Identification of the UDP-glucuronosyltransferase isozyme involved in senecionine glucuronidation in human liver microsomes

Drug Metabolism and Disposition

Volumn 38, Issue 4, 2010, Pages 626-634

  He, Yu Qi ^a   Liu, Yong ^b   Zhang, Bin Feng ^a   Liu, Hui Xin ^b   Lu, Yan Liu ^a   Yang, Li ^a   Xiong, Ai Zhen ^a   Xu, Ling Ling ^a   Wang, Chang Hong ^a   Yang, Ling ^b   Wang, Zheng Tao ^a  

^a SHANGHAI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

^b DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

[No Author keywords available]

Indexed keywords

GLUCURONIC ACID; GLUCURONOSYLTRANSFERASE 1A4; GLYCOSYLTRANSFERASE INHIBITOR; HECOGENIN; RECOMBINANT ENZYME; SENECIONINE;

ARTICLE; CHEMICAL STRUCTURE; CONTROLLED STUDY; DRUG GLUCURONIDATION; ENZYME ACTIVITY; ENZYME INHIBITION; HUMAN; LIVER MICROSOME METABOLISM; MICHAELIS CONSTANT; PRIORITY JOURNAL; TOXICOKINETICS;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; INDICATORS AND REAGENTS; ISOENZYMES; MAGNETIC RESONANCE SPECTROSCOPY; MICROSOMES, LIVER; PYRROLIZIDINE ALKALOIDS; RECOMBINANT PROTEINS; SAPOGENINS; TANDEM MASS SPECTROMETRY;

EID: 77950213268     PISSN: 00909556     EISSN: 1521009X     Source Type: Journal    
DOI: 10.1124/dmd.109.030460     Document Type: Article

References (33)

