INVOLVEMENT OF A NON-BAY-REGION DIOL-EPOXIDE IN THE FORMATION OF BENZ(A)ANTHRACENE-DNA ADDUCTS IN A RAT-LIVER MICROSOMAL SYSTEM

被引:23
作者
MACNICOLL, AD
COOPER, CS
RIBEIRO, O
GERVASI, PG
HEWER, A
WALSH, C
GROVER, PL
SIMS, P
机构
[1] Chester Beatty Research Institute, Institute of Cancer Research: Royal Cancer Hospital, London, SW3 6JB England, Fulham Road
关键词
D O I
10.1016/0006-291X(79)91548-1
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The metabolic activation of benz(a)anthracene was investigated by incubating [3H]-benz(a)anthracene with DNA, a NADPH-generating system and rat-liver microsomes. When hydrolysates of the DNA were chromatographed on Sephadex LH20 columns, three hydrocarbon-nucleoside adduct peaks were resolved and these were further examined using HPLC. One adduct probably results from the reaction of the non-bay-region diol-epoxide r-8,t-9-dihydroxy-t-10,11-oxy-8,9,10,11-tetrahydrobenz(a)anthracene (anti-BA-8,9-diol 10,11-oxide) with DNA. The other two adducts did not co-chromatograph with adducts formed from any of the four possible isomeric diolepoxides that can be formed in the 8,9,10,11-ring of benz(a)anthracene. © 1979.
引用
收藏
页码:490 / 497
页数:8
相关论文
共 16 条
  • [1] ASSOCIATION OF BACTERIAL MUTAGENICITY OF HYDROCARBON-DERIVED BAY-REGION DIHYDRODIOLS WITH THE IBALL INDEXES FOR CARCINOGENICITY AND WITH THE EXTENTS OF DNA-BINDING ON MOUSE SKIN OF THE PARENT HYDROCARBONS
    BARTSCH, H
    MALAVEILLE, C
    TIERNEY, B
    GROVER, PL
    SIMS, P
    [J]. CHEMICO-BIOLOGICAL INTERACTIONS, 1979, 26 (02) : 185 - 196
  • [2] TUMOR-INITIATING ACTIVITIES ON MOUSE SKIN OF DIHYDRODIOLS DERIVED FROM BENZO[A]PYRENE
    CHOUROULINKOV, I
    GENTIL, A
    GROVER, PL
    SIMS, P
    [J]. BRITISH JOURNAL OF CANCER, 1976, 34 (05) : 523 - 532
  • [3] METABOLIC ACTIVATION OF 7-METHYLBENZ(A)ANTHRACENE IN MOUSE SKIN - HIGH TUMOR-INITIATING ACTIVITY OF 3,4-DIHYDRODIOL
    CHOUROULINKOV, I
    GENTIL, A
    TIERNEY, B
    GROVER, P
    SIMS, P
    [J]. CANCER LETTERS, 1977, 3 (5-6) : 247 - 253
  • [4] Jerina D.M., 1977, DRUG METABOLISM MICR, P13
  • [5] (+/-)-7ALPHA,8BETA-DIHYDROXY-9BETA,10BETA-EPOXY-7,8,9,10-TETRAHYDROBENZO[A]-PYRENE IS AN INTERMEDIATE IN METABOLISM AND BINDING TO DNA OF BENZO[A]PYRENE
    KING, HWS
    OSBORNE, MR
    BELAND, FA
    HARVEY, RG
    BROOKES, P
    [J]. PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1976, 73 (08) : 2679 - 2681
  • [6] KING HWS, 1975, CANCER RES, V35, P1263
  • [7] KUBINSKI H, 1973, CANCER RES, V33, P3103
  • [8] LEHR RE, 1977, TETRAHEDRON LETT, P539
  • [9] SYNTHESIS AND PROPERTIES OF VICINAL TRANS DIHYDRODIOLS OF ANTHRACENE, PHENANTHRENE, AND BENZO[A]ANTHRACENE
    LEHR, RE
    SCHAEFERRIDDER, M
    JERINA, DM
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) : 736 - 744
  • [10] MICROSOME-MEDIATED MUTAGENICITIES OF DIHYDRODIOLS OF 7,12-DIMETHYLBENZ[A]ANTHRACENE - HIGH MUTAGENIC ACTIVITY OF 3,4-DIHYDRODIOL
    MALAVEILLE, C
    BARTSCH, H
    TIERNEY, B
    GROVER, PL
    SIMS, P
    [J]. BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1978, 83 (04) : 1468 - 1473