Synthesis, structure characterization, and enzyme screening of clenbuterol glucuronides

European Journal of Pharmaceutical Sciences

Volumn 37, Issue 5, 2009, Pages 581-587

  Alonen, Anna ^a   Gartman, Minna ^a   Aitio, Olli ^b   Finel, Moshe ^a   Yli Kauhaluoma, Jari ^a   Kostiainen, Risto ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

^b UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Clenbuterol; Glucuronidation; Koenigs Knorr reaction; Liver microsomes; Stereoselectivity

Indexed keywords

CLENBUTEROL; GLUCURONOSYLTRANSFERASE;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DRUG GLUCURONIDATION; DRUG IMPURITY; DRUG PURIFICATION; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME LOCALIZATION; HUMAN; HUMAN CELL; KOENIGS KNORR REACTION; LIVER MICROSOME METABOLISM; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; PROTEIN FUNCTION; RAT; SPECIES DIFFERENCE; STRUCTURE ANALYSIS; TANDEM MASS SPECTROMETRY;

ANIMALS; BINDING SITES; CATTLE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; CLENBUTEROL; DOGS; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MICROSOMES, LIVER; MOLECULAR STRUCTURE; RABBITS; RATS; RECOMBINANT PROTEINS; SPECIES SPECIFICITY; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY; SWINE; TANDEM MASS SPECTROMETRY;

EID: 67349117385     PISSN: 09280987     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ejps.2009.05.003     Document Type: Article

References (41)

