Search results for "Glucuronides"

showing 10 items of 13 documents

Molecular docking-based design and development of a highly selective probe substrate for UDP-glucuronosyltransferase 1A10

2018

Intestinal and hepatic glucuronidation by the UDP-glucuronosyltransferases (UGTs) greatly affect the bioavailability of phenolic compounds. UGT1A10 catalyzes glucuronidation reactions in the intestine, but not in the liver. Here, our aim was to develop selective, fluorescent substrates to easily elucidate UGT1A10 function. To this end, homology models were constructed and used to design new substrates, and subsequently, six novel C3-substituted (4-fluorophenyl, 4-hydroxyphenyl, 4-methoxyphenyl, 4-(dimethylamino)phenyl, 4-methylphenyl, or triazole) 7-hydroxycoumarin derivatives were synthesized from inexpensive starting materials. All tested compounds could be glucuronidated to nonfluorescen…

0301 basic medicineMutantGlucuronidationPharmaceutical ScienceUGT1A10030226 pharmacology & pharmacySubstrate Specificity7-hydroxycoumarin derivativechemistry.chemical_compound0302 clinical medicineDrug DiscoveryCRYSTAL-STRUCTUREGlucuronosyltransferaseta116ta317AFFINITYchemistry.chemical_classificationChemistry3. Good healthMolecular ImagingMolecular Docking Simulation7-hydroxycoumarin317 Pharmacyin silicoMolecular MedicinefluorescenceUDP-glucuronosyltransferaseEXPRESSIONENZYMEStereochemistryIn silicoKineticsFLUORESCENT-PROBETriazoleta311103 medical and health sciencesGlucuronidesMicrosomesXENOBIOTICSHumansUmbelliferonesFluorescent DyesGLUCURONIDATIONta1182glucuronidationfluoresenssiSubstrate (chemistry)drug metabolism030104 developmental biologyEnzymeDRUG-METABOLISMDrug DesignMolecular ProbesMutationMutagenesis Site-DirectedORAL BIOAVAILABILITYDrug metabolism
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Urinary tetrahydroaldosterone as a screening method for primary aldosteronism: a comparative study

2003

Abstract Background The major aldosterone metabolite 3α,5β tetrahydroaldosterone reflects up to 45% of the aldosterone secretion. Its 24-h urinary excretion is likely to provide an accurate index of the daily aldosterone production and to be an indicator for primary aldosteronism (PA). Methods In a prospective study, the validity of tetrahydroaldosterone as a screening test for PA was evaluated in comparison to serum potassium, plasma aldosterone, plasma renin activity, plasma aldosterone/renin activity ratio (PARR), as well as 24-h urinary aldosterone-18-glucuronide and free aldosterone. A total of 111 normotensive individuals, 412 PA patients and 1453 essential hypertensive patients, were…

AdultMalemedicine.medical_specialtyAdolescentmedicine.drug_classEssential hypertensionSensitivity and SpecificityPlasma renin activitychemistry.chemical_compoundGlucuronidesPrimary aldosteronismInternal medicineHyperaldosteronismReninInternal MedicinemedicineHumansMass ScreeningProspective StudiesAldosteroneMass screeningScreening proceduresAldosteronebusiness.industryMiddle Agedmedicine.diseaseHyperaldosteronismEndocrinologychemistryMineralocorticoidPotassiumFemalebusinessAmerican Journal of Hypertension
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An investigation of the stability of free and glucuronidated 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid in authentic urine samples.

2004

Preanalytical stability of a drug and its major metabolites is an important consideration in pharmacokinetic studies or whenever the analyte pattern is used to estimate drug habits. Firstly, the stability of free and glucuronidated 11-nor-delta9-tetrahydrocannabinol-9-carboxylic acid (THCCOOH, THCCOOglu) in authentic urine samples was investigated. Random urine samples of cannabis users (n = 38) were stored at -20, 4, and 20 degrees C up to 15 days and up to 5 days at 40 degrees C, and alterations of the analyte pattern during storage were followed by liquid chromatography-tandem mass spectrometry. Secondly, the influence of pH (range 5.0-8.0) on the stability of the analytes was studied us…

AnalyteSubstance-Related DisordersHealth Toxicology and MutagenesisCarboxylic acidMetaboliteUrineToxicologyHigh-performance liquid chromatographyMass SpectrometryAnalytical Chemistrychemistry.chemical_compoundGlucuronidesPharmacokineticsDrug StabilityEnvironmental ChemistryHumansDronabinolDiagnostic Errorschemistry.chemical_classificationChemical Health and SafetyChromatographyForensic MedicineHydrogen-Ion ConcentrationSubstance Abuse DetectionchemistryΔ9-tetrahydrocannabinolGlucuronideArtifactsJournal of analytical toxicology
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In silico methods for metabolomic and toxicity prediction of zearalenone, α-zearalenone and β-zearalenone.

