Cyclopenta(c,d)pyrene: a highly mutahgenic polycyclic aromatic hydrocarbon
Journal Article
·
· Proc. Natl. Acad. Sci. U.S.A.; (United States)
A polycyclic aromatic hydrocarbon recently isolated from carbon black and identified as cyclopenta(c,d)-pyrene (CPP) is highly mutagenic. By the criteria of the Salmonella/mammalian-microsome mutagenicity test, the mutagenic potency of CPP is equalled by only two other naturally occurring polycyclic aromatic hydrocarbons--benzo(a)pyrene and dibenz(a,c)anthracene. The potent mutagenicity of CPP is noteworthy for two reasons: (i) CPP is a mutagenic polycyclic aromatic hydrocarbon without a ''bay-region'' and (ii) there is evidence that it is distributed widely in the environment. On the basis of experimental observations and perturbational molecular orbital calculations we propose that a mutagenic metabolite of CPP will be the 3,4-oxide. The carbonium ion derived from opening of CPP 3,4-oxide is identical to that derived from opening of benzo(a)pyrene 7,8-diol-9,10-oxide, the metabolite now thought to be an ultimate mutagenic and carcinogenic species.
- Research Organization:
- Harvard School of Public Health, Boston
- OSTI ID:
- 6787150
- Journal Information:
- Proc. Natl. Acad. Sci. U.S.A.; (United States), Journal Name: Proc. Natl. Acad. Sci. U.S.A.; (United States) Vol. 75:4; ISSN PNASA
- Country of Publication:
- United States
- Language:
- English
Similar Records
Oxidation of cyclopenta[cd]pyrene by human and mouse liver microsomes and selected cytochrome P450 enzymes
Synthesis of the carcinogen cyclopenta(c,d)pyrene, its tritiated analog and its proposed active metabolite cyclopenta(c,d)pyrene-3,4-oxide
Metabolism and macromolecular binding of benzo(a)pyrene and its noncarcinogenic isomer benzo(e)pyrene in cell culture
Journal Article
·
· Chemical Research in Toxicology; (United States)
·
OSTI ID:6247521
Synthesis of the carcinogen cyclopenta(c,d)pyrene, its tritiated analog and its proposed active metabolite cyclopenta(c,d)pyrene-3,4-oxide
Conference
·
Fri Aug 01 00:00:00 EDT 1980
· Am. Chem. Soc., Div. Pet. Chem., Prepr.; (United States)
·
OSTI ID:7141854
Metabolism and macromolecular binding of benzo(a)pyrene and its noncarcinogenic isomer benzo(e)pyrene in cell culture
Conference
·
Sat Dec 31 23:00:00 EST 1977
·
OSTI ID:6539819
Related Subjects
500200 -- Environment
Atmospheric-- Chemicals Monitoring & Transport-- (-1989)
54 ENVIRONMENTAL SCIENCES
560301 -- Chemicals Metabolism & Toxicology-- Cells-- (-1987)
560302* -- Chemicals Metabolism & Toxicology-- Microorganisms-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AIR POLLUTION
ANIMAL CELLS
AROMATICS
BACTERIA
BIOLOGICAL EFFECTS
CARBON
CARBON BLACK
CARCINOGENESIS
CARCINOGENS
CONDENSED AROMATICS
ELEMENTS
EPOXIDES
EXHAUST GASES
GASEOUS WASTES
GENETIC EFFECTS
HYDROCARBONS
MICROORGANISMS
MUTAGENESIS
MUTAGENS
NONMETALS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PATHOGENESIS
POLLUTION
POLYCYCLIC AROMATIC HYDROCARBONS
SALMONELLA
SOOT
WASTES
Atmospheric-- Chemicals Monitoring & Transport-- (-1989)
54 ENVIRONMENTAL SCIENCES
560301 -- Chemicals Metabolism & Toxicology-- Cells-- (-1987)
560302* -- Chemicals Metabolism & Toxicology-- Microorganisms-- (-1987)
63 RADIATION, THERMAL, AND OTHER ENVIRON. POLLUTANT EFFECTS ON LIVING ORGS. AND BIOL. MAT.
AIR POLLUTION
ANIMAL CELLS
AROMATICS
BACTERIA
BIOLOGICAL EFFECTS
CARBON
CARBON BLACK
CARCINOGENESIS
CARCINOGENS
CONDENSED AROMATICS
ELEMENTS
EPOXIDES
EXHAUST GASES
GASEOUS WASTES
GENETIC EFFECTS
HYDROCARBONS
MICROORGANISMS
MUTAGENESIS
MUTAGENS
NONMETALS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PATHOGENESIS
POLLUTION
POLYCYCLIC AROMATIC HYDROCARBONS
SALMONELLA
SOOT
WASTES