A Water-soluble Near-infrared Fluorescent Probe for Cysteine/Homocysteine and Its Application in Live Cells and Mice

• Published in: Analytical Sciences Vol. 36; no. 9; pp. 1053 - 1057
• Main Authors: MEN, Yuhui, ZHOU, Xiaomin, YAN, Zhijie, NIU, Linqiang, LUO, Yang, WANG, Jiamin, WANG, Jianhong
• Format: Journal Article
• Language: English
• Published: Singapore The Japan Society for Analytical Chemistry 10.09.2020; Springer Nature Singapore; Japan Science and Technology Agency
• Subjects: Analytical Chemistry; Aqueous solutions; Cells (biology); Chemistry; cyanine; Cys/Hcy; Fluorescence; Fluorescent indicators; fluorescent probe; Homocysteine; I.R. radiation; in vivo imaging; Near infrared radiation; Near-infrared (NIR); Substitutes; Sulfur; Water chemistry; cyanine; Cys/Hcy; fluorescent probe; imaging; Near-infrared (NIR)
• ISSN: 0910-6340; 1348-2246
• DOI: 10.2116/analsci.20P016

A near-infrared (NIR) and water-soluble probe was synthesized and studied for the detection of Cys/Hcy in aqueous solution, living cells and mice. The probe was composed of cyanine derivative as the NIR fluorescent reporting unit and pyrimidiny-thioether moiety as the Cys/Hcy responsive unit. Treatment with Cys/Hcy induced the formation of sulfur-substituted products, then intramolecular rearrangement reaction would occur to produce amino-substituted products and resulting in enhanced red fluorescence emissions. It could be applied to sense Cys/Hcy both in solution with the detection limit of 0.17 μM (or 0.32 μM) and in living cells. Cell imaging experiments proved that such a probe exhibited good cell penetration. In addition, the probe could detect Cys/Hcy in live mice with strong turn-on fluorescent response.