Overview:

DansylarginineN-(3-ethyl-1,5-pentanediyl)amide,morecommonlyreferredtoasDAPA,isapotent(Ki=10-7M)andspecificsyntheticthrombininhibitor(1).OfspecialinterestaretheuniquefluorescentpropertiescontributedbythedansylmoietyofDAPA.Whenboundtothrombin,thefluorescenceintensityandlifetimeofthedansylmoietyareincreasedthreefold.Theenhancementoffluorescenceintensity,coupledwithitsinhibitoryproperties,havemadethiscompoundextremelyusefulforstudiesinvolvingthrombingeneration(2-7).Inadditiontoanincreaseinfluorescenceintensityandlifetime,thereisadecreaseindepolarizationoftheexcitationsignalwhichalsosupportsfluorescencepolarizationstudies.

TheinhibitorpropertiesofDAPAalonehavebeenusefulinavarietyofapplications.DAPAisroutinelyusedasaproteaseinhibitorduringtheisolationofproteinsthataresusceptIBLetothrombincleavage.FurThermore,byeliminatingthefeedbackofthrombinactivityduringprothrombinactivation,theisolationofreactionintermediatessuchasfragment1.2,andmeizothrombinhavebeenmadepossible(7).

DAPAissynthesizedaccordingtheproceduredescribedbyNesheim,etal.(1).HPLC,TLCandspectralanalysesareusedtodeterminethepurityofthefinalproduct.DAPAissuppliedinwater.Whenproperlystoredat-20°Candprotectedfromlight,thecompoundisstableformanyyears.

Properties:

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