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Fluorescent probe for selectively detecting H2S based on BODIPY dye targeted lysosome as well as preparation and application of fluorescent probe

A fluorescent probe and lysosome technology, applied in the field of fluorescent probes, can solve the problems of short detection fluorescence wavelength and long response time, and achieve the effects of convenient operation, simple synthesis method and obvious detection signal

Active Publication Date: 2021-05-04
上海安能健生物医药科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In the past few years, various identifications of H 2 Although great progress has been made in fluorescent probes for S, most of the developed probes have more or less limitations, such as short detection wavelength (20 min). Wait

Method used

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  • Fluorescent probe for selectively detecting H2S based on BODIPY dye targeted lysosome as well as preparation and application of fluorescent probe
  • Fluorescent probe for selectively detecting H2S based on BODIPY dye targeted lysosome as well as preparation and application of fluorescent probe
  • Fluorescent probe for selectively detecting H2S based on BODIPY dye targeted lysosome as well as preparation and application of fluorescent probe

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] The preparation steps of the probe are as follows:

[0038] (1) Preparation of Compound 1

[0039]

[0040] N 2 Under the protective ice-water bath, add 1.1 equivalents of triphenylphosphine into the tetrahydrofuran solvent to obtain a mixed solvent, dissolve 2-morpholine ethanol and p-hydroxybenzaldehyde in the mixed solvent according to the equivalent ratio of 1:1.2, and then add 1.1 An equivalent amount of diisopropyl azodicarboxylate was reacted at room temperature for 15 h, the solvent was removed under reduced pressure, and compound 1 was obtained by column chromatography;

[0041] 1 H NMR (400 MHz, CDCl 3 ) δ 9.77 (s, 1H), 7.72 (d, J = 8.7 Hz, 2H), 6.92(d, J= 8.7 Hz, 2H), 4.10 (t, J = 5.7 Hz, 2H), 3.69 – 3.54 (m, 4H), 2.73 (t, J = 5.7 Hz, 2H), 2.54 – 2.40 (m, 4H).

[0042] (2) Preparation of Compound 2

[0043]

[0044] Dissolve compound 1 in tetrahydrofuran, add 2.2 equivalents of 2,4-dimethylpyrrole, add 0.2 mL of trifluoroacetic acid, react a...

Embodiment 2

[0055] The preparation steps of the probe are as follows:

[0056] (1) Preparation of compound 1

[0057] N 2 Under the protected ice-water bath, add 1 equivalent of triphenylphosphine into the tetrahydrofuran solvent to obtain a mixed solvent, dissolve 2-morpholine ethanol and p-hydroxybenzaldehyde in the mixed solvent according to the equivalent ratio of 1:1, and then add 1.5 An equivalent amount of diisopropyl azodicarboxylate was reacted at room temperature for 12 h, the solvent was removed under reduced pressure, and compound 1 was obtained by column chromatography;

[0058] (2) Preparation of compound 2

[0059] Dissolve compound 1 in tetrahydrofuran, add 2 equivalents of 2,4-dimethylpyrrole, add 0.1 mL trifluoroacetic acid, react at room temperature for 15 h, then add 1.5 equivalents of tetrachlorobenzoquinone, react at room temperature for 0.5 h, follow Add triethylamine and boron trifluoride diethyl ether in a ratio of 5:8 equivalent, react at room temperature for ...

Embodiment 3

[0065] The preparation steps of the probe are as follows:

[0066] (1) Preparation of compound 1

[0067] N 2 Under the protective ice-water bath, 1.5 equivalents of triphenylphosphine was added to the tetrahydrofuran solvent to obtain a mixed solvent, and 2-morpholine ethanol and p-hydroxybenzaldehyde were dissolved in the mixed solvent according to the equivalent ratio of 1:1.5, and then 1 An equivalent amount of diisopropyl azodicarboxylate was reacted at room temperature for 18 h, the solvent was removed under reduced pressure, and compound 1 was obtained by column chromatography;

[0068] (2) Preparation of compound 2

[0069] Dissolve compound 1 in tetrahydrofuran, add 3 equivalents of 2,4-dimethylpyrrole, add 0.2 mL of trifluoroacetic acid, react at room temperature for 12 h, then add 1.1 equivalent of tetrachlorobenzoquinone, react at room temperature for 0.8 h, follow Add triethylamine and boron trifluoride diethyl ether at a ratio of 7:9, react at room temperature...

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Abstract

The invention provides a fluorescent probe for selectively responding to H2S based on BODIPY fluorescent dye targeting lysosome, and preparation and application of the probe. The probe selects BODIPY dye as a fluorophore and 2, 4-dinitrobenzenesulfonyl as a recognition group. A sensing mechanism is based on H2S to induce cracking of 2, 4-dinitrobenzenesulfonyl in the probe, so that a photoinduced electron transfer (PET) process is inhibited. The probe detects H2S through ultraviolet and fluorescence spectrometers and is not interfered by other amino acids, active sulfides, representative anions and the like, the detection process is simple, convenient, rapid and sensitive, and the detection limit is 4.75 nM. More importantly, the probe can target lysosome and detect H2S in cells at the same time, and has a good application prospect in the field of biological monitoring.

Description

technical field [0001] The invention relates to the field of fluorescent probes, in particular to a BODIPY-based fluorescent dye targeting lysosomes selectively responding to H 2 S fluorescent probe, preparation and application. Background technique [0002] Hydrogen sulfide (H 2 S) has received great attention from researchers because it is considered to be the third important gas signal molecule after carbon monoxide (CO) and nitric oxide (NO) in the living system. In recent years, increasing research results have shown that endogenously produced hydrogen sulfide plays an important role in a wide range of physiological and pathological processes. On the other hand, H 2 Abnormal S content is closely related to many serious diseases, such as Alzheimer's disease, Down syndrome, diabetes and liver cirrhosis, etc. Despite these findings, H 2 The underlying molecular properties of S remain unclear. Cell lysosome is an important dynamic subcellular organelle, which is respon...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F5/02C09K11/06G01N21/64
CPCC07F5/022C09K11/06C09K2211/1014C09K2211/1033C09K2211/1055G01N21/6428G01N21/6458G01N21/6486
Inventor 王佳敏张健岳金磊陶远芳王瀚王楠楠苏慧慧赵伟利
Owner 上海安能健生物医药科技有限公司
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