2020

Zearalenone (ZEA), α-zearalenol (α-ZEL) and β-zearalenol (β-ZEL) (ZEA's metabolites) are co/present in cereals, fruits or their products. All three with other compounds, constitute a cocktail-mixture that consumers (and also animals) are exposed and never entirely evaluated, nor in vitro nor in vivo. Effect of ZEA has been correlated to endocrine disruptor alterations as well as its metabolites (α-ZEL and β-ZEL); however, toxic effects associated to metabolites generated once ingested are unknown and difficult to study. The present study defines the metabolomics profile of all three mycotoxins (ZEA, α-ZEL and β-ZEL) and explores the prediction of their toxic effects proposing an in silico w…

In silicoMetaboliteToxicologyArticleAmes test03 medical and health scienceschemistry.chemical_compound0404 agricultural biotechnologyMetabolomicsGlucuronidesCytochrome P-450 Enzyme SystemIn vivoAnimalsMetabolomicsComputer SimulationMycotoxinZearalenoneZebrafish030304 developmental biology0303 health sciencesChemistryIn silicofood and beverages04 agricultural and veterinary sciencesGeneral Medicine040401 food sciencePASS onlineEndocrine disruptorBiochemistryBlood-Brain BarrierMetaToxZearalenoneSwissADMEReactive Oxygen SpeciesPredictionFood ScienceFood and chemical toxicology : an international journal published for the British Industrial Biological Research Association
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Effect of oxidative stress on UDP-glucuronosyltransferases in rat astrocytes.

2012

WOS:000309170300003; International audience; The present work reports data regarding effects of an induced oxidative stress on the mainly expressed isoforms of UDP-glucuronosyltransferases (UGTs) in the brain. UGT1A6 and UGT1A7 expression and enzymatic activities toward the 1-naphthol were analyzed in rat cultured astrocytes following the exposure for 48 h to redox-cycling xenobiotic compounds such as quinones and bipyridinium ions. The expression of NADPH:cytochrome P450 reductase and NAD(P)H:quinone oxidoreductase 1 (NQO1) was also investigated. Oxidative stress induced significant deleterious changes in astrocyte morphology, decreased cell viability and inhibited catalytic function of UG…

