Acyl glucuronides: Covalent binding and its potential relevance

Advances in Experimental Medicine and Biology

Volumn 387, Issue , 1996, Pages 313-328

  Spahn Langguth, Hildegard ^a,b   Dahms, Monika ^a   Hermening, Andreas ^a  

^a GOETHE UNIVERSITY   (Germany)

^b MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BETA GLUCURONIDASE; GLUCURONIC ACID; GLUCURONIDE; SULFATE;

CONFERENCE PAPER; CONJUGATION; COVALENT BOND; DETOXIFICATION; HYDROLYSIS; PRIORITY JOURNAL; RECEPTOR AFFINITY; RECEPTOR BINDING; XENOBIOTIC METABOLISM;

EID: 0029744251     PISSN: 00652598     EISSN: None     Source Type: Book Series    
DOI: 10.1007/978-1-4757-9480-9_39     Document Type: Conference Paper

References (60)

1. Amos HE, Wilson DV, Taussig MJ, Carlton SJ "Hypersensitivity reactions to acetylsalicylic acid" Clin Exp Immunol 8, 563-572 (1971)
2. Bakke OM, Wardell WM, Lasagna L "Drug discontinuations in the United Kingdom and the United States: 1964-1983" Clin Pharmacol Ther 35, 559-567 (1984)
3. Benet LZ, Spahn H "Acyl migration and covalent binding of drug glucuronides - potential toxicity mediators" In: Siest G, Magdalou J, Burchell B (eds) "Molecular and Cellular Aspects of Glucuronidation", Colloques INSERM/John Libbey Eurotext, Vol. 173, London, 305-309 (1988)
4. Benet LZ, Spahn-Langguth H, Iwakawa S, Volland C, Mizuma T, Mayer S, Mutschler E, Lin ET "Prediction of covalent binding of acidic drugs in man" Life Sci 53, PL 141-146 (1993)
5. Benet LZ, Bisher A, Volland C, Spahn-Langguth H "The pharmaco- and toxicokinetics of reactive and active phase II metabolites" In: Crommelin DJA, Midha KK (eds.) "Topics in Pharmaceutical Sciences" Med Pharm Scientific Publishers, Stuttgart, 533-544 (1992)
6. Blanckaert N, Compernolle F, Leroy P, Van Hautte R, Fevery J, Heirwegh KPM "The fate of bilirubin-IXα glucuronide in cholestasis and during storage in vitro" Biochem J 171, 203-214 (1978)
7. Boudinot FD, Homon CA, Jusko WJ, Ruelius HW "Protein binding of oxazepam and its glucuronide conjugates to human serum albumin" Biochem Pharmacol 39, 2115-2121 (1985)
8. 9-11-carboxytetrahydrocannabinol glucuronide" Chem Res Toxicol 2, 316-324 (1989)
9. van Breemen RB, Fenselau C "Acylation of albumin by 1-O-acyl glucuronides" Drug Metab Dispos 13, 318-320 (1985)
10. Dahms M, Spahn-Langgguth H "Acyl glucuronides as reactive intermediates: Detection of flunoxaprofen protein adducts in biological material" Naunyn Schmiedeberg's Arch Pharmacol. Suppl. (1995)
11. Dickinson RG, King AR "Studies on the reactivity of acyl glucuronides - V. Glucuronide-derived covalent binding of diflunisal to bladder tissue of rats and its modulation by urinary pH and β-glucuronidase" Biochem Pharmacol 46, 1175-1182 (1993)
12. Ding A, Ojingwa JC, McDonagh AF, Burlingame AL, Benet LZ "Evidence for covalent binding of acyl glucuronides to serum albumin via an imine mechanism as revealed by tandem mass spectrometry" Proc Nat Acad Sci USA 90, 3797-3801 (1993)
13. Dubois N, Lapicque F, Maurice MH, Pritchard M, Fournel-Gigleux S, Magdalou J, Abiteboul M, Siest G, Netter P "In vitro irreversible binding of ketoprofen glucuronide to plasma proteins" Drug Metab Dispos 21, 617-623 (1993)
14. Dudley KH "Commentary: Stereochemical formulas of β-D-glucuronides" Drug Metab Dispos 13, 524-528 (1985)
15. el Mouelhi M, Ruelius HW, Fenselau C, Dulik DM "Species-dependent enantioselective glucuronidation of three 2-arylpropionic acids: naproxen, ibuprofen and benoxaprofen" Drug Metab Dispos 16, 627-634 (1988)
16. el Mouelhi M, Schwenk M "Stereoselective glucuronidation of naproxen in isolated cells from liver, stomach, intestine, and colon of the guinea pig" Drug Metab Dispos 19, 844-845 (1991)
17. Faed EM "Properties of acyl glucuronides: Implications for studies of the pharmacokinetics and metabolism of acidic drugs" Drug Metab Rev 15, 1213-1249 (1984)
18. Fournel-Gigleux S, Hamar-Hansen C, Motassim N, Antoine B, Mothe O, Decolin D, Caldwell J, Siest G "Substrate-specificity and enantioselectivity of arylcarboxylic acid glucuronidation" Drug Metab Dispos 16, 627-634 (1988)
