Glucuronides from metabolites to medicines: a survey of the in vivo generation, chemical synthesis and properties of glucuronides

Design of Self-Immolative Linkers for Tumour-Activated Prodrug Therapy

(2013) I. Tranoy-Opalinski et al.   Anti-Cancer Agents in Medicinal Chemistry

Synthesis and Antitumor Efficacy of a β-Glucuronidase-Responsive Albumin-Binding Prodrug of Doxorubicin

(2012) Thibaut Legigan et al.   JOURNAL OF MEDICINAL CHEMISTRY

Glucosides of morphine derivatives: synthesis and characterization

(2012) András Váradi et al.   MONATSHEFTE FUR CHEMIE

Multiple NSAID-Induced Hits Injure the Small Intestine: Underlying Mechanisms and Novel Strategies

(2012) Urs A. Boelsterli et al.   TOXICOLOGICAL SCIENCES

Glucuronide directed molecularly imprinted solid-phase extraction: isolation of testosterone glucuronide from its parent drug in urine

(2011) Serena Ambrosini et al.   ANALYST

Direct quantification of deoxynivalenol glucuronide in human urine as biomarker of exposure to the Fusarium mycotoxin deoxynivalenol

(2011) Benedikt Warth et al.   ANALYTICAL AND BIOANALYTICAL CHEMISTRY

Direct quantification of cannabinoids and cannabinoid glucuronides in whole blood by liquid chromatography–tandem mass spectrometry

(2011) David M. Schwope et al.   ANALYTICAL AND BIOANALYTICAL CHEMISTRY

A Humanized Immunoenzyme with Enhanced Activity for Glucuronide Prodrug Activation in the Tumor Microenvironment

(2011) Kai-Chuan Chen et al.   BIOCONJUGATE CHEMISTRY

Chemical and Enzyme-Assisted Syntheses of Norbuprenorphine-3-β-d-glucuronide

(2011) Jinda Fan et al.   BIOCONJUGATE CHEMISTRY

Synthesis and Characterization of Biodegradable and Thermosensitive Polymeric Micelles with Covalently Bound Doxorubicin-Glucuronide Prodrug via Click Chemistry

(2011) M. Talelli et al.   BIOCONJUGATE CHEMISTRY

A Heterodimeric Glucuronide Prodrug for Cancer Tritherapy: the Double Role of the Chemical Amplifier

(2011) Marion Grinda et al.   ChemMedChem

Biosynthesis and Identification of an N-Oxide/N-Glucuronide Metabolite and First Synthesis of an N-O-Glucuronide Metabolite of Lu AA21004

(2011) H. K. Uldam et al.   DRUG METABOLISM AND DISPOSITION

Production of Ibuprofen Acyl Glucosides by Human UGT2B7

(2011) D. Buchheit et al.   DRUG METABOLISM AND DISPOSITION

Biochemical and pharmacological profile of darexaban, an oral direct factor Xa inhibitor

(2011) Yoshiyuki Iwatsuki et al.   EUROPEAN JOURNAL OF PHARMACOLOGY

Uridine Diphosphate Glucuronosyltransferase Isoform-Dependent Regiospecificity of Glucuronidation of Flavonoids

(2011) Rashim Singh et al.   JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

First Chemical Synthesis and in Vitro Characterization of the Potential Human Metabolites 5-O-Feruloylquinic Acid 4′-Sulfate and 4′-O-Glucuronide

(2011) Candice Menozzi-Smarrito et al.   JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

Chemical synthesis of allyl-[13C6]-glucuronate

(2011) Bachir Latli et al.   JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS

Development and validation of LC-HRMS and GC-NICI-MS methods for stereoselective determination of MDMA and its phase I and II metabolites in human urine

(2011) Andrea E. Schwaninger et al.   JOURNAL OF MASS SPECTROMETRY

Simultaneous determination of raltegravir and raltegravir glucuronide in human plasma by liquid chromatography-tandem mass spectrometric method

