Roles of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reactions

Chemico-Biological Interactions

Volumn 129, Issue 1-2, 2000, Pages 171-193

  Ritter, Joseph K ^a  

^a VIRGINIA COMMONWEALTH UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Acyl glucuronides; Estrogen glucuronides; Glucuronidation; Morphine 6 O glucuronide; N O Glucuronides; Retinoid glucuronides; UDP Glucuronosyltransferases

Indexed keywords

AROMATIC AMINE; CARBOXYLIC ACID; ESTROGEN; GLUCURONIDE; GLUCURONOSYLTRANSFERASE; MORPHINE; MORPHINE 6 O GLUCURONIDE; RETINOID GLUCURONIDE; UNCLASSIFIED DRUG; XENOBIOTIC AGENT;

ANALGESIA; ARTICLE; CARCINOGENESIS; CHOLESTASIS; CONJUGATION; DETOXIFICATION; DRUG ACTIVITY; DRUG EFFECT; DRUG HYPERSENSITIVITY; ENZYME MECHANISM; ENZYME SPECIFICITY; GLUCURONIDATION; HUMAN; NONHUMAN; REACTION ANALYSIS; TISSUE SPECIFICITY; XENOBIOTIC METABOLISM;

ANIMALS; BIOTRANSFORMATION; ESTROGENS; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; ISOENZYMES; RATS; SUBSTRATE SPECIFICITY; XENOBIOTICS;

EID: 0034534895     PISSN: 00092797     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-2797(00)00198-8     Document Type: Article

References (120)

