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A kind of nano fluorescent probe for ratiometric detection of HNO and its preparation method and application

A nano fluorescent probe and fluorescent probe technology, applied in the field of preparation of nano fluorescent probes, can solve the problems of limited detection range, poor water solubility of fluorescent probe molecules, etc., to solve poor water solubility, overcome the interference of reducing substances, and resist strong interference effect

Active Publication Date: 2020-05-26
HUBEI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are still deficiencies in the research work on the synthesis of such dyes, such as the poor water solubility of the designed fluorescent probe molecules, the relatively limited detection range, and most of them are used to detect exogenous small molecules, etc.

Method used

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  • A kind of nano fluorescent probe for ratiometric detection of HNO and its preparation method and application
  • A kind of nano fluorescent probe for ratiometric detection of HNO and its preparation method and application
  • A kind of nano fluorescent probe for ratiometric detection of HNO and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0072] Embodiment: the synthesis of compound P-BODIPY-N

[0073] Take 1,2-(diphenylphosphino)benzoic acid dissolved in dry CH 2 Cl 2 , stir at room temperature until completely dissolved, after cooling down to 0°C, add DPTS and DIPC, stir for 5 minutes, then add HO-BODIPY-N, slowly warm up to room temperature, add water to wash after the reaction, combine the organic phase, anhydrous sulfuric acid Sodium was dried, and column chromatography gave an orange-red solid.

[0074] The hydrogen spectrum of compound P-BODIPY-N (such as Figure 6 ), the deuterated reagent is d 6 -DMSO.

[0075] 1 H NMR (d6-DMSO, 600 MHz): δ 8.27-8.25 (q, 1H), δ 7.60-7.58 (t, 2H), δ 7.54-7.53 (d, 2H), δ 7.42-7.38 (m, 10H) , δ 7.22-7.19 (m,5H), δ 6.98-6.97(d, 1H), δ 6.93-6.92 (d, 1H), δ 6.77-6.76 (d, 1H), δ 6.56-6.55 (m, 1H) , δ4.10 (s,1H), δ3.82 (s, 1H).

[0076] High resolution mass spectrometry HRMS (m / z) of compound P-BODIPY-N (such as Figure 7 ) : Calcd for C 43 h 35 BF 2 N 3 o 3 P: 7...

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Abstract

The invention relates to a nanometer fluorescence probe used for ratio detection of HNO, and a preparation method and applications thereof. The nanometer fluorescence probe is obtained via amphotericpolymer coating of compound P-BODIPY-R; the structure general formula of the P-BODIPY-R is disclosed in the invention, wherein R1 and R2 are used for representing introduced substituent groups, are capable of adjusting the electron effects in fluorescence probe molecules, and achieving fluorescence ratio change in HNO response. The nanometer fluorescence probe can be used for ratio detection of active small molecule HNO in vivo. Introduction of amphoteric polymers and coating of fluorescence probe small molecule P-BODIPY-R are adopted to prepare nanometer micelle, so that the probe small molecule biocompatibility is improved greatly, the nanometer fluorescence probe is high in selectively on HNO, high in anti-interface performance, and sensitivity, and can be used for real-time tracking detection of HNO in living cells and zebra fish.

Description

technical field [0001] The invention belongs to the field of biochemical industry and relates to the construction of a novel ratio-type nano fluorescent probe that can be used to detect HNO in living organisms, and in particular to a preparation method and biological application of the nano fluorescent probe for detecting HNO. Background technique [0002] BODIPY compound is a fluorescent dye with excellent performance, which has a high fluorescence quantum yield. The two pyrrole rings are fixed on a plane through a boron bridge bond and a methine bond, so that the molecule has a rigid coplanar structure. Under the action of light, it can produce relatively strong fluorescence, and its highly rigid coplanar structure makes it have a high molar extinction coefficient, good photochemical and photophysical stability, excitation wavelength in the visible region, and narrow half-peak width In addition, its structure is easy to modify, and the emission wavelength can be adjusted t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): A61K49/00C09K11/02C09K11/06G01N21/64
CPCA61K49/0021A61K49/0028A61K49/0054A61K49/0082C09K11/025C09K11/06C09K2211/1029G01N21/6486
Inventor 王飞翼杨桂春陈祖兴卢翠芬袁少华
Owner HUBEI UNIV