Toxoflavin(PKF118-310)isanazapteridineantibioticproducedbysomespeciesofPseudomonas,Streptomyces,andBurkholderiaglADIolithathasantibioticandanticancerproperties.ItisalsoayellowpigmentthatactsasapHindicatorchangingbetweenyellowandcolorlessatapHof10.5.Toxoflavinisoneoftwotoxinsproducedwhenafermentedcoconutdrink,Tempebonkrek,iscontaminatedwithP.cocovenenans.
Toxoflavinistoxicbecauseitactsasanelectroncarrier,resultingintheproductionofhydrogenperoxide.
Toxoflavin(PKF118-310)isapotentantagoNISTofTcf4/b-cateninsignaling,inhibitingtheexpressionofsurvivinandinducingapoptosisinseveraltumorcelllines.ItalsohasbeenshowntoinhibitKDM4AandSIRT1/2whichshowpromiseasanticancertargets.
Toxoflavincanbeusedinpotatocelltransformation,asaselectionagent,withsimilarefficacyasthehygromycin/hptselectionsystem.Toxoflavinissolubleinethanol,methanol,DMFandDMSO.CASNumber
84-82-2
MolecularFormula
C7H7N5O2
MolecularWeight
193.2
MechanismofAction
Toxoflavin(PKF118-310)istoxicbecauseitactsasanelectroncarrier,facilitatingcytochrome-independentelectrontransfer,resultingintheproductionofhydrogenperoxideduringglycolysisandthecitricacidcycle.WhenNADHiscombinedwithtoxoflavininayeastcellextract,electronsaretransferredfromNADHtotoxoflavin.Toxoflavin(PKF118-310)thentransferstheseelectronstooxygen,producinghydrogenperoxide.Itispredictedthatthetoxiceffectoftoxoflavin(PKF118-310)isduetotheactionofhydrogenperoxideandnotduetointerferencewiththeelectrontransportchain.Yeastcells,whichexhibithighcatalaseactivity,donotshowsimilargrowthdefectsinthepresenceoftoxoflavin.Eventhoughtheyeastelectrontransportsystemisalteredbytoxoflavin(PKF118-310),theabundanceofcatalasecanneutralizetheexcesshydrogenperoxideproduced,thuspreventingcellulartoxicity.
StorageConditions
-20°C
Spectrum
Toxoflavin(PKF118-310)istoxictoplants,fungi,animalsandmicroorganisms.
