A near-infrared excitation/emission fluorescent probe for imaging of endogenous cysteine in living cells and zebrafish

• Published in: Analytical and bioanalytical chemistry Vol. 412; no. 23; pp. 5539 - 5550
• Main Authors: Xie, Ruihua, Li, Yaqian, Zhou, Zile, Pang, Xiao, Wu, Cuiyan, Yin, Peng, Li, Haitao
• Format: Journal Article
• Language: English
• Published: Berlin/Heidelberg Springer Berlin Heidelberg 01.09.2020; Springer; Springer Nature B.V
• Subjects: Analytical Chemistry; Animals; Biochemistry; Biocompatibility; Biological properties; Biological samples; Cell permeability; Cells (biology); Characterization and Evaluation of Materials; Chemistry; Chemistry and Materials Science; Cysteine; Cysteine - analysis; Cystine; Danio rerio; Emissions; Ethylmaleimide - chemistry; Excitation; Fluorescence; Fluorescent Dyes - chemistry; Fluorescent indicators; Food Science; Hep G2 Cells; Humans; I.R. radiation; Imaging; Imaging techniques; Interference; Investigations; Iodides; Laboratory Medicine; Light scattering; Methylene blue; Monitoring/Environmental Analysis; Near infrared radiation; Optical properties; Paper in Forefront; Spectroscopy, Near-Infrared - methods; Spectrum Analysis - methods; Tissues; Toxicity; Zebrafish; China; Bioimaging; Cysteine; Living cells and zebrafish; NIR excitation/emission fluorophore; Fluorescent probe
• ISSN: 1618-2642; 1618-2650
• DOI: 10.1007/s00216-020-02812-4

The fluorescence imaging technique provides an essential tool for studying biological systems. However, due to the interference of autofluorescence of biological tissues, the application of short-wavelength fluorescent probes in biological imaging was limited. The near-infrared (NIR) excitation/emission fluorescent probe possesses unique advantages in optical imaging in vivo, including less light scattering, minimal photo-damage to biological samples, deep tissue penetration, and weak autofluorescence interference from complicated biological systems. In this work, a convenient fluorophore ( E )-2-[2-(6-hydroxy-2,3-dihydro-1 H -xanthen-4-yl)vinyl]-3- methylbenzo[ d ]thiazol-3-ium iodide ( DXM-OH ) with NIR excitation and emission was rationally designed and developed. What’s more, DXM-OH was applied to construct an “OFF-ON” fluorescent probe ( E )-2-{2-[6-(acryloyloxy)-2,3-dihydro-1 H - xanthen-4-yl]vinyl}-3-methylbenzo[ d ]thiazol-3-ium iodide ( DXM ) for sensitive and selective detection of cysteine (Cys). The experimental results showed that DXM had the advantages of good cell permeability, low toxicity, and excellent optical properties (NIR excitation/emission) and it was successfully applied to image Cys of living cells and zebrafish.