(2011) Ling-Zhi Wang et al.   JOURNAL OF MASS SPECTROMETRY

Thiazolides as Novel Antiviral Agents. 1. Inhibition of Hepatitis B Virus Replication

(2011) Andrew V. Stachulski et al.   JOURNAL OF MEDICINAL CHEMISTRY

Characterization of chemo- and regioselectivity in enzyme-catalyzed consecutive hydrolytic deprotection of methyl acetyl derivatives of 1-β-O-acyl glucuronides

(2011) Akiko Baba et al.   JOURNAL OF MOLECULAR CATALYSIS B-ENZYMATIC

Experimental and Kinetic Studies of theEscherichia coliGlucuronylsynthase: An Engineered Enzyme for the Synthesis of Glucuronide Conjugates

(2011) Shane M. Wilkinson et al.   JOURNAL OF ORGANIC CHEMISTRY

Reagents for Stereoselective Preparation ofN-Carbamyl β-d-Glucuronides

(2011) William H. Bunnelle   JOURNAL OF ORGANIC CHEMISTRY

Determination of resveratrol and its sulfate and glucuronide metabolites in plasma by LC–MS/MS and their pharmacokinetics in dogs

(2011) Miguel Muzzio et al.   JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS

Synthesis of a radioiodinated antiestrogen glucuronide compound (TAM-G)

(2011) Fazilet Zumrut Biber Muftuler et al.   JOURNAL OF RADIOANALYTICAL AND NUCLEAR CHEMISTRY

Synthesis of Glycosides of Glucuronic, Galacturonic and Mannuronic Acids: An Overview

(2011) Anne Wadouachi et al.   MOLECULES

Managing the challenge of chemically reactive metabolites in drug development

(2011) B. Kevin Park et al.   NATURE REVIEWS DRUG DISCOVERY

Synthesis of simple heparanase substrates

(2011) Andrew G. Pearson et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

A new cyclopamine glucuronide prodrug with improved kinetics of drug release

(2011) Brigitte Renoux et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Rapid analysis of isomeric exogenous metabolites by differential mobility spectrometry - mass spectrometry

(2011) Whitney B. Parson et al.   RAPID COMMUNICATIONS IN MASS SPECTROMETRY

Simultaneous quantification of bisphenol A and its glucuronide metabolite (BPA-G) in plasma and urine: Applicability to toxicokinetic investigations

(2011) M.Z. Lacroix et al.   TALANTA

Regiospecific synthesis of quercetin O-β-d-glucosylated and O-β-d-glucuronidated isomers

(2011) Mohammed Kajjout et al.   TETRAHEDRON

A potential glucuronate glycosyl donor with 2-O-acyl-6,3-lactone structure: efficient synthesis of glycosaminoglycan disaccharides

(2011) Takayuki Furukawa et al.   TETRAHEDRON LETTERS

New approach in the synthesis of M6G

(2011) Claire Trécant et al.   TETRAHEDRON LETTERS

An expeditious synthesis of quercetin 3-O-β-d-glucuronide from rutin

(2011) Mohammed Kajjout et al.   TETRAHEDRON LETTERS

Assessment of UDP-glucuronosyltransferase catalyzed formation of Picroside II glucuronide in microsomes of different species and recombinant UGTs

(2011) Tingting Li et al.   XENOBIOTICA

Synthesis and Evaluation of [18F]-FEAnGA as a PET Tracer for β-Glucuronidase Activity

(2010) Inês F. Antunes et al.   BIOCONJUGATE CHEMISTRY

Acyl glucuronides: the good, the bad and the ugly

(2010) Sophie L. Regan et al.   BIOPHARMACEUTICS & DRUG DISPOSITION

Enzymatic Synthesis of Uracil Glucuronide, Labeling with 125/131I, and In Vitro Evaluation on Adenocarcinoma Cells

