50-32-8 Benzo ajpyrene

A-Hydroxy-4- acetylaminobiphenyl Benzo [a] pyrene diol epoxide Human TK6 lymphoblastoid Custom A-Hydroxy-4- acetylaminobiphenyl 10 xMfor27h Benzo[ajpyrene diol epoxide 10 xM for Ih Gene name, gene symbol, gene bank accession fold change in a table All data available online 116... 

The presence of polycyclic aromatic hydrocarbons in the environment is of obvious concern and, apart from specific occupational environments, human exposure to these compounds derives from combustion products released into the atmosphere. Estimates of the total annual benzo[aJpyrene emissions in the United States range from 900 tons (19) to about 1300 tons (20). These totals are derived from heat and power generation (37-38%), open-refuse burning (42-46%), coke production (15-19%) and motor vehicle emissions (1-1.5%) (19,20). Since the vast majority of these emissions are from stationary sources, local levels of air pollution obviously vary. Benzo[aJpyrene levels of less than 1 pg/1,000 m correspond to clean air (20). At this level, it can be estimated that the average person would inhale about 0.02 pg of benzo[aJpyrene per day, and this could increase to 1.5 pg/day in polluted air (21). 

The search for an alternative reactive metabolite for the polycyclic hydrocarbon carcinogens was soon successful. Also in 1973, Borgen et al. (54) reported that, in the presence of a microsomal system from hamster liver, trans 7,8-dihydro-7,8-dihydroxybenzola]-pyrene (a metabolite of benzo[aJpyrene) was bound to DNA in vitro some ten times more extensively than was benzo[a]pyrene itself. 

In the newborn mouse system (Table II), the (+) anti dihydrodiol epoxide is clearly more effective than benzo[ajpyrene but this is not the case in initiation-promotion studies or in complete carcinogenesis studies on mouse skin. Nevertheless, there is always... 

Mix, M.C. and Schaffer, R.L. (1979). Benzo(aJpyrene concentrations in mussels (Mytilus eduUs) from Yaquina Bay, Oregon during June 1976-May 1978, BuU. Environ. Contain. IbxicoL 23,677. 

Haake JM, Merrill JC, Safe S. 1985. The in vitro metabolism of benzo [ajpyrene by polychlorinated and polybrominated biphenyl induced rat hepatic microsomal monooxygenases. Can J Physiol Pharmacol 63 1096-1100. 

Hamdan S, Morse B, Reinhold D. 1999. Nickel subsulfide is similar to potassium dichromate in protecting normal human fibroblasts from the mutagenic effects of benzo [ajpyrene diolepoxide. Environ Mol Mutagen 33 211-218. 

Wiebel FJ, Leutz JC, Diamond L, Gelboin HV. 1971. Aryl hydrocarbon (benzo-[ajpyrene) hydroxylase in microsomes from rat tissues differential inhibition and stimulation by benzoflavones and organic solvents. Arch. Biochem. Biophys. 144 78-86... 

Paine AJ. 1976. Induction of benzo-[ajpyrene mono-oxygenase in liver cell culture by the photochemical generation of active oxygen species. Biochem. J. 158 109-17... 

Cosma GN, Jamabi R, Marchok AC. 1988a. Growth inhibition and DNA damage induced by benzo[ajpyrene and formaldehyde in primary cultures of rat tracheal epithelial cells. Mutat Res 201 161-168. 

Blanton RH, Myers MJ, Bick PH. 1988. Modulation of immunocompetent cell populations by benzo( ajpyrene. Toxicol Appl Pharmacol 93 267-274. 

Lyte M, Blanton RH, Myers MJ, et. al. 1987. Effect of in v/vo administration of the carcinogen benzo( ajpyrene on interleukin-2 and interleukin-3 production. Int J Immunopharmacol 9 307-312. 

The coplanarity of benzo[ajpyrene and many carcinogenic polycyclic hydrocarbons is of interest. It has been suggested that this flat structure allows intercalation of the hydrocarbon within the DNA molecule, thereby facilitating reaction of the intermediate with the nucleic acid. 

It is clear that the effects of induction or inhibition of the metabolism will be complex, due to the large number of possible metabolic pathways through which benzo [ajpyrene may be metabolized. For instance, the microsomal enzyme inducer 5,6-benzoflavone inhibits the carcinogenicity of benzo [a] pyrene to mouse lung and skin, whereas inhibitors such as SKF 525A may increase the tumour production from certain polycyclic hydrocarbons. 

SANTELLA ET AL. Human Exposure to Benzo[aJpyrene and Afiatoxin Bj 237... 

US EPA. 1994b. Toxicity Summary for BENZO[AJPYRENE. [on line]. [2009-01-20]. URL < http //rais.oml.gov/tox/ profiles/bap.slitnil>... 

U. S. EPA. 1991. Dose-Response Analysis of Ingested Benzo[ajpyrene (CAS No. 50-32-8). Human Health Assessment Group, Office of Health and Environmental Assessment, Washington, DC. EPA/600/R-92/045. 

McElroy AE, Cahill JM, Sisson JD, Kleinow KM (1991) Relative bioavailability and DNA adduct formation of benzo[ajpyrene and metabolites in the diet of the winter flounder. Comp Biochem Physiol 100C 29-32. 

Benzo [ajpyrene benzo [a]pyrenediolepoxide asp/glu Benzo [a] pyrene-tetrols NCI 53, ii... 

---