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consumption of very well-done fried beef (199). In the United States, the urinary excretion of 8-MeIQx and total acid-labile phase II conjugates of 8MeIQx in male African-American subjects was 1.3- and 3.0-fold higher than in Asians and Caucasians, respectively (200). These differences in urinary 8MeIQx content are probably due to racial dietary preferences for consuming fried beef or bacon rather than racial genetic differences. The urinary concentrations of 8-MelQx were positively associated with intake frequencies of bacon, pork/ham, and sausage/luncheon meats among study subjects. However, the urinary excretion concentrations of PhIP did not correlate with intake frequencies of any cooked meat, when the self-administered dietary questionnaire responses of the same group of subjects were analyzed (201). Therefore, urinary excretion levels of a single HAA may not serve as a reliable predictor of other levels of HAAs, in estimates of exposure to these compounds, for humans consuming unrestricted diets. Individual expression of P450 1A2 can affect the metabolism and genotoxic potency of HAAs (202). The constitutive P450 1A2 mRNA expression levels in human liver can vary by as much as 15-fold (203, 204), and interindividual expression of P450 1A2 protein may vary by 60-fold in human liver (205 208). The variable expression of P450 1A2 in humans is attributed to environmental and dietary factors, such as smoking (209 211) and frequent consumption of cruciferous vegetables (212, 213) and grilled meats (214), all of which induce P450 1A2 expression. Several genetic polymorphisms (215, 216) and a variation in the extent of CpG methylation (204) have been detected in the upstream 5 -regulatory region of the P450 1A2 gene; these can affect the level of P4501A2 mRNA expression, and can lead to variation in the level of protein expression. In the case of 8-MeIQx, lower concentrations of the unchanged compound were found in the urine of individuals with high P450 1A2 activity, indicating that P450 1A2 is an important enzyme in the metabolism of 8-MeIQx in vivo (217). The contribution of P450 1A2 to the metabolism of PhIP in humans was reported to be less important than the enzyme s contribution to the metabolism of 8-MeIQx (218). However, glutathione S-transferases (GSTs) are able to reduce N-hydroxy-PhIP and N-acetoxy-PhIP back to the parent amine, and the occurrence of this reverse reaction can obscure the relationship between rapid P450 1A2 activity and PhIP metabolism (168). The importance of P450 1A2 in the metabolism of MeIQx and PhIP in humans was demonstrated in a pharmacokinetic study that used furafylline, a mechanism-based inhibitor of P450 1A2 (219). In that study, as much as 91% of the MeIQx and 70% of the PhIP following consumption of grilled meat were estimated to undergo metabolism by the enzyme (195). The major pathways of metabolism of 8-MeIQx and PhIP in humans have been characterized (196, 220 222). Direct glucuronidation of these HAAs and their genotoxic N-hydroxylated metabolites was reported to be the major pathways of metabolism (Fig. 2.3.6). The levels of glucuronide conjugates of N-hydroxy-MeIQx and N-hydroxy-PhIP in urine were signi cantly higher than the levels measured in the urine of rodents (196, 197, 213), a nding consistent with the superior catalytic ef ciency of human P450 1A2, relative
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METABOLISM OF HAAs AND IMPLEMENTATION (a)
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N HO O HO OH HO OH HON-PhIP-N 3 -Gl HON-PhIP-N 2-Gl UGT1A1 P450 1A1, 1A2, 1B1 CH3 H N NADPH N N OH Reductase
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OH O
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H3 C N N N OH N N CH 3 O HO O OH HO OH N H3C N N H N O HO O H 3C OH HO OH N MeIQx-N 2SO3 H N IQx-8-CH2OH N O OH HN S O N N CH HO-H2C 3 NH 2 N N N CH 3 HO O C N N N IQx-8-COOH P450 1A2 N CH 3 NH 2
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