1. Bjornsson TD, Callaghan JT, Einolf HJ, Fischer V, Gan L, Grimm S, Kao J, King SP, Miwa G, Ni L, et al. (2003) The conduct of in vitro and in vivo drug-drug interaction studies: a Pharmaceutical Research and Manufacturers of America (PhRMA) perspective. Drug Metab Dispos 31:815-832.
2. Chen G, Blevins-Primeau AS, Dellinger RW, Muscat JE, and Lazarus P (2007) Glucuronidation of nicotine and cotinine by UGT2B10: loss of function by the UGT2B10 codon 67 (Asp>Tyr) polymorphism. Cancer Res 67:9024-9029.
3. Chen G, Dellinger RW, Sun D, Spratt TE, and Lazarus P (2008) Glucuronidation of tobacco-specific nitrosamines by UGT2B10. Drug Metab Dispos 36:824-830.
4. Chiu SH and Huskey SW (1998) Species differences in N-glucuronidation. Drug Metab Dispos 26:838-847.
5. Couet CE, Hopley J, and Hanley AB (1996) Metabolic activation of pyrrolizidine alkaloids by human, rat and avocado microsomes. Toxicon 34:1058-1061.
6. Crews C, Startin JR, and Clarke PA (1997) Determination of pyrrolizidine alkaloids in honey from selected sites by solid phase extraction and HPLC-MS. Food Addit Contam 14:419-428.
7. Dueker SR, Lamé MW, and Segall HJ (1992) Hydrolysis of pyrrolizidine alkaloids by guinea pig hepatic carboxylesterases. Toxicol Appl Pharmacol 117:116-121.
8. Fu PP, Xia Q, Lin G, and Chou MW (2004) Pyrrolizidine alkaloids - genotoxicity, metabolism enzymes, metabolic activation, and mechanisms. Drug Metab Rev 36:1-55.
9. Green MD, King CD, Mojarrabi B, Mackenzie PI, and Tephly TR (1998) Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab Dispos 26:507-512.
10. Hanioka N, Jinno H, Tanaka-Kagawa T, Nishimura T, and Ando M (2001) Determination of UDP-glucuronosyltransferase UGT1A6 activity in human and rat liver microsomes by HPLC with UV detection. J Pharm Biomed Anal 25:65-75.
11. Hartmann T (2008) Pyrrolizidine alkaloids: the successful adoption of a plant chemical defense, in Tiger Moths and Woolly Bears: Behavior, Ecology, and Evolution of the Arctiidae (Conner WE ed), Oxford University Press, New York.
12. Huan JY, Miranda CL, Buhler DR, and Cheeke PR (1998) Species differences in the hepatic microsomal enzyme metabolism of the pyrrolizidine alkaloids. Toxicol Lett 99:127-137.
13. Kaivosaari S, Toivonen P, Aitio O, Sipilä J, Koskinen M, Salonen JS, and Finel M (2008) Regioand stereospecific N-glucuronidation of medetomidine: the differences between UDP glucuronosyltransferase (UGT) 1A4 and UGT2B10 account for the complex kinetics of human liver microsomes. Drug Metab Dispos 36:1529-1537.
14. Kaivosaari S, Toivonen P, Hesse LM, Koskinen M, Court MH, and Finel M (2007) Nicotine glucuronidation and the human UDP-glucuronosyltransferase UGT2B10. Mol Pharmacol 72:761-768.
15. King CD, Rios GR, Green MD, and Tephly TR (2000) UDP- glucuronosyltransferases. Curr Drug Metab 1:143-161.
16. Lin G, Cui YY, and Hawes EM (2000) Characterization of rat liver microsomal metabolites of clivorine, an hepatotoxic otonecine-type pyrrolizidine alkaloid. Drug Metab Dispos 28:1475-1483.
17. Liu HX, He YQ, Hu Y, Liu Y, Zhang JW, Li W, Wang ZT, and Yang L (2008a) Determination of UDP-glucuronosyltransferase UGT2B7 activity in human liver microsomes by ultraperformance liquid chromatography with MS detection. J Chromatogr B Analyt Technol Biomed Life Sci 870:84-90.
18. Liu HX, Liu Y, Zhang JW, Li W, Liu HT, and Yang L (2008b) UDP-glucuronosyltransferase 1A6 is the major isozyme responsible for protocatechuic aldehyde glucuronidation in human liver microsomes. Drug Metab Dispos 36:1562-1569.
19. Luo H, Hawes EM, McKay G, and Midha KK (1992) Synthesis and characterization of quaternary ammonium-linked glucuronide metabolites of drugs with an aliphatic tertiary amine group. J Pharm Sci 81:1079-1083.
20. Nobre VM, Dantas AF, Riet-Correa F, Barbosa Filho JM, Tabosa IM, and Vasconcelos JS (2005) Acute intoxication by Crotalaria retusa in sheep. Toxicon 45:347-352.
21. Prakash AS, Pereira TN, Reilly PE, and Seawright AA (1999) Pyrrolizidine alkaloids in human diet Mutat Res 443:53-67.
22. Ritter JK, Chen F, Sheen YY, Tran HM, Kimura S, Yeatman MT, and Owens IS (1992) A novel complex locus UGT1 encodes human bilirubin, phenol, and other UDP-glucuronosyltransferase-isozymes with identical carboxyl termini. J Biol Chem 267:3257-3261.
23. Ritter JK, Crawford JM, and Owens IS (1991) Cloning of two human liver bilirubin UDPglucuronosyltransferase cDNAs with expression in COS-1 cells. J Biol Chem 266:1043-1047.
24. Roeder E (1990) Carbon-13 NMR spectroscopy of pyrrolizidine alkaloids. Phytochemistry 39:11-29.
25. Roeder E (1995) Medicinal plants in Europe containing pyrrolizidine alkaloids. Pharmazie 50:83-98.
26. Roeder E (2000) Medicinal plants in China containing pyrrolizidine alkaloids. Pharmazie 55:711-726.
27. Soars MG, Petullo DM, Eckstein JA, Kasper SC, and Wrighton SA (2004) An assessment of UDP-glucuronosyltransferase induction using primary human hepatocytes. Drug Metab Dispos 32:140-148.
28. Stegelmeier B, Gardner D, and Davis TZ (2009) Livestock poisoning with pyrrolizidinealkaloid-containing plants (Senecio, Crotalaria, Cynoglossum, Amsinckia, Heliotropium, and Echium spp.). Rangelands 31:35-37.
29. Stegelmeier BL, Edgar JA, Colegate SM, Gardner DR, Schoch TK, Coulombe RA, and Molyneux RJ (1999) Pyrrolizidine alkaloid plants, metabolism and toxicity. J Nat Toxins 8:95-116.
30. Tang J, Akao T, Nakamura N, Wang ZT, Takagawa K, Sasahara M, and Hattori M(2007) In vitro metabolism of isoline, a pyrrolizidine alkaloid from Ligularia duciformis, by rodent liver microsomal esterase and enhanced hepatotoxicity by esterase inhibitors. Drug Metab Dispos 35:1832-1839.
31. Uchaipichat V, Mackenzie PI, Elliot DJ, and Miners JO (2006a) Selectivity of substrate (trifluoperazine) and inhibitor (amitriptyline, androsterone, canrenoic acid, hecogenin, phenylbutazone, quinidine, quinine, and sulfinpyrazone) "probes" for human UDP-glucuronosyltransferases. Drug Metab Dispos 34:449-456.
32. Uchaipichat V, Winner LK, Mackenzie PI, Elliot DJ, Williams JA, and Miners JO (2006b) Quantitative prediction of in vivo inhibitory interactions involving glucuronidated drugs from in vitro data: the effect of fluconazole on zidovudine glucuronidation. Br J Clin Pharmacol 61:427-439.
33. Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, and Ball SE (2004) Drug-drug interactions for UDP- glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos 32:1201-1208.