Development of water-soluble far-red fluorogenic dyes for enzyme sensing
Development of water-soluble far-red fluorogenic dyes for enzyme sensing
复制标题
DOI：
10.1016/j.tet.2005.10.020
复制
发表时间：
2006-01-23
期刊：
影响因子：
2.1
通讯作者：
Tung, CS
中科院分区：
文献类型：
--
作者：
Ho, NH;Weissleder, R;Tung, CS
在高氯酸存在下，N-烷基或N-磺基丙基4-芳基偶氮取代的3-羟基苯胺与4-芳基偶氮取代的1-萘胺或8-氨基-2-萘磺酸缩合，合成了一系列尼罗蓝类似物5-氨基-9-二烷基氨基苯并[a]吩恶嗪染料7-9。这些荧光染料分别在640和680 rim附近具有激发和发射最大值。水溶液中的荧光强度随着另外的磺酸盐基团被添加到苯并[a]吩恶嗪核而增加。化合物7有两个磺酸基，比尼罗蓝亮十倍。合成了含有该亲水性远红染料的荧光底物，并将其应用于检测两种模型蛋白酶胰蛋白酶和亮氨酸氨肽酶的酶活性。鉴于其优异的荧光性质，这些新型远红染料应可用于生物测定中的酶传感。(c)2005爱思唯尔有限公司保留所有权利。
A series of Nile Blue analogs, 5-amino-9-dialkylamino benzo[a]phenoxazine dyes, 7-9, were prepared by condensation of N-alkyl or N-sulfo-propyl 4-arylazo-substituted 3-hydroxyaniline with 4-arylazo-substituted 1-naphthlamines or 8-amino-2-naphthalene-sulfonic acid in the presence of perchloric acid. These fluorochromes have excitation and emission maxima near 640 and 680 rim, respectively. The fluorescence intensity in aqueous solution increases as additional sulfonate groups are added to the benzo[a]phenoxazine core. Compound 7, which has two sulfonate groups, is ten-times brighter than Nile Blue. Fluorogenic substrates containing this hydrophilic far-red dye were synthesized and applied to detect enzymatic activities of two model proteases, trypsin and leucine aminopeptidase. Given their excellent fluorogenic property, these novel far-red dyes should be useful for enzyme sensing in biological assays. (c) 2005 Elsevier Ltd. All rights reserved.