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

No abstract is available for this paper.

• Publication year

  2011

• Venue

  Journal of Pharmacology and Experimental Therapeutics

• Publication date

  2011-02-01

• Fields of study

  Medicine, Chemistry

• Identifiers
  DOI 10.1124/jpet.110.175356PMID 21068207PMCID PMC3033718
• External record

  Open on Semantic Scholar

• Source metadata

  Semantic Scholar, PubMed

• No claims are published for this paper.

• No concepts are published for this paper.

• Identification of the position of mono-O-glucuronide of flavones and flavonols by analyzing shift in online UV spectrum (lambdamax) generated from an online diode array detector.

  2010cited by this paper
• Phase II drug metabolizing enzymes.

  2010cited by this paper
• Use of glucuronidation fingerprinting to describe and predict mono- and dihydroxyflavone metabolism by recombinant UGT isoforms and human intestinal and liver microsomes.

  2010cited by this paper
• A Molecular Model of the Human UDP-Glucuronosyltransferase 1A1, Its Membrane Orientation, and the Interactions between Different Parts of the Enzyme

  2010cited by this paper
• Structure and concentration changes affect characterization of UGT isoform-specific metabolism of isoflavones.

  2009cited by this paper
• In silico and in vitro approaches to elucidate the thermal stability of human UDP-glucuronosyltransferase (UGT) 1A9.

  2009cited by this paper
• Metabolism, oral bioavailability and pharmacokinetics of chemopreventive kaempferol in rats.

  2009cited by this paper
• Substrate specificity of plant UDP-dependent glycosyltransferases predicted from crystal structures and homology modeling.

  2009cited by this paper
• Determination of mRNA Expression of Human UDP-Glucuronosyltransferases and Application for Localization in Various Human Tissues by Real-Time Reverse Transcriptase-Polymerase Chain Reaction

  2009cited by this paper
• Structure–activity relationships of the glucuronidation of flavonoids by human glucuronosyltransferases

  2009cited by this paper
• Recent advances in the in silico modelling of UDP glucuronosyltransferase substrates.

  2008influential reference
• Glucuronidation of flavonoids by recombinant UGT1A3 and UGT1A9.

  2008influential reference
• Mutation analysis in UGT1A9 suggests a relationship between substrate and catalytic residues in UDP-glucuronosyltransferases.

  2008influential reference
• Molecular mechanism of phase I and phase II drug-metabolizing enzymes: implications for detoxification.

  2007cited by this paper
• Comparative molecular field analysis of flavonoid inhibitors of the PIM-1 kinase.

  2007cited by this paper
• Polyphenols, dietary sources and bioavailability.

  2007cited by this paper
• Disposition of flavonoids via enteric recycling: enzyme stability affects characterization of prunetin glucuronidation across species, organs, and UGT isoforms.

  2007cited by this paper
• Quantitative structure activity relationships in drug metabolism.

  2006cited by this paper
• Bioavailability of Quercetin From Berries and the Diet

  2006cited by this paper
• IN VITRO CHARACTERIZATION OF LAMOTRIGINE N2-GLUCURONIDATION AND THE LAMOTRIGINE-VALPROIC ACID INTERACTION

  2006cited by this paper
• KINETIC CHARACTERIZATION OF THE 1A SUBFAMILY OF RECOMBINANT HUMAN UDP-GLUCURONOSYLTRANSFERASES

  2005cited by this paper
• Quantitative regioselectivity of glucuronidation of quercetin by recombinant UDP-glucuronosyltransferases 1A9 and 1A3 using enzymatic kinetic parameters

  2005cited by this paper
• Nomenclature update for the mammalian UDP glycosyltransferase (UGT) gene superfamily.

  2005cited by this paper
• Binding model construction of antifungal 2-aryl-4-chromanones using CoMFA, CoMSIA, and QSAR analyses.

  2005cited by this paper
• Towards integrated ADME prediction: past, present and future directions for modelling metabolism by UDP-glucuronosyltransferases.

  2004influential reference
• Predicting human drug glucuronidation parameters: application of in vitro and in silico modeling approaches.

  2004influential reference
• Comparative molecular field analysis and QSAR on substrates binding to cytochrome p450 2D6.

  2003cited by this paper
• In silico insights: Chemical and structural characteristics associated with uridine diphosphate‐glucuronosyltransferase substrate selectivity

  2003cited by this paper
• Quantitative structure activity relationships for the glucuronidation of simple phenols by expressed human UGT1A6 and UGT1A9.

  2002cited by this paper
• Comparative Molecular Field Analysis (CoMFA)

  2002cited by this paper
• Pharmacophore and quantitative structure activity relationship modelling of UDP-glucuronosyltransferase 1A1 (UGT1A1) substrates.

  2002influential reference
• Glucuronidation versus oxidation of the flavonoid galangin by human liver microsomes and hepatocytes.

  2002cited by this paper
• Dietary flavonoids: bioavailability, metabolic effects, and safety.

  2002influential reference
• Dietary agents in cancer prevention: flavonoids and isoflavonoids.

  2001influential reference
• The role of hepatic and extrahepatic UDP-glucuronosyltransferases in human drug metabolism*†

  2001cited by this paper
• Beyond Eyeballing: Fitting Models to Experimental Data

  2000cited by this paper
• Comparative molecular field analysis (CoMFA) and docking studies of non-nucleoside HIV-1 RT inhibitors (NNIs).

