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A Ratiometric Fluorescent Probe for Detecting Hypochlorous Acid with Large Stokes Shift

A fluorescent probe and displacement detection technology, applied in the field of chemical analysis and detection, can solve the problems of cumbersome steps and limited application

Active Publication Date: 2021-05-25
CENT SOUTH UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the steps of these methods are cumbersome, and many methods must be carried out in organic media or organic / aqueous media, which limits their application in biology.

Method used

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  • A Ratiometric Fluorescent Probe for Detecting Hypochlorous Acid with Large Stokes Shift
  • A Ratiometric Fluorescent Probe for Detecting Hypochlorous Acid with Large Stokes Shift
  • A Ratiometric Fluorescent Probe for Detecting Hypochlorous Acid with Large Stokes Shift

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Example 1: Synthesis of Probe Molecules Synthesis of Compound 1

[0024] Take potassium hydroxide (25mg, 0.45mmol) in a 10mL round bottom flask, add 5mL of absolute ethanol, add PTZ (56mg, 0.2mmol) and 2-hydroxyacetophenone (47mg, 0.35mmol) under stirring, After reacting at 65°C for 7 hours, the reaction solution was directly spin-dried by a rotary evaporator, and then purified by silica gel column chromatography to obtain 18 mg of compound 1 as a dark red solid with a yield of 22.5%.

[0025] 1 H NMR (400MHz, CDCl 3 )δH 12.92(s,1H),7.92(d,J=7.7Hz,1H),7.85(d,J=14.3Hz,1H),7.52–7.43(m,3H),7.38(d,J=5.9Hz ,1H),7.13(d,J=7.2Hz,2H),7.02(d,J=8.3Hz,1H),6.94(t,J=7.5Hz,1H),6.84(d,J=7.1Hz,3H ), 4.04 (s, 2H), 1.85–1.73 (m, 2H), 1.48 (dd, J=14.8, 7.4Hz, 2H), 0.97 (t, J=7.3Hz, 3H).

[0026] 13 C NMR (400MHz, CDCl 3 )δC 163.5, 147.8, 144.5, 143.9, 136.2, 129.5, 129.3, 128.8, 127.5, 126.7, 125.1, 123.7, 123.1, 120.1, 118.8, 118.6, 117.5, 115.7, 115.2, 481.4, 28.1.

[0027] Synthe...

Embodiment 2

[0031] Embodiment 2: the application of fluorescent probe of the present invention

[0032] Fluorescent probe (10.0×10 -6 mol / L) in HEPES buffer solution (20.0mM, containing 1.0mM CTAB) at pH 7.4, add PBS, 1 o 2 ,H 2 o 2 ,O 2 - ,NO - ,-OH,ONOO - ,ROO - ,TBHP,Hcy,Cys,GSH,SH - , HSO 3 - ,S 2 o 3 2- , SO 4 2- ,Br - , I - ,K + , Na + ,Fe 3+ After adding hypochlorous acid (HClO), there was no obvious change in the emission peak of the probe itself, but it caused a change in fluorescence, indicating that the probe has excellent selectivity. Moreover, the probe is fast enough to detect hypochlorous acid (HClO), showing a fast response rate, while cytotoxicity experiments and imaging experiments in zebrafish indicate that the probe has good biological application prospects.

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Abstract

The invention discloses a ratio-type fluorescent probe with a large Stokes shift for detecting hypochlorous acid. It is a fluorescent probe capable of rapid monitoring or cell imaging of hypochlorous acid in vitro or in living cells, and has a good biological application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemical analysis and detection, and specifically relates to a ratio-type fluorescent probe with a large Stokes shift for identifying hypochlorous acid and an application thereof. Background technique [0002] Hypochlorous acid (HClO), as a typical reactive oxygen species (ROS) species, plays an important role in both physiological and pathological processes. Different reactive oxygen species in the human body are generated through different physiological pathways, and hypochlorous acid is produced by the reaction of hydrogen peroxide and chloride ions through the enzyme myeloperoxidase (MPO). An appropriate amount of hypochlorous acid helps organisms destroy bacteria, but excessive hypochlorous acid is very harmful to people, leading to many diseases, such as cardiovascular disease, arthritis, arteriosclerosis, cancer and so on. Therefore, it is essential to monitor the concentration change of hypochlor...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C09K11/06C09B21/00C07D417/04A61K49/00
Inventor 宋相志廖立德何龙
Owner CENT SOUTH UNIV