Simple one-pot preparation of water-soluble, cysteine-reactive cyanine and merocyanine dyes for biological imaging
Simple one-pot preparation of water-soluble, cysteine-reactive cyanine and merocyanine dyes for biological imaging
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DOI：
10.1021/bc060376n
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发表时间：
2007-07-01
影响因子：
4.7
通讯作者：
Hahn, Klaus M.
中科院分区：
文献类型：
--
作者：
Toutchkine, Alexei;Nguyen, Dan-Vinh;Hahn, Klaus M.
开发了一种简单的一锅法来制备蛋白质反应性水溶性部花青和花青染料。 1-(3-氨丙基)-2,3,3-三甲基-3H-吲哚-5-磺酸溴化物(1)用作常见的起始中间体。该方法可以轻松制备具有氯乙酰胺侧链和碘乙酰胺侧链的染料，以共价连接到半胱氨酸。通过将磺基直接放置在染料荧光团系统上，生成了在水中具有高荧光量子产率的染料。碘代和氯代乙酰胺衍生物均被证明可用于蛋白质标记。反应性较低的氯乙酰胺将优先用于选择性标记反应性最强的半胱氨酸。
A simple one-pot-procedure for preparation of protein-reactive, water-soluble merocyanine and cyanine dyes has been developed. The 1-(3-ammoniopropyl)-2,3,3-trimethyl-3H-indolium-5-sulfonate bromide (1) was used as a common starting intermediate. The method allows easy preparation of dyes with chloro- and iodoacetamide side chains for covalent attachment to cysteine. By placing a sulfonato group directly on the dye fluorophore system, dyes with high fluorescence quantum yields in water were generated. Both iodo- and chloroacetamido derivatives were shown to be useful in protein labeling. Less reactive chloroacetamides will be preferential for selective labeling of the most reactive cysteines.