(2010) Ilker Emin Medine et al.   CANCER BIOTHERAPY AND RADIOPHARMACEUTICALS

Development of an Automated Synthesis System for Preparation of Glucuronides Using a Solid-Phase Extraction Column Loaded with Microsomes

(2010) Yousuke Kashima et al.   CHEMICAL & PHARMACEUTICAL BULLETIN

Direct Analysis of Glucuronides with Liquid Chromatography-Mass Spectrometric Techniques and Methods

(2010) Raimo A. Ketola et al.   CURRENT DRUG METABOLISM

Chemical Synthesis of Citrus Flavanone Glucuronides

(2010) Muhammad Kamran Khan et al.   JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

Application of one-step liquid chromatography–electrospray tandem MS/MS and collision-induced dissociation to quantification of ezetimibe and identification of its glucuronated metabolite in human serum: A pharmacokinetic study

(2010) Gholamreza Bahrami et al.   JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES

Hydrophilic interaction liquid chromatography and accurate mass measurement for quantification and confirmation of morphine, codeine and their glucuronide conjugates in human urine

(2010) M. Kolmonen et al.   JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES

SnCl4- and TiCl4-Catalyzed Anomerization of AcylatedO- andS-Glycosides: Analysis of Factors That Lead to Higher α:β Anomer Ratios and Reaction Rates

(2010) Wayne Pilgrim et al.   JOURNAL OF ORGANIC CHEMISTRY

Characterisation and identification of the human N+-glucuronide metabolite of cediranib

(2010) Eva M. Lenz et al.   JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS

Retinoyl β-Glucuronide: A Biologically Active Form of Vitamin A

(2010) Arun B. Barua   NUTRITION REVIEWS

First synthesis, characterization, and evidence for the presence of hydroxycinnamic acid sulfate and glucuronide conjugates in human biological fluids as a result of coffee consumption

(2010) René Fumeaux et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Synthesis of a series of phenylacetic acid 1-β-O-acyl glucosides and comparison of their acyl migration and hydrolysis kinetics with the corresponding acyl glucuronides

(2010) Lisa Iddon et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

High-performance liquid chromatography/mass spectrometric and proton nuclear magnetic resonance spectroscopic studies of the transacylation and hydrolysis of the acyl glucuronides of a series of phenylacetic acids in buffer and human plasma

(2010) Elin S. Karlsson et al.   RAPID COMMUNICATIONS IN MASS SPECTROMETRY

First synthesis and full characterization of mexiletine N-carbonyloxy β-d-glucuronide

(2010) Maria Maddalena Cavalluzzi et al.   TETRAHEDRON LETTERS

Production of human phase 1 and 2 metabolites by whole-cell biotransformation with recombinant microbes

(2010) Andy Zöllner et al.   Bioanalysis

Efficient synthesis of glycyrrhetinic acid glycoside/glucuronide derivatives using silver zeolite as promoter

(2009) Maria Carmen del Ruiz Ruiz et al.   CARBOHYDRATE RESEARCH

A concise synthesis of glucuronide metabolites of urolithin-B, resveratrol, and hydroxytyrosol

(2009) Ricardo Lucas et al.   CARBOHYDRATE RESEARCH

4-Hydroxy-3-methoxymethamphetamine Glucuronide as a Phase II Metabolite of 3,4-Methylenedioxymethamphetamine: Enzyme-Assisted Synthesis and Involvement of Human Hepatic Uridine 5′-Diphosphate-Glucuronosyltransferase 2B15 in the Glucuronidation

(2009) Takuji Shoda et al.   CHEMICAL & PHARMACEUTICAL BULLETIN

Structure−Activity Relationships for the Degradation Reaction of 1-β-O-Acyl Glucuronides. Part 3: Electronic and Steric Descriptors Predicting the Reactivity of Aralkyl Carboxylic Acid 1-β-O-Acyl Glucuronides

(2009) Akiko Baba et al.   CHEMICAL RESEARCH IN TOXICOLOGY

Current Synthesis of Triterpene Saponins

(2009) Biao Yu et al.   Chemistry-An Asian Journal

Metabolism and Excretion of the Novel Bioreductive Prodrug PR-104 in Mice, Rats, Dogs, and Humans

