Adipogen/Shikonin/AGCN20487M010/10 mg

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ProductDetails
Synonyms	(+)-Shikonin;(R)-Shikonin;TokyoViolet;NSC252844;Isoarnebin4;C.I.75535;(R)-5,8-Dihydroxy-2-(1-hydroxy-4-methylpent-3-en-1-yl)naphthalene-1,4-dione
ProductType	Chemical
Properties
Formula	C₁₆H₁₆O₅
MW	288.3
CAS	517-89-5
Source/HostChemicals	IsolatedfromAlkannasp.
PurityChemicals	≥98%(HPLC)
Appearance	Purpleredsolid.
Solubility	SolubleinDMSOorDMF.Sparinglysolubleinethanol,methanolorwater.
Identity	Determinedby¹H-NMR.
InChiKey	NEZONWMXZKDMKF-SNVBAGLBSA-N
ShippingandHandling
Shipping	AMBIENT
ShortTermStorage	+4°C
LongTermStorage	-20°C
HandlingAdvice	Keepcoolanddry. Protectfromlight.
Use/Stability	Stableforatleast2yearsafterreceiptwhenstoredat-20°C.
Documents
MSDS	DownloadPDF
ProductSpecificationSheet
Datasheet	DownloadPDF

Anticancercompound.InhibitsTNF-α-inducedandB-16melanoma-inducedangiogenesis.
InducesapoptosisandRIP1-andRIP3-dependentnecroptosisinseveralcancercells.Circumventscancerantidrugresistancethroughthenecroptosispathway.
Proteasomeinhibitor.Autophagyinducer.
TopoisomeraseIinhibitor.
Inhibitsglycolysisincancercellsbyinhibitingtumor-specificpyruvatekinaseM2(PKM2).
Anti-inflammatorycompound.Inhibitsleukocytemigration,downregulateschemokinereceptorexpression,andinhibitsHIV-1replication.
InhibitstheactivationofNLRP3andAIM2inflammasome.Showntodirectlytargetcaspase-1andasainhibitorofPKM2toblockPKM2-mediatedglycolysisthatpromotesinflammasomeactivationbymodulatingEIF2AK2phosphorylationinmacrophages.
Antioxidant.Freeradicalscavenger.
Directlyinhibitsnitricoxidesynthase(NOS).
Regulatorofsystemicglucosetolerance,energybalanceandadiposity/obesity.Adipogenesisinhibitor.Showntoinhibitfataccumulationinadipocytes.
Antibacterialandantifungalagent.

ProductReferences

Antitumoractivityofshikoninanditsderivatives:U. Sankawa,etal.;Chem.Pharm.Bull.(Tokyo)25,2392(1977)
Acomparativestudyonanti-inflammatoryactivitiesoftheenantiomers,shikoninandalkannin:S.Tanaka,etal.;J.Nat.Prod.49,466(1986)
Shikonin,aningredientofLithospermumerythrorhizon,inhibitsangiogenesisinvivoandinvitro:T.Hisa,etal.;AnticancerRes.18,783(1998)
Shikonin,acomponentofantiinflammatoryChineseherbalmedicine,selectivelyblockschemokinebindingtoCCchemokinereceptor-1:X.Chen,etal.;Int.Immunopharmacol.1,229(2001)
Shikonin,acomponentofchineseherbalmedicine,inhibitschemokinereceptorfunctionandsuppresseshumanimmunodeficiencyvirustype1:X.Chen,etal.;Antimicrob.AgentsChemother.47,2810(2003)
InductionofapoptosisbyshikoninthroughaROS/JNK-mediatedprocessinBcr/Abl-positivechronicmyelogenousleukemia(CML)cells:X.Mao,etal.;CellRes.18,879(2008)
DualroleofshikonininearlyandlatestagesofcollagentypeIIarthritis:Q.Dai,etal.;Mol.Biol.Rep.36,1597(2009)
Shikoninexertsantitumoractivityviaproteasomeinhibitionandcelldeathinductioninvitroandinvivo:H.Yang,etal.;Int.J.Cancer124,2450(2009)
Shikonininhibitsfataccumulationin3T3-L1adipocytes:H.Lee,etal.;Phytother.Res.24,344(2010)
Shikonindirectlyinhibitsnitricoxidesynthases:possibletargetsthataffectthoracicaortarelaxationresponseandnitricoxidereleasefromRAW264.7macrophages:L.S.Yoshida,etal.;J.Pharmacol.Sci.112,343(2010)
ShikonininhibitsadipogenesisbymodulationoftheWNT/β-cateninpathway:H.Lee,etal.;LifeSci.88,294(2011)
Shikoninanditsanalogsinhibitcancercellglycolysisbytargetingtumorpyruvatekinase-M2:J.Chen,etal.;Oncogene30,4297(2011)
Shikonindirectlytargetsmitochondriaandcausesmitochondrialdysfunctionincancercells:B.Wiench,etal.;Evid.BasedComplementAlternat.Med.2012,726025(2012)
InhibitoryeffectofShikoninonCandidaalbicansgrowth:H.Miao,etal.;Biol.Pharm.Bull.35,1956(2012)
TopoisomeraseIinhibitors,shikoninandtopotecan,inhibitgrowthandinduceapoptosisofgliomacellsandgliomastemcells:F.L.Zhang,etal.;PLoSOne8,e81815(2013)
Theanti-tumoreffectofshikoninonosteosarcomabyinducingRIP1andRIP3dependentnecroptosis:Z.Fu,etal.;BMCCancer13,580(2013)
Evaluationofradicalscavengingpropertiesofshikonin:L.S.Yoshida,etal.;J.Clin.Biochem.Nutr.55,90(2014)
ShikoninpromotesautophagyinBXPC-3humanpancreaticcancercellsthroughthePI3K/Aktsignalingpathway:S.Shi&H.Cao;Oncol.Lett.8,1087(2014)
TheMechanismUnderlyingtheAntibacterialActivityofShikoninagainstMethicillin-ResistantStaphylococcusaureus:Y.S.Lee,etal.;Evid.BasedComplementAlternat.Med.2015,520578(2015)
Decreasedadiposityandenhancedglucosetoleranceinshikonintreatedmice:A.Bettaieb,etal.;Obesity23,2269(2015)
ShikoninSuppressesNLRP3andAIM2InflammasomesbyDirectInhibitionofCaspase-1:J.Zorman,etal.;PLoSOne11,e0159826(2016)
PKM2-dependentglycolysispromotesNLRP3andAIM2inflammasomeactivation:M.Xie,etal.;Nat.Commun.7,13280(2016)

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Adipogen/Shikonin/AGCN20487M010/10 mg