Novel water-soluble sulfydryl fluorescent probe, and preparation method and application thereof
A fluorescent probe, water-soluble technology, applied in the field of new water-soluble sulfhydryl fluorescent probes and their preparation, can solve the problems of light instability, low signal-to-noise ratio, easy loss of fluorophores in products, etc., and achieve high sulfhydryl determination sensitivity , good biocompatibility, rapid fluorescence change effect
A fluorescent probe, water-soluble technology, applied in the field of new water-soluble sulfhydryl fluorescent probes and their preparation, can solve the problems of light instability, low signal-to-noise ratio, easy loss of fluorophores in products, etc., and achieve high sulfhydryl determination sensitivity , good biocompatibility, rapid fluorescence change effect
CN102585802AInactive Publication Date: 2012-07-18TIANJIN UNIVERSITY OF TECHNOLOGY
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[0035] A preparation method of the novel water-soluble thiol fluorescent probe, the steps are as follows:
[0036] 1) Dissolve 4.66g of aniline in 40mL of water to obtain aniline aqueous solution, add 15mL of concentrated hydrochloric acid with a mass percentage concentration of 37% to completely dissolve the aniline, cool to 0°C in an ice bath, and obtain aniline hydrochloride solution, and dissolve 3.6g of sodium nitrite Dissolve it in 12mL of water to obtain an aqueous solution of sodium nitrite, cool it to 0°C in an ice bath, and add it dropwise to the above-mentioned aniline hydrochloride solution at a rate of 2 drops per second to prepare aniline diazonium salt solution;
[0037] 2) adding 300mL of 1% NaOH aqueous solution into 6.1g salicylaldehyde to obtain a salicylaldehyde solution, and adding the aniline diazonium salt solution dropwise to the salicylaldehyde alkali aqueous solution at a rate of 3 drops per second at 0°C In, dropwise add the Na that the mass percenta...
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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 ...
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Patent Timeline
18 Jul 2012
Publication
CN102585802A
- IPC
- C09K11/06; C07D235/18; G01N33/52; G01N21/64; C12Q1/02
- Inventors
- 欧阳杰; 王秋生