  1999cited by this paper
• INHIBITION OF BILIRUBIN UDP-GLUCURONOSYLTRANSFERASE : A COMPARATIVE MOLECULAR FIELD ANALYSIS (COMFA)

  1996cited by this paper
• Comparative molecular field analysis (CoMFA). 1. Effect of shape on binding of steroids to carrier proteins.

  1988cited by this paper

• Insight into the structure, oligomerization, and the role in drug resistance of human UDP-glucuronosyltransferases

  2025cites this paper
• In Silico ADME Methods Used in the Evaluation of Natural Products

  2025cites this paper
• Simple preparation and greatly improved oral bioavailability: The supersaturated drug delivery system of quercetin based on PVP K30

  2024cites this paper
• Antioxidant Activity, Metabolism, and Bioavailability of Polyphenols in the Diet of Animals

  2023influential citation
• Homology Modeling of Human Uridine-5′-diphosphate-glucuronosyltransferase 1A6 Reveals Insights into Factors Influencing Substrate and Cosubstrate Binding

  2020cites this paper
• SAR Studies and Biological Characterization of a Chromen-4-one Derivative as an Anti-Trypanosoma brucei Agent.

  2019cites this paper
• Overcoming Drug Resistance through the Development of Selective Inhibitors of UDP-Glucuronosyltransferase Enzymes.

  2019cites this paper
• Identification of UGTs and BCRP as potential pharmacokinetic determinants of the natural flavonoid alpinetin

  2019cites this paper
• Drug interaction study of flavonoids toward CYP3A4 and their quantitative structure activity relationship (QSAR) analysis for predicting potential effects.

  2018cites this paper
• Establishment and use of new MDCK II cells overexpressing both UGT1A1 and MRP2 to characterize flavonoid metabolism via the glucuronidation pathway.

  2016cites this paper
• Disposition of flavonoids via recycling: Direct biliary excretion of enterically or extrahepatically derived flavonoid glucuronides.

  2016cites this paper
• Predicting substrate selectivity between UGT1A9 and UGT1A10 using molecular modelling and molecular dynamics approach

  2016cites this paper
• Drug interaction study of natural steroids from herbs specifically toward human UDP-glucuronosyltransferase (UGT) 1A4 and their quantitative structure activity relationship (QSAR) analysis for prediction.

  2016cites this paper
• C-8 Mannich base derivatives of baicalein display improved glucuronidation stability: exploring the mechanism by experimentation and theoretical calculations

  2015cites this paper
• HQSAR and topomer CoMFA for predicting melanocortin-4 receptor binding affinities of trans-4-(4-chlorophenyl) pyrrolidine-3-carboxamides

  2015cites this paper
• Flavonoid interactions during digestion, absorption, distribution and metabolism: a sequential structure–activity/property relationship-based approach in the study of bioavailability and bioactivity

  2015influential citation
• Absolute quantification of UGT1A1 in various tissues and cell lines using isotope label-free UPLC-MS/MS method determines its turnover number and correlates with its glucuronidation activities.

  2014cites this paper
• SVM Classification and CoMSIA Modeling of UGT1A6 Interacting Molecules

  2014cites this paper
• Pharmacophore‐Based Methods for Predicting the Inhibition and Induction of Metabolic Enzymes

  2014cites this paper
• Revolving door action of breast cancer resistance protein (BCRP) facilitates or controls the efflux of flavone glucuronides from UGT1A9-overexpressing HeLa cells.

  2013cites this paper
• Substrate selectivity of human intestinal UDP-glucuronosyltransferases (UGTs): in silico and in vitro insights

  2013influential citation
• Mutual regioselective inhibition of human UGT1A1-mediated glucuronidation of four flavonoids.

  2013cites this paper
• Toward in silico structure-based ADMET prediction in drug discovery.

  2012cites this paper
• Systematic studies of sulfation and glucuronidation of 12 flavonoids in the mouse liver S9 fraction reveal both unique and shared positional preferences.

  2012cites this paper
• A New Strategy to Rapidly Evaluate Kinetics of Glucuronide Efflux by Breast Cancer Resistance Protein (BCRP/ABCG2)

  2012cites this paper
• In silico modeling of UDP-glucuronosyltransferase 1A10 substrates using the VolSurf approach.

  2012cites this paper
• Accurate Prediction of Glucuronidation of Structurally Diverse Phenolics by Human UGT1A9 Using Combined Experimental and In Silico Approaches

  2012cites this paper
• Understanding substrate selectivity of human UDP-glucuronosyltransferases through QSAR modeling and analysis of homologous enzymes

  2012cites this paper
• What are the Real Causes of Substrate Inhibition in the Glucuronidation Reaction

  2012cites this paper
• 3D-QSAR studies on UDP-glucuronosyltransferase 2B7 substrates using the pharmacophore and VolSurf approaches

  2012cites this paper
• Uridine diphosphate glucuronosyltransferase isoform-dependent regiospecificity of glucuronidation of flavonoids.

  2011cites this paper
• Regioselective sulfation and glucuronidation of phenolics: insights into the structural basis.

  2011cites this paper
• Evaluation of 3,3',4'-trihydroxyflavone and 3,6,4'-trihydroxyflavone (4'-O-glucuronidation) as the in vitro functional markers for hepatic UGT1A1.

  2011cites this paper
• Regioselective Glucuronidation of Flavonols by Six Human UGT1A Isoforms

  2011cites this paper
• Translational research insights into pharmacokinetic herb-drug interactions.

  2011cites this paper
• First-pass metabolism via UDP-glucuronosyltransferase: a barrier to oral bioavailability of phenolics.

  2011cites this paper