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Organic compound based on cyanine and application

An organic compound and compound technology, applied in the field of fluorescent probes, can solve problems such as being unsuitable for real-time detection, and achieve the effect of reducing interference and improving detection accuracy

Inactive Publication Date: 2018-04-24
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

However, these methods require sample pretreatment, such as cell disruption, tissue homogenization, etc., and require large-scale detection equipment, so they are not suitable for in situ and real-time detection in vivo

Method used

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  • Organic compound based on cyanine and application
  • Organic compound based on cyanine and application
  • Organic compound based on cyanine and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1. Preparation of cyanine-based organic compounds:

specific Embodiment

[0034] The present invention is a cyanine-based organic compound. The cyanine fluorophore shown in the compound of formula I is commercially available, and then different detection groups are modified at the designated positions of the fluorophore to obtain the corresponding cyanine compound. Specific examples are as follows:

[0035] (1) Preparation of compound II

[0036] Dissolve 1-(4-nitrophenyl)ethan-1-ol (0.067g, 0.4mmol) in a 20ml round-bottomed flask of anhydrous DMF, add 0.0167g of sodium hydride at room temperature, and Stir for 15 minutes. Then cyanine fluorophore (0.255g, 0.4mmol) was added to the above solution, reacted at room temperature for 1 hour, washed with excess saturated potassium iodide solution, extracted with dichloromethane after washing, and rotary evaporated to obtain a crude product. The crude product was purified by column chromatography using dichloromethane and methanol (6:1 / v / v) as the eluent to obtain 0.148 g (0.23 mmol) of compound II as a ...

Embodiment 2

[0042] The prepared compound of formula I is used as a probe in water system, simulated physiological environment and intracellular for O 2 ·- and H 2 S n The detection of each of the following experiments under simulated physiological conditions was carried out under the condition of pH 7.4 (HEPES buffer solution, the concentration was 10 mM), and the probe concentration was 10 μM. For each experiment in the following cells, the probe concentration was 1 μM.

[0043] Above-mentioned preparation gained formula I compound is as probe pair O 2 ·- the response to:

[0044] Add 1 mL of different concentrations of O 2 ·- into a 10mL colorimetric tube, and then diluted to 10.0mL with 10mM HEPES buffer (pH 7.4). Compound of formula I (10 [mu]M) was added last. After the mixed solution was equilibrated for 10 minutes, absorb 1mL of the working solution in each colorimetric tube and pour it into a fluorescent dish to measure the fluorescence spectrum, and measure the fluoresce...

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PUM

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Abstract

The invention relates to a fluorescent probe, in particular to an organic compound based on cyanine and application of the organic compound. The organic compound based on the cyanine is as shown in structural formula I, and the cyanine compound is used as a fluorescent probe for detecting O2<.> and H2Sn. According to the fluorescent probe, in the presence of O2<.> and H2Sn, the corresponding fluorescence transmission wavelength and intensity are apparently changed, and the fluorescent probe can be used for detecting O2<.> and H2Sn. The compound is high in sensitivity and good in selectivity. The compound serving as fluorescent probe can be used for detecting O2<.> and H2Sn in a complex biological sample, and has important biological significance for researching the cell signal transductionof O2<.> and H2Sn, further researching the metabolism and effect of biological active substances in cells and discovering the effect of O2<.> and H2Sn in health and disease. (The formula I is shown in description).

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a cyanine-based organic compound and its application. Background technique [0002] There are a variety of endogenous active species in cells, including active oxygen species, active sulfur species, and active nitrogen species. They all have special physiological functions and play a very important role in various physiological activities of living organisms. Hydrogen sulfide is an active sulfur species, and as an endogenous signal molecule, it mainly plays a role in regulating the cardiovascular and cerebrovascular systems and the nervous system, and balancing the redox homeostasis of the body. At present, studies have shown that hydrogen polysulfide is the real signal molecule, and hydrogen sulfide is only a release product after hydrogen polysulfide plays a physiological role. Hydrogen polysulfide is more reductive than hydrogen sulfide, so when cells are oxidatively damaged, it can pl...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/12C09K11/06G01N21/64
CPCC07D209/12C09K11/06C09K2211/1007C09K2211/1029G01N21/643
Inventor 陈令新高敏于法标
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI