硼酸及其衍生物在荧光分子开关中的应用

(300071),40,,,E2mail:[e-mail](29872019)2001209224,2002206213,,,AbstractTherearemanytypesofcombinationsbetweenthehostsandguestsinfluorescentmolecularswitch.Amongthem,boricacidderivativeswithfluorophoremayselectivelyrecognizesaccharidesorhydroxylcompoundsthroughtheformationofcovalentbond.Sincethechemistryofsaccharidesplaysasignificantroleinlifescience,therecognitionanddetectionofsaccharidesareveryimportantinmedicine,cellular,biologicalscienceandotherfields.Asasortofefficientfluroescentmolecularsensors,theboricacidderivativesaresensitiveandselectiveintherecogni2tionofsomesaccharidesandhaveattractedextensiveattentionsofmanychemists.Inthiscontext,therelativeresultsofresearchaboutthistypeoffluroescentmolecularswitchesinrecentyearswerereviewed.KeywordsBoricacid,Fluorescence,Switch,Sensor,Saccharide,[13],,22CH2vanderWaals,[4,5],[68],;;[9,10],[11],,,;,;,,[12],(PhotoinducedElec2056200210http:PPhxtb.icas.ac.cntronTransterSystems,PET),,:,,,,1,[13],,,CDUV,[14],,,1[15]1[15]Fig.1Thevariationoffluorescencebeforeandafterthecombinationofboricacidderivativeswithsaccharides[15]1,,1a,11b,1b1,1b1c,,1a1cPETpH(),,234[16],,(1);(2);(3)pH;(4);(5)[17,18],James5[19],,,PET156http:PPhxtb.icas.ac.cn200210pH,52[19]5,,5a,PET,5apH5b,,5a5c,,(sp2sp3),,NB,PET5pH,pH2pH[19]Fig.2TheeffectofpHonthefluorescenceofboricacidderivatives[19]22.12,[20],6[2123],5,111211,D2(011013mmolL-1)D2(011mmolL-1)D2(011mmolL-1),67[23],,6(excimer),7,,711,,PET,12,256200210http:PPhxtb.icas.ac.cn11123Fig.3Thevariationoffluorescencebeforeandafterthecombinationofdiboricacidderivativeswithsaccharides8[2426]811,DL,PET,8,8RD2,8(RS)DL,[27,28]119,915225(Na+Ba2+Sr2+),9b,,,,356http:PPhxtb.icas.ac.cn2002109Li+Cs+,9a,,,4Fig.4Theeffectofcationsonfluorescenceinthecompoundsformedbydiboricacidderivativesandsaccharides,pH,10[29,30],[4]22,1011122.21,2211[31],,,1111a,,113,,N2(92)12,456200210http:PPhxtb.icas.ac.cn5Fig.5ThefluorescentsensorofdiboricacidderivativesrespondingtodisaccharidesPET,,12a,,PET,pH,13,13,,PET,13a,pH,[32],,,,[1]deSilverAP,FoxDB,MoodyTSetal.TrendsinBiotechnology,2001,19(1):2934.[2]RurackK.SpectrochimicaActaPartA:MolecularandBiomolecularSpectroscopy,2001,57(11):21612195.[3]deSilverAP,FoxDB,DavidBetal.CoordinationChemistryReviews,1999,1852186:297306.[4]BieleckiM,EggertH,NorrildJC.J.Chem.Soc.,PerkinTrans.2,1999:449.[5]CooperCR,JamesTD.Chem.Lett.,1998,9:883884.[6]LindbergSE,Wallschl¾gerD,PrestboEMetal.AtmosphericEnvironment,2001,35(23):40114015.556http:PPhxtb.icas.ac.cn200210[7]MallavarapuA,SawinK,MitchisonT.CurrentBiology,1999,9(23):14231426.[8]ImJunS,WookLeeJ,SakamotoSetal.TetrahedronLetters,2000,41(4):471475.[9]YamamotoT,SeinoY,FukumotoHetal.Biochem.Biophys.Res.Commun.,1990,170:223224.[10]YasudaH,KurokawaT,FjuiYetal.Biochim.Biophys.Acta,1990,1021:114117.[11]GuptaUC.BoronandItsRoleinCropProduction.BocaRaton:CRCPress,1993.[12]deSilverAP,GunaratneHQN,GunnlaugssinTetal.Chem.Rev.,1997,97:15151566.[13]SubrahmanyamS,PiletskySA,PiletskaEVetal.BiosensorsandBioelectronics,2001,16(912):631637.[14]CzarnikAW.Acc.Chem.Res.,1994,27(10):302308.[15]YoonJ,CzarnikAW.J.Am.Chem.Soc.,1992,114(14):58745875.[16]NagaiY,MkabayashiK,ToiHetal.Bull.Chem.Soc.Jpn.,1993,66(10):29652971.[17]BisselRA,deSilvaAP,GunaratnaHQMetal.Top.Curr.Chem.,1993,168:223227.[18]BisselR,deSilvaAP,GunaratnaHQN.Chem.Soc.Rev.,1992,21(3):187195.[19]JamesTD,SandanayakeKRAS,ShinkaiS.J.Chem.Soc.,Chem.Commun.,1994:477478.[20]HanneE,JohnF,ChristopheMetal.J.Org.Chem.,1999,64:38463852.[21]RebekJ.Acc.Chem.Res.,1990,23(10):338344.[22]NorrildJC,EggertH.J.Am.Chem.Soc.,1995,117(5):14791484.[23]SandanayakeKRASV,JamesTD,ShinkaiS.Chem.Lett.,1996:503504.[24]CramDJ.Angew.Chem.,Int.Ed.Engl.,1986,25(12):10391057.[25]JamesTD,SandanayakeKRAS,ShinkaiS.Nature,1995,374:345349.[26]KoshlandDEJ.TheEnzymes.NewYork:AcademicPress,1970,1:341.[27]JamesTD,SandanayakeKRAS,ShinkaiS.Angew.Chem.,Int.Ed.Engl.,1994,33(21):22072209.[28]GokelGW.CrownEthersandCryptands.CambridgeandLondon:RoyalSocietyofChemistey,1991,3:190.[29]VicensJ,BohmerV.CalixarenesaVersatileClassofMacrocyclicCompound.DorgechtPBostonPLondon:KluwerAcademicPublishers,1991:263.[30]GutscheCD.Calixarenes.CambridgeandLondon:RoyslSocietyofChemistry,1989,1:223.[31]SandanayakeKRAS.J.Chem.Soc.,Chem.Commun.,1994,16211622.[32]WangW,SpringsteenG,GaoSetal.Chem.Commun.,2000,1283.,,:(1);(2);(3),45;(4)::(1),,;(2)::041124379070041124379307:041124694447E2mail:[e-mail]@dicp.ac.cn656200210http:PPhxtb.icas.ac.cn