新型羧基BODIPY及基于BODIPY的近红外荧光探针的设计、合成与应用.pdf 全文

  本文关键词：新型羧基BODIPY及基于BODIPY的近红外荧光探针的设计、合成与应用，由笔耕文化传播整理发布。

网友kh6797近日为您收集整理了关于新型羧基BODIPY及基于BODIPY的近红外荧光探针的设计、合成与应用的文档，希望对您的工作和学习有所帮助。以下是文档介绍：NovelBODIPYswith carboxylsubstituentontheboroncenterandBODIPYs basedNIRfluorescentprobes:Design,Synthesis andApplicationADissertationSubmitted totheGraduateSchoolofHenanUniversityinPartial Fulfillment of theRequirementsfor theDegreeofMaster ofScienceByZhangjianSupervisor: Prof. JiangXindongandZhaoWeiliDate:May,2013I摘要***硼二吡咯甲川(BODIPY)类染料是一种性能优越的染料,因其良好的光化学稳定性、高摩尔消光系数、高荧光量子产率、分子结构易于修饰、荧光光谱半峰宽窄、对溶剂极性和pH的耐受性好等众多优点而被广泛应用于光电器件、生物标记以及荧光探针等领域。在现代生物技术和生命科学研究的诸多检测识别方法中,荧光分析技术由于其灵敏度高、检测限低、选择性好等优点,在生物化学分析领域具有无法替代的作用,而荧光染料在其中扮演着极其重要的角色。本文中,设计合成了一系列新型可见光区羧酸根单双取代的BODIPY染料,及四个基于BODIPY或Aza-BODIPY的近红外荧光探针。羧酸根单双取代BODIPY染料及荧光探针均经1H-NMR、13C-NMR和HRMS等鉴定。利用紫外?可见光和荧光光谱法系统研究了荧光探针对目标物的识别性能及识别机理。1、利用one-pot反应,成功设计合成了十二个新型可见光区羧酸根单双取代BODIPY染料1-12。对十二个化合物测定了紫外和荧光光谱性质,对化合物1和7,测试了pH耐受性、光化学稳定性、水溶性、电化学性质(循环伏安)并进行了理论计算。与母体BODIPY相比,化合物1和7的光稳定性良好,水溶性得到提高,使其在生物检测、靶向治疗方面具有潜在的应用。2、在BODIPY的8位引入醛基,合成了off-on型近红外荧光探针BDT1。:H2O=4:1体系下可以同时检测识别半胱氨酸(Cys)与同型半胱氨酸(Hcy),其荧光强度分别增强9倍、30倍。3、***基乙酸乙酯与BODIPY的8位醛基缩合,合成了off-on型近红外荧光探针BDT2。:H2O=4:1体系下检测识别中性小分子H2S,探针与HS?结合后,紫外吸收从683nm蓝移至674nm,荧光强度增强60多倍。4、乙硫醇与BODIPY的8位醛基缩合,合成了on-off型近红外荧光探针BDT3。:H2O=4:1体系下检测识别Hg2+,探针与Hg2+结合后,紫外吸收从672nm红移至769nm,荧光从690nm蓝移至668nm且强度降低27倍。5、Aza-BODIPY与2,4-二硝基苯磺酰***反应,合成了off-on型近红外荧光探针BDT4。:H2O:DMSO=79:20:1体系下检测识别硫醇类化合物,探针与半II胱氨酸结合后,紫外吸收从717nm红移至735nm,荧光从734nm红移至755nm且强度增强11倍。关键词:BODIPY,近红外荧光探针,Cys,Hcy,H2S,Hg2+IIIABSTRACTBorondipyrromethene(BODIPY)asafluorophorehastremendoussuperiority,suchashighstability,bigmolarextinctioncoefficient,highfluorescencequantumyield,easilymodified,sharpabsorptionandfluorescencepeakshaveactedasgoodcandidatesforelectro-luminescentfilms,biologicallabelingand fluorescentprobes.Manydetectionmeansare applied to the researchofmodern biotechnologyandlifesciences,becauseofgoodsensitivity,lowdetectabilityandgoodselectivity,fluorescenceanalysistechnologyhasplayedanirreplaceableroleinthebioanalyticalfield.HereinaseriesofnovelBODIPYswithcarboxylandfourNIRfluorescentProbesbasedonBODIPYorAza-BODIPYweredesignedandsynthesized.poundswerecharacterizedby1HNMR,MRandHRMS.TheirphotophysicalpropertiesandresponsestoanalytesweresystematicallyinvestigatedbymeansofUV-visandfluorescencemethods.1、Byone-potreaction,twelvenovelBODIPYswithcarboxyl1-12weredesignedandsynthesized.poundsweremeasured.ThepHtolerance,photochemicalstability,awater-soluble,electrochemicalproperties(cyclicvoltammetry),pounds1and7havebetterlightstability,watersolubilityandhavepotentialapplicationsinbiologicaltestingandtargetedtherapy.2、Anoff-onNIRfluorescentprobesBDT1wassynthesizedthroughintroducingaaldehydeto8-positionofBODIPY.Cysteine(Cys)andhomocysteine(Hcy)weredetectedinsolution(:H2O=4:1)andtheirfluorescenceintensitywereenhanced9-foldand30-foldrespectively.Bydifferentresponserate,the twodetection canbedistincted.3、Anoff-onNIRfluorescentprobesBDT2wassynthesizedthroughconjugatingethylcyanoacetatewith8-aldehydeofBODIPY.H2Swasdetectedinsolution(:H2O=4:1).WhenprobereactedwithHS-,theUVabsorpti

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  本文关键词：新型羧基BODIPY及基于BODIPY的近红外荧光探针的设计、合成与应用，由笔耕文化传播整理发布。