Synthesis and characterization of deoxycholyl 2-deoxyglucuronide: A water-soluble affinity labeling reagent

Lipids

Volumn 38, Issue 8, 2003, Pages 873-879

  Mano, Nariyasu ^a   Nishijima, Akira ^a   Saito, Shuntaro ^a   Ikegawa, Shigeo ^b   Goto, Junichi ^a,c  

^a TOHOKU UNIVERSITY   (Japan)

^b KINKI UNIVERSITY   (Japan)

^c TOHOKU UNIVERSITY HOSPITAL   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; CARBOXYLIC ACIDS; DETOXIFICATION; PROTEINS; SOLUBILITY; SOLUTIONS;

IMINE MECHANISMS;

LIPIDS;

CARBOXYLIC ACID; DEOXYCHOLIC ACID; DEOXYCHOLYL 2 DEOXYGLUCURONIDE; GLUCURONIDE; PEPTIDE; REAGENT; UNCLASSIFIED DRUG; WATER;

ACYLATION; AQUEOUS SOLUTION; ARTICLE; CHEMICAL STRUCTURE; COVALENT BOND; DETOXIFICATION; ENZYME ACTIVITY; LIPOPHILICITY; REACTION ANALYSIS; SOLUBILITY; STRUCTURE ANALYSIS; SYNTHESIS; TRANSACYLATION;

AFFINITY LABELS; DEOXYCHOLIC ACID; GLUCURONIDES; HYDROGEN-ION CONCENTRATION; MOLECULAR STRUCTURE; SOLUBILITY; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION; WATER;

EID: 0141816530     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-003-1138-1     Document Type: Article

References (31)

