Publication Cover
Xenobiotica
the fate of foreign compounds in biological systems
Volume 45, 2015 - Issue 8
166
Views
2
CrossRef citations to date
0
Altmetric
General Xenobiochemistry

Establishment of pharmacophore and VolSurf models to predict the substrates of UDP-glucuronosyltransferase1A3

, , &
Pages 653-662 | Received 12 Jan 2015, Accepted 03 Feb 2015, Published online: 02 Apr 2015

References

  • Ako R, Dong D, Wu B. (2012). 3D-QSAR studies on UDP-glucuronosyltransferase 2B7 substrates using the pharmacophore and VolSurf approaches. Xenobiotica 42:891–900
  • Alonen A, Finel M, Kostiainen R. (2008). The human UDP-glucuronosyltransferase UGT1A3 is highly selective towards N2 in the tetrazole ring of losartan, candesartan, and zolarsartan. Biochem Pharmacol 76:763–72
  • Argikar UA, Remmel RP. (2009). Variation in glucuronidation of lamotrigine in human liver microsomes. Xenobiotica 39:355–63
  • Bauman JN, Goosen TC, Tugnait M, et al. (2005). UDP-glucuronosyltransferase 2B7 is the major enzyme responsible for gemcabene glucuronidation in human liver microsomes. Drug Metab Dispos 33:1349–54
  • Buckle DR, Erhardt PW, Ganellin CR, et al. (2013). Glossary of terms used in medicinal chemistry part II (IUPAC recommendations 2013). Ann Rep Med Chem 48:387–418
  • Chen YK, Xie SG, Chen SQ, Zeng S. (2008). Glucuronidation of flavonoids by recombinant UGT1A3 and UGT1A9. Biochem Pharmacol 76:416–25
  • Cianchetta G, Mannhold R, Cruciani G, et al. (2004). Chemometric studies on the bactericidal activity of quinolones via an extended VolSurf approach. J Med Chem 47:3193–201
  • Cramer RD, Patterson DE, Bunce JD. (1988). Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110:5959–67
  • Crivori P, Cruciani G, Carrupt PA, Testa B. (2000). Predicting blood-brain barrier permeation from three-dimensional molecular structure. J Med Chem 43:2204–16
  • Cruciani C, Crivori P, Carrupt PA, Testa B. (2000a). Molecular fields in quantitative structure-permeation relationships: the VolSurf approach. J Mol Struct Theochem 503:17–30
  • Cruciani G, Pastor M, Guba W. (2000b). VolSurf: a new tool for the pharmacokinetic optimization of lead compounds. Eur J Pharm Sci 11:S29–39
  • Dellinger RW, Garcia AM, Meyskens FL. Jr. (2014). Differences in the glucuronidation of resveratrol and pterostilbene: altered enzyme specificity and potential gender differences. Drug Metab Pharmacokinet 29:112–19
  • Dong D, Ako R, Hu M, Wu BJ. (2012). Understanding substrate selectivity of human UDP-glucuronosyltransferases through QSAR modeling and analysis of homologous enzymes. Xenobiotica 42:808–20
  • Dong D, Wu B. (2012). In silico modeling of UDP-glucuronosyltransferase 1A10 substrates using the VolSurf approach. J Pharm Sci 101:3531–9
  • Ekins S, Bravi G, Binkley S, et al. (2000a). Three- and four-dimensional-quantitative structure activity relationship (3D/4D-QSAR) analyses of CYP2C9 inhibitors. Drug Metab Dispos 28:994–1002
  • Ekins S, Waller CL, Swaan PW, et al. (2000b). Progress in predicting human ADME parameters in silico. J Pharmacol Toxicol Methods 44:251–72
  • Ghosal A, Hapangama N, Yuan Y, et al. (2004). Identification of human UDP-glucuronosyltransferase enzyme(s) responsible for the glucuronidation of ezetimibe (Zetia). Drug Metab Dispos 32:314–20
  • Iwai M, Maruo Y, Ito M, et al. (2004). Six novel UDP-glucuronosyltransferase (UGT1A3) polymorphisms with varying activity. J Hum Genet 49:123–8
  • Jakoby WB, Ziegler DM. (1990). The enzymes of detoxication. J Biol Chem 265:20715–18
  • Jeong ES, Kim YW, Kim HJ, et al. (2015). Glucuronidation of fimasartan, a new angiotensin receptor antagonist, is mainly mediated by UGT1A3. Xenobiotica 45:10–18
  • John S, Thangapandian S, Sakkiah S, Lee KW. (2011). Potent bace-1 inhibitor design using pharmacophore modeling, in silico screening and molecular docking studies. BMC Bioinformatics 12:S28
  • Koga T, Fujiwara R, Nakajima M, Yokoi T. (2011). Toxicological evaluation of acyl glucuronides of nonsteroidal anti-inflammatory drugs using human embryonic kidney 293 cells stably expressing human UDP-glucuronosyltransferase and human hepatocytes. Drug Metab Dispos 39:54–60
  • Kuehl GE, Lampe JW, Potter JD, Bigler J. (2005). Glucuronidation of nonsteroidal anti-inflammatory drugs: identifying the enzymes responsible in human liver microsomes. Drug Metab Dispos 33:1027–35
  • Mackenzie PI, Bock KW, Burchell B, et al. (2005). Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily. Pharmacogenet Genomics 15:677–85