MESH : Oxidative StressMESH : RNA MessengerAntioxidantTranscription Geneticmedicine.medical_treatmentToxicologyNAD(P)H:quinone oxidoreductase 1MESH: GlucuronosyltransferaseAntioxidantsSubstrate SpecificityRats Sprague-Dawley0302 clinical medicineMESH: NADPH-Ferrihemoprotein ReductaseMESH: GlucuronidesNAD(P)H Dehydrogenase (Quinone)MESH : CatalysisMESH: AnimalsMESH : NAD(P)H Dehydrogenase (Quinone)GlucuronosyltransferaseCells Culturedchemistry.chemical_classificationMESH : Cell Survival0303 health sciencesMESH : Substrate SpecificityMESH : Animals NewbornCytochrome P450 reductaseGeneral MedicineMESH: Cell SurvivalMESH: Pyridinium CompoundsMESH : AntioxidantsMESH: Cells CulturedOxidative phosphorylationGene Expression Regulation EnzymologicMESH : QuinonesMESH : Glucuronides03 medical and health sciencesRNA MessengerCell ShapeNADPH-Ferrihemoprotein ReductaseMESH : Oxidation-ReductionMESH : Pyridinium CompoundsMESH: NaphtholsMESH : GlucuronosyltransferaseMESH: AntioxidantsMESH: CatalysischemistryOxidative stressAstrocytesReactive Oxygen Species030217 neurology & neurosurgeryMESH: Oxidation-ReductionTime Factors[ SDV.AEN ] Life Sciences [q-bio]/Food and NutritionMESH : Reactive Oxygen SpeciesNADPH:cytochrome P450 reductasePyridinium CompoundsNaphtholsMESH: Rats Sprague-DawleyProtein oxidationmedicine.disease_causeMESH: Animals NewbornMESH: NAD(P)H Dehydrogenase (Quinone)Protein CarbonylationMESH : OxidantsMESH: OxidantsMelatoninMESH: MelatoninMESH: Oxidative StressMESH : MelatoninMESH : RatsMESH: Gene Expression Regulation EnzymologicQuinonesMESH: Reactive Oxygen SpeciesOxidantsBiochemistryMESH : Protein CarbonylationOxidation-ReductionUDP-glucuronosyltransferaseMESH : Time FactorsMESH: Protein CarbonylationMESH: RatsCell SurvivalMESH : NaphtholsBiologyCatalysisMESH: QuinonesMESH : Gene Expression Regulation EnzymologicGlucuronidesMESH : Cells CulturedmedicineAnimalsMESH: Cell Shape030304 developmental biologyMESH: RNA MessengerReactive oxygen speciesMESH: Transcription GeneticMESH: Time FactorsMESH : AstrocytesMESH : Transcription GeneticNAD(P)H Dehydrogenase (Quinone)MESH : Rats Sprague-DawleyRatsMESH: AstrocytesAnimals NewbornMESH : NADPH-Ferrihemoprotein ReductaseMESH: Substrate SpecificityMESH : AnimalsNAD+ kinaseMESH : Cell Shape[SDV.AEN]Life Sciences [q-bio]/Food and NutritionOxidative stress
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Metabolism of apigenin by rat liver phase I and phase II enzymes and by isolated perfused rat liver

2004

The metabolism of apigenin, a low estrogenic flavonoid phytochemical, was investigated in rat using liver models both in vitro (subcellular fractions) and ex vivo (isolated perfused liver). In vitro, phase I metabolism led to the formation of three monohydroxylated derivatives: luteolin which was the major metabolite (K(m) = 22.5 +/- 1.5 microM; V(max) = 5.605 +/- 0.090 nmol/min/mg protein, means +/- S.E.M.), scutellarein, and iso-scutellarein. These oxidative pathways were mediated by cytochrome P450 monooxygenases (P450s). The use of P450 inhibitors and inducers showed that CYP1A1, CYP2B, and CYP2E1 are involved. In vitro studies of phase II metabolism indicated that apigenin underwent co…

MaleFMN ReductaseMetabolite[SDV]Life Sciences [q-bio]Pharmaceutical ScienceIn Vitro TechniquesMethylation030226 pharmacology & pharmacyMass Spectrometry03 medical and health scienceschemistry.chemical_compoundGlucuronides0302 clinical medicineCytochrome P-450 Enzyme SystemAnimalsApigeninEnzyme InhibitorsRats WistarLuteolinBiotransformationChromatography High Pressure LiquidComputingMilieux_MISCELLANEOUS030304 developmental biologyFlavonoidsPharmacologySex Characteristics0303 health sciencesbiologySulfatesScutellareinCytochrome P450MonooxygenaseDiosmetinRats3. Good health[SDV] Life Sciences [q-bio]KineticsLiverBiochemistrychemistryApigeninbiology.proteinRATFemaleSpectrophotometry UltravioletLuteolinNADPDrug metabolismSubcellular Fractions
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Impact of glucuronide interferences on therapeutic drug monitoring of posaconazole by tandem mass spectrometry.

2010

Abstract Background: Posaconazole is a novel antifungal drug for oral application intended especially for therapy of invasive mycoses. Due to variable gastrointestinal absorption, adverse side effects, and suspected drug-drug interactions, therapeutic drug monitoring (TDM) of posaconazole is recommended. Method: A fast ultra performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method for quantification of posaconazole with a run-time <3 min was developed and compared to a LC-MS/MS method and HPLC method with fluorescence detection. Results: During evaluation of UPLC-MS/MS, two earlier eluting peaks were observed in the MRM trace of posaconazole. This was only seen in p…

Observer VariationPosaconazoleElectrosprayChromatographyAntifungal Agentsmedicine.diagnostic_testChemistryBiochemistry (medical)Clinical BiochemistryAntifungal drugGeneral MedicineTriazolesMass spectrometryTandem mass spectrometryHigh-performance liquid chromatographyGlucuronidesTherapeutic drug monitoringTandem Mass SpectrometrymedicineHumansDrug MonitoringGlucuronidemedicine.drugClinical chemistry and laboratory medicine
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Partition coefficient, blood to plasma ratio, protein binding and short-term stability of 11-nor-Delta(9)-carboxy tetrahydrocannabinol glucuronide.

