“一步法”合成新型不对称三甲川吲哚菁荧光染料及荧光标记
收稿日期: 2015-11-12
修回日期: 2016-01-16
网络出版日期: 2016-03-11
基金资助
国家自然科学基金（No.21202036）资助项目.
One-Step Synthesis of Novel Asymmetric Trimethine Indocyanine Fluorescent Dye and Fluorescent Labeling
Received date: 2015-11-12
Revised date: 2016-01-16
Online published: 2016-03-11
Supported by
Project supported by the National Natural Science Foundation of China (No. 21202036).
首次合成了一种含非离子水溶性基团的水溶性不对称三甲川吲哚菁荧光染料. 以N-（3，5-二（2-（2-甲氧乙氧基）乙氧基）乙氧基）苄基-2，3，3-三甲基-5-磺酸基-3H-吲哚、N-对羧苄基-2，3，3-三甲基-5-磺酸基-3H-吲哚和缩合剂N，N′-二苯基二甲脒为原料，采用“一步法”合成，用自制简易C18反相硅胶填料柱分离即可得到纯品，目标染料经HRMS、NMR表征； 测试了染料的紫外光谱性能、荧光光谱性能和光稳定性能； 研究了染料标记牛血清白蛋白（BSA）和细胞染色. 结果表明： 在吲哚“N”原子上引入具有PEG链的非离子水溶性基团，使目标染料合成简便，纯化简单，产率达到73%； 荧光量子产率（Φ）达到0.3； 标记蛋白质标示率（D/P）为1.87； 染料对固定细胞和活细胞染色结果有显著差异，能有效区分细胞存活状态.
汤昆 , 张鹏超 , 王升 , 邱娜 , 张付利 . “一步法”合成新型不对称三甲川吲哚菁荧光染料及荧光标记[J]. 有机化学, 2016 , 36(7) : 1700 -1705 . DOI: 10.6023/cjoc201511020
A novel water-soluble asymmetric trimethine cyanine dye which contains one nonionic hydrophilic group was first synthesized, which was prepared from one-step synthesis with N-carboxybenzyl-2,3,3-trimethyl-3H-indol-5-sulfonic acid, N,N′-diphenylformamidine and 2,3,3-trimethyl-3H-indol-5-sulfonic acid with PEG. The pure title compound could be obtained by using the self-made C18 reversed-phase chromatographic column. The structure of the product was identified by NMR and HRMS. The spectra character and photostability of this dye were detected, protein labeling of albumin bovine serum (BSA) and cell stain with this dye were investigated. The results showed that the yield of the target compound could reach 73% by simple synthesis and purification, the fluorescence quantum yield was 0.3, the D/P of protein labeling was 1.87. The dye could effectively distinguish between the fixed cells and living cells, because of the significant differences in the staining results.
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