Comparative oncogenic activation of 7H-dibenzo[c,g]carbazole and dibenze[a,j]acridine

被引:0
|
作者
Warshawsky, D [1 ]
Mitchell, K [1 ]
Xue, WL [1 ]
Jaeger, M [1 ]
Schneider, J [1 ]
Talaska, G [1 ]
机构
[1] Univ Cincinnati, Dept Environm Hlth, Cincinnati, OH 45267 USA
关键词
7H-dibenzo[c; g]carbazole; dibenz[a; j]acridine; oncogenic activation; oncogenes; ras;
D O I
10.1080/10406639908020584
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
7H-Dibenzo[c,g]carbazole (DBC) is a potent liver, lung and skin carcinogen while dibenz[a,j]acridine (DBA) is a moderate skin carcinogen. DEC is metabolized to phenols and DBC-DNA adducts are formed through the 2-, 3-, and 4-phenols or directly through radical cations. Mutations in ras as a result of DEC, activation are found exclusively in codon 61 in liver, lung and skin. DBA is metabolized to dihydrodiols, and phenols and DBA-DNA adducts are formed through the diol-epoxides and possibly through bis-diol-epoxides. Mutations in ras, as a result of DBA activation, are found in codons 12, 13, and 61. These results indicate that although the two compounds are structurally similar, differing by one carbon in the middle ring, there are differences in their metabolism, DNA binding, mutational spectra and target-organ carcinogenesis.
引用
收藏
页码:173 / 179
页数:7
相关论文
共 50 条
  • [1] Comparative carcinogenicity, metabolism, mutagenicity, and DNA binding of 7H-dibenzo[c,g]carbazole and dibenz[a,j]acridine
    Warshawsky, D
    Talaska, G
    Xue, WL
    Schneider, J
    CRITICAL REVIEWS IN TOXICOLOGY, 1996, 26 (02) : 213 - 249
  • [2] COMPARATIVE METABOLISM OF 7H-DIBENZO[C,G]CARBAZOLE AND DIBENZ[A,J]ACRIDINE BY MOUSE AND RAT-LIVER MICROSOMES
    WAN, LP
    XUE, WL
    SCHNEIDER, J
    REILMAN, R
    RADIKE, M
    WARSHAWSKY, D
    CHEMICO-BIOLOGICAL INTERACTIONS, 1992, 81 (1-2) : 131 - 147
  • [3] COMPARATIVE TUMOR-INITIATING ABILITY OF 7H-DIBENZO(C,G)CARBAZOLE AND DIBENZ(A,J)ACRIDINE IN MOUSE SKIN
    WARSHAWSKY, D
    BARKLEY, W
    MILLER, ML
    LADOW, K
    ANDRINGA, A
    TOXICOLOGY, 1992, 71 (03) : 233 - 243
  • [4] COMPARATIVE CARCINOGENIC POTENCIES OF 7H-DIBENZO[C,G]CARBAZOLE, DIBENZ[A,J]ACRIDINE AND BENZO[A]PYRENE IN MOUSE SKIN
    WARSHAWSKY, D
    BARKLEY, W
    CANCER LETTERS, 1987, 37 (03) : 337 - 344
  • [5] FLUORESCENCE SPECTROSCOPIC STUDIES ON THE IDENTIFICATION AND QUANTIFICATION OF 7H-DIBENZO[C,G]CARBAZOLE AND DIBENZ[A,J]ACRIDINE METABOLITES
    SCHNEIDER, J
    XUE, WL
    WARSHAWSKY, D
    CHEMICO-BIOLOGICAL INTERACTIONS, 1994, 93 (02) : 139 - 153
  • [6] GENETIC TOXICOLOGY OF 7H-DIBENZO (C,G) CARBAZOLE
    WARSHAWSKY, D
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1989, 198 : 9 - CHAS
  • [7] 7H-Dibenzo[c,g]carbazole: Metabolic pathways and toxicity
    Gabelova, Alena
    CHEMICO-BIOLOGICAL INTERACTIONS, 2020, 323
  • [8] MECHANISM OF ALUMINUM CHLORIDE-CATALYZED REARRANGEMENT OF 7H-DIBENZO[C,G]CARBAZOLE TO 7H-DIBENZO[A,G]CARBAZOLE AND OF RELATED AROMATIC SKELETON REARRANGEMENTS
    BLUMER, GP
    GUNDERMANN, KD
    ZANDER, M
    CHEMISCHE BERICHTE-RECUEIL, 1977, 110 (05): : 2005 - 2011
  • [9] CARCINOGENICITY OF 7H-DIBENZO [C,G]CARBAZOLE, DIBENZ[A,J]ACRIDINE AND BENZO[A]PYRENE IN MOUSE SKIN AND LIVER FOLLOWING TOPICAL APPLICATION
    WARSHAWSKY, D
    BARKLEY, W
    MILLER, ML
    LADOW, K
    ANDRINGA, A
    TOXICOLOGY, 1994, 93 (2-3) : 135 - 149
  • [10] SYNTHESIS AND CHARACTERIZATION OF MONOHYDROXYLATED DERIVATIVES OF 7H-DIBENZO[C,G]CARBAZOLE
    XUE, WL
    WARSHAWSKY, D
    CHEMICAL RESEARCH IN TOXICOLOGY, 1992, 5 (01) : 130 - 133