BODIPY derivative for measuring CysSnSSH and application thereof

A technology of cysteine ​​fluoroboron pyrrole and fluorophore, which is applied in the field of fluorescent probes, can solve the problems that fluorescent probes have not been developed, and achieve the effects of reducing sample processing time, improving detection accuracy, and reducing detection costs

Active Publication Date: 2015-10-28
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Currently used for specific detection of CysS n Fluorescent probes for SSH have not yet been developed

Method used

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  • BODIPY derivative for measuring CysSnSSH and application thereof
  • BODIPY derivative for measuring CysSnSSH and application thereof
  • BODIPY derivative for measuring CysSnSSH and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] Example 1. Preparation of polysulfide cysteine ​​fluoroboron pyrrole fluorophore (BODIPY) derivatives:

specific Embodiment

[0041] The fluorophore (BODIPY) derivatives used for the determination of polysulfide cysteine ​​shown in the general formula Ⅰ are reacted with commercially available p-hydroxyacetophenone and benzaldehyde to synthesize the corresponding fluorophore BODIPY, and then in the fluorescence The corresponding positions of the groups are respectively modified with different positioning groups. Finally, the fluorophore of the modified positioning group is reacted with dithiophthalic acid in dichloromethane solvent, catalyzed by DMAP and EDC, and then reduced by dithiothreitol to generate the corresponding polysulfide cysteine. Fluoropyrrole-like fluorophore (BODIPY) derivatives. Specific examples are as follows:

[0042] Preparation of a compound of formula:

[0043] Under the protection of argon, the BODIPY fluorophore (92.6mg, 0.1mmol) with triphenylphosphine group, 2,2'-diselenodibenzoic acid (40.0mg, 0.1mmol), 1-(3- Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, ...

Embodiment 2

[0051] The prepared compound of formula one is used as a probe in water system, simulated physiological environment and intracellular for CysS n The detection of SSH simulates physiological conditions. The following experiments are all carried out under the condition of pH=7.4 (HEPES buffer solution, the concentration is 10 mM), and the probe concentration is 10 μM.

[0052] Above-mentioned preparation gained formula two compound pair CysS n Spectral response of SSH; add 10μM compound of formula 1 to 10ml colorimetric tube, then add 10mM HEPES, then add 0-10μM CysS n SSH, dilute to 10ml with ultrapure water, shake the solution to balance for 10min, then add the above working solution into the fluorescence dish to measure the fluorescence spectrum. Fluorescence spectral changes and UV spectra such as figure 1 shown. Depend on figure 1 The compound shown can be used to realize CysS in vivo n SSH detection. Simultaneously, the probe provided by the embodiment of the present...

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Abstract

The invention relates to a fluorescent probe for detecting CysSnSSH (n is larger than one), in particular to a BODIPY derivative for measuring the CysSnSSH and application thereof. The BODIPY derivative is shown in the general formula I. In the general formula I, R1 (a detection group) is a sulfydryl benzoyl group or an aryl selenol benzoyl group or a tellurium phenol benzoyl group; R2 (a positioning functional group) is a sulfydryl benzoyl group, an aryl selenol benzoyl group, a tellurium phenol benzoyl group, a butyl triphenyl phosphonium group, an N-propyl morpholino group, a biotin group, a folic acid group, a glycosyl chain group or a C1-25 alkyl group; X represents H or halogen; Y represents N or C; Z represents N or O. In the presence of CysSnSSH, corresponding fluorescence intensity changes, and the compound like the CysSnSSH fluorescent probe can be used for detecting CysSnSSH, interference of external detection conditions can be greatly reduced, the sample treatment time is saved, and the detection precision is improved.

Description

technical field [0001] The present invention relates to be used for detecting cysteine ​​polysulfide (CysS n SSH, n>1) fluorescent probe, specifically a kind of polysulfide cysteine ​​fluoroboryrrole fluorophore (BODIPY) derivative and its application. Background technique [0002] Intracellular active sulfur species is a general term for sulfur-containing biomolecules, such as glutathione, cysteine, and hydrogen sulfide. These molecules participate in important physiological and pathological functions in living organisms. The production of endogenous hydrogen sulfide and its physiological role in biological systems make this gas an important member of the family of nitric oxide and carbon monoxide gas signaling molecules. Under normal physiological conditions, hydrogen sulfide mainly forms as H2S - exist. That is to say, HS - It may be responsible for the regulation and metabolism of various important substances. Hydrogen sulfide will be converted into sulfane sulf...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1007C09K2211/1022C09K2211/1029G01N21/64
Inventor 于法标陈令新高敏韩潇玥
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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