1. Implication of the conjugation of drugs and other exogenous compounds
2. Reactions in vitro of some tissue nucleophiles with the glucuronide of the carcinogen N-hydroxy-2-acetylaminofluorene
3. Properties of acyl glucuronides: Implications for studies of the pharmacokinetics and metabolism of acidic drugs
4. Acyl glucuronides revisited: Is the glucuronidation process a toxification as well as a detoxification mechanism?
5. Pharmacological characterization of morphine-6-beta-glucuronide, a very potent morphine metabolite
6. Enhancement of biological activity by conjugation reactions
7. Cholestatic properties and hepatic transport of steroid glucuronides
8. Biologically active conjugates of drugs and toxic chemicals
9. Molecular cloning and characterization of the human and mouse UDP-glucose dehydrogenase genes
10. Identification and cloning of a novel androgen-responsive gene, uridine diphosphoglucose dehydrogenase, in human breast cancer cells
11. The UDP glycosyltransferase gene superfamily: Recommended nomenclature update based on evolutionary divergence
12. A novel complex locus UGT1 encodes human bilirubin, phenol, and other UDP-glucuronosyltransferase isozymes with identical carboxyl termini
13. Drug-responsive and tissue-specific alternative expression of multiple first exons in rat UDP-glucuronosyltransferase family 1 (UGT1) gene complex
14. Isolation and characterization of the human UGT2B15 gene, localized within a cluster of UGT2B genes and pseudogenes on chromosome 4
15. Reaction of the glucuronide of the carcinogen N-hydroxy-2- acetylaminofluorene with nucleic acids
16. Arylhydroxylamines and arylhydroxamic acids: Conjugation reactions
17. Enzyme-catalyzed reactions of the carcinogen N-hydroxy-2- fluorenylacetamide with nucleic acid
18. Metabolic activation of N-hydroxy compounds by conjugation
19. Glucuronide conjugates of 4-aminobiphenyl and its N-hydroxy metabolites. pH stability and synthesis by human and dog liver
20. Disposition of the aromatic amine, benzidine, in the rat: Characterization of mutagenic urinary and biliary metabolites
21. Glucuronidation of N-hydroxy metabolites of N-acetylbenzidine
22. Influence of the aryl group on the reaction of glucuronides of N-arylacethydroxamic acids with polynucleotides
23. Glucuronidation of carcinogen metabolites by complementary DNA-expressed uridine 5′-diphosphate glucuronosyltransferases
24. Microsomal metabolism of the carcinogen, N-2-fluorenyl-acetamide, by the mammary gland and liver of female rats. II. Glucuronidation of ring- and N-hydroxylated metabolites of N-2-fluorenylacetamide
25. cDNA cloning and expression of two new members of the human liver UDP-glucuronosyltransferase 2B subfamily
26. Characterization of two UDP glucuronosyltransferases that are predominantly expressed in human colon
27. Glucuronidation of benzidine and its metabolites by cDNA-expressed human UDP-glucuronosyltransferases and pH stability of glucuronides
28. Acyl glucuronides as chemically reactive intermediates
29. Covalent binding of zomepirac glucuronide to proteins: Evidence for a Schiff base mechanism
30. Mechanism of covalent adduct formation of diclofenac to rat hepatic microsomal proteins. Retention of the glucuronic acid moiety in the adduct
31. Disposition and covalent binding of diflunisal and diflunisal acyl glucuronide in the isolated perfused rat liver
32. The clinical importance of a protein-bound fraction of serum bilirubin in patients with hyperbilirubinemia
33. Irreversible binding of zomepirac to plasma protein in vitro and in vivo
34. Covalent binding of suprofen to renal tissue of rat correlates with excretion of its acyl glucuronide
35. Studies on the reactivity of acyl glucuronides - III. Glucuronide-derived adducts of valproic acid and plasma protein and anti-adduct antibodies in humans
36. Influence of renal failure in rats on the disposition of salicyl acyl glucuronide and covalent binding of salicylate to plasma proteins
37. Chemical and immunochemical comparison of protein adduct formation of four carboxylate drugs in rat liver and plasma
38. Diclofenac covalent protein binding is dependent on acyl glucuronide formation and is inversely related to P450-mediated acute cell injury in cultured rat hepatocytes
39. Reactivity of mefenamic acid 1-o-acyl glucuronide with proteins in vitro and ex vivo
40. Genotoxicity of acyl glucuronide metabolites formed from clofibric acid and gemfibrozil: A novel role for phase-II-mediated bioactivation in the hepatocarcinogenicity of the parent aglycones?
41. Studies on the reactivity of acyl glucuronides - VI. Modulation of reversible and covalent interaction of diflunisal acyl glucuronide and its isomers with human plasma protein in vitro
42. Effect of selective phase II enzyme inducers on glucuronidation of benoxaprofen in rats