2002

11-Nor-Delta(9)-carboxy tetrahydrocannabinol glucuronide (THCCOOglu) is a major metabolite of tetrahydrocannabinol in blood. Despite its mass spectrometric identification already in 1980, further physicochemical data of THCCOOglu have not been established. Therefore, the octanol/buffer partition coefficient P and the blood to plasma ratio b/p for THCCOOglu concentrations of 100 and 500ng/ml were investigated. Protein binding of the glucuronide was established from spiked albumin solutions at a level of 250ng/ml as well as from authentic samples. The data were compared to those of 11-nor-Delta(9)-carboxy tetrahydrocannabinol (THCCOOH). In addition, the short-term stability of THCCOOglu in pl…

OctanolBlood Specimen CollectionChromatographyMetaboliteAlbuminPlasma protein bindingForensic MedicineMass spectrometryMass SpectrometryPathology and Forensic MedicinePartition coefficientchemistry.chemical_compoundGlucuronideschemistryDrug StabilityBlood plasmaHumansDronabinolGlucuronideLawProtein BindingForensic science international
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Resveratrol metabolites inhibit human metastatic colon cancer cells progression and synergize with chemotherapeutic drugs to induce cell death.

2012

Scope Resveratrol (RSV) has been proposed to prevent tumor growth; nevertheless, these preventive effects are controversial since RSV pharmacokinetics studies show a low bioavailability. Recent clinical trials show that patients with colorectal cancer and receiving oral RSV have high levels of RSV conjugates in the colorectum, mainly RSV-3-O-sulfate (R3S), RSV-3-O-glucuronide, and RSV-4′-O-glucuronide. However, their potential biological activity has not yet been established. This study thus investigated in human colorectal cancer cell lines whether RSV main metabolites retain anticarcinogenic properties as their parental molecule. Methods and results Proliferation, apoptosis assays and cel…

Programmed cell deathColorectal cancerCell SurvivalvirusesApoptosisBiologyResveratrolPharmacologychemistry.chemical_compoundGlucuronidesIn vivoCell Line TumorStilbenesmedicineHumansCell ProliferationCell Cyclevirus diseasesBiological activityDrug Synergismrespiratory systemCell cyclemedicine.diseaseAntineoplastic Agents PhytogenicchemistryCell cultureApoptosisResveratrolColonic NeoplasmsFood ScienceBiotechnologyMolecular nutritionfood research
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Biomarkers to disclose recent intake of alcohol: potential of 5-hydroxytryptophol glucuronide testing using new direct UPLC-tandem MS and ELISA metho…

2007

Aims: This study compared two new methods for direct determination of 5-hydroxytryptophol glucuronide (GTOL) in urine, a biomarker for detection of recent alcohol consumption. Methods: Urine samples were collected from ten alcoholic patients during recovery from intoxication. A direct injection ultra-performance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method for measurement of the urinary GTOL to 5-hydroxyindoleacetic acid (5-HIAA) ratio, and an ELISA assay for direct measurement of GTOL, were used. Comparison was made with the urinary ethanol and ethyl glucuronide (EtG) concentrations. Results: The breath ethanol concentration on admission ranged between 1.0-3.1 g/l. Th…

Spectrometry Mass Electrospray IonizationAlcohol DrinkingUrinary systemEnzyme-Linked Immunosorbent AssayAlcoholUrineHigh-performance liquid chromatographychemistry.chemical_compoundGlucuronidesEthyl glucuronideTandem Mass SpectrometryHumansMedicineChromatography High Pressure LiquidEthanolChromatographyEthanolbusiness.industryCentral Nervous System DepressantsGeneral MedicineHydroxyindoleacetic AcidAlcoholismBreath TestschemistryBiochemistryHydroxytryptopholBiomarker (medicine)GlucuronidebusinessBiomarkersAlcohol and Alcoholism
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