Preparation and application of cyanine dye-based targeting cysteine fluorescent probe

Abstract

The invention relates to preparation and application of a targeting cysteine fluorescent probe based on a cyanine dye, and the structural formula of the fluorescent probe is shown in the specification. The invention provides a preparation method for synthesizing the fluorescent probe by taking the cyanine fluorescent dye, D-biotin, 3, 4-dimethoxythiophenol and the like as raw materials. The fluorescent probe is a cysteine fluorescent probe which has near-infrared emission and high selectivity and can target cells. Firstly, the fluorescent probe shows very high sensitivity to Cys, and fluorescence is remarkably enhanced after the probe reacts with Cys; secondly, the fluorescent probe shows good selectivity on Cys and is not interfered by other common inorganic ions, active oxygen, active nitrogen, active sulfur, amino acid and biological mercaptan; in addition, the fluorescent probe has been successfully used for Cys imaging in cells, and can be used for detecting the cysteine level in the cells.

Description

Preparation and application of targeted cysteine ​​fluorescent probes based on cyanine dyes technical field The invention belongs to the technical field of fluorescent probes, be specifically related to the targeted cysteine ​​fluorescent probes based on cyanine dyes Needle preparation and application. Background technique Cysteine ​​(Cys) is an important biological thiol and plays an important role in various life activities (S.Y.Zhang, C.N.Ong and H.M.Shen, Cancer Lett., 2004, 208, 143‑153; A. Sharma, M.G.Lee,M.Won,S.Koo,J.F.Arambula,J.L.Sessler,J.Am.Chem.Soc.,2019,141,15611‑ 15618). Scientific research has shown that abnormal metabolism of Cys is associated with many diseases, including cancer, Ringworm, edema, liver damage, etc. (L.Cui, Y.Baek, S.Lee, N.Kwon, J.Yoon, J.Mater.Chem.C, 2016, 4, 2909‑2914; G. Liu, D. Liu, X. Han, X. Sheng, Z. Xu, S. H. Liu, L. Zeng, J. Yin, Talanta, 2017, 170, 406‑412). However, Cys is extremely low in living cells, and detec...

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Problems solved by technology

However, these Cys probes have some disadvantages: (1) The analysis wavelength is short, so it is easily interfered by the autofluorescence signal generated by biomolecules in vivo, and the tissue penetration ability is weak, which limits the application in vivo;( 2) Cannot actively target cells and tissues, it is difficult to gather in specific tissues, scattered probes will reduce the detection efficiency and further enhance the background fluorescence

However, there is no fluorescent probe that can simultaneously target cells and detect Cys

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