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Cyanine compound and application thereof

A compound and cyanine technology applied in the field of fluorescent probes to improve detection accuracy and reduce interference

Active Publication Date: 2015-11-04
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 sulfane sulfur in the mitochondria of cells is regulated by O 2 - Regulation and opening of signal transduction pathways still need to be further clarified

Method used

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  • Cyanine compound and application thereof
  • Cyanine compound and application thereof
  • Cyanine compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1. Preparation of cyanine compound:

specific Embodiment

[0051] The cyanine-based fluorophore shown in the general formula I comes from commercially available products, and then different positioning groups are respectively modified on the corresponding positions of the fluorophore. Finally, the corresponding cyanine compound is obtained by reacting the fluorophore modifying the positioning group and the substituted benzoic acid in dichloromethane solvent. Specific examples are as follows:

[0052] Preparation of a compound of formula:

[0053] Under argon protection, 2,2'-dithiodibenzoic acid (1.53g, 5mmol) and oxalyl chloride (2.96g, 23.3mmol) were reacted in 100ml of dichloromethane for 3 hours in an ice-water bath, and the solvent was evaporated to dryness stand-by. Under the ice-water bath, the cyanine fluorophore (500mg, 1.08mmol) was dissolved in dichloromethane, then 2,2'-dithiodibenzoyl chloride was added dropwise, reacted under the ice bath for 1 hour, and then washed with water until neutral. Then dichloromethane (100m...

Embodiment 2

[0067] The prepared compound of formula one is used as a probe in the water system, simulated physiological environment and intracellular detection of sulfane sulfur, simulated physiological conditions, the following experiments are all carried out under the condition of pH=7.4 (HEPES buffer solution, concentration 40 mM), the probe concentration was 2 μM.

[0068] The response of the above-mentioned prepared compound formula to superoxide anion:

[0069] pH was controlled with HEPES buffer solution. Add 2μM compound formula 1 to a 10ml colorimetric tube, then add 40mM HEPES, then add 5μM superoxide anion, dilute the volume to 10ml with ultrapure water, shake the solution, and equilibrate for 10min, then add the above working solution into a fluorescent dish to measure the fluorescence spectrum. The changes of the fluorescence spectrum before and after the detection of superoxide anion are as follows: figure 1 shown. The compound can be used to realize the detection of sup...

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PUM

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Abstract

The invention relates to a fluorescent probe for detecting superoxide anions (O2-) and sulfane sulfur, in particular to a cyanine compound and application thereof. The cyanine compound is as shown in general formula I and serves as the fluorescent probe for hydrogen sulfide. In the presence of the superoxide anions (O2-) and sulfane sulfur, the corresponding fluorescence-emission wavelength and strength of the fluorescent probe vary, and the fluorescent probe can be used for detecting the superoxide anions (O2-) and sulfane sulfur, can greatly reduce the interference of external detection conditions and is high in detection signal-to-noise ratio and good in sensitivity and selectivity. The compound serving as the fluorescent probe can be used for linkage detection of the level of the superoxide anions (O2-) and sulfane sulfur in complex biological samples and is of great biomedicine significance for studying cellular signal transduction of the superoxide anions (O2-) and sulfane sulfur. Formula I.

Description

technical field [0001] The present invention relates to be used for detecting superoxide anion (O 2 - ) and a fluorescent probe of sulfane sulfur, specifically a kind of cyanine compound and its application. Background technique [0002] The high concentration of H in the organism 2 S inhibits mitochondrial respiration, whereas sulfane sulfur has very low cytotoxicity. In mouse tissues, high rates of H 2 The process of S generation and degradation depends on the catabolism of reactive oxygen species in mitochondria to balance. O produced by mitochondria 2 - H can be 2 S is rapidly converted to sulfane sulfur and stored stably until released in response to physiological signals. The content of sulfane sulfur in mitochondria accounts for more than 60% of the total content of cells. There is evidence that controlled O 2 - The resulting process can activate the reversible interconversion state of hydrogen sulfide and sulfane sulfur, thereby mediating cell signal trans...

Claims

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Application Information

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IPC IPC(8): C07D209/12C07F9/572C09B23/10C09K11/06G01N21/64
CPCC07D209/12C07F9/572C09B23/10C09K11/06C09K2211/1033C09K2211/104G01N21/64
Inventor 于法标陈令新陈浩高敏景晓彤
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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