2018
Synthesis and Biological Evaluation of an Indazole-Based Selective Protein Arginine Deiminase 4 (PAD4) Inhibitor
Tjin CC, Wissner RF, Jamali H, Schepartz A, Ellman JA. Synthesis and Biological Evaluation of an Indazole-Based Selective Protein Arginine Deiminase 4 (PAD4) Inhibitor. ACS Medicinal Chemistry Letters 2018, 9: 1013-1018. PMID: 30344909, PMCID: PMC6187405, DOI: 10.1021/acsmedchemlett.8b00283.Peer-Reviewed Original ResearchProtein arginine deiminase 4Potent PAD4 inhibitorPAD4 inhibitorsBiological evaluationCalcium-dependent enzymesTarget proteinsConversion of arginineHuman diseasesHL-60 granulocytesFold selectivityNew classCompoundsSynthesisInhibitorsSelectivityPAD3IndazoleProteinPAD1EnzymePAD2ConversionArginineDysregulationCitrullination
2016
Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling
Kim B, Chinn AJ, Fandrick DR, Senanayake CH, Singer RA, Miller SJ. Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling. Journal Of The American Chemical Society 2016, 138: 7939-7945. PMID: 27254785, PMCID: PMC5127171, DOI: 10.1021/jacs.6b03444.Peer-Reviewed Original Research
2015
Phosphothreonine as a Catalytic Residue in Peptide‐Mediated Asymmetric Transfer Hydrogenations of 8‐Aminoquinolines
Shugrue CR, Miller SJ. Phosphothreonine as a Catalytic Residue in Peptide‐Mediated Asymmetric Transfer Hydrogenations of 8‐Aminoquinolines. Angewandte Chemie International Edition 2015, 54: 11173-11176. PMID: 26246129, PMCID: PMC4628550, DOI: 10.1002/anie.201505898.Peer-Reviewed Original ResearchConceptsTransfer hydrogenationChiral phosphoric acid catalystHydrogen bonding interactionsPhosphoric acid catalystAsymmetric transfer hydrogenationEnantioselective transfer hydrogenationAsymmetric catalystsAcid catalystStrong complexationNMR studiesSubstrate classesCatalystHydrogenationNew classCatalytic residuesPeptidesComplexationEnantioselectivityQuinolinePhosphopeptidesSubstrateResiduesTetrafluorophenoxymethyl ketone cruzain inhibitors with improved pharmacokinetic properties as therapeutic leads for Chagas’ disease
Neitz RJ, Bryant C, Chen S, Gut J, Caselli EH, Ponce S, Chowdhury S, Xu H, Arkin MR, Ellman JA, Renslo AR. Tetrafluorophenoxymethyl ketone cruzain inhibitors with improved pharmacokinetic properties as therapeutic leads for Chagas’ disease. Bioorganic & Medicinal Chemistry Letters 2015, 25: 4834-4837. PMID: 26144347, PMCID: PMC4737481, DOI: 10.1016/j.bmcl.2015.06.066.Peer-Reviewed Original ResearchConceptsCruzain inhibitorsCysteine protease cruzainAnimal modelsSubstrate Activity ScreeningPharmacokinetic propertiesImproved pharmacokinetic propertiesVivo pharmacokinetic propertiesNew chemotherapeutic approachesKetone inhibitorsNew analoguesPromising efficacyReduced lipophilicityOral exposureTherapeutic leadsChemotherapeutic approachesCruzainEfficacious effectsChagas diseaseTherapeutic hypothesesDiseaseNew classInhibitorsTrypanosoma cruziP3 positionPotency
2013
Rhodium(III)-Catalyzed Indazole Synthesis by C–H Bond Functionalization and Cyclative Capture
Lian Y, Bergman RG, Lavis LD, Ellman JA. Rhodium(III)-Catalyzed Indazole Synthesis by C–H Bond Functionalization and Cyclative Capture. Journal Of The American Chemical Society 2013, 135: 7122-7125. PMID: 23642256, PMCID: PMC3656829, DOI: 10.1021/ja402761p.Peer-Reviewed Original ResearchConceptsH bond functionalizationInitial spectroscopic characterizationH bond additionBond functionalizationSpectroscopic characterizationBond additionIndazole productsAryl groupsRegioselective couplingN-substitutionUnsymmetrical azobenzenesAzobenzeneOne-stepIndazoleNew classSynthesisFunctionalizationAldehydesFluorophoresPreparationCharacterizationProducts
2011
Transition-Metal-Centered Nine-Membered Boron Rings: MⓒB9 and MⓒB9 – (M = Rh, Ir)
Li W, Romanescu C, Galeev T, Piazza Z, Boldyrev A, Wang L. Transition-Metal-Centered Nine-Membered Boron Rings: MⓒB9 and MⓒB9 – (M = Rh, Ir). Journal Of The American Chemical Society 2011, 134: 165-168. PMID: 22148745, DOI: 10.1021/ja209808k.Peer-Reviewed Original ResearchBoron ringsLaser-vaporization supersonic molecular beamsCentral metal atomLarge HOMO-LUMO gapChemical bonding analysisHOMO-LUMO gapAb initio calculationsAnion photoelectron spectraSupersonic molecular beamBonding analysisPhotoelectron spectroscopyMetal atomsMolecular wheelsTransition metalsInitio calculationsΣ electronsPhotoelectron spectraIRTheoretical calculationsB-ringMolecular beamNew classRhShell speciesRingAssembly factors as a new class of disease genes for mitochondrial complex I deficiency: cause, pathology and treatment options
