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Figure 7.2 UPGMA tree of 54 puffer sh (fugu), 60 human, and 8 other sh P450s. Species are indicated by f , h, z, c, k, s, and t for fugu, human, zebra sh, cat sh, killi sh, seabass, and trout, respectively. (Reprinted from D. R. Nelson, Archives of Biochemistry and Biophysics 409, pp. 18 24. 2003, with permission from Academic Press.)
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Because these two highly homologous forms are so highly conserved among species, it is thought that both may possess important endogenous functions that have yet to be elucidated. CYP2E1 is the only other CYP that retains the same gene designation in many different species. CYP1A1 and CYP1A2 possess distinct but overlapping substrate speci cities: CYP1A1 preferring neutral polycyclic aromatic hydrocarbons (PAHs), and the latter preferring polyaromatic and heterocyclic amines and amides. Because of the preference of this family for molecules with highly planar molecular structures, CYP1 family members are closely associated with metabolic activation of many procarcinogens and mutagens including benzo(a)pyrene, a atoxin B1, dimethylbenzanthracene, naphthylamine, 4-aminobiphenyl, 2-acetylamino ourene, and benzidine. Figure 7.3 illustrates a typical reaction sequence leading to the formation of epoxide and the epoxide diols that are often implicated in the formation of carcinogenic metabolites formed by these enzymes. Many of the planar PAH compounds induce their own metabolism by inducing transcription of the aryl hydrocarbon receptor (Ah receptor). Although expression of CYP1A1 and 1A2 is often coordinately induced, there are clear differences in regulation, not only with respect to substrate speci city but also in their biological expression. For example, CYP1A1 does not appear to be expressed in human liver unless induced,
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Examples of epoxidation reactions.
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whereas CYP1A2 is endogenously expressed in the liver. CYP1A1, however, is present in many extrahepatic tissues including the lung, where there is a possible association between CYP-mediated activation of benzo(a)pyrene and other related chemicals present in cigarette smoke and lung cancer in humans. The CYP2 family consists of 10 subfamilies, ve of which are present in mammalian liver. Some of the more important isoforms found in humans within this family are CYP2A6, -2B6, -2C8, -2C9, -2C19, -2D6, and -2E1. The enzyme CYP2A6 is expressed primarily in liver tissue, where it represents 1 10% of total CYP content. CYP2A6 is responsible for the 7-hydroxylation of the naturally occurring plant compound coumarin and its activity is often phenotyped by monitoring this particular metabolic pathway. Other drugs metabolized by CYP2A6 include nicotine, 2-acetylamino uorene, methoxy urane, halothane, valproic acid, and disul ram. Precarcinogens likely activated by 2A6 include a atoxin B1, 1,3 butadiene, 2,6-dichlorobenzonitrile, and a number of nitrosamines. Because CYP2A6 is responsible for up to 80% of the human metabolism of nicotine, a number of studies have been conducted to determine whether individuals with 2A6 polymorphisms have reduced risk of lung cancers. Although theoretically individuals lacking 2A6 would be expected to smoke less and be less likely to activate carcinogens found in tobacco smoke, studies have not conclusively demonstrated any clear associations between 2A6 polymorphisms and risk of lung cancer. Like CYP2A6, the human isoform CYP2B6 has recently gained greater recognition for its role in metabolism of many clinical drugs. Some common pharmaceutical substrates for CYP2B6 include cyclophosphamide, nevirapine, S-mephobarbitol, artemisinin, bupropion, propofol, ifosfamide, ketamine, selegiline, and methadone. CYP2B6 has also been demonstrated to have a role in the activation of the organophosphate, chlorpyrifos, and in the degradation of the commonly used insecticide repellant, diethyl toluamide (DEET). Historically it was thought that CYP2B6 is found in a small proportion of livers (<25%), but more recent data using antibodies prepared from human proteins have demonstrated that most liver samples have detectable levels of 2B6, though greater than 20-fold differences in levels of protein have been observed. In contrast with CYP2A6 and CYP2B6, members of the CYP2C family constitute a fairly large percentage of CYP in human liver (ca. 20%) and are responsible for the metabolism of several drugs. All four members of the subfamily in humans exhibit genetic polymorphisms, many of which have important clinical consequences in affected individuals. Genetic polymorphisms in CYP2C19 were shown to be responsible for one of the rst described polymorphic effects, that involving mephenytoin metabolism. This polymorphism signi cantly reduces the metabolism of mephenytoin, resulting in the classi cation of those individuals possessing this trait as poor metabolizers (PM). Among Caucasians, PMs represent only 3 5% of the populations, while in Asian and Polynesian populations 12 23% and 38 79% of the populations are represented, respectively. At least seven different mutations in this allele have been described, some of which negatively affect catalytic activity while others prevent expression of the protein. Other important drugs affected by these CYP2C19 polymorphisms include the anti-ulcer drug omeprazole, other important proton pump inhibitors, barbiturates, certain tricyclic antidepressants such as imipramine, and the antimalarial drug proguanil. Other important members of the CYP2C family in humans include CYP2C8, -2C9, and -2C18. Substrates metabolized exclusively by CYP2C8 include retinol, retinoic acid, taxol, and arachidonic acid. CYP2C9, the principal CYP2C in
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