Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 17, 1987 - Issue 12
27
Views
40
CrossRef citations to date
0
Altmetric
Original Article

Interactions between oxaprozin glucuronide and human serum albumin

, &
Pages 1437-1449 | Received 01 Jul 1986, Accepted 18 Aug 1986, Published online: 30 Sep 2009

References

  • Bradford M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Analytical Biochemistry 1976; 72: 248–254
  • Compernolle F., Blankaert N., Heirwegh K. The fate of bilirubin-IXα glucuronides in cholestatic bile: sequential migration of the 1-acylaglycone to the 2-, 3- and 4-positions of glucuronic acid. Biochemical Society Transactions 1977; 5: 317–319
  • Cunningham V. J., Hay L., Stoner H. B. The binding of L-tryptophan to serum albumins in the presence of non-esterified fatty acids. Biochemical Journal 1975; 146: 653–658
  • Dickinson R. G., Hooper W. D., Eadie M. J. pH-Dependent rearrangement of the biosynthetic ester glucuronide of valproic acid to β-glucuronidase-resistant forms. Drug Metabolism and Disposition 1984; 12: 247–252
  • Eggers N. J., Doust K. Isolation and identification of probenecid acyl glucuronide. Journal of Pharmacy and Pharmacology 1981; 33: 123–124
  • Ellman G. L. Tissue sulfhydryl groups. Archives of Biochemistry and Biophysics 1959; 82: 70–77
  • Faed E. M. Properties of acyl glucuronides: implications for studies of the pharmacokinetics and metabolism of acidic drugs. Drug Metabolism Reviews 1984; 15: 1213–1249
  • Faed E. M., Mcqueen E. G. Separation of two conjugates of clofibric acid (CPIB) found in the urine of subjects taking clofibrate. Clinical and Experimental Pharmacology and Physiology 1978; 5: 195–198
  • Faed E. M., Mcqueen E. G. Plasma half-life of clofibric acid in renal failure. British Journal of Clinical Pharmacology 1979; 7: 407–410
  • Fehske K. J., Muller W. E., Wollert U. A highly reactive tyrosine residue as part of the indole and benzodiazepine binding site of human serum albumin. Biochimica et Biophysica Acta 1979; 577: 346–359
  • Fehske K. J., Muller W. E., Wollert U. Direct demonstration of the highly reactive tyrosine residue of human serum albumin located in fragment 299–585. Archives of Biochemistry and Biophysics 1980; 205: 217–221
  • Fehske K. J., Muller W. E., Schlafer U., Wollert U. Characterisation of two important drug binding sites on human serum albumin. Progress in Drug Protein Binding. Proc. Lect. Symp. 2nd 1981; 5–15
  • Gautam A., Seligson H., Gordon E. R., Seligson D., Boyer J. L. Irreversible binding of conjugated bilirubin to albumin in cholestatic rats. Journal of Clinical Investigation 1984; 73: 873–877
  • Gregory J. D. The stability of n-ethylmaleimide and its reaction with sulfhydryl groups. Journal of the American Chemical Society 1955; 77: 3922–3923
  • Gugler R. The effect of disease on the response to drugs. Proceedings of the 7th International Congress of Pharmacology, P. Duchene-Mairwaz. Pergamon Press, Oxford 1979
  • Hasegawa J., Smith P. C., Benet L. Z. Apparent intramolecular acyl migrations of zomepirac glucuronide. Drug Metabolism and Disposition 1982; 10: 469–473
  • Hughes W. L., Saroff H. A., Carney A. L. Preparation and properties of serum and plasma proteins. XXII. A crystallizable guanidinated derivative of human serum albumin. Journal of the American Chemical Society 1949; 71: 2476–2480
  • Illing H. P., Wilson I. D. PH dependent formation of β-glucuronidase resistant conjugates from the biosynthetic ester glucuronide of isoxepac. Biochemical Pharmacology 1981; 30: 3381–3384
  • Jacobsen C., Jacobsen J. Dansylation of human serum albumin in the study of the primary binding sites of bilirubin and L-tryptophan. Biochemical Journal 1979; 181: 251–253
  • Janssen F. W., Chiang S. T., Walker B. R., Ruelius H. W. Disposition of oxaprozin in healthy subjects and certain disease states. Current Therapeutic Research 1984; 35: 363–376
  • Janssen F. W., Kirkman S. K., Fenselau C., Stogniew M., Hofmann B. R., Young E. M., Ruelius H. W. Metabolic formation of N- and O-glucuronides of 3-(p-chlorophenyl)thiazolo[3,2-a]benzimidazoie-2-acetic acid. Rearrangement of the 1-O-acyl glucuronide. Drug Metabolism and Disposition 1982; 10: 599–604