  • Miners JO, Bowalgaha K, Elliot DJ, et al. (2011). Characterization of niflumic acid as a selective inhibitor of human liver microsomal UDP-glucuronosyltransferase 1A9: application to the reaction phenotyping of acetaminophen glucuronidation. Drug Metab Dispos 39:644–52
  • Muzeeb S, Basha SJ, Shashikumar D, et al. (2006). Glucuronidation of DRF-6574, hydroxy metabolite of DRF-4367 (a novel COX-2 inhibitor) by pooled human liver, intestinal microsomes and recombinant human UDP-glucuronosyltransferases (UGT): role of UGT1A1, 1A3 and 1A8. Eur J Drug Metab Pharmacokinet 31:299–309
  • Oda S, Nakajima M, Hatakeyama M, et al. (2012). Preparation of a specific monoclonal antibody against human UDP-glucuronosyltransferase (UGT) 1A9 and evaluation of UGT1A9 protein levels in human tissues. Drug Metab Dispos 40:1620–7
  • Ortega SS, Cara LC, Salvador MK. (2012). In silico pharmacology for a multidisciplinary drug discovery process. Drug Metabol Drug Interact 27:199–207
  • Ritter JK. (2000). Roles of glucuronidation and UDP-glucuronosyltransferases in xenobiotic bioactivation reactions. Chem Biol Interact 129:171–93
  • Rouguieg K, Picard N, Sauvage FL, et al. (2010). Contribution of the different UDP-glucuronosyltransferase (UGT) isoforms to buprenorphine and norbuprenorphine metabolism and relationship with the main UGT polymorphisms in a bank of human liver microsomes. Drug Metab Dispos 38:40–5
  • Sakaguchi K, Green M, Stock N, et al. (2004). Glucuronidation of carboxylic acid containing compounds by UDP-glucuronosyltransferase isoforms. Arch Biochem Biophys 424:219–25
  • Sakkiah S, Baek A, Lee KW. (2012). Pharmacophore modeling and molecular dynamics simulation to identify the critical chemical features against human sirtuin 2 inhibitors. J Mol Struct 1011:66–75
  • Shahlaei M. (2013). Descriptor selection methods in quantitative structure-activity relationship studies: a review study. Chem Rev 113:8093–103
  • Sheweita SA. (2000). Drug-metabolizing enzymes: mechanisms and functions. Curr Drug Metab 1:107–32
  • Smith PA, Sorich MJ, McKinnon RA, Miners JO. (2003). Pharmacophore and quantitative structure-activity relationship modeling: complementary approaches for the rationalization and prediction of UDP-glucuronosyltransferase 1A4 substrate selectivity. J Med Chem 46:1617–26
  • Sorich MJ, Miners JO, McKinnon RA, Smith PA. (2004). Multiple pharmacophores for the investigation of human UDP-glucuronosyltransferase isoform substrate selectivity. Mol Pharmacol 65:301–8
  • Sorich MJ, Smith PA, McKinnon RA, Miners JO. (2002). Pharmacophore and quantitative structure activity relationship modelling of UDP-glucuronosyltransferase 1A1 (UGT1A1) substrates. Pharmacogenetics 12:635–45
  • Stanton DT. (2012). QSAR and QSPR model interpretation using partial least squares (PLS) analysis. Curr Comput Aided Drug Des 8:107–27
  • Toffoli G, Cecchin E, Corona G, Boiocchi M. (2003). Pharmacogenetics of irinotecan. Curr Med Chem Anticancer Agents 3:225–37
  • Turgeon D, Chouinard S, Belanger P, et al. (2003). Glucuronidation of arachidonic and linoleic acid metabolites by human UDP-glucuronosyltransferases. J Lipid Res 44:1182–91
  • Wang M, Lu J, Li J, et al. (2014). Steviol glucuronidation and its potential interaction with UDP-glucuronosyltransferase 2B7 substrates. Food Chem Toxicol 64:135–43
  • Wolber G, Seidel T, Bendix F, Langer T. (2008). Molecule-pharmacophore superpositioning and pattern matching in computational drug design. Drug Discov Today 13:23–9
  • Wu B, Dong D, Hu M, Zhang S. (2013). Quantitative prediction of glucuronidation in humans using the in vitro-in vivo extrapolation approach. Curr Top Med Chem 13:1343–52
  • Wu B, Kulkarni K, Basu S, et al. (2011a). First-pass metabolism via UDP-glucuronosyltransferase: a barrier to oral bioavailability of phenolics. J Pharm Sci 100:3655–81
  • Wu B, Xu B, Hu M. (2011b). Regioselective glucuronidation of flavonols by six human UGT1A isoforms. Pharm Res 28:1905–18
  • Xie S, Chen Y, Chen S, Zeng S. (2011). Structure-metabolism relationships for the glucuronidation of flavonoids by UGT1A3 and UGT1A9. J Pharm Pharmacol 63:297–304
  • Yamanaka H, Nakajima M, Katoh M, Yokoi T. (2007). Glucuronidation of thyroxine in human liver, jejunum, and kidney microsomes. Drug Metab Dispos 35:1642–8
  • Yu L, Lu S, Lin Y, Zeng S. (2007). Carboxyl-glucuronidation of mitiglinide by human UDP-glucuronosyltransferases. Biochem Pharmacol 73:1842–51

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.