Research paperGlucuronide conjugates of 4-aminobiphenyl and its N-hydroxy metabolites: pH stability and synthesis by human and dog liver☆
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Cited by (48)
Recent technical and biological development in the analysis of biomarker N-deoxyguanosine-C8-4-aminobiphenyl
2018, Journal of Chromatography B: Analytical Technologies in the Biomedical and Life SciencesCitation Excerpt :The sulfation in the liver has been shown to be related with the formation of DNA adducts in liver, as the metabolites may be highly labile and reactive [18] and may cause liver cancer. In contrast, glucuronidation in the liver may lead to bladder cancer, as the metabolites, once excreted in the urine, may be labile especially in acidic urine and may deliver carcinogenic species to the bladder epithelium [19,20]. 4-ABP binds primarily to the C-8 site of guanine and forms dG-C8-4-ABP to cause what is referred to as nucleobase lesions on the DNA sequence.
Impact of enzymatic hydrolysis on the quantification of total urinary concentrations of chemical biomarkers
2018, ChemosphereCitation Excerpt :For samples with relatively low triclocarban concentrations, 5 units H-1 enzyme/μL urine completely hydrolyzed N-glucuronide triclocarban, but only after at least 31 h, too long of an incubation time for large-scale biomonitoring studies which favor high throughput analytical methods. The results from this experiment also supported β-glucuronidase preferential hydrolysis of O-glucuronides over N-glucuronides, as reported before (Babu et al., 1996; Hawes, 1998; Zenser et al., 1999). We then tested the efficiency of N-glucuronide triclocarban hydrolysis with variable amounts of H-1 enzyme (equivalent to 5, 20, 30, or 36 units/μL urine) added to 100 μL of urine (S6 and S7), and incubated at 37 °C for 4, 8, 24, or 48 h. Hydrolysis was complete within 4 h of incubation when using 30 units enzyme/μL urine (Fig. 1B and C), 6 times more than the amount used previously for the quantification of environmental phenols (Ye et al., 2005a; Zhou et al., 2014).
Chapter 3 Glucuronidation-Dependent Toxicity and Bioactivation
2008, Advances in Molecular ToxicologyCitation Excerpt :Interestingly, UGTs do not appear to catalyse the formation of N-O-linked glucuronide conjugates of arylhydroxylamines, and these species may be formed only as decomposition products of arylhydroxamic acid N-O-linked glucuronides. At physiological pH and temperature, the half-lives of the N-O-glucuronides of arylhydroxamic acids in aqueous buffered solutions range from >24 h for N-OH-N,N′-diacetylbenzidine O-glucuronide [74] to 2 h and 68 min for N-OH-N-acetylbenzidine O-glucuronide [74] and N-OH-N-acetyl-4-aminobiphenyl O-glucuronide [75], respectively, suggesting that the aryl chemical structure significantly affects reactivity. The formation of N-linked glucuronide conjugates of arylhydroxylamines and arylamines is also catalysed by UGTs and, although acid-labile, they are not considered bioactivation products [74–76], but are thought to influence the carcinogenicity of arylamines and heterocyclic amines by acting as shuttles for CYP and N-acetyltransferase bioactivation products to the bladder and gastrointestinal tract (see Section 6.2).
Urine pH and Risk of Bladder Cancer in Northern New England
2023, Cancer Epidemiology Biomarkers and Prevention
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This work was supported by the Department of Veterans Affairs (T.V.Z. and B.B.D.).