Hydrocarbons carcinogenic

Lee H, RG Harvey (1986) Synthesis of the active diol epoxide metabolites of the potent carcinogenic hydrocarbon 7,12-dunethybenz[a]anthacene. J Am Chem Soc 51 3502-3507. 

Immediately after the first few carcinogenic hydrocarbons were identified, scientists puzzled over the developing structure-activity relationships and tried to identify the structural features of the hydrocarbons which are associated with their carcinogenic activity. 

The structure-activity considerations at that time naturally enough focussed interest on epoxides formed at the K-regions of the carcinogenic hydrocarbons (Figure 3), but it was not until 1964 that the synthesis of such putative metabolites was achieved (46). 

There have also been reports of neoplasms in native bottomfeeding fish with a suggestion that carcinogenic hydrocarbons from motor boat exhausts, rotenone and insecticides such as DDT may be involved as causative agents (59.). Similarly (an) unidentified carcinogen(s) are suspected in the case of adematous polyps of gastric mucosa of fish, reported recently (60). The diet of these fish was free of aflatoxins. 

Berwald, Y. and Sachs, L. (1965). In vitro transformation of normal cells to tumor cells by carcinogenic hydrocarbons, J. Natl. Cancer Inst. 35,641. 

Chen, T.T. and Heidelberger, C. (1969). Quantitative studies on the malignant transformation of mouse prostate cells by carcinogenic hydrocarbons in vitro, Int. J. Cancer 4,166. 

Huberman, E. and Sachs, L. (1966). Cell susceptibility to transformation and cytotoxicity by the carcinogenic hydrocarbon benzo[a]pyrene, Proc. Natl. Acad. Sd. 56,1123,... 

Other cycloadditions of interest include the photoaddition [Eq. (52)] of pyrimidine derivatives such as cytosine to the carcinogenic hydrocarbon benzo[a]pyrene,191 and the photoaddition of allene as a vital step [Eq. (53)] in the synthesis of an annotinine derivative.192... 

STRUCTURAL SIMILARITY BETWEEN SOME ANTINEOPLASTIC AGENTS AND POLYCYCLIC CARCINOGENIC HYDROCARBONS 37... 

Humans have used fire for cooking since about 105 years ago. The presence of polycyclic aromatic hydrocarbons in broiled foods such as beefsteak and broiled fish has been reported (1, 2). The presence of genotoxic substances in broiled foods other than typical carcinogenic hydrocarbons was detected after the development of Ames Salmonella/mammalian-microsome test (3). Charred parts of broiled fish and meat showed mutagenicity towards Salmonella typhirmcrium TA98, a fraraeshift mutant of histidine auxotroph, in the presence of S9 mix, a mixture of rat liver... 

Recent work on the relation between film structure and constitution Incorporation of carcinogenic hydrocarbons in sterol 61ms. ... 

The remarkable progress achieved by Vouros et al. [120,121] in the CEC analysis of isomeric polyaromatic hydrocarbon deoxyribonucleic acid (DNA) adducts derived from in-vitro reactions of carcinogenic hydrocarbons with calf thymus DNA has been illustrated in a previous section. This work represents an... 

Substitution of a methyl group (electron donor) at a position of high free valency increases the action (the 10-methyl derivative is active). In 1, 2, 5, 6-dibenzanthracene, one of the first known carcinogenic hydrocarbons, there are two bonds, 3—4 and 7—8, which both possess a high TT-electron density. The difference between the inactive 1, 2-benzopyrene and the active 3, 4-benzopyrene from coal tar would be due to the fact that the former possesses one K region, the 6—7 bond, the latter, however, has also the 1—2 bond as such. 

Hypersensitivity reactions are rare, but a few have been reported after inhalation. Delayed hypersensitivity reactions, particularly affecting vascular tissue, have been recorded with chronic systemic administration. Tumor-inducing effects are difficult to attribute to cannabis alone. Animal studies have shown neoplastic pulmonary lesions superimposed on chronic inflammation, but such pathology may be primarily associated with the tar produced by burning marijuana. The most serious potential adverse effects of cannabis use come from the inhalation of the same carcinogenic hydrocarbons that are present in tobacco, and some data suggest that heavy cannabis users are at risk of chronic respiratory diseases and lung cancer. 

The same idea accounts for the site selectivity in the reactions of the carcinogenic hydrocarbons 6.282 and 6.283, both of which react with osmium tetroxide in the K-region. The contrast is with the behaviour of these hydrocarbons with other oxidising agents, like lead tetraacetate, chromic acid and sulfuryl chloride, which react only at one site at a time none of the hydrocarbons 6.280, 6.282 or 6.283 reacts in the K-region with these reagents. Instead, reaction takes place at... 

One of the many enzyme functions of hepatocytes is the hydroxyla-tion of various drugs (aminopyrine, codeine, hexobarbital, etc.) cyclic compounds, and carcinogenic hydrocarbons (benzopyrenes, benzanthracene), steroid hormones (testosterone), fatty acids (lauric acid), etc. All these functions are carried out by an organized multienzyme system in the endoplasmic reticulum membrane (Gillette and Gram, 1969). The endoplasmic reticulum can be obtained by differential centrifugation in the form of membranous vesicles called microsomes. 

According to Hall (80a) adsorption on silica-alumina in the presence of isoctane, displays for pyrene bands at 462 and 467, and for 3,4-benzopyrene, the carcinogenic hydrocarbon, bands at 520 and 782 mju., corresponding evidently to similar cation radicals and to carbonium cations. It was presumed that these latter are not of the protonated form, but represent a positively charged configuration, covalently bound to an electrophilic (Al) site, like that schematically represented in Section VD for chemisorbed olefins. 

Daniel PM, Pratt OE, Prichard MML. 1967. Metabolism of labelled carcinogenic hydrocarbons in rats. Nature 215 1142-1146. 

Hoch-Ligeti C. 1941. Studies on the changes in the lymphoid tissue of mice treated with carcinogenic and non-carcinogenic hydrocarbons. Cancer Res 1 484-488. 

Lorenz E, Stewart HL. 1948. Tumors of alimentary tract in mice fed carcinogenic hydrocarbons in mineral oil emulsions. J Natl Cancer Inst 9 173. 

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