1. Alonen A., Aitio O., Hakala K., Luukkanen L., Finel M., and Kostiainen R. Biosynthesis of dobutamine monoglucuronides and glucuronidation of dobutamine by recombinant human UDP-glucuronosyltransferases. Drug Metab. Dispos. 33 (2005) 657-663
2. Alonen A., Jansson J., Kallonen S., Kiriazis A., Aitio O., Finel M., and Kostiainen R. Enzyme-assisted synthesis and structure characterization of glucuronic acid conjugates of losartan, candesartan, and zolarsartan. Bioorg. Chem. 36 (2008) 148-155
3. Brambilla G., Cenci T., Franconi F., Galarini R., Macri A., Rondoni F., Strozzi M., and Loizzo A. Clinical and pharmacological profile in a clenbuterol epidemic poisoning of contaminated beef meat in Italy. Toxicol. Lett. 114 (2000) 47-53
4. Brambilla G., di Bez S., Pietraforte D., Minetti M., Campanella L., and Loizzo A. Ex vivo formation of gastric metabolites of clenbuterol: preliminary characterisation of their chemical structure. Anal. Chim. Acta 586 (2007) 426-431
5. Chan T.Y. Health hazards due to clenbuterol residues in food. J. Toxicol. Clin. Toxicol. 37 (1999) 517-519
6. Duus J., Gotfredsen CH., and Bock K. Carbohydrate structural determination by NMR spectroscopy: modern methods and limitations. Chem. Rev. 100 (2000) 4589-4614
7. Fenselau C., and Johnson L.P. Analysis of intact glucuronides by mass spectrometry and gas chromatography-mass spectrometry. A review. Drug Metab. Dispos. 8 (1980) 274-283
8. Garegg P.J. Synthesis and reactions of glycosides. Adv. Carbohydr. Chem. Biochem. 59 (2004) 69-134
9. Hintikka L., Kuuranne T., Aitio O., Thevis M., Schänzer W., and Kostiainen R. Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of eleven anabolic steroid metabolites. Steroids 73 (2008) 257-265
10. Jäntti S.E., Kiriazis A., Reinilä R.R., Kostiainen R.K., and Ketola R.A. Enzyme-assisted synthesis and characterization of glucuronide conjugates of neuroactive steroids. Steroids 72 (2007) 287-296
11. Jørgensen O., Egsgaard H., and Larsen E. Synthesis of deuterated clenbuterol. J. Label. Compd. Rad. 38 (1996) 1007-1014
12. Kaspersen F.M., and Van Boeckel C.A. A review of the methods of chemical synthesis of sulphate and glucuronide conjugates. Xenobiotica 17 (1987) 1451-1471
13. Kiang T.K., Ensom M.H., and Chang T.K. UDP-glucuronosyltransferases and clinical drug-drug interactions. Pharmacol. Ther. 106 (2005) 97-132
14. King C.D., Rios G.R., Green M.D., and Tephly T.R. UDP-glucuronosyltransferases. Curr. Drug Metab. 1 (2000) 143-161
15. Kurkela M., Patana A.S., Mackenzie P.I., Court M.H., Tate C.G., Hirvonen J., Goldman A., and Finel M. Interactions with other human UDP-glucuronosyltransferases attenuate the consequences of the Y485D mutation on the activity and substrate affinity of UGT1A6. Pharmacogenet. Genomics 17 (2007) 115-126
16. Kuuranne T., Aitio O., Vahermo M., Elovaara E., and Kostiainen R. Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of methyltestosterone (17α-methylandrost-4-en-17β-ol-3-one) and nandrolone (estr-4-en-17β-ol-3-one) metabolites. Bioconjug. Chem. 13 (2002) 194-199
17. Lemieux R.U., Kullnig R.K., Bernstein H.J., and Schneider W.G. Configurational effects on the proton magnetic resonance spectra of six-membered ring compounds. J. Am. Chem. Soc. 80 (1958) 6098-6105
18. Luukkanen L., Elovaara E., Lautala P., Taskinen J., and Vainio H. Characterization of 1-hydroxypyrene as a novel marker substrate of 3-methylcholanthrene-inducible phenol UDP-glucuronosyltransferase(s). Pharmacol. Toxicol. 80 (1997) 152-158
19. Luukkanen L., Kilpeläinen I., Kangas H., Ottoila P., Elovaara E., and Taskinen J. Enzyme-assisted synthesis and structural characterization of nitrocatechol glucuronides. Bioconjug. Chem. 10 (1999) 150-154
20. Mackenzie P.I., Walter Bock K., Burchell B., Guillemette C., Ikushiro S., Iyanagi T., Miners J.O., Owens I.S., and Nebert D.W. Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet. Genomics 15 (2005) 677-685
21. Martinez-Navarro J.F. Food poisoning related to consumption of illicit β-agonist in liver. Lancet 336 (1990) 1311
22. Montesissa C., Anfossi P., Biancotto G., and Angeletti R. In vitro metabolism of clenbuterol and bromobuterol by pig liver microsomes. Xenobiotica 28 (1998) 1049-1060
23. Niemeijer N.R., Gerding T.K., and De Zeeuw R.A. Glucuronidation of labetalol at the two hydroxy positions by bovine liver microsomes. Isolation, purification, and structure elucidation of the glucuronides of labetalol. Drug Metab. Dispos. 19 (1991) 20-23
24. Ouzzine M., Barre L., Netter P., Magdalou J., and Fournel-Gigleux S. The human UDP-glucuronosyltransferases: structural aspects and drug glucuronidation. Drug Metab. Rev. 35 (2003) 287-303
25. Prezelj A., Obreza A., and Pecar S. Abuse of clenbuterol and its detection. Curr. Med. Chem. 10 (2003) 281-290
26. Reiss P., Burnett D.A., and Zaks A. An enzymatic synthesis of glucuronides of azetidinone-based cholesterol absorption inhibitors. Bioorg. Med. Chem. 7 (1999) 2199-2202
27. Ritter J.K. Roles of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reactions. Chem. Biol. Interact. 129 (2000) 171-193
28. Salonen J.S. Tissue-specificity of hydroxylation and N-methylation of arylalkylimidazoles. Pharmacol. Toxicol. 69 (1991) 1-4
29. 2-agonist abuse in food producing animals: use of in vitro liver preparations to assess biotransformation and potential target residues for surveillance. Xenobiotica 29 (1999) 483-497
30. Schmid J., Prox A., Zimmer A., Keck J., and Kaschke S. Biotransformation of clenbuterol. Fresenius J. Anal. Chem. 337 (1990) 121
31. Shelver W.L., and Smith D.J. Evaluation of commercial immunoassays for cross-reactivity to clenbuterol stereoisomers and bovine metabolites. Food Addit. Contam. 17 (2000) 837-845
32. Smith D.J. The pharmacokinetics, metabolism, and tissue residues of β-adrenergic agonists in livestock. J. Anim. Sci. 76 (1998) 173-194
33. Soars M.G., Mattiuz E.L., Jackson D.A., Kulanthaivel P., Ehlhardt W.J., and Wrighton S.A. Biosynthesis of drug glucuronides for use as authentic standards. J. Pharmacol. Toxicol. Methods 47 (2002) 161-168
34. Stachulski A.V., and Jenkins G.N. The synthesis of O-glucuronides. Nat. Prod. Rep. 15 (1998) 173-186
35. Stevenson D.E., and Hubl U. Optimization of β-d-glucuronide synthesis using UDP-glucuronyl transferase. Enzyme Microb. Technol. 24 (1999) 388-396
36. Tukey R.H., and Strassburg C.P. Human UDP-glucuronosyltransferases: metabolism, expression, and disease. Annu. Rev. Pharmacol. Toxicol. 40 (2000) 581-616
37. Wen Z., Tallman M.N., Ali S.Y., and Smith P.C. UDP-glucuronosyltransferase 1A1 is the principal enzyme responsible for etoposide glucuronidation in human liver and intestinal microsomes: structural characterization of phenolic and alcoholic glucuronides of etoposide and estimation of enzyme kinetics. Drug Metab. Dispos. 35 (2007) 371-380
38. Zalko D., Debrauwer L., Bories G., and Tulliez J. Evidence for a new and major metabolic pathway of clenbuterol involving in vivo formation of an N-hydroxyarylamine. Chem. Res. Toxicol. 10 (1997) 197-204
39. Zalko D., Bories G., and Tulliez J. Metabolic fate of clenbuterol in calves. J. Agric. Food Chem. 46 (1998) 1935-1943
40. Zalko D., Debrauwer L., Bories G., and Tulliez J. Metabolism of clenbuterol in rats. Drug Metab. Dispos. 26 (1998) 891-899
41. Zalko D., Perdu-Durand E., Debrauwer L., Bec-Ferte M.P., and Tulliez J. Comparative metabolism of clenbuterol by rat and bovine liver microsomes and slices. Drug Metab. Dispos. 26 (1998) 28-35