43. Identification and analysis of drug-responsive expression of UDP-glucuronosyltransferase family 1 (UGT1) isozyme in rat hepatic microsomes using anti-peptide antibodies
44. Bilirubin UDP-glucuronosyltransferase 1 is the only relevant bilirubin glucuronidating isoform in man
45. Glucuronidation of retinoids by rat recombinant UDP: Glucuronosyltransferase 1.1 (bilirubin UGT)
46. Investigation of the substrate specificity of a cloned expressed human bilirubin UDP-glucuronosyltransferase: UDP-sugar specificity and involvement in steroid and xenobiotic glucuronidation
47. Stereoselective glucuronidation of (R)- and (S)-naproxen by recombinant rat phenol UDP-glucuronosyltransferase (UGT1A1) and its human orthologue
48. Substrate specificities of two stably expressed human liver UDP-glucuronosyltransferases of the UGT1 gene family
49. Complementary deoxyribonucleic acid cloning and expression of a human liver uridine diphosphate-glucuronosyltransferase glucuronidating carboxylic acid-containing drugs
50. A recombinant phenobarbital-inducible rat liver UDP-glucuronosyltransferase (UDP-glucuronosyltransferase 2B1) stably expressed in V79 cells catalyzes the glucuronidation of morphine, phenols, and carboxylic acids
51. Stereoselective (S)- and (R)-naproxen glucuronosyl transferases of rat liver
52. Hepatic microsomal glucuronidation of clofibric acid in the adult and neonate albino rat
53. Substrate specificity and enantioselectivity of arylcarboxylic acid glucuronidation
54. Effect of inducers and inhibitors of glucuronidation on the biliary excretion and choleretic action of valproic acid in the rat
55. Glucuronidation of 2-arylpropionic acids pirprofen, flurbiprofen, and ibuprofen by liver microsomes
56. Analgesic activity of morphine-6-glucuronide
57. Morphine and metabolite behavior after different routes of morphine administration: Demonstration of the importance of the active metabolite morphine-6-glucuronide
58. Chronic morphine therapy for cancer pain: Plasma and cerebrospinal fluid morphine and morphine-6-glucuronide concentrations
59. Isolation and purification of rat liver morphine UDP-glucuronosyltransferase
60. Isolation and purification of two human liver UDP-glucuronosyltransferases
61. In vitro evidence for the involvement of at least two forms of human liver UDP-glucuronosyltransferase in morphine 3-glucuronidation
62. The enantioselective glucuronidation of morphine in rats and humans. Evidence for the involvement of more than one UDP-glucuronosyltransferase isoenzyme
63. Cloning and stable expression of a cDNA encoding a rat liver UDP-glucuronosyltransferase (UDP-glucuronosyltransferase 1.1) that catalyzes the glucuronidation of opioids and bilirubin
64. Purification of a phenobarbital-inducible morphine UDP-glucuronyltransferase isoform, absent from Gunn rat liver
65. Comparison of stably expressed rat UGT1.1 and UGT2B1 in the glucuronidation of opioid compounds
66. Induction of two UDP-glucuronosyltransferase isoforms sensitive to phenobarbital that are involved in morphine glucuronidation: Production of isoform-selective antipeptide antibodies toward UGT1.1r and UGT2B1
67. Cloning and expression of a rat liver phenobarbital-inducible UDP-glucuronosyltransferase (2B12) with specificity for monoterpenoid alcohols
68. Human UGT2B7 catalyzes morphine glucuronidation
69. The glucuronidation of opioids, other xenobiotics, and androgens by human UGT2B7Y(268) and UGT2B7H(268)
70. Expression of UDP-glucuronosyltransferases (UGTs) 2B7 and 1A6 in the human brain and identification of 5-hydroxytryptamine as a substrate
71. Characterization of retinyl beta-glucuronide in human blood
72. Retinoyl beta-glucuronide: An endogenous compound of human blood
73. Bioactivities of N-(4-hydroxyphenyl) retinamide and retinoyl beta- glucuronide
74. Effects of retinoid glucuronides on mammary gland development in organ culture
75. Enhancement of the expression of activation markers on human peripheral blood mononuclear cells by in vitro culture with retinoids and carotenoids
76. Comparative teratogenicity and metabolism of all-trans retinoic acid, all-trans retinoyl beta-glucose, and all-trans retinoyl beta-glucuronide in pregnant Sprague-Dawley rats
77. Formation of beta-glucuronides and of beta-galacturonides of various retinoids catalyzed by induced and noninduced microsomal UDP-glucuronosyltransferases of rat liver
78. Glucuronidation of all-trans-retinoic acid and 5,6-epoxy-all-trans-retinoic acid. Activation of rat liver microsomal UDP-glucuronosyltransferase activity by alamethicin
79. Identification of a rat oltipraz-inducible UDP-glucuronosyltransferase (UGT1A7) with activity towards benzo(a)pyrene-7,8-dihydrodiol
80. Studies on the substrate specificity of human intestinal UDP-lucuronosyltransferases 1A8 and 1A10