(2009) Y. Gu et al.   DRUG METABOLISM AND DISPOSITION

Glucuronide Production by Whole-Cell Biotransformation Using Genetically Engineered Fission Yeast Schizosaccharomyces pombe

(2009) C.-A. Dragan et al.   DRUG METABOLISM AND DISPOSITION

The crystal structure of human UDP-glucuronosyltransferase 2B7 C-terminal end is the first mammalian UGT target to be revealed: the significance for human UGTs from both the 1A and 2B families

(2009) Anna Radominska-Pandya et al.   DRUG METABOLISM REVIEWS

Synthesis, structure characterization, and enzyme screening of clenbuterol glucuronides

(2009) Anna Alonen et al.   EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES

Applicability of Methyl 2,3,4-Tri-O-benzoyl-1-methanesulfonyl-a-D-glucopyranuronate as a Novel Quaternary Glucuronyl Reagent for Tertiary Amines

(2009) Ichiro Araya et al.   HETEROCYCLES

Efficient Synthesis of Flavanone Glucuronides

(2009) Ahcene Boumendjel et al.   JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

Preparation and Characterization of Catechin Sulfates, Glucuronides, and Methylethers with Metabolic Interest

(2009) Susana González-Manzano et al.   JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

Glucuronidase-assisted Transglycosylation for the Synthesis of Highly Functional Disaccharides: β-D-Glucuronyl 6-O-Sulfo-β-D-Gluco- and -β-D-Galactopyranosides

(2009) Takehiro Nagatsuka et al.   JOURNAL OF CARBOHYDRATE CHEMISTRY

Improved method for identifying and quantifying olive oil phenolic compounds and their metabolites in human plasma by microelution solid-phase extraction plate and liquid chromatography–tandem mass spectrometry

(2009) Manuel Suárez et al.   JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES

Synthesis of three isotopically labeled versions and a metabolite of Aurora A kinase inhibitor

(2009) Yuexian Li et al.   JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS

Synthesis, Conformation, and Biological Characterization of a Sugar Derivative of Morphine that is a Potent, Long-Lasting, and Nontolerant Antinociceptive

(2009) Gemma Arsequell et al.   JOURNAL OF MEDICINAL CHEMISTRY

Synthesis, transacylation kinetics and computational chemistry of a set of arylacetic acid 1β-O-acyl glucuronides

(2009) Neil G. Berry et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

Corticosteroids 21-glucuronides: Synthesis and complete characterization by 1H and 13C NMR

(2009) Pierangela Ciuffreda et al.   STEROIDS

Sample cleanup-free determination of mycophenolic acid and its glucuronide in serum and plasma using the novel technology of ultra-performance liquid chromatography–electrospray ionization tandem mass spectrometry

(2009) Joachim Kuhn et al.   TALANTA

A convenient new synthesis of quaternary ammonium glucuronides of drug molecules

(2009) Lisa Iddon et al.   TETRAHEDRON

Synthesis of isotopically labelled SGLT inhibitors and their metabolites

(2009) Volker Derdau et al.   TETRAHEDRON

Convenient syntheses of the in vivo carbohydrate metabolites of mycophenolic acid: reactivity of the acyl glucuronide

(2009) Amy E. Jones et al.   TETRAHEDRON LETTERS

Variation in glucuronidation of lamotrigine in human liver microsomes

(2009) U. A. Argikar et al.   XENOBIOTICA

High-performance liquid chromatography–tandem mass spectrometry in the identification and determination of phase I and phase II drug metabolites

(2008) M. Holčapek et al.   ANALYTICAL AND BIOANALYTICAL CHEMISTRY

The human UDP-glucuronosyltransferase UGT1A3 is highly selective towards N2 in the tetrazole ring of losartan, candesartan, and zolarsartan

