TubastatinAisapotentandselectiveHDAC6inhibitor.TubastatinAdemonstrates1093-foldselectivityoverHDAC1(IC50valuesof15nMforHDAC6vs16.4µMforHDAC1).TubastatinAwassubstantiallymoreselectivethantheknownHDAC6inhibitorTubacinatallisozymesexceptHDAC8.TubastatinAisapotentHDAC6inhibitorwithanIC50valueof15nM.Comparatively,itdemonstratesover1,000-foldselectivityagainstallotherHDACisoforms(IC50>16μM),excludingHDAC8(IC50=0.9μM).TubastatinAinducesα-tubulinhyperacetylationat2.5μMinprimarycorticalneuroncultures.Inamodelofoxidativestressinducedbyglutathionedepletion,tubastatinAdisplaysdose-dependentneuronalprotectionofprimarycorticalneuronculturesat5-10μM.

MedKooCat#:403550
Name:TubastatinA
CAS#:1252003-15-8(freebase)
ChemicalFormula:C20H21N3O2
ExactMass:335.16338
MolecularWeight:335.4
ElementalAnalysis:C,71.62;H,6.31;N,12.53;O,9.54


RelatedCAS#:1310693-92-5(HCl) 1252003-15-8(freebase)  

Synonym:TubastatinA

IUPAC/ChemicalName:N-hydroxy-4-((2-methyl-3,4-dihydro-1H-pyrido[4,3-b]indol-5(2H)-yl)methyl)benzamide

InChiKey:GOVYBPLHWIEHEJ-UHFFFAOYSA-N

InChiCode:InChI=1S/C20H21N3O2/c1-22-11-10-19-17(13-22)16-4-2-3-5-18(16)23(19)12-14-6-8-15(9-7-14)20(24)21-25/h2-9,25H,10-13H2,1H3,(H,21,24)

SMILESCode:O=C(NO)C1=CC=C(CN2C3=C(CN(C)CC3)C4=C2C=CC=C4)C=C1


TechnicalData

Appearance:
whitesolidpowder

Purity:
>98%(orrefertotheCertificateofAnalysis)

CertificateofAnalysis:
ViewCoA:currentbatch,Lot#BBC70207

QCData:
ViewQCdata:currentbatch,Lot#BBC70207

SafetyDataSheet(MSDS):
ViewMaterialSafetyDataSheet(MSDS)(willbeavailablefordownloadwhenitisinstock)
ViewMaterialSafetyDataSheet(MSDS)

ShippingCondition:
Shippedunderambienttemperatureasnon-hazardouschemical.ThisproductisstableenoughforafewweeksduringordinaryshippingandtimespentinCustoms.

StorageCondition:
Dry,darkandat0-4Cforshortterm(daystoweeks)or-20Cforlongterm(monthstoyears).

Solubility:
SolubleinDMSO,notinwater

ShelfLife:
>2yearsifstoredproperly

DrugFormulation:
ThisdrugmaybeformulatedinDMSO

StockSolutionStorage:
0-4Cforshortterm(daystoweeks),or-20Cforlongterm(months).

HarmonizedSystemCode:
293490


AdditionalInformation

   
 
 


References

1:KozlovMV,KleymenovaAA,KonduktorovKA,MalikovaAZ,KochetkovSN.Selectiveinhibitorofhistonedeacetylase6(tubastatinA)suppressesproliferationofhepatitisCvirusrepliconincultureofhumanhepatocytes.Biochemistry(Mosc).2014Jul;79(7):637-42.doi:10.1134/S0006297914070050.PubMedPMID:25108326.

2:ZhangY,LiuCM,CaoXC,ZangY,ZhouYB,LiJ.InvolvementoftranscriptionfactorXBP1sintheresistanceofHDAC6inhibitorTubastatinAtosuperoxidationviaacetylation-mediatedproteasomaldegradation.BiochemBiophysResCommun.2014Jul18;450(1):433-9.doi:10.1016/j.bbrc.2014.05.134.Epub2014Jun6.PubMedPMID:24909686.

3:ZhangL,LiuC,WuJ,TaoJJ,SuiXL,YaoZG,XuYF,HuangL,ZhuH,ShengSL,QinC.TubastatinA/ACY-1215improvescognitioninAlzheimer'sdiseasetransgenicmice.JAlzheimersDis.2014;41(4):1193-205.doi:10.3233/JAD-140066.PubMedPMID:24844691.

4:KozlovMV,KleĭmenovaAA,KonduktorovKA,KochetkovSN.[Newsynthesisofhighlyselectiveinhibitorofhistonedeacetylase6--N-hydroxy-4-(2-methyl-1,2,3,4-tetrahydro-pyrido[4,3b]indol-5-ylmethyl)benzamide--TubastatinA].BioorgKhim.2013Jan-Feb;39(1):117-20.Russian.PubMedPMID:23844513.

5:VishwakarmaS,IyerLR,MuleyM,SinghPK,ShastryA,SaxenaA,KulathingalJ,VijaykanthG,RaghulJ,RajeshN,RathinasamyS,KachhadiaV,KilambiN,RajgopalS,BalasubramanianG,NarayananS.Tubastatin,aselectivehistonedeacetylase6inhibitorshowsanti-inflammatoryandanti-rheumaticeffects.IntImmunopharmacol.2013May;16(1):72-8.doi:10.1016/j.intimp.2013.03.016.Epub2013Mar27.PubMedPMID:23541634.

6:DeVreeseR,VerhaegheT,DesmetT,D'hoogheM.PotentandselectiveHDAC6inhibitoryactivityofN-(4-hydroxycarbamoylbenzyl)-1,2,4,9-tetrahydro-3-thia-9-azafluorenesasnovelsulfuranaloguesofTubastatinA.ChemCommun(Camb).2013May8;49(36):3775-7.doi:10.1039/c3cc41422a.Epub2013Mar28.PubMedPMID:23538448.

7:ButlerKV,KalinJ,BrochierC,VistoliG,LangleyB,KozikowskiAP.Rationaldesignandsimplechemistryyieldasuperior,neuroprotectiveHDAC6inhibitor,tubastatinA.JAmChemSoc.2010Aug11;132(31):10842-6.doi:10.1021/ja102758v.PubMedPMID:20614936;PubMedCentralPMCID:PMC2916045.