程中化学发光的特异性。
Proc Natl Acad Sci U S A. 1981 Feb;78(2):940-2. doi: 10.1073/pnas.78.2.940.
6
Fluorescence study of DNA-binding metabolites of benzo(a)pyrene formed in hepatocytes isolated from 3-methylcholanthrene-treated rats.从经3-甲基胆蒽处理的大鼠分离出的肝细胞中形成的苯并(a)芘DNA结合代谢物的荧光研究。
Cancer Res. 1978 Aug;38(8):2600-7.
7
Immunochemical study on the contributions of two molecular species of microsomal cytochrome P-450 to the metabolism of benzo(a)pyrene by rat liver microsomes.关于微粒体细胞色素P-450的两种分子形式对大鼠肝脏微粒体代谢苯并(a)芘贡献的免疫化学研究。
Cancer Res. 1983 Aug;43(8):3604-8.
8
Pyrrolizidine alkaloid-induced alterations in benzo[alpha]pyrene metabolism and binding of benzo[alpha]pyrene metabolites to deoxyribonucleic acid.
Biochem Pharmacol. 1983 Aug 15;32(16):2443-7. doi: 10.1016/0006-2952(83)90689-5.
9
The benzo(alpha)pyrene deoxyribonucleoside products isolated from DNA after metabolism of benzo(alpha)pyrene by rat liver microsomes in the presence of DNA.在DNA存在的情况下，大鼠肝脏微粒体对苯并（α）芘进行代谢后，从DNA中分离出的苯并（α）芘脱氧核糖核苷产物。
Cancer Res. 1975 May;35(5):1263-9.
10
Metabolism of benzo[a]pyrene. VI. Stereoselective metabolism of benzo[a]pyrene and benzo[a]pyrene 7,8-dihydrodiol to diol epoxides.苯并[a]芘的代谢。VI. 苯并[a]芘和苯并[a]芘7,8-二氢二醇向二醇环氧化物的立体选择性代谢。
Chem Biol Interact. 1977 Mar;16(3):281-300. doi: 10.1016/0009-2797(77)90108-9.

本文引用的文献

1
A microsome-dependent binding of benzo[a]pyrene to DNA.微粒体介导的苯并[a]芘与DNA的结合。
Cancer Res. 1969 Jun;29(6):1272-6.
2
Metabolic activation of benzo(a)pyrene proceeds by a diol-epoxide.苯并(a)芘的代谢活化通过二醇环氧化物进行。
Nature. 1974 Nov 22;252(5481):326-8. doi: 10.1038/252326a0.
3
Determination of protein: a modification of the Lowry method that gives a linear photometric response.蛋白质的测定：一种改进的洛瑞法，可产生线性光度响应。
Anal Biochem. 1972 Aug;48(2):422-7. doi: 10.1016/0003-2697(72)90094-2.
4
Fluorescence spectral evidence that benzo(a)pyrene-DNA products in mouse skin arise from diol-epoxides.荧光光谱证据表明，小鼠皮肤中的苯并(a)芘-DNA产物源自二醇环氧化物。
FEBS Lett. 1975 Oct 1;57(3):250-3. doi: 10.1016/0014-5793(75)80310-3.
5
Tumorigenicity studies with diol-epoxides of benzo(a)pyrene which indicate that (+/-)-trans-7beta,8alpha-dihydroxy-9alpha,10alpha-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene is an ultimate carcinogen in newborn mice.苯并(a)芘二醇环氧化物的致癌性研究表明，(±)-反式-7β,8α-二羟基-9α,10α-环氧-7,8,9,10-四氢苯并(a)芘是新生小鼠的一种最终致癌物。
Cancer Res. 1978 Feb;38(2):354-8.

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.

DOI:10.1093/nar/15.22.9487
PMID:3684601
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC306482/
Abstract

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.

摘要

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。