Acetylamino uorene in VS .NET

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8.6.6 Acetylamino uorene
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In the case of the hepatocarcinogen, 2-acetylamino uorene (2-AAF), two activation steps are necessary to form the reactive metabolites (Figure 8.4). The initial reaction, N -hydroxylation, is a CYP-dependent phase I reaction, whereas the second reaction, resulting in the formation of the unstable sulfate ester, is a phase II conjugation reaction that results in the formation of the reactive intermediate. Another phase II reaction, glucuronide conjugation, is a detoxication step, resulting in a readily excreted conjugation product. In some animal species, 2-AAF is known to be carcinogenic, whereas in other species it is noncarcinogenic. The species- and sex-speci c carcinogenic potential of
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COCH3 N NHCOCH3 2-Acetylaminofluorene 2-AAF OH N-Hydroxy AAF N O -glucuronide Glucuronide conjugate (detoxication) COCH3 N OSO3 + Binding to tissue macromolecules COCH3
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P450
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COCH3 + N
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Sulfate conjugate
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Figure 8.4 Bioactivation of 2-acetylamino uorene.
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REACTIVE METABOLITES
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2-AAF is correlated with the ability of the organism to sequentially produce the N hydroxylated metabolite followed by the sulfate ester. Therefore in an animal such as the guinea pig, which does not produce the N -hydroxylated metabolite, 2-AAF is not carcinogenic. In contrast, both male and female rats produce the N -hydroxylated metabolite, but only male rats have high rates of tumor formation. This is because male rats have up to 10-fold greater expression of sulfotransferase 1C1 than female rats, which has been implicated in the sulfate conjugation of 2-AAF resulting in higher production of the carcinogenic metabolite.
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Benzo(a)pyrene
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The polycyclic aromatic hydrocarbons are a group of chemicals consisting of two or more condensed aromatic rings that are formed primarily from incomplete combustion of organic materials including wood, coal, mineral oil, motor vehicle exhaust, and cigarette smoke. Early studies of cancer in the 1920s involving the fractionation of coal tar identi ed the carcinogenic potency of pure polycyclic aromatic hydrocarbons, including dibenz(a,h)anthracene and benzo(a)pyrene. Although several hundred different polycyclic aromatic hydrocarbons are known, environmental monitoring usually only detects a few compounds, one of the most important of which is benzo(a)pyrene. Benzo(a)pyrene is also one of the most prevalent polycyclic aromatic hydrocarbons found in cigarette smoke. Extensive studies of metabolism of benzo(a)pyrene have identi ed at least 15 phase I metabolites. The majority of these are the result of CYP1A1 and epoxide hydrolase reactions. Many of these metabolites are further metabolized by phase II enzymes to produce numerous different metabolites. Studies examining the carcinogenicity of this compound have identi ed the 7,8-oxide and 7,8-dihydrodiol as proximate carcinogens and the 7,8-diol-9,10 epoxide as a strong mutagen and ultimate carcinogen. Because of the stereoselective metabolizing abilities of CYP isoforms, the reactive 7,8-diol-9,10epoxide can appear as four different isomers. (Figure 8.5). Interestingly only one of these isomers(+)-benzo(a)pyrene 7,8-diol-9,10 epoxide-2 has signi cant carcinogenic potential. Comparative studies with several other polycyclic aromatic hydrocarbons have demonstrated that only those substances that are epoxidized in the bay region of the ring system possess carcinogenic properties.
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Acetaminophen
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A good example of the importance of tissue availability of the conjugating chemical is found with acetaminophen. At normal therapeutic doses, acetaminophen is safe, but can be hepatotoxic at high doses. The major portion of acetaminophen is conjugated with either sulfate or glucuronic acid to form water-soluble, readily excreted metabolites and only small amounts of the reactive intermediate, believed to be quinoneimine, are formed by the CYP enzymes (Figure 8.6). When therapeutic doses of acetaminophen are ingested, the small amount of reactive intermediate forms is ef ciently deactivated by conjugation with glutathione. When large doses are ingested, however, the sulfate and glucuronide cofactors (PAPS and UDPGA) become depleted, resulting in more of the acetaminophen being metabolized to the reactive intermediate.
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EXAMPLES OF ACTIVATING REACTIONS
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O Benzo(a)pyrene 7,8 epoxide of benzo(a)pyrene
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HO OH HO O OH 7,8 dihydrodiol of benzo(a)pyrene
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HO OH 7,8-diol-9,10-epoxides of benozo(a)pyrene
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Figure 8.5 Selected stages of biotransformation of benzo(a)pyrene. The diol epoxide can exist in four diastereoisomeric forms of which the key carcinogenic metabolite is (+)-benzo(a)pyrene 7,8-diol-9,10-epoxide.
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As long as glutathione (GSH) is available, most of the reactive intermediate can be detoxi ed. When the concentration of GSH in the liver also becomes depleted, however, covalent binding to sulfhydryl (-SH) groups of various cellular proteins increases, resulting in hepatic necrosis. If suf ciently large amounts of acetaminophen are ingested, as in drug overdoses and suicide attempts, extensive liver damage and death may result.
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