COMPARATIVE METABOLISM AND DNA-BINDING OF 7,12-DIMETHYLBENZ[A]ANTHRACENE AND ITS WEAKLY CARCINOGENIC 5-FLUORO ANALOG

被引:22
作者
DANIEL, FB
CAZER, FD
DAMBROSIO, SM
HART, RW
KIM, WH
WITIAK, DT
机构
[1] OHIO STATE UNIV,COLL PHARM,DEPT MED CHEM,COLUMBUS,OH 43210
[2] OHIO STATE UNIV,COLL MED,DEPT RADIOL & PHARMACOL,COLUMBUS,OH 43210
[3] OHIO STATE UNIV,CTR COMPREHENS CANC,COLUMBUS,OH 43210
关键词
D O I
10.1016/S0304-3835(79)80044-0
中图分类号
R73 [肿瘤学];
学科分类号
100214 ;
摘要
Cultured Syrian hamster embryo cells readily convert both the carcinogenic polycyclic aromatic hydrocarbon, 7,12-dimethylbenz[a] anthracene (DMBA), and its weakly carcinogenic analogue, 5-fluoro-7,12-dimethylbenz[a] anthracene (5F-DMBA), to water soluble metabolites. DMBA, however, binds to the hamster cell DNA at least 2.8-3.0 times more extensively than 5F-DMBA. Likewise, 5F-DMBA is converted to water soluble metabolites by liver microsomal preparations at a rate equal to DMBA, but the latter compound binds to DNA 2.6-3.2 times more effectively. © 1979 Elsevier/North-Holland Scientific Publishers Ltd., All rights reserved.
引用
收藏
页码:263 / 272
页数:10
相关论文
共 26 条
[1]   The synthesis of growth-inhibitory polycyclic compounds Part I [J].
Badger, GM ;
Cook, JW .
JOURNAL OF THE CHEMICAL SOCIETY, 1939, :802-806
[2]  
BERWALD Y, 1965, J NATL CANCER I, V35, P641
[3]   DIFFERENCES BETWEEN PRODUCTS OF BINDING OF 7,12-DIMETHYLBENZ[A]ANTHRACENE TO DNA IN MOUSE SKIN AND IN A RAT-LIVER MICROSOMAL SYSTEM [J].
BIGGER, CAH ;
TOMASZEWSKI, JE ;
DIPPLE, A .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1978, 80 (01) :229-235
[4]   BINDING OF 7,12-DIMETHYLBENZ[A]ANTHRACENE TO DNA INVESTIGATED BY TRITIUM DISPLACEMENT [J].
BLACKBURN, GM ;
FLAVELL, AJ ;
TAUSSIG, PE ;
WILL, JP .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (09) :358-359
[5]   PRODUCTS OBTAINED AFTER INVITRO REACTION OF 7,12-DIMETHYLBENZ[A]ANTHRACENE 5,6-OXIDE WITH NUCLEIC-ACIDS [J].
BLOBSTEIN, SH ;
WEINSTEIN, IB ;
GRUNBERGER, D ;
WEISGRAS, J ;
HARVEY, RG .
BIOCHEMISTRY, 1975, 14 (15) :3451-3458
[6]   EVIDENCE FOR BINDING OF POLYNUCLEAR AROMATIC HYDRO-CARBONS TO NUCLEIC ACIDS OF MOUSE SKIN - RELATION BETWEEN CARCINOGENIC POWER OF HYDROCARBONS + THEIR BINDING TO DEOXYRIBONUCLEIC ACID [J].
BROOKES, P ;
LAWLEY, PD .
NATURE, 1964, 202 (493) :781-&
[7]   CARCINOGENIC HYDROCARBONS AND HUMAN CELLS IN CULTURE [J].
BROOKES, P ;
DUNCAN, ME .
NATURE, 1971, 234 (5323) :40-&
[8]  
BROOKES P, 1969, CANCER RES, V29, P157
[9]   ROLE OF EPIDERMAL ARYL-HYDROCARBON HYDROXYLASE IN COVALENT BINDING OF POLYCYCLIC HYDROCARBON TO DNA AND ITS RELATIONSHIP TO TUMOR INITIATION [J].
BUTY, SG ;
THOMPSON, S ;
SLAGA, TJ .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1976, 70 (04) :1102-1108
[10]   RELIABLE, SENSITIVE, AND CONVENIENT RADIOACTIVE ASSAY FOR BENZPYRENE MONOOXYGENASE [J].
DEPIERRE, JW ;
MORON, MS ;
JOHANNESEN, KA ;
ERNSTER, L .
ANALYTICAL BIOCHEMISTRY, 1975, 63 (02) :470-484