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dodecyl sulfate polyacrylamide gel electrophoresis (SDS-PAGE), which could then be related to distinct CYPs present in the original microsomes. Puri cation of CYP and its usual constituent isoforms was, for many years, an elusive goal; one, however, that has been largely resolved. The problem of instability on solubilization was resolved by the use of glycerol and dithiothreitol as protectants, and the problem of reaggregation by maintaining a low concentration of a suitable detergent, such as Emulgen 911 (Kao-Atlas, Tokyo), throughout the procedure. Multiple CYP isoforms, as discussed previously, may be separated from each other and puri ed as separate entities, although individual isoforms are now routinely cloned and expressed as single entities. The lengthy processes of column puri cation of CYPs have now been largely superceded by the cloning and expression of transgenic isoforms in a variety of expression systems. Systems reconstituted from puri ed CYP, NADPH-cytochrome P450 reductase and phosphatidylchloline will, in the presence of NADPH and O2 , oxidize xenobiotics such as benzphetamine, often at rates comparable to microsomes. Although systems reconstituted from this minimal number of components are enzymatically active, other microsomal components, such as cytochrome b5 , may facilitate activity either in vivo or in vitro or may even be essential for the oxidation of certain substrates. One important nding from puri cation studies as well as cloning and expressing of individual isoforms is that the lack of substrate speci city of microsomes for monooxygenase activity is not an artifact caused by the presence of several speci c cytochromes. Rather, it appears that many of the cytochromes isolated are still relatively nonspeci c. The relative activity toward different substrates does nevertheless vary greatly from one CYP isoform to another even when both are relatively nonspeci c. This lack of speci city is illustrated in Table 7.2, using human isoforms as examples.
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Classi cation and Evolution of Cytochrome P450. The techniques of molecular biology have been applied extensively to the study of CYP. More than 1925 genes have been characterized as of 2002, and the nucleotide and derived amino acid sequences compared. In some cases the location of the gene on a particular chromosome has been determined and the mechanism of gene expression investigated. A system of nomenclature proposed in 1987 has since been updated several times, most recently in 1996. The accepted guidelines from nomenclature designate cytochrome P450 genes as CYP (or cyp in the case of mouse genes). The CYP designation is followed by an Arabic numeral to denote the gene family, followed by a letter designating the subfamily. The individual isoform is then identi ed using a second Arabic numeral following the subfamily designation. Polymorphic isoforms of genes are indicated by an asterisk followed by an arabic numeral. If there are no subfamilies or if there is only a single gene within the family or subfamily, the letter and/or the second numeral may be omitted (e.g., CYP17). The name of the gene is italicized, whereas the protein (enzyme) is not. In general, enzymes within a gene family share more than 40% amino acid sequence identity. Protein sequences within subfamilies have greater than 55% similarity in the case of mammalian genes, or 46% in the case of nonmammalian genes. So far, genes in the same subfamily have been found to lie on the same chromosome within the same gene cluster and are nonsegregating, suggesting a common origin through gene duplication events. Sequences showing less than 3% divergence are arbitrarily designated allelic variants unless other evidence exists to the contrary. Known sequences t
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METABOLISM OF TOXICANTS
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Table 7.2 P450 1A1
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Some Important Human Cytochrome P450 Isozymes and Selected Substrates Drugs Carcinogens/Toxicants/ Endogenous Substrates Diagnostic Substrates In vivo [In vitro] [Ethoxyresoru n, benzo(a)pyrene] Caffeine, [acetanilide, methoxyresoru n, ethoxyresoru n] Coumarin [7-ethoxy-4-tri uoromethyl coumarin] [Chloromethyl uorescein diethyl ether] [Diclofenac (4 -OH)]
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Verlukast (very few drugs) Benzo(a)pyrene, dimethylbenz(a)anthracene 1A2 Phenacetin, theophylline, Aromatic amines, acetaminophen, arylhydrocarbons, NNK,3 a atoxin, estradiol warfarin, caffeine, cimetidine 2A6 Coumarin, nicotine A atoxin, diethylnitrosamine, NNK3 2B6 Cyclophosphamide, 6 Aminochrysene, a atoxin, ifosphamide, nicotine NNK3 2C8 Taxol, tolbutamide, carbamazepine 2C9 Tienilic acid, tolbutamide, warfarin, phenytoin, THC, hexobarbital, diclofenac 2C19 S-Mephenytoin, diazepam, phenytoin, omeprazole, indomethacin, impramine, propanolol, proguanil 2D6 Debrisoquine, sparteine, NNK3 bufuralol, propanolol, thioridazine, quinidine, phenytoin, uoxetine 2E1 Chlorzoxazone, isoniazid, Dimethylnitrosamine, benacetaminophen, zene, halogenated alkanes halothane, en urane, (eg, CCl4 ) acylonitrile, alcohols, aniline, styrene, methoxy urane vinyl chloride 3A4 Nifedipine, ethylmorphine, A atoxin, 1-nitropyrene, warfarin, quinidine, benzo(a)pyrene 7,8-diol, 6 taxol, ketoconazole, aminochrysene, estradiol, verapamil, progesterone, testosterone, erythromycin, diazepam other steroids, bile acids 4A9/11 (Very few drugs) Fatty acids, prostaglandins, thromboxane, prostacyclin
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[S-Mephentoin (4 -OH)]
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Dextromethorphan, [bufuralol (4 -OH)
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