  • Kurono Y., Maki T., Yatsuyanagi T., Ikeda K. Esterase-like activity of human serum albumin: structure-activity relationships for the reactions with phenyl acetates and p-nitrophenyl esters. Chemical and Pharmaceutical Bulletin 1979; 27: 2781–2786
  • Lauff J. J., Kasper M. E., Wu T. W., Ambrose R. T. Isolation and preliminary characterization of a fraction of bilirubin in serum that is firmly bound to protein. Clinical Chemistry 1982; 28: 629–637
  • Lewis A. J., Carlson R. P., Chang J., Gilman S. C., Nielsen S., Rosenthale M. E., Janssen F. W., Ruelius H. W. The pharmacological profile of oxaprozin, an antiinflammatory and analgesic agent with low gastrointestinal toxicity. Current Therapeutic Research 1983; 34: 777–794
  • Lundblad R. L., Noyes C. M. Chemical Reagents for Protein Modification. CRC Press, Boca Raton 1984; Vol I: 55, 127
  • Mcdonagh A. F., Palma L. A., Lauff J. J., Wu J. W. Origin of mammalian biliprotein and rearrangement of bilirubin glucuronides in vivo in the rat. Journal of Clinical Investigation 1984; 74: 763–769
  • Means G. E., Bender M. L. Acetylation of human serum albumin by p-nitrophenyl acetate. Biochemistry 1975; 14: 4989–4994
  • Means G. E., Wu H. L. The reactive tyrosine residue of human serum albumin; characterization of its reaction with diisopropylfluorophosphate. Archives of Biochemistry and Biophysics 1979; 194: 526–530
  • Muller W. E., Wollert U. High stereospecificity of the benzodiazepine binding site on human serum albumin. Studies with d- and l-oxazepam hemisuccinate. Molecular Pharmacology 1975; 11: 52–60
  • Musson D. G., Lin J. H., Lyon C., Tocco D. J., Yeh K. C. Assay methodology for quantification of the ester and ether glucuronide conjugates of diflunisal in human urine. Journal of Chromatography 1985; 337: 363–378
  • Ohta N., Kurono Y., Ikeda K. Esterase-like activity of human serum albumin II: reaction with N-trans-cinnamoylimidazoles. Journal of Pharmaceutical Science 1983; 72: 385–388
  • Rachmel A., Hazelton G. A., Yergey A. L., Liberato D. J. Furosemide 1-O-acyl glucuronide. In vitro biosynthesis and pH-dependent isomerization to β-glucuronidase-resistant forms. Drug Metabolism and Disposition 1985; 13: 705–710
  • Ruelius H. W., Kirkman S. K., Young E. M., Janssen F. W. Reactions of oxaprozin-1-O-acyl glucuronide in solutions of human plasma and albumin. Biological Reactive Intermediates III, J. J. Kocsis, D. J. Jollow, C. M. Witmer, J. O. Nelson, R. Snyder. Plenum Press, New York 1986, In press
  • Ruelius H. W., Young E. M., Kirkman S. K., Schillings R. T., Sisenwine S. F., Janssen F. W. Biological fate of acyl glucuronides in the rat. The role of rearrangement, intestinal enzymes and reabsorption. Biochemical Pharmacology 1985; 34: 451–452
  • Sinclair K. A., Caldwell J. The formation of β-glucuronidase resistant glucuronides by the intramolecular rearrangement of glucuronic acid conjugates at mild alkaline pH. Biochemical Pharmacology 1982; 31: 953–957
  • Sjöholm I., Ekman B., Kober A., Ljungstedt-Pahlman I., Seiving B., Sjodin T. Binding of drugs to human serum albumin: XI. The specificity of three binding sites as studied with albumin immobilized in microparticles. Molecular Pharmacology 1979; 16: 767–777
  • Smith P. C., Mcdonaugh A. F., Benet L. Z. Irreversible binding of zomepirac to plasma protein in vitro and in vivo. Journal of Clinical Investigation 1986; 77: 934–939
  • Sokolovsky M., Riordan J. F., Vallee B. L. Tetranitromethane. A reagent for the nitration of tyrosyl residues in proteins. Biochemistry 1966; 5: 3582–3589
  • Sudlow G., Birkett D. J., Wade D. N. Further characterization of specific drug binding sites on human serum albumin. Molecular Pharmacology 1976; 12: 1052–1061
  • Van Breemen R. B., Fenselau C. Acylation of albumin by 1-O-acyl glucuronides. Drug Metabolism and Disposition 1985; 13: 318–320
  • Walker J. E. Lysine residue 199 of human serum albumin is modified by acetylsalicylic acid. FEBS Letters 1976; 66: 173–175
  • Weber C. J. A modification of Sakaguchi's reaction for the quantitative determination of arginine. Journal of Biological Chemistry 1930; 86: 217–222

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.