SYNTHESIS OF 3-NITROBENZO[A]PYRENE BAY-REGION TRANS-7,8-DIOL ANTI-9,10-EPOXIDE AND THE CORRESPONDING N(2)-DEOXYGUANOSINE ADDUCT

被引:10
作者
FU, PP [1 ]
WU, YS [1 ]
VONTUNGELN, LS [1 ]
LAI, JS [1 ]
CHIARELLI, MP [1 ]
EVANS, FE [1 ]
机构
[1] PROVIDENCE UNIV, INST APPL CHEM, TAICHUNG, TAIWAN
关键词
D O I
10.1021/tx00035a003
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
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-dihydroxy-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.
引用
收藏
页码:603 / 608
页数:6
相关论文
共 18 条
[1]   MULTIPLE METABOLIC PATHWAYS FOR THE MUTAGENIC ACTIVATION OF 3-NITROBENZO[A]PYRENE [J].
CHOU, MW ;
HEFLICH, RH ;
FU, PP .
CARCINOGENESIS, 1985, 6 (08) :1235-1238
[2]   METABOLISM OF THE CARCINOGEN [H-3] 6-NITROCHRYSENE IN THE PREWEANLING MOUSE - IDENTIFICATION OF 6-AMINOCHRYSENE-1,2-DIHYDRODIOL AS THE PROBABLE PROXIMATE CARCINOGENIC METABOLITE [J].
DELCLOS, KB ;
ELBAYOUMY, K ;
HECHT, SS ;
WALKER, RP ;
KADLUBAR, FF .
CARCINOGENESIS, 1988, 9 (10) :1875-1884
[3]  
Dipple A., 1984, ACS MONOGR SER, V182, P41, DOI DOI 10.1074/JBC.M409155200
[4]  
DJURIC Z, 1986, CARCINOGENESIS, V7, P1703
[5]   METABOLISM OF NITRO-POLYCYCLIC AROMATIC-HYDROCARBONS [J].
FU, PP .
DRUG METABOLISM REVIEWS, 1990, 22 (2-3) :209-268
[6]   MUTAGENICITY OF THE MONONITROBENZO[A]PYRENES IN CHINESE-HAMSTER OVARY CELLS MEDIATED BY RAT HEPATOCYTES OR LIVER S9 [J].
HASS, BS ;
HEFLICH, RH ;
SCHOL, HM ;
CHOU, MW ;
FU, PP ;
CASCIANO, DA .
CARCINOGENESIS, 1986, 7 (04) :681-684
[7]   HEPATOCYTE-MEDIATED MUTAGENICITY OF MONONITROBENZO[A]PYRENES IN SALMONELLA-TYPHIMURIUM STRAINS [J].
HASS, BS ;
HEFLICH, RH ;
CHOU, MW ;
WHITE, GL ;
FU, PP ;
CASCIANO, DA .
MUTATION RESEARCH, 1986, 171 (2-3) :123-129
[8]   FORMATION OF THE ADDUCT 6-(DEOXYGUANOSIN-N-2-YL)-3-AMINO-BENZO[A]PYRENE FROM THE MUTAGENIC ENVIRONMENTAL CONTAMINANT 3-NITROBENZO[A]PYRENE [J].
HERRENOSAENZ, D ;
EVANS, FE ;
ABIAN, J ;
FU, PP .
CARCINOGENESIS, 1993, 14 (05) :1065-1067
[9]  
HOWARD PC, 1990, NITROARENES OCCURREN, V40
[10]   ATMOSPHERIC REACTIONS OF POLYCYCLIC AROMATIC-HYDROCARBONS - FACILE FORMATION OF MUTAGENIC NITRO-DERIVATIVES [J].
PITTS, JN ;
VANCAUWENBERGHE, KA ;
GROSJEAN, D ;
SCHMID, JP ;
FITZ, DR ;
BELSER, WL ;
KNUDSON, GB ;
HYNDS, PM .
SCIENCE, 1978, 202 (4367) :515-519