81. 4-Hydroxyretinoic acid, a novel substrate for human liver microsomal UDP-glucuronosyltransferase(s) and recombinant UGT2B7
82. The glucuronidation of exogenous and endogenous compounds by stably expressed rat and human UDP-glucuronosyltransferase 1.1
83. Characterization of cholestasis induced by estradiol-17 beta-D-glucuronide in the rat
84. Biliary excretion of estradiol-17 beta-glucuronide in the rat
85. Steroid UDP glucuronosyltransferases: Characterization and regulation
86. Characterization of UDP-glucuronosyltransferases active on steroid hormones
87. Rat liver UDP-glucuronosyltransferase. Identification of cDNAs encoding two enzymes which glucuronidate testosterone, dihydrotestosterone, and beta-estradiol
88. Human bilirubin UDP-glucuronosyltransferase catalyzes the glucuronidation of ethinylestradiol
89. Cloning and expression of human liver UDP-glucuronosyltransferase in COS-1 cells. 3,4-Catechol estrogens and estriol as primary substrates
90. Differential glucuronidation of bile acids, androgens and estrogens by human UGT1A3 and 2B7
91. Characterization of a cloned human dihydrotestosterone/androstanediol UDP-glucuronosyltransferase and its comparison to other steroid isoforms
92. Alteration of human UDP-glucuronosyltransferase UGT2B17 regio- specificity by a single amino acid substitution
93. cDNA cloning and characterization of the human UDP glucuronosyltransferase, UGT1A3
94. Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3
95. Glucuronidation of amines and hydroxylated xenobiotics and endobiotics catalyzed by expressed human UGT1.4 protein
96. Differential expression of the UGT1A locus in human liver, biliary, and gastric tissue: Identification of UGT1A7 and UGT1A10 transcripts in extrahepatic tissue
97. Expression and inducibility of the human bilirubin UDP- glucuronosyltransferase UGT1A1 in liver and cultured primary hepatocytes: Evidence for both genetic and environmental influences
98. The genetic basis of the reduced expression of bilirubin UDP-glucuronosyltransferase 1 in Gilbert's syndrome
99. Genetic defect of bilirubin UDP-glucuronosyltransferase in the hyperbilirubinemic Gunn rat
100. Tissue-specific constitutive and inducible expression of rat phenol UDP-glucuronosyltransferase
101. Paracetamol glucuronidation by recombinant rat and human phenol UDP-glucuronosyltransferases
102. Induction of a rat liver benzo[a]pyrene-trans-7,8-dihydrodiol glucuronidating activity by oltipraz and beta-naphthoflavone
103. UDP-glucuronosyltransferase UGT1A7 induced in rat small intestinal mucosa by oral administration of 2-naphthoflavone
104. Transcriptional activation of the UDP-glucuronosyltransferase 1A7 gene in rat liver by aryl hydrocarbon receptor ligands and oltipraz
105. Phase II-selective induction of hepatic drug-metabolizing enzymes by oltipraz-5-(2-pyrazinyl)-4-methyl-1,2-dithiol-3-thione-, 1,7-phenanthroline, and 2,2′-dipyridyl in rats is not accompanied by induction of intestinal enzymes
106. Cloning and characterization of DNA complementary to rat liver UDP-glucuronosyltransferase mRNA
107. Rat liver UDP-glucuronosyltransferase. cDNA sequence and expression of a form glucuronidating 3-hydroxyandrogens
108. Polymorphic expression of the UDP-glucuronosyltransferase UGT1A gene locus in human gastric epithelium
109. Expression of the UDP-glucuronosyltransferase 1A locus in human colon. Identification and characterization of the novel extrahepatic UGT1A8
110. UDP-glucuronosyltransferase activity in human liver and colon
111. Gilbert's syndrome is caused by a heterozygous missense mutation in the gene for bilirubin UDP-glucuronosyltransferase
112. The expression of UDP-glucuronosyltransferases of the UGT1 family in human liver and kidney and in response to drugs
113. Genetic polymorphism in the human UGT1A6 (planar phenol) UDP-glucuronosyltransferase: Pharmacological implications
114. Induction of human UDP glucuronosyltransferases (UGT1A6, UGT1A9, and UGT2B7) by t-butylhydroquinone and 2,3,7,8-tetrachlorodibenzo-p-dioxin in Caco-2 cells
115. Regulation and function of family 1 and family 2 UDP-glucuronosyltransferase genes (UGT1A, UGT2B) in human oesophagus
116. Cloning and expression of human UDP-glucuronosyltransferase (UGT) 1A8
117. The monkey and human uridine diphosphate-glucuronosyltransferase UGT1A9, expressed in steroid target tissues, are estrogen-conjugating enzymes
118. Two human liver cDNAs encode UDP-glucuronosyltransferases with 2 log differences in activity toward parallel substrates including hyodeoxycholic acid and certain estrogen derivatives
119. UDP-glucuronosyltransferases in human intestinal mucosa
120. Isolation and characterization of UGT2B15(Y85): A UDP-glucuronosyltransferase encoded by a polymorphic gene