Biological thiol fluorescent probe as well as preparation method and application thereof

Abstract

The invention discloses a biological thiol fluorescent probe. According to the biological thiol fluorescent probe, a first fluorophore is used as an energy donor for emitting fluorescence, and a second fluorophore or quenching group is used as an energy acceptor for absorbing fluorescence. The biological thiol fluorescent probe has the structure of R-S-S-R', wherein R comprises the first fluorophore, and the R' comprises the second fluorophore or quenching group. The invention further provides a preparation method and an application of the biological thiol fluorescent probe. The biological thiol fluorescent probe uses the fluorescence intensity per se to attenuate or quench, thus the imaging signal to noise ratio is increased. In addition, the biological thiol fluorescent probe has high fluorescence stability after the thiol is subjected to reaction. The biological thiol fluorescent probe is easy to prepare and can be prepared at normal temperature and pressure and neutral pH value.

Description

technical field [0001] The invention relates to the technical field of biological detection, in particular to a biological thiol fluorescent probe and its preparation and application in the determination of thiol content in active cells or living organisms. Background technique [0002] Sulfhydryl (-SH) is the most chemically active group in cells. In proteins, the sulfhydryl moiety is the most reactive functional group related to enzyme activity. Two sulfhydryl groups dehydrogenate to form a disulfide bond (-S-S-), which enables the connection of adjacent polypeptides, which is very important for maintaining the integrity of the protein structure. The sulfhydryl group in cells, especially glutathione (GHS), acts as a nucleophile and reducing agent in cells, which can protect cells from hypoxia, toxins, mutagenesis, radioactivity and carcinogens. A large number of biological phenomena are dependent on thiols including thiols, such as redox reactions, methyl transfer reactio...

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Problems solved by technology

[0004] The thiol fluorescent probes in the prior art mainly contain the following classes: the first class is aromatic halides, dansylaziridines, pyrenes, etc., which have good selectivity and sensitivity, but these probes themselves have relatively high Strong fluorescence, which will cause a low signal-to-noise ratio when used in live cell imaging; the second type is benzofuransulfonyl halide probes, which have weak autofluorescence and need to be combined with sulfhydryl groups under alkaline and high temperature conditions. It is not suitable for thiol detection in living organisms; the third category is acetyl halide derivative reagents, which have poor photostability and easy inactivation of fluorescent groups, which cannot meet the requirements of thiol detection in living organisms.

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