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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.
A metabolite of benzo[]pyrene forms an intercalated DNA adduct, at center. In molecular genetics, a DNA adduct is a segment of DNA bound to a cancer-causing chemical.This process could lead to the development of cancerous cells, or carcinogenesis.
Chemical structure of benzo[a]pyrene Chemical structure of benzo[e]pyrene. A benzopyrene is an organic compound with the formula C 20 H 12.Structurally speaking, the colorless isomers of benzopyrene are pentacyclic hydrocarbons and are fusion products of pyrene and a phenylene group.
The metabolism of the tobacco smoke procarcinogen benzo[a]pyrene involves three distinct steps – the introduction of an epoxide group in the 7,8-position, its hydration to a vicinal diol and the introduction of an epoxide in the 9,10-position.
The Ames test is a widely employed method that uses bacteria to test whether a given chemical can cause mutations in the DNA of the test organism. More formally, it is a biological assay to assess the mutagenic potential of chemical compounds. [ 1 ]
One significant compound the bacteria can biodegrade is benzo(a)pyrene (BaP). [13] BaP is a polycyclic aromatic hydrocarbon (PAH), well-known organic pollutant associated with properties of teratogenicity, mutagenicity, and carcinogenicity. BaP is a degradation-resistant compound; thus, it is more inclined to accumulate in the environment. [14]
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An example is benzo(a)pyrene that is metabolized in two steps, oxidation and conjugation. Oxidation produces epoxide carcinogens that are rapidly detoxified by conjugation, but some molecules may escape to the nucleus of the cell and bind to DNA causing a mutation, resulting in cancer initiation.