Human and Escherichia coli β-glucuronidase hydrolysis of glucuronide conjugates of benzidine and 4-aminobiphenyl, and their hydroxy metabolites

Drug Metabolism and Disposition

Volumn 27, Issue 9, 1999, Pages 1064-1067

  Zenser, Terry V ^a,b   Lakshmi, Vijaya M ^a   Davis, Bernard B ^a  

^a SAINT LOUIS UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b VETERANS AFFAIRS MEDICAL CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 BIPHENYLAMINE; BENZIDINE; BETA GLUCURONIDASE; GLUCURONIDE;

ARTICLE; CONCENTRATION RESPONSE; DNA ADDUCT; DRUG CONJUGATION; DRUG METABOLISM; ENZYME ACTIVITY; ENZYME SUBSTRATE; ESCHERICHIA COLI; GENOTOXICITY; GLUCURONIDATION; HYDROLYSIS; NONHUMAN; PRIORITY JOURNAL;

AMINOBIPHENYL COMPOUNDS; BENZIDINES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; ESCHERICHIA COLI; GLUCURONATES; GLUCURONIDASE; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; HYDROXYLATION; KINETICS; RECOMBINANT PROTEINS;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 0032878806     PISSN: 00909556     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (27)

1. Babu SR, Lakshmi VM, Hsu FF, Kane KE III, Zenser TV and Davis BB (1993) N-Acetylbenzidine-N′-glucuronidation by human, dog, and rat liver. Carcinogenesis 14:2605-2611.
2. Babu SR, Lakshmi VM, Hsu FF, Zenser TV and Davis BB (1992) Role of N-glucuronidation inbenzidine-induced bladder cancer in dog. Carcinogenesis 13:1235-1240.
3. Babu SR, Lakshmi VM, Hsu FF, Zenser TV and Davis BB (1995) Glucuronidation of N-hydroxy metabolites of N-acetylbenzidine. Carcinogenesis 16:3069-3074.
4. Babu SR, Lakshmi VM, Huang GP, Zenser TV and Davis BB (1996) Glucuronide conjugates of 4-aminobiphenyl and its N-hydroxy metabolites: pH stability and synthesis by human and dog liver. Biochem Pharmacol 51:1679-1687.
5. Bank N and Bailine SH (1965) Urinary beta-glucoronidase activity in patients with urinary tract infection. N Engl J Med 272:70-75.
6. Beland FA, Beranek DT, Dooley KL, Heflich RH and Kadlubar FF (1983) Arylamine-DNA adducts in vitro and in vivo: Their role in bacterial mutagenesis and urinary bladder carcinogenesis. Environ Health Perspect 49:125-134.
7. Ciotti M, Lakshmi VM, Nikhil B, Davis BB, Owens IS and Zenser TV (1999) Glucuronidation of benzidine and its metabolites by cDNA-expressed human UDP-glucuronosyltransferases and pH stability of glucuronides. Carcinogenesis, in press.
8. Doll R and Peto R (1981) The Causes of Cancer. Oxford University Press, New York.
9. Fox TR, Schumann AM, Watanabe PG, Yano BL, Maher VM and McCormick JJ (1990) Mutational analysis of the H-ras oncogene in spontaneous C57BL/6 × C3H/He mouse liver tumors and tumors induced with genotoxic and nongenotoxic hepatocarcinogens. Cancer Res 50:4014-4019.
10. Glaser JH and Sly WS (1973) β-Glucuronidase deficiency mucopolysaccharidosis: Methods for enzymatic diagnosis. J Lab Clin Med 82:969-977.
11. Gonick HC, Kramer HJ and Schapiro AE (1973) Urinary β-glucuronidase activity in renal disease. Arch Intern Med 132:63-69.
12. Guerin MR and Buchanan MV (1988) Environmental exposure to N-aryl compounds, in Carcinogenic and Mulagenic Responses to Aromatic Amines and Nitroarenes (King CM, Romano LJ and Schuetzle D eds) pp 37-45, Elsevier Science Publishing Co., Inc., New York.
13. Harris RE, Thomas VL, Underwood JM and Gaudot F (1978) A comparison of two indirect methods for localizing the site of urinary infection: Beta glucuronidase levels and the presence of antibody-coated bacteria Am J Obstet Gynecol 131:647-649.
14. Heflich RH, Morris SM, Beranek DT, McGarrity LJ, Chen JJ and Beland FA (1986) Relationships between the DNA adducts and the mutations and sister-chromatid exchanges produced in Chinese hamster ovary cells by N-hydroxy-2-aminofluorene, N-hydroxy-N′-acetylbenzidine and 1-nitrosopyrene. Mutagenesis 1:201-206.
15. Ho Y and Ho K (1985) Differential quantitation of urinary β-glucuronidase of human and bacterial origins. J Urol 134:1227-1230.
16. Kadlubar FF, Miller JA and Miller EC (1977) Hepatic microsomal N-glucuronidation and nucleic acid binding of N-hydroxy arylamines in relation to urinary bladder carcinogenesis. Cancer Res 37:805-814.
17. Lakshmi VM, Mattammal MB, Spry LA, Kadlubar FF, Zenser TV and Davis BB (1990) Metabolism and disposition of benzidine in the dog. Carcinogenesis 11:139-144.
18. Lakshmi VM, Zenser TV and Davis BB (1997) Rat liver cytochrome P450 metabolism of N-acetylbenzidine and N,N′-diacetylbenzidine, Drug Metab Dispos 25:481-488.
19. Lakshmi VM, Zenser TV and Davis BB (1998) N′-(3′-monophospho-deoxyguanosin-8-yl)-N-acetylbenzidine formation by peroxidative metabolism. Carcinogenesis 19:911-917.
20. Lakshmi VM, Zenser NT, Hsu FF, Mattammal MB, Zenser TV and Davis BB (1996) NADPH-dependent oxidation of benzidine by rat liver. Carcinogenesis 17:1941-1947.
21. Melchior WB Jr, Marques MM and Beland FA (1994) Mutations induced by aromatic amine DNA adducts in pBR322. Carcinogenesis 15:889-899.
22. Paigen B, Yarfitz S and Tabron D (1984) Urinary glucuronidase and arylsulfatases in identical twins of bladder cancer patients. Cancer Res 44:3624-3626.
23. Ross RK, Paganini-Hill A and Henderson BE (1988) Epidemiology of bladder cancer, in Diagnosis and Management of Genitourinary Cancer (Skinner DG and Lieskovsky G eds) pp 23-31, W.B. Saunders Co., Philadelphia.
24. Rothman N, Talaska G, Hayes R, Bhatnagar V, Bell D, Lakshmi V, Kashyap S, Dosemeci M, Kashyap R, Hsu F, Jaeger M, Hirvonen A, Parikh D, Davis B and Zenser T (1997) Acidic urine pH is associated with elevated levels of free urinary benzidine and N-acetylbenzidine and urothelial cell DNA adducts in exposed workers. Cancer Epidemiol Biomarkers Prev 6:1039-1042.
25. Wachstein M (1955) Histochemical staining reactions of the normally functioning and abnormal kidney. J Histochem Cytochem 3:246-270.
26. Watanabe H, Grubb JH and Sly WS (1990) The overexpressed human 46-kDa mannose-6-phosphate receptor mediates endocytosis and sorting of B-glucuronidase. Proc Natl Acad Sci USA 87:8036-8040.
27. Zenser TV, Mattammal MB and Davis BB (1978) Differential distribution of the mixed-function oxidase activities in rabbit kidney. J Pharmacol Exp Ther 207:719-725.