Nouws J, Nijtmans L, Smeitink J, Vogel R. Assembly factors as a new class of disease genes for mitochondrial complex I deficiency: cause, pathology and treatment options. Brain 2011, 135: 12-22. PMID: 22036961, DOI: 10.1093/brain/awr261.Peer-Reviewed Original ResearchConceptsComplex I deficiencyAssembly factorsDisease genesI deficiencySpecific assembly factorsGeneral molecular mechanismMitochondrial complex I deficiencyOxidative phosphorylation disordersDisease-causing mutationsSuch genesMolecular mechanismsComplex IGenesLarge diversityProgressive encephalomyopathyChaperonesDiversityMutationsEncephalomyopathyDeficiencyNew classLinear and cyclic C -glycosides as surfactants
Foley P, Phimphachanh A, Beach E, Zimmerman J, Anastas P. Linear and cyclic C -glycosides as surfactants. Green Chemistry 2011, 13: 321-325. DOI: 10.1039/c0gc00407c.Peer-Reviewed Original ResearchCarbohydrate-based surfactantsAlkyl aldehydesC bond formationGlycosidic linkagesFacile synthesisBond formationReaction conditionsSurfactant propertiesGood yieldsSurfactantsAdditional analoguesRenewable feedstockC-glycosidesCarbohydrate CAldehydesMost carbohydratesNew classDesirable performance propertiesPerformance propertiesChemistryPyrrolidineRecent advancesPropertiesSynthesisStoichiometry
2008
Toward Green Nano
Eckelman M, Zimmerman J, Anastas P. Toward Green Nano. Journal Of Industrial Ecology 2008, 12: 316-328. DOI: 10.1111/j.1530-9290.2008.00043.x.Peer-Reviewed Original ResearchGreen nanoE-factorSynthesis of nanomaterialsGreener synthesis routesGreen chemistry metricsGold nanoparticlesNanomaterial productionMetal nanoparticlesSpecific nanomaterialsCarbon nanotubesGreen chemistryTraditional synthesisSynthesis routeNanoNanomaterialsPotential applicationsDifferent production methodsNanotechnologyNanoparticlesProduction methodsResearch interestEnvironmental implicationsNew classSynthesisOrders of magnitudeIdentification of a New Class of Nonpeptidic Inhibitors of Cruzain
Brak K, Doyle PS, McKerrow JH, Ellman JA. Identification of a New Class of Nonpeptidic Inhibitors of Cruzain. Journal Of The American Chemical Society 2008, 130: 6404-6410. PMID: 18435536, PMCID: PMC2765048, DOI: 10.1021/ja710254m.Peer-Reviewed Original ResearchConceptsVinyl sulfonesNonpeptidic inhibitorsAdditional binding interactionsStructure-based designMajor cysteine proteaseMammalian cell cultureChagas diseasePotent nonpeptidic inhibitorsCruzain inhibitorsT. cruzi parasiteCruzain inhibitionCruzainCysteine proteasesBinding interactionsProtease substratesS3 pocketTrypanosoma cruziPeptidic inhibitorsCruzi parasitesMechanistic insightsNew chemotherapeuticsCleavage efficiencySulfoneNew classCell culturesSynthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C−H Activation
Colby DA, Bergman RG, Ellman JA. Synthesis of Dihydropyridines and Pyridines from Imines and Alkynes via C−H Activation. Journal Of The American Chemical Society 2008, 130: 3645-3651. PMID: 18302381, PMCID: PMC3057408, DOI: 10.1021/ja7104784.Peer-Reviewed Original ResearchConceptsSynthesis of dihydropyridinesReductive elimination stepOne-pot CX-ray analysisFacile COxidative additionDihydropyridine intermediatesPyridine derivativesH activationStructure determinationElimination stepAromatization sequenceRate constantsAlkynesLigandsNew classSynthesisKinetic simulationsBroad scopePyridineIminesKetiminesAldiminesIntermediatesComplexes
2007
Enantioselective Aza-Henry Reaction with an N-Sulfinyl Urea Organocatalyst
Robak MT, Trincado M, Ellman JA. Enantioselective Aza-Henry Reaction with an N-Sulfinyl Urea Organocatalyst. Journal Of The American Chemical Society 2007, 129: 15110-15111. PMID: 18004853, DOI: 10.1021/ja075653v.Peer-Reviewed Original ResearchHydrophobic Forces and Hydrogen Bonds in the Adhesion between Retinoid-Coated Surfaces
Tareste D, Pincet F, Lebeau L, Perez É. Hydrophobic Forces and Hydrogen Bonds in the Adhesion between Retinoid-Coated Surfaces. Langmuir 2007, 23: 3225-3229. PMID: 17266339, DOI: 10.1021/la0629779.Peer-Reviewed Original ResearchConceptsHydrophobic forcesHydrogen bondsPure waterShort-range attractive forcesLipid layerHydrophilic headgroupLong-range attractionHydrophobic chainsTris bufferHydrophobic effectLipid monolayersApolar characterMolecular interactionsAttractive forceBondsLipid bilayersExponential forceHeadgroupsNew classForce measurementsDistance profilesWaterBufferInteractionMonolayers
1999
Chemistry and Biology of Multifunctional DNA Binding Agents
Farrell N, Qu Y, Roberts J. Chemistry and Biology of Multifunctional DNA Binding Agents. Topics In Biological Inorganic Chemistry 1999, 99-115. DOI: 10.1007/978-3-662-03815-4_4.Peer-Reviewed Original Research
1992
Antisense c-myb oligonucleotides inhibit intimal arterial smooth muscle cell accumulation in vivo
Simons M, Edelman E, DeKeyser J, Langer R, Rosenberg R. Antisense c-myb oligonucleotides inhibit intimal arterial smooth muscle cell accumulation in vivo. Nature 1992, 359: 67-70. PMID: 1522889, DOI: 10.1038/359067a0.Peer-Reviewed Original Research
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