19. Gräfe AK "PK/PD Correlation model for the triglyceride-lowering effect of lipid-regulating agents and the effect of the patients' age: Gemfibrozil and its metabolites" PhD Thesis, Johann Wolfgang Goethe-University, Frankfurt/M., 1994
20. Grubb N, Weil A, Caldwell J "Studies on the in vitro reactivity of clofibryl and fenofibryl glucuronides. Evidence for protein binding via a Schiff*s base mechanism" Pharmacology 46, 357-364 (1993)
21. Gugler R, Kurten JW, Jensen CJ, Klehr U, Hartlapp J "Clofibrate disposition in renal failure and acute and chronic liver disease" Eur J Clin Pharmacol 230, 237-241 (1979)
22. Hargus SJ, Martin BM, Pohl LR "Covalent modification of rat liver dipeptidyl peptidase IV by diclofenac metabolites" The Fifth International Symposium on Biological Reactive Intermediates, Munich, Jan 1995, Abstract Volume, p. 74 (1995)
23. Hasegawa J, Smith PC, Benet LZ "Apparent intramolecular acyl migration of zomepirac glucuronide" Drug Metab Dispos 10, 469-473 (1982)
24. Hayball PJ, Nation RL, Bochner F "Stereoselective interactions of ketoprofen glucuronides with human plasma protein and serum albumin" Biochem Pharmacol 44, 291-299 (1992)
25. Hayball PJ, Nation RL, Bochner F, Sansom LN, Ahern MJ, Smith MD "The influence of renal function on the enantioselective pharmacokinetics and pharmacodynamics of ketoprofen in patients with rheumatoid arthritis" Br J clin Pharmac 31, 546-550 (1991)
26. Hermening A, Gräfe AK, Mayer S, Mutschler E, Spahn-Langguth H "Pharmacokinetics of fibrates and their acyl glucuronides: Inclusion of a reversible metabolic step and cvalent binding into kinetic modelling" Naunyn Schmiedeberg's Arch Pharmacol, Suppl (1995)
27. Iwakawa S, Suganuma T, Lee SF, Spahn H, Benet LY, Lin ET "Direct determination of diastereomeric carprofen glucuronides in human plasma and urine and preliminary measurements of stereoselective metabolic and renal elimination after oral administration of carprofen in man" Drug Metab Dispos 17, 474-480 (1989)
28. Iwakawa S, Spahn H, Benet LZ, Lin ET "Stereoselective disposition of carprofen, flunoxaprofen, and naproxen in rats" Drug Metab Dispos 19, 853-857 (1991)
29. Iwakawa S, Spahn H, Benet LZ, Lin ET "Carprofen glucuronides: Stereoselective degradation and interaction with human serum albumin" Pharmaceut Res 5 (Suppl), 5214 (1988)
30. King AR, Dickinson RG "Studies on the reactivity of acyl glucuronides - IV. Covalent binding of diflunisal to tissues of the rat" Biochem Pharmacol 45, 10431047 (1993)
31. Kroemer HK, Klotz U "Glucuronidation of drugs. A re-evaluation of the pharmacological significance of the conjugates and modulating factors" Clin Pharmacokinet 23, 292-310 (1992)
32. Mayer S, Spahn-Langguth H, Gikalov I, Mutschler E "Pharmacokinetics of beclobric acid enantiomers and their glucuronides after single and multiple p.o. dosage of rac-beclobrate" Arzneim Forsch/Drug Res 42-2, 1354-1358 (1993)
33. Mayer S, Mutschler E, Benet LY, Spahn-Langguth H "In vitro and in vivo irreversible plasma protein binding of beclobric acid enantiomers" Chirality 5, 120-125 (1993)
34. McKinnon GE, Dickinson RG "Covalent binding of diflunisal and probenecid to plasma protein in humans: Persistence of the adducts in the circulation" Res Commun Chem Pathol Pharmacol 66, 339-354 (1989)
35. Ojingwa J, Spahn-Langguth H, Benet LZ "Reversible binding of tolmetin, zomepirac and their glucuronide conjugates to human serum albumin" J Pharmacokin Biopharm 22, 19-40 (1994)
36. Ojingwa J, Spahn-Langguth H, Benet LZ "Irreversible binding of tolmetin to macromolecules via its glucuronide: Bindng to blood constituents, tissue homogenates and subcellular fractions in vitro" Xenobiotica 24, 495-506 (1994)
37. Ott RJ, Giacomini KM "Stereoselective transport of drugs across epithelia" In: Wainer IW (ed) "Drug stereochemistry: Analytical methods and pharmacology" Marcel Dekker Inc, New York, Basel, Hong Kong, 281-314 (1993)
38. Rowe BJ, Meffin PJ "Diisopropylfluorophosphate increases clofibric acid clearance: Supporting evidence for a futile cycle" J Pharmacol Exp Ther 230, 237-241 (1984)
39. Rubin A, Warrick RL, Wolen SM, Chernish SM, Ridolfo AS, Gruber CM "Physiological disposition of fenoprofen in man. III. Metabolism and protein binding of fenoprofen" J Pharmacol Exp Ther 183, 449-457 (1972)
