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Benzo[a]pyrene (BaP or B[a]P) is a polycyclic aromatic hydrocarbon and the result of incomplete combustion of organic matter at temperatures between 300 °C (572 °F) and 600 °C (1,112 °F). The ubiquitous compound can be found in coal tar, tobacco smoke and many foods, especially grilled meats.
The mechanism of action of benzo[a]pyrene-related DNA modification has been investigated extensively and relates to the activity of cytochrome P450 subclass 1A1 . [3] Seemingly, the high activity of CYP1A1 in the intestinal mucosa prevents major amounts of ingested benzo[a]pyrene from entering portal blood and systemic circulation. [4]
Genes of enzymes activating the breakdown of foreign and often toxic compounds are classic examples of such genes (enzyme induction). TCDD increases the enzymes breaking down, e.g., carcinogenic polycyclic hydrocarbons such as benzo(a)pyrene. [10] These polycyclic hydrocarbons also activate the AH receptor, but less than TCDD and only ...
In this reaction, the oxidation of benzo[a]pyrene is catalysed by CYP1A1 to form BaP-7,8-epoxide, which can be further oxidized by epoxide hydrolase (EH) to form BaP-7,8-dihydrodiol. Finally, CYP1A1 catalyses this intermediate to form BaP-7,8-dihydrodiol-9,10-epoxide , which is a carcinogen .
Benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide is a metabolite of benzo[a]pyrene formed by the introduction of vicinal hydroxyl and epoxide functional groups to the fifth benzene ring. [7] These oxidations are stereoselective , producing the pair of enantiomers with the hydroxyl groups on opposite sides of the pyrene plane and with the epoxide on ...
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Pyrene is a polycyclic aromatic hydrocarbon (PAH) consisting of four fused benzene rings, resulting in a flat aromatic system. The chemical formula is C 16 H 10. This yellow-green solid is the smallest peri-fused PAH (one where the rings are fused through more than one face). Pyrene forms during incomplete combustion of organic compounds. [10]
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