Regioselective glucuronidation of flavonols by six human UGT1A isoforms

Pharmaceutical Research

Volumn 28, Issue 8, 2011, Pages 1905-1918

  Wu, Baojian ^a   Xu, Beibei ^a   Hu, Ming ^a  

^a UNIVERSITY OF HOUSTON   (United States)

Author keywords

flavonols; glucuronidation; regioselectivity; substrate inhibition; UGTs

Indexed keywords

3,7 DIHYDROXYFLAVONE; 3,7,4' TRIHYDROXYFLAVONE; FLAVONOL DERIVATIVE; GALANGIN; GLUCURONOSYLTRANSFERASE 1A1; GLUCURONOSYLTRANSFERASE 1A10; GLUCURONOSYLTRANSFERASE 1A3; GLUCURONOSYLTRANSFERASE 1A7; GLUCURONOSYLTRANSFERASE 1A8; GLUCURONOSYLTRANSFERASE 1A9; KAEMPFEROL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION KINETICS; DRUG GLUCURONIDATION; DRUG METABOLISM; DRUG STRUCTURE; IN VITRO STUDY; PRIORITY JOURNAL; PROTEIN EXPRESSION;

BINDING SITES; CATALYTIC DOMAIN; FLAVONOLS; GLUCURONIDES; GLUCURONOSYLTRANSFERASE; HUMANS; KINETICS; PROTEIN ISOFORMS;

EID: 79961171351     PISSN: 07248741     EISSN: 1573904X     Source Type: Journal    
DOI: 10.1007/s11095-011-0418-5     Document Type: Article

References (33)

