Fluorescent probe for ratio detection of hypochloric acid and application thereof in biological systems

A technology for detecting hypochlorous acid and fluorescent probes, which is applied in the field of fluorescent probes and can solve the problem that the probes do not have biological system detection.

Active Publication Date: 2014-10-29
ZHANGJIAGANG IND TECH RES INST CO LTD DALIAN INST OF CHEM PHYSICS CHINESE ACADEMY OF SCI
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this probe has not been used for detection in biological systems

Method used

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  • Fluorescent probe for ratio detection of hypochloric acid and application thereof in biological systems
  • Fluorescent probe for ratio detection of hypochloric acid and application thereof in biological systems
  • Fluorescent probe for ratio detection of hypochloric acid and application thereof in biological systems

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Example 1 (synthesis and properties of Cy7-NR1):

[0038] Synthesis of Cy7-NR1: Under nitrogen, 0.60g Cy7-Cl (available for purchase) and 1.07g morpholine were dissolved in 25ml N,N-dimethylformamide, heated to 90°C for 3 hours. The solvent was evaporated under vacuum, and the obtained solid was purified by column chromatography to obtain the target compound Cy7-NR1.

[0039] Cy7-NR1: 1 H NMR (400MHz, CDCl 3 )δ(ppm):7.77(d,J=12Hz,2H),7.37-7.32(m,4H),7.16(t,J=8Hz,2H),7.03(d,J=8Hz,2H),5.93( d,J=16Hz,2H),4.11-4.06(m,4H),3.98(t,J=4Hz,4H),3.72(t,J=4Hz,4H),2.56(t,J=6Hz,4H) ,1.88(t,J=6Hz,2H),1.69(s,12H),1.44(t,J=6Hz,6H). 13 C NMR (400MHz, CDCl 3 )δ (ppm): 171.78, 168.91, 142.16, 141.59, 140.39, 128.65, 125.31, 123.97, 122.10, 109.57, 96.91, 68.31, 55.01, 48.30, 39.05, 28.84, 25.31, 21.069,

[0040] HRMS: m / z C 38 h 48 N 3 o + Calcd 562.3797, found 562.2762.

[0041] The effect of pH on fluorescence of Cy7-NR1 solution: pH was controlled by PBS buffer solution. Add ...

Embodiment 2

[0047] Embodiment 2 (the synthesis of Cy7-NR2 and the selectivity to hypochlorous acid):

[0048] Synthesis of Cy7-NR2: Under nitrogen, 0.60g Cy7-Cl (available for purchase) and 10 equivalents of piperidine were dissolved in 25ml N,N-dimethylformamide, heated to 90°C for 3 hours. The solvent was evaporated under vacuum, and the obtained solid was purified by column chromatography to obtain the target compound Cy7-NR2.

[0049] Cy7-NR2: 1 H NMR (400MHz, CDCl 3 )δ(ppm):7.55(d,J=16Hz,2H),7.34-7.27(m,4H),7.11(t,J=8Hz,2H),6.95(d,J=8Hz,2H),5.75( d,J=12Hz,2H),3.97(t,J=6Hz,4H),3.67-3.64(m,4H),2.50(t,J=6Hz,4H),1.92-1.82(m,8H),1.66 (s,12H),1.38(t,J=8Hz,6H).HRMS:m / z C 39 h 50 N 3 + Calcd 560.4005, found 560.3985.

[0050] Selectivity of Cy7-NR2 to hypochlorous acid: add 5.0μMCy7-NR2 to a 10ml colorimetric tube, then add 10ml of PBS (pH=7.4) with a concentration of 20mM, shake well, and then add various substances to be tested (each For the amount of the measured substance, see t...

Embodiment 3

[0051] Embodiment 3 (the synthesis of Cy7-NR3 and the selectivity to hypochlorous acid):

[0052] Synthesis of Cy7-NR3: Under nitrogen, 0.60g Cy7-Cl (available for purchase) and 10 equivalents of piperazine were dissolved in 25ml N,N-dimethylformamide, heated to 90°C for 3 hours. The solvent was evaporated under vacuum, and the obtained solid was purified by column chromatography to obtain the target compound Cy7-NR3.

[0053] Cy7-NR3: 1H NMR (400MHz, CDCl 3 )δ(ppm):7.85(d,J=12Hz,2H),7.42(d,J=8Hz,2H),7.36(t,J=6Hz,2H),7.19(t,J=8Hz,2H), 7.05(d,J=8Hz,2H),5.90(d,J=16Hz,2H),4.05(t,J=8Hz,8H),3.53(s,4H),2.52(t,J=6Hz,4H) ,1.88-1.85(m,2H),1.80(s,12H),1.44(t,J=8Hz,6H).HRMS:m / z C 38 h 49 N 4 + Calcd 561.3957, found 561.3971.

[0054] Selectivity of Cy7-NR3 to hypochlorous acid: add 5.0μMCy7-NR3 to a 10ml colorimetric tube, then add 10ml of PBS (pH=7.4) with a concentration of 20mM, shake well, and then add various substances to be tested (each For the amount of the measured subs...

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Abstract

The invention relates to a fluorescent probe for ratio detection of hypochlorous acid and application thereof in biological systems. Specifically, in the presence of hypochlorous acid, fluorescence wavelength of the probe may change. The invention provides the fluorescent probe for selective ratio detection of the hypochlorous acid in solution systems, cells, animal tissues or individual animals. The fluorescent probe adopts a cyanine dyes as a fluorescent matrix, a secondary amine is introduced onto the middle position of the cyanine matrix, selective detection of the hypochlorous acid can be realized by using the properties that the cyanine matrix is high in electron cloud density and easy to be oxidized by the hypochlorous acid; after the cyanine matrix is oxidized by the hypochlorous acid, blue shift of the fluorescence wavelength of the probe is occurred, the intensity of long wavelength fluorescent light is decreased gradually along with the increase of the hypochlorous acid content, the intensity of newly-occurred short wavelength fluorescent light is gradually increased, and the fluorescent probe is used for ratio detection of the hypochlorous acid.

Description

technical field [0001] The present invention relates to a class of fluorescent probes for ratiometric detection of hypochlorous acid (HClO). Specifically, it is a kind of compound whose fluorescence wavelength changes in the presence of HClO, so as to be able to ratiometrically detect the fluorescent probe of hypochlorous acid in solution system, cells, animal tissues or individual animals. Background technique [0002] Hypochlorous acid (HClO), as a kind of active oxygen in organisms, is of great significance to organisms. Unlike other reactive oxygen species in living organisms, hypochlorous acid is also widely used as a disinfectant, antibacterial agent, and bleaching agent in daily life. Endogenous hypochlorous acid is produced by myeloperoxidase MPO catalyzing hydrogen peroxide and chloride ions. Under physiological conditions, hypochlorous acid will be decomposed into hypochlorite anion (ClO-) with strong oxidative properties, which has antibacterial properties and c...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06G01N21/64
Inventor 楼张蓉韩克利李鹏
Owner ZHANGJIAGANG IND TECH RES INST CO LTD DALIAN INST OF CHEM PHYSICS CHINESE ACADEMY OF SCI
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