(2008) Anna Alonen et al.   BIOCHEMICAL PHARMACOLOGY

Synthesis and biological evaluation of glucuronide prodrugs of the histone deacetylase inhibitor CI-994 for application in selective cancer chemotherapy

(2008) Mickaël Thomas et al.   BIOORGANIC & MEDICINAL CHEMISTRY

Duocarmycin-based prodrugs for cancer prodrug monotherapy

(2008) Lutz F. Tietze et al.   BIOORGANIC & MEDICINAL CHEMISTRY

Enzyme-assisted synthesis and structure characterization of glucuronic acid conjugates of losartan, candesartan, and zolarsartan

(2008) Anna Alonen et al.   BIOORGANIC CHEMISTRY

Structure−Activity Relationships for Degradation Reaction of 1-β-O-Acyl Glucuronides: Kinetic Description and Prediction of Intrinsic Electrophilic Reactivity under Physiological Conditions

(2008) Akiko Baba et al.   CHEMICAL RESEARCH IN TOXICOLOGY

An Efficient Method for the Glycosylation of Isoflavones

(2008) Nawaf Al-Maharik et al.   EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Metabolic activation of carboxylic acids

(2008) Christian Skonberg et al.   Expert Opinion on Drug Metabolism & Toxicology

Preparative Enzymatic Synthesis of Glucuronides of Zearalenone and Five of Its Metabolites

(2008) David E. Stevenson et al.   JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY

Stereoselective Synthesis of Di- and Trisaccharide Fucoidan Fragments Bearing α-D-Glucuronic Acid Residue∗

(2008) Natalia S. Zlotina et al.   JOURNAL OF CARBOHYDRATE CHEMISTRY

Selective isolation of in vitro phase II conjugates using a lipophilic anionic exchange solid phase extraction method

(2008) Sébastien Gagné et al.   JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES

Synthesis of [14C] - and [13C6]-labeled tipranavir and its potential hydroxyl metabolite and the glucuronide conjugate

(2008) Bachir Latli et al.   JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS

Synthesis of Betavulgaroside III, a Representative Triterpeneseco-Glycoside

(2008) Shilei Zhu et al.   JOURNAL OF ORGANIC CHEMISTRY

Acyl Group Migration and Cleavage in Selectively Protected β-d-Galactopyranosides as Studied by NMR Spectroscopy and Kinetic Calculations

(2008) Mattias U. Roslund et al.   JOURNAL OF THE AMERICAN CHEMICAL SOCIETY

Synthesis of hydroxycinnamic acid glucuronides and investigation of their affinity for human serum albumin

(2008) Stéphanie Galland et al.   ORGANIC & BIOMOLECULAR CHEMISTRY

EscherichiacoliGlucuronylsynthase:  An Engineered Enzyme for the Synthesis of β-Glucuronides

(2008) Shane M. Wilkinson et al.   ORGANIC LETTERS

17α- and 17β-boldenone 17-glucuronides: Synthesis and complete characterization by 1H and 13C NMR

(2008) Silvana Casati et al.   STEROIDS

Synthesis of betulinic acid acyl glucuronide for application in anticancer prodrug monotherapy

(2008) Charles Gauthier et al.   TETRAHEDRON LETTERS

Ion mobility spectrometry detection for gas chromatography

(2007) Abu B. Kanu et al.   JOURNAL OF CHROMATOGRAPHY A

Simultaneous determination of mycophenolic acid and its acyl and phenol glucuronide metabolites in human serum by capillary zone electrophoresis

(2007) Kaname Ohyama et al.   JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS

Regioselectivity of human UDP-glucuronosyl-transferase 1A1 in the synthesis of flavonoid glucuronides determined by metal complexation and tandem mass spectrometry

(2007) Barry D. Davis et al.   JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY

Enzyme-assisted synthesis and structure characterization of glucuronide conjugates of eleven anabolic steroid metabolites

(2007) Laura Hintikka et al.   STEROIDS