Corpus ID: 44689160

Mutagenicity and cytotoxicity of benzo(a)pyrene arene oxides, phenols, quinones, and dihydrodiols in bacterial and mammalian cells.

  title={Mutagenicity and cytotoxicity of benzo(a)pyrene arene oxides, phenols, quinones, and dihydrodiols in bacterial and mammalian cells.},
  author={P. Wislocki and A. Wood and R. Chang and W. Levin and H. Yagi and O. Hernandez and P. Dansette and D. M. Herina and A. Conney},
  journal={Cancer research},
  volume={36 9 pt.1},
Twenty-nine benzo(a)pyrene derivatives were tested for mutagenic acitivity without metabolic activation in Salmonella typhimurium strains TA98, TA100, and TA1538 and in Chinese hamster V79 cells. The compounds studied included 4 arene oxides, all 12 isomeric phenols, 5 quinones, and 8 dihydrodiols. Benzo(a)pyrene 4,5-oxide was the most mutagenic of the compounds tested in both the bacterial and mammalian systems. The other arene oxides [benzo(a)pyrene 7,8-, 9,10-, and 11,12-oxides] were only… Expand
Mutagenicity and cytotoxicity of benzo(a)pyrene benzo-ring epoxides.
Four benzo-ring epoxides of the environmental carcinogen benzo(a)pyrene (BP) were tested for mutagenic and cytotoxic activity in 3 strains of Salmonella typhimurium and in Chinese hamster V79 cells. Expand
Mutagenesis of certain benzo(a)pyrene phenols in vitro following further metabolism by mouse liver.
The addition of the substrate for sulfotransferase(s), 3-phosphoadenosine 5'-phosphate sulfate, prevents about half of the mutagenesis caused by 1-hydroxy- or 3-Hydroxybenzo[a]pyrene, and the combination of UDP-glucuronic acid and UDP- N -acetylglucosamine provides an even higher level of protection. Expand
Inhibitory effect of 3-hydroxybenzo(a)pyrene on the mutagenicity and tumorigenicity of (±)-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene
Three isomeric phenols of benzo( a )pyrene were tested for their ability to inhibit the mutagenic activity of (±)-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo-2, and 3-HO-B(a)P was the most effective antimutagen of the B( a)P phenols tested. Expand
Modulation of the cytotoxicity and mutagenicity of benzo[a]pyrene and benzo[a]pyrene 7,8-diol by glutathione and glutathione S-transferases in mammalian cells (CHO/HGPRT assay).
It is indicated that biochemical mechanisms of detoxication can affect the biological activity of a carcinogen, such as BP or BP-diol as profoundly as bioactivation by the MFO system. Expand
Glucuronide conjugation reduces the cytotoxicity but not the mutagenicity of benzo(a)pyrene in the CHO/HGPRT assay.
  • L. Recio, A. Hsie
  • Chemistry, Medicine
  • Teratogenesis, carcinogenesis, and mutagenesis
  • 1984
The reduction of B(a)P and B( a)P 6-OH-induced cytotoxicity by glucuronide conjugation is likely due to the elimination of cytotoxic phenols and quinones. Expand
Screening of antioxidants and other compounds for antimutagenic properties towards benzo[a]pyrene-induced mutagenicity in strain TA98 of Salmonella typhimurium.
Antioxidants and several other compounds, some of which are known to inhibit carcinogenicity, have been screened for their effectiveness as inhibitors of benzo[a]pyrene (BP) mutagenicity towards Salmonella typhimurium strain TA98 in the Ames test, finding that retinol, phenothiazine, disulfiram, phenethylisothiocyanate and phenylisothuyanate were the most effective inhibitors. Expand
Carcinogenicity of benzo-ring derivatives of benzo(a)pyrene on mouse skin.
Results indicate the importance of the double bond at position 9,10 for the carcinogenic activity of (+/-)-trans-7-8-dihydroxy-7,8- dihydrobenzo(a)pyrene and the high reactivity of the three epoxides may account for their inactivity or their weak carcinogen activity on mouse skin. Expand
Mutagenicity and tumor-initiating activity of fluorinated derivatives of 7,12-dimethylbenz(a)anthracene.
Results suggest that carbon positions 1 and 2 of DMBA, which are located in the bay region, and position 5, which is located at the K-region, are involved in the metabolic activation of DM BA into mutagenic and carcinogenic metabolites. Expand
Carcinogenicity and mutagenicity of benz(a)anthracene diols and diol-epoxides.
The results suggest that the bay-region diol-epoxide of BA may be the ultimate carcinogen and mutagenic form of BA. Expand
Non-enzymic activation of polycyclic aromatic hydrocarbons as mutagens.
It is suggested that Salmonella typhimurium may be oxidized in air by radiation-induced processes to products whose mutagenicity resembles that of liver-microsomal metabolites of the parent polycyclic aromatic hydrocarbon. Expand


Comparison of the cellular DNA-bound products of benzo(alpha)pyrene with the products formed by the reaction of benzo(alpha)pyrene-4,5-oxide with DNA.
The metabolic activation of benzo(alpha)pyrene that results in this hydrocarbon becoming covalently bound to DNA in mouse embryo cells in culture may be more complex than simply formation of a K-region epoxide and reaction of that compound with the cellular DNA. Expand
Methods for detecting carcinogens and mutagens with the Salmonella/mammalian-microsome mutagenicity test.
The methods described include the standard plate test, the use and storage of the bacterial tester strains, preparation and use of the liver homogenates, and the methods of inducing the rats for elevated microsomal enzyme activity. Expand