AUTOXIDATION OF 6-HYDROXYBENZO[A]PYRENE AND 6-OXOBENZO[A]PYRENE RADICAL, REACTIVE METABOLITES OF BENZO[A]PYRENE
AUTOXIDATION OF 6-HYDROXYBENZO[A]PYRENE AND 6-OXOBENZO[A]PYRENE RADICAL, REACTIVE METABOLITES OF BENZO[A]PYRENE
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DOI：
10.1021/bi00689a007
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发表时间：
1975-01-01
期刊：
影响因子：
2.9
通讯作者：
TSO, POP
中科院分区：
文献类型：
--
作者：
LORENTZEN, RJ;CASPARY, WJ;TSO, POP
罗纳德J.洛伦岑，威廉J.卡斯帕里，* 斯蒂芬A. Lesko和P.O.曹丕 * 摘要：致癌物苯并[a]芘的不稳定代谢产物6-羟基苯并[a]芘在缓冲-乙醇水溶液中自氧化生成三种稳定的6，12-1，6-和3，6-苯并[a]芘二酮和少量未鉴定的顺磁性紫色物质。在该反应中，氧被还原成过氧化氢，并且也可能被还原成其他活性还原氧物质。6-羟基苯并[a]芘经单电子氧化产生的自由基6-oxobenzo [a] pyrene radical，很可能是这种自氧化反应的必然中间体，其形成和衰变动力学表明了这一点。此外，在苯中，用钾水溶液氧化6-OH-B [a] P可定量产生这种自由基。3Fe（CN）e，并在无氧条件下分离。像6-
Ronald J. Lorentzen, William J. Caspary,* Stephen A. Lesko, and P. O. P. Ts’o* abstract: A labile metabolite of the carcinogen benzo-[ojpyrene, 6-hydroxybenzo [a] pyrene, is autoxidized in aqueous buffer-ethanol solutions to produce the three stable 6, 12-1, 6-, and 3, 6-benzo [a] pyrene diones and a small amount of an unidentified paramagnetic, violet-colored ma-terial. In this reaction, oxygen is reduced to hydrogen per-oxide and probably to other reactive reduced oxygen species as well. A free radical derived from 6-hydroxybenzo [a] py-rene by one-electron oxidation, 6-oxobenzo [a] pyrene radi-cal, is most likely an obligatory intermediate in this autox-idation as indicated by its kinetics of formation and decay. In addition, this free radical can be produced quantitatively in benzene by oxidation of6-OH-B [a] P with aqueous K. 3Fe (CN) e and isolated in the absence of oxygen. Like 6-