Fu P P, Wu Y S, Von Tungeln L S, Lai J S, Chiarelli M P, Evans F E
National Center for Toxicological Research, Jefferson, Arkansas 72079.
Chem Res Toxicol. 1993 Sep-Oct;6(5):603-8. doi: 10.1021/tx00035a003.
3-Nitrobenzo[a]pyrene (3-nitro-BaP) is a potent mutagenic environmental contaminant, and its biological activities have been intensively studied. It is significant to prepare its reactive metabolites and the corresponding modified DNA adducts for biological studies. The synthesis of its oxidized proximate metabolite trans-7,8-dihydro-3-nitrobenzo[a]pyrene (3-nitro-BaP-trans-7,8-dihydrodiol, 1), its oxidized ultimate metabolite trans-7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahydro-3- nitrobenzo[a]pyrene (3-nitro-BaP-DE, 2), and the corresponding DNA adduct 10-(deoxyguanosin-N2-yl)-7,8,9-trihydroxy-7,8,9,10-tetrahydro-3- nitrobenzo[a]pyrene is described.
3-硝基苯并[a]芘（3-硝基-BaP）是一种具有强诱变作用的环境污染物，其生物学活性已得到深入研究。制备其活性代谢物及相应的修饰DNA加合物用于生物学研究具有重要意义。本文描述了其氧化近程代谢物反式-7,8-二氢-3-硝基苯并[a]芘（3-硝基-BaP-反式-7,8-二氢二醇，1）、氧化终程代谢物反式-7,8-二羟基-反式-9,10-环氧-7,8,9,10-四氢-3-硝基苯并[a]芘（3-硝基-BaP-DE，2）以及相应的DNA加合物10-(脱氧鸟苷-N2-基)-7,8,9-三羟基-7,8,9,10-四氢-3-硝基苯并[a]芘的合成方法。