1. Dutton, G.J. (1980) Glucuronidation of Drugs and Other Compounds, CRC Press, Boca Raton.
2. Magdalou, J., Chajes, V., Lafaurie, C., and Siest, G. (1990) Glucuronidation of 2-Arylpropionic Acids Pirprofen, Flurbiprofen, and Ibuprofen by Liver Microsomes, Drug Metab. Dispos. 18, 692-697.
3. Ikegawa, S., Murao, N., Oohashi, J., and Goto, J. (1998) Separatory Determination of Diastereomeric Ibuprofen Glucuronides in Human Urine by Liquid Chromatography/Electrospray Ionization-Mass Spectrometry, Biomed. Chromatogr. 12, 317-321.
4. Ding, A., Ojingwa, J.C., McDonagh, A.F., Burlingame, A.L., and Benet, L.Z. (1993) Evidence for Covalent Binding of Acyl Glucuronides to Serum Albumin via in Imine Mechanism as Revealed by Tandem Mass Spectrometry, Proc. Natl. Acad. Sci. USA 90, 3797-3801.
5. Smith, P.C., and Liu, J.H. (1993) Covalent Binding of Suprofen Acyl Glucuronide to Albumin in vitro, Xenobiotica 23, 337-348.
6. Williams, A.M., and Dickinson, R.G. (1994) 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, Biochem. Pharmacol. 47, 457-467.
7. Ding, A., Zia-Amirhosseini, P., McDonagh, A.F., Burlingame, A.L., and Benet, L.Z. (1995) Reactivity of Tolmetin Glucuronide with Human Serum Albumin. Identification of Binding Sites and Mechanisms of Reaction by Tandem Mass Spectrometry, Drug Metab. Dispos. 23, 369-376.
8. Worrall, S., and Dickinson, R.G. (1995) Rat Serum Albumin Modified by Diflunisal Acyl Glucuronide Is Immunogenic in Rats, Life Sci. 56, 1921-1930.
9. Smith, P.C., and Liu, J.H. (1995) Covalent Binding of Suprofen to Renal Tissue of Rat Correlates with Excretion of Its Acyl Glucuronide, Xenobiotica 25, 531-540.
10. 13C Labeling and Nuclear Magnetic Resonance Spectroscopy, Drug Metab. Dispos. 26, 457-464.
11. Back, P., Spaczinski, K., and Gerok, W. (1974) Bile-Salt Glucuronides in Urine, Hoppe-Seyler's Z. Physiol. Chem. 355, 749-752.
12. Back, P. (1976) Bile Acid Glucuronides. II. Isolation and Identification of a Chenodeoxycholic Acid Glucuronide from Human Plasma in Intrahepatic Cholestasis, Hoppe-Seyler's Z. Physiol. Chem. 357, 213-217.
13. Almé, B., and Sjövall, J. (1980) Analysis of Bile Acid Glucuronides in Urine. Identification of 27-Nor-5β-cholestan-3α ,7α,12α,24ξ,25ξ-pentol in Man, J. Steroid Biochem. 13, 907-916.
14. Ikegawa, S., Murao, N., Motoyama, T., Yanagihara, T., Niwa, T., and Goto, J. (1996) Separation and Detection of Bile Acid 3-Glucuronides in Human Urine by Liquid Chromatography/Electrospray Ionization-Mass Spectrometry, Biomed. Chromatogr. 10, 313-317.
15. Goto, J., Murao, N., Nakada, C., Motoyama, T., Oohashi, J., Yanagihara, T., Niwa, T., and Ikegawa, S. (1998) Separation and Characterization of Carboxyl-Linked Glucuronides of Bile Acids in Incubation Mixture of Rat Liver Microsomes, Steroids 63, 186-192.
16. Ikegawa, S., Okuyama, H., Oohashi, J., Murao, N., and Goto, J. (1999) Separation and Detection of Bile Acid 24-Glucuronides in Human Urine by Liquid Chromatography Combined Electrospray Ionization Mass Spectrometry, Anal. Sci. 15, 625-631.
17. Ikegawa, S., Murao, N., Nagata, M., Ohba, S., and Goto, J. (1999) Covalent Binding of Bile Acid Acyl Glucuronide with Protein, Anal. Sci. 15, 213-215.
18. Hoj, P.B., Condron, R., Traeger, J.C., McAuliffe, J.C., and Stone, B.A. (1996) Identification of Glutamic Acid 105 at the Active Site of Bacillus amyloliquefaciens 1,3-1,4-β-D-Glucanohydrolase Using Epoxide-Based Inhibitors, J. Biol. Chem. 267, 25059-25066.
19. Tull, D., Burgoyne, D.L., Chow, D.T., Withers, S.G., and Aebersold, R. (1996) A Mass Spectrometry-Based Approach for Probing Enzyme Active Sites: Identification of Glu 127 in Cellulomonas fimi Exoglycanase as the Residue Modified by N-Bromoacetyl Cellobiosylamine, Anal. Biochem. 234, 119-125.
20. Mills, J.S., Miettinen, H.M., Bamidge, D., Vlases, M.J., Wimer-Mackin, S., Dratz, E.A., Sunner, J., and Jesaitis, A.J. (1998) Identification of a Ligand Binding Site in the Human Neutrophil Formyl Peptide Receptor Using a Site-Specific Fluorescent Photoaffinity Label and Mass Spectrometry, J. Biol. Chem. 273, 10428-10435.
21. Swamy, N., Dutta, A., and Ray, R. (1997) Roles of the Structure and Orientation of Ligands and Mimics Inside the Ligand-Binding Pocket of the Vitamin D-Binding Protein, Biochemistry 36, 7432-7436.
22. +-ATPase by N-Hydroxysuccinimidyl Derivatives of Digoxigenin, Eur. J. Biochem. 227, 61-67.
23. Ullman, E.F., Milburn, G., Jelesoko, J., Radika, K., Pirio, M., Kempe, T., and Skold, C. (1993) Anti-Immune Complex Anti-bodies Enhance Affinity and Specificity of Primary Antibodies, Proc. Natl. Acad. Sci. USA 90, 1184-1189.
24. Panfil, I., Lehman, P.A., Zimniak, M., Ernest, B., Franz, T., Lester, R., and Radominska, A. (1992) Biosynthesis and Chemical Synthesis of Carboxyl-Linked Glucuronides of Lithocholic Acid, Biochim. Biophys. Acta 1126, 221-228.
25. Mitsunobu, O. (1981) The Use of Diethylazodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products, Synthesis 7, 1-28.
26. Goto, J., Murao, N., Oohashi, J., and Ikegawa, S. (1998) Synthesis of Bile Acid 24-Acyl Glucuronides, Steroids 63, 180-185.
27. Roepstorff, P., and Fohlman, J. (1984) Proposal for a Common Nomenclature for Sequence Ions in Mass Spectra of Peptides, Biomed. Mass Spectrom. 11, 601.
28. Bieman, K. (1989) Tandem Mass Spectrometry Applied to Protein Structure Problems, Biochem. Soc. Trans. 17, 237-243.
29. Makishima, M., Okamoto, Y., Repa, J.J., Tu, H., Learned, R.M., Luk, A., Hull, M.V., Lustig, K.D., Mangelsdorf, D.J., and Shan, B. (1999) Identification of a Nuclear Receptor for Bile Acids, Science 284, 1362-1365.
30. Parks, D.J., Blanchard, S.G., Bledsoe, R.K., Chandra, G., Consler, T.G., Kliewer, S.A., Stimmel, J.B., Willson, T.M., Zavacki, A.M., Moore, D.D., and Lehmann, J.M. (1999) Bile Acids: Natural Ligands for an Orphan Nuclear Receptor, Science 284, 1365-1368.
31. Mano, N., Nishimura, K., Narui, T., Ikegawa, S., and Goto, J. (2002) Characterization of Rat Liver Bile Acid Acyl Glucuronosyltransferase, Steroids 67, 257-262.