40. Sallustio BC, Knights KM, Roberts BJ, Zacest R "In vivo covalent binding of clofibric acid to human plasma proteins and rat liver proteins" Biochem Pharmacol 42, 1421-1425 (1991)
41. Smith PC, Langendijk PNJ, Hasegawa J, Benet LZ "Effect of probenecid on the formation and elimination of acyl glucuronides: Studies with zomepirac" Clin Pharmacol Ther 38, 121-127 (1985)
42. Smith PC, Benet LZ "Characterization of the isomeric esters of zomepirac glucuronide by proton NMR" Drug Metab Dispos 14, 503-505 (1986)
43. Smith PC, Benet LZ, McDonagh A "Covalent binding of zomepirac glucuronide to proteins: Evidence for a Schiff base mechanism" Drug Metab Dispos 18, 639-644 (1990a)
44. Smith PC, McDonagh AF, Benet LZ "Irreversible binding of zomepirac to plasma protein in vitro and in vivo" J Clin Invest 77, 934-939 (1986)
45. Smith PC, McDonagh AF, Benet LZ "Effect of an esterase inhibitor on the disposition of zomepirac and its covalent binding to plasma proteins in the guinea pig" J Pharmacol Exp Ther 230, 218-224 (1990b)
46. Smith PC, Song WQ, Rodriguez RJ "Covalent binding of etodolac acyl glucuronide to albumin in vitro" Drug Metab Dispos 20, 962-965 (1992)
47. Spahn H, Iwakawa S, Lin ET, Benet LZ "Influence of probenecid on the urinary excretion rates of the diastereomeric benoxaprofen glucuronides" Eur J Drug Metab Pharmacokinet 12, 233-239 (1987)
48. Spahn H, Iwakawa S, Lin ET, Benet LZ "Procedures to properly characterize formation of acyl glucuronides: Studies with benoxaprofen" Pharm Res 6, 125-132 (1989)
49. Spahn H, Zia-Amirhosseini P, Näthke I, Mohri K, Benet LZ "Characterization of drug adducts - formed with proteins via acyl glucuronides - by electrophoresis and blotting" Pharm Res 7 (Suppl). S-257 (1990)
50. Spahn H, Spahn I, Benet LZ "Probenecid-induced changes in the clearance of carprofen enantiomers - A preliminary study" Clin Pharmacol Ther 45, 500-505 (1989)
51. Spahn-Langguth H, Benet LZ "Active and reactive phase-II metabolites: The glucuronides pathway" In: Crommelin DJA, Midha KK (eds.) "Topics in Pharmaceutical Sciences" Med Pharm Scientific Publishers, Stuttgart, 533-544 (1992a)
52. Spahn-Langguth H, Benet LZ "Acyl glucuronides revisited: Is the glucuronidation process a toxification as well as a detoxification mechanism?" Drug Metab Rev 24, 5-48 (1992b)
53. Spahn-Langguth H, Zia-Amirhosseini P, Iwakawa S, Ojingwa J, Büschges R, Benet LZ "Aktive und reaktive Glucuronide: Reversible und irreversible Interaktionen mit Proteinen" In: Dengler HJ, Mutschler E (eds) "Fremdstoffmetabolismus und Klinische Pharmakologie, Gustav Fischer Verlag, Stuttgart, 29-50 (1994)
54. Spahn-Langguth H, Gräfe AK, Mayer S, Büschges R, Benet LZ "Fibrates: The occurrence of active and reactive metabolites" In: Reid E, Hill HM, Wilson ID (eds) "Biofluid and tissue analysis for drugs including hyperlipidaemics." Methodological Surveys in Bioanalysis of Drugs, Vol. 23, The Royal Society of Chemistry, Cambridge, 87-102 (1994)
55. Stogniew M, Fenselau C "Electrophilic reactions of acyl-linked glucuronides: Formation of clofibrate mercapturate in humans" Drug Metab Dispos 10, 609-613 (1982)
56. Wells DS, Janssen FW, Ruelius HW "Interactions between oxaprozin glucuronide and human serum albumin" Xenobiotica 17, 1437-1449 (1987)
57. Williams AM, Worrall S, DeJersey J, Dickinson RG "Studies on the reactivity of acyl glucuronides: Glucuronide-derived adducts of valproic acid and plasma proteins and anti-adduct antibodies in humans" Biochem Pharmacol 43, 745-755 (1992)
58. Vree TB, Hekster YA, Anderson PG "Contribution of the human kidney to the metabolic clearance of drugs" Ann Pharmacother 26, 1421-1428 (1992)
59. Zia-Amirhosseini P "Hypersensitivity to nonsteroidal anti-inflammatory drugs: Exploration of a theory" Ph.D. Thesis, School of Pharmacy, University of California, San Francisco, 1994
60. Zia-Amirhosseini P, Ojingwa J, Spahn-Langguth H, McDonagh AF, Benet LZ "Enhanced covalent binding of tolmetin to proteins in humans after multiple dosing" Clin Pharmacol Ther 55, 21-27 (1994)