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Click Chemistry Based Method for the Preparation of Maleinimide-Type Thiol-Reactive Labels
Link, Martin1; Li, Xiaohua1,2; Kleim, Jana1; Wolfbeis, Otto S.1
2010-12-01
Source PublicationEUROPEAN JOURNAL OF ORGANIC CHEMISTRY
ISSN1434-193X
Issue36Pages:6922-6927
AbstractMaleinimides are widely used to label proteins and to derivatize thiols. The so-called click reaction was shown to allow the efficient introduction of the maleinimido group into azido-modified fluorophores (benzoxazines) by reacting them with an alkyne-modified maleinimide to yield new thiol-reactive fluorescent labels 5-7. The reaction proceeds under mild experimental conditions and provides a new strategy with which to introduce the maleimide group, as exemplified here for fluorophores. Conceivably, it may be extended to radioactive, electro-active, isotopic, or spin labels. Previously reported methods for the formation of such maleinimides starting from open-ring precursors require rather harsh conditions. The new benzoxazines 5-7 are characterized by a fairly long and flexible linker between the chromophore and the maleinimide functional group, and their fluorescence can be photoexcited with diode lasers (which are preferred light sources in fluorometry). They were conjugated to: (a) the aminothiol cysteamine, (b) the peptide glutathione, and (c) to human serum albumin. The fluorescence of the phenoxazinone 5 is strongly solvatochromic, which suggests its use as a polarity-sensitive probe.
KeywordClick Chemistry Fluorescent Probes Imaging Agents Proteins Thiols
DOI10.1002/ejoc.201001085
Indexed BySCI ; IC
Language英语
WOS IDWOS:000285311000006
PublisherWILEY-BLACKWELL
Citation statistics
Cited Times:6[WOS]   [WOS Record]     [Related Records in WOS]
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/70142
Collection中国科学院化学研究所
Corresponding AuthorWolfbeis, Otto S.
Affiliation1.Univ Regensburg, Inst Analyt Chem Chemo & Biosensors, D-93040 Regensburg, Germany
2.Chinese Acad Sci, Beijing Natl Lab Mol Sci, Key Lab Analyt Chem Living Biosyst, Inst Chem, Beijing 100190, Peoples R China
Recommended Citation
GB/T 7714
Link, Martin,Li, Xiaohua,Kleim, Jana,et al. Click Chemistry Based Method for the Preparation of Maleinimide-Type Thiol-Reactive Labels[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY,2010(36):6922-6927.
APA Link, Martin,Li, Xiaohua,Kleim, Jana,&Wolfbeis, Otto S..(2010).Click Chemistry Based Method for the Preparation of Maleinimide-Type Thiol-Reactive Labels.EUROPEAN JOURNAL OF ORGANIC CHEMISTRY(36),6922-6927.
MLA Link, Martin,et al."Click Chemistry Based Method for the Preparation of Maleinimide-Type Thiol-Reactive Labels".EUROPEAN JOURNAL OF ORGANIC CHEMISTRY .36(2010):6922-6927.
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