FORMATION OF DIHYDRODIOLS FROM BENZO[A]PYRENE BY OXIDATION WITH AN ASCORBIC ACID-FERROUS SULFATE-EDTA SYSTEM

被引:15
作者
HEWER, A
RIBEIRO, O
WALSH, C
GROVER, PL
SIMS, P
机构
[1] The Chester Beatty Research Institute, Institute of Cancer Research: Royal Cancer Hospital, London, SW3 6JB, Fulham Road
基金
英国医学研究理事会;
关键词
D O I
10.1016/0009-2797(79)90018-8
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
In the oxidation of benzo [a] pyrene in an ascorbic acid-ferrous sulphate-EDTA system, our dihydrodiola were detected. Three, trans-4,5-dihydro-4,5-dihydroxybenzo [a] pyrene, trans-7,8-dihydro-7,8-dihydroxybenzo[a] pyrene and trans-9,10-dihydro-9,10-dihydroxybenzo[a] pyrene were identified by their UV spectra and by direct comparisons of their chromatographic properties, using HPLC, with those of the authentic compounds. The fourth compound appeared to be trans-11, 12-dihydro-11,12-dihydroxybenzo[a] pyrene since its ultraviolet spectrum was identical to that of the cis-dihydrodiol. Time-course experiments showed that the maximum amounts of products were obtained after 8 h of oxidation. A re-examination of the dihydrodiols formed from benzo[a]pyrene by rat-liver microsomal fractions failed to show the formation of the trans-11,12-dihydrodiol. © 1979.
引用
收藏
页码:147 / 154
页数:8
相关论文
共 16 条
[1]   SYNTHESIS AND PROPERTIES OF VICINAL TRANS DIHYDRODIOLS OF ANTHRACENE, PHENANTHRENE, AND BENZO[A]ANTHRACENE [J].
LEHR, RE ;
SCHAEFERRIDDER, M ;
JERINA, DM .
JOURNAL OF ORGANIC CHEMISTRY, 1977, 42 (04) :736-744
[2]  
MCCAUSTLAND DJ, 1975, TETRAHEDRON LETT, P2549
[3]  
MCCAUSTLAND DJ, 1976, CARCINOGENESIS, V1, P349
[4]   METABOLISM OF BENZO[ALPHA]PYRENE .5. EFFECT OF 3-METHYLCHOLANTHRENE PRETREATMENT ON METABOLISM BY MICROSOMES FROM LUNGS OF GENETICALLY RESPONSIVE AND NONRESPONSIVE MICE [J].
SEIFRIED, HE ;
BIRKETT, DJ ;
LEVIN, W ;
LU, AYH ;
CONNEY, AH ;
JERINA, DM .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1977, 178 (01) :256-263
[5]   METABOLIC ACTIVATION OF BENZO(A)PYRENE PROCEEDS BY A DIOL-EPOXIDE [J].
SIMS, P ;
GROVER, PL ;
SWAISLAN.A ;
PAL, K ;
HEWER, A .
NATURE, 1974, 252 (5481) :326-328
[6]  
Sims P, 1974, Adv Cancer Res, V20, P165, DOI 10.1016/S0065-230X(08)60111-6
[8]   METABOLISM OF BENZO[A]PYRENE BY RAT-LIVER HOMOGENATES [J].
SIMS, P .
BIOCHEMICAL PHARMACOLOGY, 1967, 16 (04) :613-&
[9]   PREPARATION OF DIHYDRODIOLS FROM 7-METHYLBENZ[A]-ANTHRACENE [J].
TIERNEY, B ;
ABERCROMBIE, B ;
WALSH, C ;
HEWER, A ;
GROVER, PL ;
SIMS, P .
CHEMICO-BIOLOGICAL INTERACTIONS, 1978, 21 (2-3) :289-298
[10]   FORMATION OF DIHYDRODIOLS BY CHEMICAL OR ENZYMIC OXIDATION OF 3-METHYLCHOLANTHRENE [J].
TIERNEY, B ;
HEWER, A ;
RATTLE, H ;
GROVER, PL ;
SIMS, P .
CHEMICO-BIOLOGICAL INTERACTIONS, 1978, 23 (01) :121-135