One-Step Synthesis of Novel Asymmetric Trimethine Indocyanine Fluorescent Dye and Fluorescent Labeling

doi:10.6023/cjoc201511020

Chin. J. Org. Chem. ›› 2016, Vol. 36 ›› Issue (7): 1700-1705.DOI: 10.6023/cjoc201511020 Previous Articles Next Articles

Notes

“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

汤昆^a, 张鹏超^a,b, 王升^a,b, 邱娜^a, 张付利^a

a. 河南大学医学院环境医学研究所开封 475004;
b. 河南大学药学院开封 475004

收稿日期:2015-11-12 修回日期:2016-01-16 发布日期:2016-03-11
通讯作者: 张付利 E-mail:hdzfl508@163.com
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

Tang Kun^a, Zhang Pengchao^a,b, Wang Sheng^a,b, Qiu Na^a, Zhang Fuli^a

a. Research Institute of Environmental Medicine, Medical College of Henan University, Kaifeng 475004;
b. Pharmaceutical College of Henan University, Kaifeng 475004

Received:2015-11-12 Revised:2016-01-16 Published:2016-03-11
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21202036).

1. One-Step Synthesis of Novel Asymmetric Trimethine Indocyanine Fluorescent Dye and Fluorescent Labeling.PDF(291KB)

Abstract

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.

Key words: trimethine indocyanine, nonionic hydrophilic group, fluorescence quantum yield, protein labeling, cell stain

Cite this article

Tang Kun, Zhang Pengchao, Wang Sheng, Qiu Na, Zhang Fuli. One-Step Synthesis of Novel Asymmetric Trimethine Indocyanine Fluorescent Dye and Fluorescent Labeling[J]. Chin. J. Org. Chem., 2016, 36(7): 1700-1705.

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“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

One-Step Synthesis of Novel Asymmetric Trimethine Indocyanine Fluorescent Dye and Fluorescent Labeling

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