Novel water-soluble sulfydryl fluorescent probe, and preparation method and application thereof

Abstract

The invention relates to a novel water-soluble sulfydryl fluorescent probe which is a 2-(2'-hydroxyphenyl) benzimidazole (HPBI) compound modified by quaternary ammonium salt. The compound has the structure of 2-[5-(trimethyl quaternary ammonium salt)-acetamido-2'-hydroxyphenyl) benzimidazole. The fluorescent probe can be used for detecting a biological sulfhydryl compound in aqueous solution and living tumor cell, i.e. the novel water-soluble sulfydryl fluorescent probe is selectively coordinated with cupric ions and an obtained coordination compound can enter the living cell to be reacted with the sulfhydryl compound, so that a fluorescent compound is changed into ionic molecules again and fluorescent light is recovered. The novel water-soluble sulfydryl fluorescent probe has the advantages that the novel water-soluble sulfydryl fluorescent probe has excellent water solubility and biocompatibility and high sulfhydryl measurement sensitivity; before and after GSH (glutathione) reaction, the fluorescent light is rapidly changed and is stable; the novel water-soluble sulfydryl fluorescent probe can be stored and used for a long time; and according to the fluorescent probe, a good research method is provided for researching a biological signal channel related to the biological sulfydryl and the significance and diagnosis of the sulfydryl in the in vivo process of diseases or organisms.

Description

technical field [0001] The invention belongs to the technical field of biological detection, and in particular relates to a novel water-soluble sulfhydryl fluorescent probe and its preparation method and application. Background technique [0002] Sulfhydryl (-SH) is one of the most chemically active groups in cells. In proteins, the sulfhydryl moiety is the most reactive functional group associated with enzymatic activity. The sulfhydryl compounds in cells, especially glutathione, are important antioxidants in living organisms. They can eliminate free radicals in the human body, clean and purify the environmental pollution in the human body, thereby improving human physical and mental health. In particular, reduced glutathione (GSH) itself is susceptible to oxidation by certain substances, so it can protect the sulfhydryl groups in many proteins and enzymes in the body from being oxidized by harmful substances such as free radicals, thereby allowing proteins and enzymes to ...

AI Technical Summary

Problems solved by technology

[0004] The reported sulfhydryl fluorescent probes include aryl halides, dansylaziridines, etc., which have good sensitivity, and the detection limit of thiol is generally around nanomolar (nmol), but these probes themselves have Strong fluorescence, which will cause low signal-to-noise ratio when used in live cell imaging; there is also a class such as benzofuransulfonyl halide, although its autofluorescence is weak, but it needs to be combined with sulfhydryl under alkaline conditions and above room temperature derivation and cannot be applied to live cell imaging

The most commonly used reagents for derivatizing sulfhydryl groups are acetyl halide derivatives, mainly iodoacetamide derivatives, which react quickly with sulfhydryl groups and can be carried out at room temperature and physiological pH, but the products are prone to lose fluorophores and are unstable to light

These existing sulfhydryl fluorescent probes cannot well meet the requirements of bioluminescence detection and fluorescence imaging.

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