1. DF Birt S Hendrich W Wang 2001 Dietary agents in cancer prevention: flavonoids and isoflavonoids Pharmacol Ther 90 2-3 157 177 11578656 10.1016/S0163-7258(01)00137-1 1:CAS:528:DC%2BD3MXntV2htbc%3D (Pubitemid 32913477)
2. JA Ross CM Kasum 2002 Dietary flavonoids: bioavailability, metabolic effects, and safety Annu Rev Nutr 22 19 34 12055336 10.1146/annurev.nutr.22. 111401.144957 1:CAS:528:DC%2BD38XmtF2ht7o%3D (Pubitemid 35221452)
3. J Chen H Lin M Hu 2003 Metabolism of flavonoids via enteric recycling: role of intestinal disposition J Pharmacol Exp Ther 304 3 1228 1235 12604700 10.1124/jpet.102.046409 1:CAS:528:DC%2BD3sXit1eisL4%3D (Pubitemid 36254436)
4. KD Setchell NM Brown P Desai L Zimmer-Nechemias BE Wolfe WT Brashear AS Kirschner A Cassidy JE Heubi 2001 Bioavailability of pure isoflavones in healthy humans and analysis of commercial soy isoflavone supplements J Nutr 131 4 Suppl 1362S 1375S 11285356 1:CAS:528:DC%2BD3MXjsl2itb0%3D (Pubitemid 32268489)
5. A Barve C Chen V Hebbar J Desiderio CL Saw AN Kong 2009 Metabolism, oral bioavailability and pharmacokinetics of chemopreventive kaempferol in rats Biopharm Drug Dispos 30 7 356 65 19722166 10.1002/bdd.677 1:CAS:528: DC%2BD1MXhtFKnt7vO
6. RH Tukey CP Strassburg 2000 Human UDP-glucuronosyltransferases: metabolism, expression, and disease Annu Rev Pharmacol Toxicol 40 581 616 10836148 10.1146/annurev.pharmtox.40.1.581 1:CAS:528:DC%2BD3cXjs1yht7k%3D (Pubitemid 30340694)
7. A Radominska-Pandya M Ouzzine S Fournel-Gigleux J Magdalou 2005 Structure of UDP-glucuronosyltransferases in membranes Methods Enzymol. 400 116 147 16399347 10.1016/S0076-6879(05)00008-X 1:CAS:528:DC%2BD28XoslCjsb0%3D (Pubitemid 43052419)
8. PI Mackenzie KW Bock B Burchell C Guillemette S Ikushiro T Iyanagi JO Miners IS Owens DW Nebert 2005 Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily Pharmacogenetics Genomics 15 677 685 10.1097/01.fpc.0000173483.13689.56 1:CAS:528:DC%2BD2MXpslahtLY%3D (Pubitemid 41345319)
9. MB Fisher MF Paine TJ Strelevitz SA Wrighton 2001 The role of hepatic and extrahepatic UDP-glucuronosyltransferases in human drug metabolism Drug Metab Rev 33 3-4 273 297 11768770 10.1081/DMR-120000653 1:CAS:528: DC%2BD38XjvVGqsg%3D%3D (Pubitemid 33136266)
10. S Ohno S Nakajin 2009 Determination of mRNA expression of human UDP-glucuronosyltransferases and application for localization in various human tissues by real-time reverse transcriptase-polymerase chain reaction Drug Metab Dispos. 37 1 32 40 18838504 10.1124/dmd.108.023598 1:CAS:528: DC%2BD1MXhsVSnuw%3D%3D
11. JO Miners KM Knights JB Houston PI Mackenzie 2006 In vitro-in vivo correlation for drugs and other compounds eliminated by glucuronidation in humans: pitfalls and promises Biochem Pharmacol 71 11 1531 9 16455060 10.1016/j.bcp.2005.12.019 1:CAS:528:DC%2BD28XktVOqtLo%3D
12. JO Miners PI Mackenzie KM Knights 2010 The prediction of drug-glucuronidation parameters in humans: UDP-glucuronosyltransferase enzyme-selective substrate and inhibitor probes for reaction phenotyping and in vitro-in vivo extrapolation of drug clearance and drug-drug interaction potential Drug Metab Rev 42 1 189 201 10.3109/03602530903210716
13. S Aprile E Del Grosso G Grosa 2010 Identification of the human UDP-glucuronosyltransferases involved in the glucuronidation of combretastatin A-4 Drug Metab Dispos. 38 7 1141 6 20375181 10.1124/dmd.109.031435 1:CAS:528:DC%2BC3cXos1Klsb4%3D
14. L Tang R Singh Z Liu M Hu 2009 Structure and concentration changes affect characterization of UGT isoform-specific metabolism of isoflavones Mol Pharm. 6 5 1466 82 19545173 10.1021/mp8002557 1:CAS:528:DC%2BD1MXovVemtrk%3D
15. Q Zhou Z Zheng B Xia L Tang C Lv W Liu Z Liu M Hu 2010 Use of Isoform-Specific UGT Metabolism to Determine and Describe Rates and Profiles of Glucuronidation of Wogonin and Oroxylin A by Human Liver and Intestinal Microsomes Pharm Res 27 8 1568 83 20411407 10.1007/s11095-010-0148-0
16. MJ Sorich PA Smith JO Miners PI Mackenzie R McKinnon 2008 Recent advances in the in silico modelling of UDP glucuronosyltransferase substrates Curr Drug Metab 9 1 60 9 18220572 10.2174/138920008783331167 1:CAS:528: DC%2BD1cXhsFSitbs%3D (Pubitemid 351201671)
