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Phase I reactions include microsomal monooxygenations, cytosolic and mitochondrial oxidations, co-oxidations in the prostaglandin synthetase reaction, reductions, hydrolyses, and epoxide hydration. All of these reactions, with the exception of reductions, introduce polar groups to the molecule that, in most cases, can be conjugated during phase II metabolism. The major phase I reactions are summarized in Table 7.1.
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7.2.1 The Endoplasmic Reticulum, Microsomal Preparation, and Monooxygenations
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Monooxygenation of xenobiotics are catalyzed either by the cytochrome P450 (CYP)dependent monooxygenase system or by avin-containing monooxygenases (FMO).
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Table 7.1 Summary of Some Important Oxidative and Reductive Reactions of Xenobiotics Examples Aldrin, benzo(a)pyrene, a atoxin, bromobenzene Ethylmorphine, atrazine, p-nitroanisole, methylmercaptan Thiobenzamide, chlorpromazine, 2-acetylamino uorene Parathion, carbon disul de Carbon tetrachloride, chloroform Nitrobenzene O-Aminoazotoluene Nicotine, imiprimine, thiourea, methimazole Fonofos Acetaminophen, benzidine, epinephrine Benzphetamine, dimethylaniline Benzo(a)pyrene, 2-amino uorene, phenylbutazone FANFT, ANFT, bilirubin Purines, pteridine, methotrexate, 6-deoxycyclovir Aromatic nitrocompounds, azo dyes, nitrosoamines Methanol, ethanol, glycols, glycol ethers Aldehydes and ketones Aldehydes resulting from alcohol and glycol oxidations Parathion, paraoxon, dimethoate Benzo(a)pyrene epoxide, styrene oxide
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Enzymes and Reactions Cytochrome P450 Epoxidation/hydroxylation N-, O-, S-Dealkylation N-, S-, P -Oxidation Desulfuration Dehalogenation Nitro reduction Azo reduction Flavin-containing monooxygenase N-, S-, P -Oxidation Desulfuration Prostaglandin synthetase cooxidation Dehydrogenation N-Dealkylation Epoxidation/hydroxylation Oxidation Molybdenum hydroxylases Oxidation Reductions Alcohol dehydrogenase Oxidation Reduction Aldehyde dehydrogenase Oxidation Esterases and amidases Hydrolysis Epoxide hydrolase Hydrolysis
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Both are located in the endoplasmic reticulum of the cell and have been studied in many tissues and organisms. This is particularly true of CYPs, probably the most studied of all enzymes. Microsomes are derived from the endoplasmic reticulum as a result of tissue homogenization and are isolated by centrifugation of the postmitochondrial supernatant fraction, described below. The endoplasmic reticulum is an anastomosing network of lipoprotein membranes extending from the plasma membrane to the nucleus and mitochrondria, whereas the microsomal fraction derived from it consists of membranous vesicles contaminated with free ribosomes, glycogen granules, and fragments of other subcellular structures such as mitochondria and Golgi apparatus. The endoplasmic reticulum, and consequently the microsomes derived from it, consists of two types, rough and smooth, the former having an outer membrane studded with ribosomes, which the latter characteristically lack. Although both rough and smooth microsomes have all of the components of the CYP-dependent monooxygenase system, the speci c activity of the smooth type is usually higher. The preparation of microsomal fractions, S9, and cytosolic fractions from tissue homogenates involves the use of two to three centrifugation steps. Following tissue extraction, careful mincing, and rinses of tissue for blood removal, the tissues are typically homogenized in buffer and centrifuged at 10,000 g for 20 minutes. The resulting supernatant, often referred to as the S9 fraction, can be used in studies where both microsomal and cytosolic enzymes are desired. More often, however, the S9 fraction is centrifuged at 100,000 g for 60 minutes to yield a microsomal pellet and a cytosolic supernatant. The pellet is typically resuspended in a volume of buffer, which will give 20 to 50 mg protein/ml and stored at 20 to 70 C. Often, the microsomal pellet is resuspended a second time and resedimented at 100,000 g for 60 minutes to further remove contaminating hemoglobin and other proteins. As described above, enzymes within the microsomal fraction (or microsomes) include CYPs, FMOs, cyclooxygenases, and other membrane-bound enzymes, including necessary coenzymes such as NADPH cytochrome P450 reductase for CYP. Enzymes found in the cytosolic fraction (derived from the supernatant of the rst 100,000 g spin) include hydrolases and most of the conjugating enzymes such as glutathione transferases, glucuronidases, sulfotransferases, methyl transferases, and acetylases. It is important to note that some cytosolic enzymes can also be found in microsomal fractions, although the opposite is not generally the case. Monooxygenations, previously known as mixed-function oxidations, are those oxidations in which one atom of a molecule of oxygen is incorporated into the substrate while the other is reduced to water. Because the electrons involved in the reduction of CYPs or FMOs are derived from NADPH, the overall reaction can be written as follows (where RH is the substrate): RH + O2 + NADPH + H+ NADP+ + ROH + H2 O.
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