Pham Wellington, Medarova Zdravka, Moore Anna
Athinoula A. Martinos Center for Biomedical Imaging, Department of Radiology, Massachusetts General Hospital, Charlestown, Massachusetts 02129, USA.
Bioconjug Chem. 2005 May-Jun;16(3):735-40. doi: 10.1021/bc049700+.
A novel water-soluble 2-[2-(2-chloro-3-{2-[3,3-dimethyl-5-sulfo-1-(4-sulfo-butyl)-3H-indol-2-yl]-vinyl}-cyclohex-2-enylidene)-ethylidene]-3,3-dimethyl-1-(4-sulfo-butyl)-2,3-dihydro-1H-indole-5-carboxylic acid (dye 2) was developed via an asymmetric approach. With an additional sulfonate group, the near-infrared feature of this dye exhibited a 2-fold increase in quantum yield compared to the previous generation. The current synthetic strategy provided a single carboxylic group as a handle for conjugation, thus allowing selectivity for bioconjugation. The stability of this dye was demonstrated by labeling peptides via solid-phase peptide chemistry. The in vivo optical imaging showed potential and broad applications of this dye in developing molecular-based beacons for cancer detection.
通过不对称方法开发了一种新型水溶性2-[2-(2-氯-3-{2-[3,3-二甲基-5-磺基-1-(4-磺基丁基)-3H-吲哚-2-基]-乙烯基}-环己-2-烯亚基)-亚乙基]-3,3-二甲基-1-(4-磺基丁基)-2,3-二氢-1H-吲哚-5-羧酸（染料2）。由于额外的磺酸根基团，该染料的近红外特性与上一代相比量子产率提高了2倍。当前的合成策略提供了一个单一的羧基作为共轭基团，从而实现生物共轭的选择性。通过固相肽化学标记肽证明了该染料的稳定性。体内光学成像显示该染料在开发用于癌症检测的基于分子的信标方面具有潜力和广泛应用。
