A fluorescent probe for detecting nitrosyl peroxide by cleavage of amide bond and its application

A technology of peroxynitrosyl and fluorescent probes, applied in the field of fluorescent probes, can solve problems such as inability to achieve quantitative detection

Active Publication Date: 2015-07-29
ZHANGJIAGANG IND TECH RES INST CO LTD DALIAN INST OF CHEM PHYSICS CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above-mentioned probes are fluorescence-enhanced probes, and there is no change in wavelength, so quantitative detection cannot be realized

Method used

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  • A fluorescent probe for detecting nitrosyl peroxide by cleavage of amide bond and its application
  • A fluorescent probe for detecting nitrosyl peroxide by cleavage of amide bond and its application
  • A fluorescent probe for detecting nitrosyl peroxide by cleavage of amide bond and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Embodiment 1 (synthesis of intermediate compound BOD):

[0059] Such as image 3 As shown, the structure of the probe compound used in the examples is represented by the code BODSe, and the dye matrix used in the synthesis of the probe compound is represented by the code BOD.

[0060] Synthesis of BOD: raw material BODIPY (J.Phys.Chem.A 1998,102,10211-10220) 0.76g, p-ethylaminobenzaldehyde (JOC 2011,76,1180-1183) 0.3g, 1mL piperidine as catalyst, 20mL of o-dichlorobenzene was used as a solvent, protected by nitrogen, reacted at 140°C for 6h, and evaporated to dryness. Purify by column separation, collect the red fluorescent components, and evaporate the solvent to obtain a green shiny solid.

[0061] 1 H NMR (400MHz, CDCl 3 -D 1 )δ(ppm):7.49-7.17(m,8H),6.58-6.56(s,2H),5.96(s,2H),3.90(s,2H),3.22-3.20(q,2H),2.58(s ,3H),1.54(s,3H),1.41-1.37(s,3H),1.27-1.26(t,3H).GC-MS(API-ES):m / z C 28 h 28 BF 2 N 3 Calcd 455.2, found 455.2.

Embodiment 2

[0062] Embodiment 2 (synthesis of probe BODSe):

[0063] Synthesis of probe BODSe: Dissolve 0.3g of o-phenylseleniumbenzoic acid (Organic Syntheses Coll.1988, 6,533, J.Chem.Soc., Perkin Trans.1999,1, 1915-1916) and 2mL of thionyl chloride in 5mL In dichloromethane, react at 65°C for 7 h, evaporate the solvent to dryness under reduced pressure, and dissolve the obtained solid with 10 mL of benzene. The acid chloride solution was dropped into a solution formed by dissolving 0.41 g of BOD in 10 mL of benzene, stirred at room temperature for 10 hours, and evaporated to dryness. The obtained solid was purified by column chromatography to obtain the target compound BODSe.

[0064] 1 H NMR (400MHz, CDCl 3 -D 1 )δ(ppm):7.60-7.29(m,8H),7.16-6.96(m,12H), 6.55(s,1H),6.03(s,1H),4.10-3.99(q,2H),2.60(s ,3H),1.59(s,3H),1.42-1.39(d,3H),1.27-1.26(m,3H). 13 CNMR (100MHz, CDCl 3 -D 1 )δ(ppm):182.25,168.70,153.79,151.82,143.62,142.94,141.93,141.54,141.37,139.41,135.62,132.36,131.69,131.62,...

Embodiment 3

[0065] Embodiment 3 (synthesis of intermediate compound NA):

[0066] Such as Figure 4 As shown, the structure of the probe compound used in the examples is represented by the code NASe, and the dye precursor used in the synthesis of the probe compound is represented by the code NA.

[0067] 2.77g of 4-bromo-1,8-naphthoic anhydride, 5mL of 40% methylamine aqueous solution, 20mL of ethylene glycol monomethyl ether, reacted at 135°C for 18h under the protection of nitrogen, poured the reaction liquid into 200mL of water, dichloromethane Extract until the aqueous layer is colorless, combine the organic layers, and dry over anhydrous sodium sulfate. Purified by column separation to obtain 1.8 g of yellow powder.

[0068] 1 H NMR (400MHz, CDCl 3 ,ppm)δ8.45(d,1H,J=8.0Hz),8.30(d,1H,J=8.0Hz),8.25(d,1H,J=8.4Hz),7.92(t,1H,J=8.0 Hz),7.17(d,1H,J=8.4Hz),4.76(s,1H),3.62(s,3H),3.52(s,3H).

[0069] GC-MS(API-ES): m / z C 14 h 12 N 2 o 2 [M+H] + Calcd: 241.0899, found: 241.0932.

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Abstract

The invention discloses a fluorescence probe for detecting nitrosyl peroxide by utilizing amido bond rupture and application of the fluorescence probe and relates to fluorescence probes of which fluorescence wavelengths have obvious displacement in the presence of ONOO<->. The invention provides a fluorescence probe capable of selectively detecting ONOO<-> in cells. A BODIPY dye and a naphthalimide dye serve as fluorescence matrixes respectively, an o-benzene selenium (tellurium) benzamide structure is introduced to serve as an activity center reacting with ONOO<->, and the ONOO<-> is selectively detected by utilizing the process of rupturing the amido bond after oxidization of organic selenium (tellurium) ether. Moreover, the influence on the fluorescence wavelength of the whole compound serves as a detection signal for probe identification before and after the amido bond rupture, and the probe is used for detecting fluorescence imaging of the ONOO<-> in the cells.

Description

technical field [0001] The present invention relates to a class for detecting nitrosyl peroxide (ONOO - ) fluorescent probes, specifically, are a class of onoo - Fluorescent probes that undergo a significant change in fluorescence wavelength in the presence. Background technique [0002] Nitrosyl peroxide (ONOO - ) is a short-lived active species with strong oxidative properties, which is produced by the reaction of nitric oxide and superoxide negative ions in the human body. ONOO - It can act on harmful substances such as germs recognized by the immune system to inactivate them, thereby protecting the body from harmful substances and maintaining the normal functions of cells and tissues. However, under pathological conditions such as bacterial infection, a large number of ONOO - The generation of ischemia-reperfusion injury, rheumatoid arthritis, sepsis, stroke, multiple sclerosis, arteriosclerosis, enteritis, cancer and various neurodegenerative diseases. However, fo...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): G01N21/64C09K11/06A61K49/00C12Q1/02
Inventor 韩克利王炳帅于法标李鹏孙小飞
Owner ZHANGJIAGANG IND TECH RES INST CO LTD DALIAN INST OF CHEM PHYSICS CHINESE ACADEMY OF SCI
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