Broadpharm基础篇什么是点击化学（什么叫点击化学）

ClickChemistryisachemicalreactionbetweenpairsofreagents(namedclickchemistryreagents)toexclusivelyreactwitheachotherundermildconditionsandiseffectivelyinerttonaturallyoccurringfunctionalgroupssuchasaminegroups.Theterm"ClickChemistry"wasfirstcoinedbySharplessin2001inanefforttodesignamethodtoeasilysynthesizemoleculesundermildconditionsandtheproductcanbeeasilyisolated.

Broadpharm基础篇什么是点击化学（什么叫点击化学）

ClickChemistryreactionscanbecategorizedintothreegenerations:

(1)

ThefirstgenerationofClickChemistryinvolvedthereactionofazidewithalkynecatalyzedbyCu(I).Thecoppercatalystallowsforthisreactiontobecarriedoutefficientlyundermildconditionsinwaterwhereasthereactionwouldrequirehightemperatureandhighpressurewithoutthecoppercatalyst.CoppercatalyzedClickChemistryhasbeenfoundtohavethesecondfastestrateconstantof10-100M-1

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Duetothetoxicnatureofcoppertolivingstructuresandbiosystems,coppercatalyzedClickChemistryisnotaviablemethodofcarryingoutreactionsinlivingsystemswhichhasledtothedevelopmentofthefollowingtwogenerationsofClickChemistry.

(2)

DBCOreagentorBCNreagentcanbeusedtoperformClickChemistrywithazidemoleculeswithouttheneedofheavy-metalcatalysis.

Figure2:Strain-promotedAzide-DBCOClickChemistry

Thebondstraincreatedbythebondangleofthecyclooctyne(DBCOorBCN)requireslessenergyforthecyclooctynetoformthe(3+2)cycloadditionwhichreleasesenthalpicenergycausedbytheringstrainofthecyclooctyne.Thisgenerationdoesnotrequirecopperasacatalystanditcanbeusedincellsurfaceandinvivolabeling.Therateconstantis10-2

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(3)

ThethirdgenerationofClickChemistryistheligationbetweentetrazinewithtrans-Cyclooctene(TCO).Themechanismforthisligationutilizesringstrainfromthetrans-CycloocteneandaninverseDiels-Alderreactionbetweentheelectronrichtrans-Cycloocteneandtheelectronpoortetrazine.ThisligationhasbeenfoundtobethefastestgenerationofClickChemistrythusfarwitharateconstantof1-106

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ApplicationsofClickChemistry

ClickChemistryhasbeenwidelyusedindrugdiscovery,bioconjugation,labeling,andmaterialsciencesinthepharmaceuticalandbiotechindustryduetoitsmildconditionsandhighselectivity.

ClickChemistryinDrugDiscovery

ClickChemistryisutilizedintheformationofADClinkersinantibodydrugconjugates.Forexample,Trodelvy(SacituzumabGovitecan),alsoknownasIMMU-132(Figure4),isanimmunetargettherapymedicinefortriple-negativebreastcancerwhichcontainssacituzumabandSN-38boundwithalinker.ClickChemistryisusedintheformationofthelinkertoformatriazolethatlinksSMCCtoaPEG8moiety.

Figure4:

ClickChemistryinJointCartilageTherapy

ClickChemistryhasalsobeenusedincell-basedtherapytotreatdamageinjointcartilage,relievepain,andimprovefunction.Autologouschondrocytetransplantationtargetsapoptoticchondrocytesincartilagewhichcanbeidentifiedbyasixaminoacidpeptide,ApoPep-1,andbybindinginjectedhealthychondrocytesfromunaffectedcartilage.ApoPep-1carriesatrans-CycloocteneboundbyaPEGLinkertoapoptoticchondrocyteswhichcanthenbindhealthychondrocytesviaClickChemistrytotetrazinetoencouragecartilageregeneration(Figure5).

Figure5:

ClickChemistryTools

Asaleadingclickchemistyreagentsupplierworldwide,BroadPharmprovidesover500highpurityClickChemistryReagents(tools)andKitswithanarrayoffunctionalgroupssuchas:Azide,Alkyne,DBCO,TCO,Tetrazine,BCNtoempowerourclientsadvancedresearchanddrugdevelopment.

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