Carcinogens polycyclic aromatic hydrocarbons

Metabolites of carcinogenic polycyclic aromatic hydrocarbons (PAH) such as ( ) trans-7,8-dihydroxy-anti-9,10-epoxy-7,8,9,10-tetrahy-drobenzo[a]pyrene (BPDE) and 7,8,9,10-tetrahydroxytetrahydroben-zo[ a] pyrene (BPT) participate in tt binding interactions with nucleotide bases (1-19) which lead to the reversible formation of... 

Grimmer, G. (ed.). 1983. Environmental Carcinogens Polycyclic Aromatic Hydrocarbons. Chemistry, Occurrence, Biochemistry, Carcinogenicity. CRC Press, Boca Raton, FL. 261 pp. 

Tong C, Fazio M, Williams GM. 1981. Rat hepatocyte-mediated mutagenesis of human cells by carcinogenic polycyclic aromatic hydrocarbons but not organochlorine pesticides. Proc Soc Exp Biol Med 167(4) 572-575. 

Fig. 5 Typical deformations detected in 96 hpf zebrafish embryos exposed at the indicated concentrations of the carcinogenic polycyclic aromatic hydrocarbons Benzo[a]Pyrene (b) and Benazo [k]Fluoranthene (c), or to the reportedly nontoxic AhR-ligand (3-naphthofiavone (d). A nonexposed, normal specimen is shown in (a). Arrows indicate (a) pericardial edema, (b) malformation of the lower jaw, (c) malformation of the tail, (tf) color of the yolk, and (e) coagulation...

Use of Response/Effect Addition in the Risk Assessment of Mixtures OF Carcinogenic Polycyclic Aromatic Hydrocarbons... 

Schmahl, D., R. P. Deutsch-Wenzel, H. Brune, P. Schneider, U. Mohr, M. Habs, F. Pott, and D. Steinhoff, Biological Activity, in Environmental Carcinogens Polycyclic Aromatic Hydrocarbons (G. Grimmer, Ed.), pp. 157-220, CRC Press, Boca Raton, FL, 1983. 

Initially, particular attention was focused on the epoxides of the so-called K region. As in the case of benzo [a] pyrene and certain other polycyclic aromatic hydrocarbons, these were more carcinogenic than the parent compound. The K region had attracted particular interest, as it is electronically the most reactive portion of the polycyclic aromatic hydrocarbon molecule. However, with other carcinogenic polycyclic aromatic hydrocarbons, this was not found to be the case. It now seems that the ultimate carcinogen is an epoxide of a dihydrodiol metabolite, where the epoxide is adjacent to the so-called bay region (Fig. 7.2). 

Carcinogenic polycyclic aromatic hydrocarbons can contaminate smoked food (Bartle, 1991), although the main dietary sources of these compounds in the UK appear to be early in food production. 

GRIMMER G (eds) Environmental Carcinogens Polycyclic Aromatic Hydrocarbons, CRC Press, Boca Raton, 1983. 

One of the most potent carcinogenic polycyclic aromatic hydrocarbons. In animals, large single and multiple doses produce tumors of the skin, breast, and stomach or leukemias, regardless of route of administration. It is a strong mutagen after metabolic activation.2-4... 

H. Yu, Environmental carcinogenic polycyclic aromatic hydrocarbons Photochemistry and phototoxicity. J. Environ. Sci. Health C. Environ. Carcinog. Ecotoxicol. Rev. C20, 149-183... 

Dickhut, R.M., Canuel, E.A., Gustafson, K.E., Liu, K., Arzayus, K.M., Walker, S.E., Edgecombe, G., Gaylor, M.O., and Macdonald, E.H. (2000) Automotive sources of carcinogenic polycyclic aromatic hydrocarbons associated with particulate matter in the Chesapeake bay region. Environ. Sci. Technol. 34, 4635-4640. 

S. M. Adams and L. S. Kaminsky, Mol. Pharmacol., 22, 459 (1982). Molecular Orbital Studies of Epoxide Stability of Carcinogenic Polycyclic Aromatic Hydrocarbon Diol Epoxides. 

Garcia, C., Gonzalez, V, Cornejo, C., Palma-Fleming, H., and Lagos N., 2004. First evidence of dinophysistoxin-1 ester and carcinogenic polycyclic aromatic hydrocarbons in smoked bivalves collected in the Patagonia fjords. Toxicon, 43(2), 121-131. 

Another carcinogenic polycyclic aromatic hydrocarbon, 7,l2-dimethylben/.lajanthracene. also forms covalent adducts with nucleic acids (RNA)."" The ultimate carcinogenic reactive species apparently is the S.6-oxidc that results from epoxidation of the 5,6-double bond in this aromatic hydrocarbon. The arene oxide intermediate binds covalently to guanosinc residues of RNA to yield the two adducts. 

Low concentrations of carcinogenic polycyclic aromatic hydrocarbons (PAHs) have also been evaluated for a potential hormetic effect. Exposure of grunion embryos (Leuresthes tenuis-, a freshwater tel-eost) to 7ppb of benzo [a]pyrene resulted in significantly increased respiration rates compared with unexposed controls, whereas at higher concentrations of 24.2, 361, or 868.8 ppb, respiration rates were not... 

Baird WM, Hooven LA, Mahadevan B. Carcinogenic polycyclic aromatic hydrocarbon-DNA aducts and mechanism of action. Environ Mol Mutagen 2005 45(2-3) 106 14. 

Index Chemical Chemical selected as the basis for standardization of toxicity of components in a chemical class (e.g., 2,3,7,8-tetrachlorodibenzo-p-dioxin [TCDD] for the assessment of dioxin-like compounds benzo[a]pyrene for the assessment of carcinogenic polycyclic aromatic hydrocarbons [PAHs]). 

Pfeiffer EH. 1977. Oncogenic interaction of carcinogenic and non-carcinogenic polycyclic aromatic hydrocarbons in mice lARC Scientific Publication No. 16. Air pollution and cancer in man. Lyon, France International Agency for Research on Cancer, 69-77. 

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