17. MJ Sorich PA Smith RA McKinnon JO Miners 2002 Pharmacophore and quantitative structure activity relationship modelling of UDP- glucuronosyltransferase 1A1 (UGT1A1) substrates Pharmacogenetics 12 8 635 645 12439224 10.1097/00008571-200211000-00008 1:CAS:528:DC%2BD38XovVeitbw%3D (Pubitemid 36005673)
18. PA Smith MJ Sorich RA McKinnon JO Miners 2003 In silico insights: chemical and structural characteristics associated with uridine diphosphate glucuronosyltransferase substrate selectivity Clin Exp Pharmacol Physiol 30 11 836 840 14678246 10.1046/j.1440-1681.2003.03923.x 1:CAS:528:DC%2BD3sXps1ensbc%3D (Pubitemid 37506149)
19. L Tang L Ye R Singh B Wu J Zhao C Lv Z Liu M Hu 2010 Use of Glucuronidation Fingerprinting to Describe and Predict mono- and di- Hydroxyflavone Metabolism by Recombinant UGT Isoforms and Human Intestinal and Liver Microsomes Mol Pharm 7 3 664 79 20297805 10.1021/mp900223c 1:CAS:528:DC%2BC3cXkvVKru7w%3D
20. KK Chohan SW Paine NJ Waters 2006 Quantitative structure activity relationships in drug metabolism Curr Top Med Chem 6 15 1569 1578 16918469 10.2174/156802606778108960 1:CAS:528:DC%2BD28XhtVCgsLvE (Pubitemid 44304615)
21. YC Wong L Zhang G Lin Z Zuo 2009 Structure-activity relationships of the glucuronidation of flavonoids by human glucuronosyltransferases Expert Opin Drug Metab Toxicol 5 11 1399 1419 19663742 10.1517/17425250903179300 1:CAS:528:DC%2BD1MXhtlersrvP
22. MG Boersma H van der Woude J Bogaards S Boeren J Vervoort NH Cnubben ML van Iersel PJ van Bladeren IM Rietjens 2002 Regioselectivity of phase II metabolism of luteolin and quercetin by UDP-glucuronosyl transferases Chem Res Toxicol. 15 5 662 670 12018987 10.1021/tx0101705 1:CAS:528:DC%2BD38XivFWitb8%3D (Pubitemid 34535121)
23. BD Davis JS Brodbelt 2008 Regioselectivity of human UDP-glucuronosyl- transferase 1A1 in the synthesis of flavonoid glucuronides determined by metal complexation and tandem mass spectrometry J Am Soc Mass Spectrom 19 2 246 256 18083528 10.1016/j.jasms.2007.11.004 1:CAS:528:DC%2BD1cXitlyktb4%3D
24. JO Miners PA Smith MJ Sorich RA McKinnon PI Mackenzie 2004 Predicting human drug glucuronidation parameters: application of in vitro and in silico modeling approaches Annu Rev Pharmacol Toxicol. 44 1 25 14744236 10.1146/annurev.pharmtox.44.101802.121546 1:CAS:528:DC%2BD2cXhvVCkt78%3D (Pubitemid 38268090)
25. B Wu J Morrow R Singh S Zhang M Hu 2011 Three-Dimensional Quantitative Structure-Activity Relationship Studies on UGT1A9-Mediated 3-O-Glucuronidation of Natural Flavonols Using a Pharmacophore-Based Comparative Molecular Field Analysis Model J Pharmacol Exp Ther 336 2 403 13 21068207 10.1124/jpet.110. 175356 1:CAS:528:DC%2BC3MXhslWhs7s%3D
26. R Singh BJ Wu L Tang ZQ Liu M Hu 2010 Identification of the Position of Mono-O-Glucuronide of Flavones and Flavonols by Analyzing Shift in Online UV Spectrum (λmax) Generated from an Online Diode-arrayed Detector J Agric Food Chem 58 17 9384 9395 20687611 10.1021/jf904561e 1:CAS:528: DC%2BC3cXpslGqurk%3D
27. A Christopoulos MJ Lew 2000 Beyond eyeballing: fitting models to experimental data Crit Rev Biochem Mol Biol. 35 5 359 391 11099051 10.1080/10409230091169212 1:STN:280:DC%2BD3MzgsVKhtQ%3D%3D
28. L Luukkanen J Taskinen M Kurkela R Kostiainen J Hirvonen M Finel 2005 Kinetic characterization of the 1A subfamily of recombinant human UDP-glucuronosyltransferases Drug Metab Dispos 33 7 1017 1026 15802387 10.1124/dmd.105.004093 1:CAS:528:DC%2BD2MXlslWqsLg%3D (Pubitemid 41002784)
29. G Williamson D Barron K Shimoi J Terao 2005 In vitro biological properties of flavonoid conjugates found in vivo Free Radic Res 39 5 457 69 16036321 10.1080/10715760500053610 1:CAS:528:DC%2BD2MXjvFajtr4%3D (Pubitemid 40711878)
30. JM Hutzler TS Tracy 2002 Atypical kinetic profiles in drug metabolism reactions Drug Metab Dispos 30 4 355 62 11901086 10.1124/dmd.30.4.355 1:CAS:528:DC%2BD38Xis1Ols7s%3D (Pubitemid 34263817)
31. Segel IH. Enzyme kinetics: behavior and analysis of rapid equilibrium and steady state enzyme systems, New edn. New York: Wiley; 1993.
32. C Li Q Wu 2007 Adaptive evolution of multiple-variable exons and structural diversity of drugmetabolizing enzymes BMC Evol Biol. 7 69 17475008 10.1186/1471-2148-7-69 (Pubitemid 46876381)
33. L Laakkonen M Finel 2010 A molecular model of the human UGT1A1, its membrane orientation and the interactions between different parts of the enzyme Mol Pharmacol 77 6 931 939 20215562 10.1124/mol.109.063289 1:CAS:528: DC%2BC3cXmslKntr8%3D