Click Chemistry Based Method for the Preparation of Maleinimide-Type Thiol-Reactive Labels

doi:10.1002/ejoc.201001085

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	Click Chemistry Based Method for the Preparation of Maleinimide-Type Thiol-Reactive Labels
	Link, Martin 1; Li, Xiaohua 1,2; Kleim, Jana 1; Wolfbeis, Otto S.1
刊名	EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
	2010-12-01
期号	36 页码:6922-6927
关键词	Click Chemistry Fluorescent Probes Imaging Agents Proteins Thiols
ISSN号	1434-193X
DOI	10.1002/ejoc.201001085
英文摘要	Maleinimides 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.
语种	英语
出版者	WILEY-BLACKWELL
WOS记录号	WOS:000285311000006
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/70141]
专题	中国科学院化学研究所
通讯作者	Wolfbeis, Otto S.
作者单位	1.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
推荐引用方式 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.