2012
Synthesis and evaluation of 11β-(4-Substituted phenyl) estradiol analogs: Transition from estrogen receptor agonists to antagonists
Hanson RN, Hua E, Hendricks JA, Labaree D, Hochberg RB. Synthesis and evaluation of 11β-(4-Substituted phenyl) estradiol analogs: Transition from estrogen receptor agonists to antagonists. Bioorganic & Medicinal Chemistry 2012, 20: 3768-3780. PMID: 22608920, PMCID: PMC3581310, DOI: 10.1016/j.bmc.2012.04.041.Peer-Reviewed Original ResearchConceptsSynthetic strategyNew compoundsERα-LBDPotential drug delivery systemPrevious synthetic studiesSeries of compoundsDrug delivery systemsClass of compoundsSynthetic methodTerminal groupsFacile accessSynthetic studiesDrug conjugationSpecific structural featuresCompetitive ligandCompoundsSteroidal agonistsDelivery systemRepresentative scaffoldsStructural featuresERβ-LBDSubtype selectivityActive groupAnaloguesScaffoldsTargeting the estrogen receptor with metal-carbonyl derivatives of estradiol
Hanson RN, Kirss R, McCaskill E, Hua E, Tongcharoensirikul P, Olmsted SL, Labaree D, Hochberg RB. Targeting the estrogen receptor with metal-carbonyl derivatives of estradiol. Bioorganic & Medicinal Chemistry Letters 2012, 22: 1670-1673. PMID: 22277281, PMCID: PMC3274643, DOI: 10.1016/j.bmcl.2011.12.111.Peer-Reviewed Original Research
2001
Estradiol-16α-carboxylic Acid Esters as Locally Active Estrogens
Labaree D, Reynolds T, Hochberg R. Estradiol-16α-carboxylic Acid Esters as Locally Active Estrogens. Journal Of Medicinal Chemistry 2001, 44: 1802-1814. PMID: 11356114, DOI: 10.1021/jm000523h.Peer-Reviewed Original ResearchMeSH KeywordsAlkaline PhosphataseAnimalsBinding, CompetitiveEnzyme InductionEstersEstradiolEstradiol CongenersEstrogen Receptor alphaEstrogen Receptor betaFemaleHumansIn Vitro TechniquesMiceMicrosomes, LiverOrgan SizeOvariectomyOxidoreductasesRatsRats, Sprague-DawleyReceptors, EstrogenStructure-Activity RelationshipTumor Cells, CulturedUterusVaginaConceptsEstrogenic actionActive estrogensAnalogues of estradiolRat uterine weightEstrogenic potencyEstrogen receptor bindingSystemic estrogenRat hepatic microsomesUterine weightIshikawa cellsVivo modelEstrogenTherapeutic treatmentHepatic microsomesReceptor bindingFluoroethyl esterSystemic actionER affinityHigh ER affinityEstradiolEsterase hydrolysisPotencyDyspareuniaLocal actionMenopause
1999
Regiospecific Esterification of Estrogens by Lecithin:Cholesterol Acyltransferase1
Kanji S, Kuohung W, Labaree D, Hochberg R. Regiospecific Esterification of Estrogens by Lecithin:Cholesterol Acyltransferase1. The Journal Of Clinical Endocrinology & Metabolism 1999, 84: 2481-2488. PMID: 10404824, DOI: 10.1210/jcem.84.7.5755.Peer-Reviewed Original ResearchConceptsLow-density lipoproteinEsterification of estradiolCholesterol acyltransferasePowerful antioxidant actionD-ring structureDensity lipoproteinEstrogenPolar oestrogensEstradiolEstradiol estersAntioxidant actionSteroidsLCAT substrateBloodDifferent steroidsPowerful antioxidantLCATHuman LCATEstriolTissueCholesterolGroup7α-Iodo and 7α-Fluoro Steroids as Androgen Receptor-Mediated Imaging Agents
Labaree D, Hoyte R, Nazareth L, Weigel N, Hochberg R. 7α-Iodo and 7α-Fluoro Steroids as Androgen Receptor-Mediated Imaging Agents. Journal Of Medicinal Chemistry 1999, 42: 2021-2034. PMID: 10354410, DOI: 10.1021/jm990064o.Peer-Reviewed Original ResearchConceptsAndrogen receptorAndrogen-responsive reporter geneHigh androgenic activityImaging agentReceptor-mediated uptakeDHT 4Rat prostatic cytosolReceptor binding propertiesHigh affinityMale ratsRat prostateAndrogenic activityResponsive reporter geneProstatic cytosolDiagnostic imaging agentsReceptorsHigh binding activitySteroidsIodinated compoundBiological activityDegrees CHigher bindingMetabolic oxidationDHTBiological potency
1998
Iodinated and fluorinated steroid 2′-aryl-[3,2-c] pyrazoles as potential glucocorticoid receptor imaging agents
Hoyte R, Labaree D, Fede J, Harris C, Hochberg R. Iodinated and fluorinated steroid 2′-aryl-[3,2-c] pyrazoles as potential glucocorticoid receptor imaging agents. Steroids 1998, 63: 595-602. PMID: 9830686, DOI: 10.1016/s0039-128x(98)00069-5.Peer-Reviewed Original ResearchConceptsPotent glucocorticoidGlucocorticoid receptorTrihydroxy-16Potential glucocorticoid receptorReceptor imaging agentImaging agentPositron emission tomographyHeLa cell assayGlucocorticoid potencyEmission tomographySteroidsGlucocorticoidsReceptorsCell assayDexamethasoneAlkaline phosphataseSteroids 2PotencyAgentsPara positionBromo analogueBest ligandSide chainsCortivazolFluoro analogue