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Fluorophore derivative for detecting superoxide anions and hydrogen polysulfide and application thereof

A technology of superoxide anion and hydrogen polysulfide, applied in the field of fluorescent probes, to improve detection accuracy and reduce interference

Active Publication Date: 2015-10-28
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, to what extent and by what mechanism is hydrogen polysulfide in cellular mitochondria 2 ·- Regulation and opening of signal transduction pathways still need to be further clarified

Method used

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  • Fluorophore derivative for detecting superoxide anions and hydrogen polysulfide and application thereof
  • Fluorophore derivative for detecting superoxide anions and hydrogen polysulfide and application thereof
  • Fluorophore derivative for detecting superoxide anions and hydrogen polysulfide and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0051] Example 1. Preparation of cyanine compounds:

specific Embodiment

[0052] The cyanine fluorophore shown in the general formula I is from a commercial product, and then different positioning groups are modified at the corresponding positions of the fluorophore. Finally, the corresponding cyanine compounds are obtained by reacting the fluorophore of the modified positioning group and the substituted benzoic acid in dichloromethane solvent. Specific examples are as follows:

[0053] To prepare a compound of formula I:

[0054] m-nitrophenol (0.696 g, 5.00 mmol) was dissolved in a 30 ml round-bottomed flask of anhydrous DMF, 0.208 g (60% in oil) NaH was added at room temperature, and stirred for 15 min under argon protection. The heptacyanine fluorophore (0.5 g, 0.83 mmol) was added to the above solution as described above, and the reaction was stirred at room temperature for 24 h, washed with saturated potassium iodide solution, extracted with dichloromethane, and rotary evaporated. The crude product was purified by column chromatography using...

Embodiment 2

[0064] The compound of formula 1 prepared was used as a probe to detect superoxide anion and hydrogen polysulfide in a water system, simulated physiological environment and cells, and simulated physiological conditions. The following experiments were all carried out under the condition of pH=7.4 (HEPES buffer solution at a concentration of 40 mM) and a probe concentration of 10 μM.

[0065] The response of the compound formula obtained above to a pair of superoxide anions:

[0066] pH was controlled with HEPES buffer solution. Add 10μM compound of formula 1 to a 10ml colorimetric tube, then add 40mM HEPES, then add 10μM superoxide anion, make up to 10ml with ultrapure water, shake the solution, and after equilibrating for 2min, add the above working solution to a fluorescent dish to measure the fluorescence spectrum. The change of fluorescence spectrum before and after detection of superoxide anion is as follows: figure 1 shown. To evaluate compounds of formula I for O 2 ...

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Abstract

The invention relates to a fluorescent probe used for conducting linkage detection on superoxide anions (O2.-) and hydrogen polysulfide, in particular to a fluorophore derivative for detecting superoxide anions and hydrogen polysulfide and application thereof. The fluorophore derivative is shown in the general formula I. In the general formula I, R1 represents a C1-22 alkyl group or a halogenated benzyl group or C1-C12 organic acid ester chains; R2 represents hydrogen, a sulfonic group or an amino group or a carboxyl group or a nitro group or halogen; X (a positioning functional group) represents -OH, a butyl triphenyl phosphonium group, an N-propyl morpholino group, a biotin group, a folic acid group, a glycosyl chain group, benzyl chloride or a C1-22 alkyl group; Y1 represents N, O or S; Y2 represents N, O or S. In the presence of the superoxide anions (O2.-) and the hydrogen polysulfide, corresponding fluorescence emission wavelength and intensity change, and the fluorescent probe can be used for detecting the superoxide anions (O2.-) and the hydrogen polysulfide in organisms, interference of external detection conditions can be greatly reduced, the detection signal to noise ratio is high, and sensitivity and selectivity are good. The fluorophore derivative has important significance in biomedicine.

Description

technical field [0001] The present invention relates to be used for linkage detection superoxide anion (O 2 ·- ) and a fluorescent probe of hydrogen polysulfide, specifically a fluorophore derivative and application thereof for measuring superoxide anion and hydrogen polysulfide. Background technique [0002] Hydrogen sulfide is an endogenous gas signal molecule that has been studied more in recent years, and it plays a vital role in regulating the cardiovascular system and nervous system of the living body. However, some studies have found that hydrogen sulfide is actually the release of polyhydrogen sulfide in cells, and what actually works in cells is hydrogen polysulfide, which can act as an antioxidant in cell damage and oxidative stress. Hydrogen polysulfide, H 2 S and other polysulfides can produce a series of physiological reactions to maintain the health of cells. We also found that the production of hydrogen polysulfide is dependent on O 2 ·- Stimulation of c...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D209/14C07D209/12G01N21/64
Inventor 陈令新于法标黄严付龙文
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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