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Organic compound based on cyanine and application thereof

A technology for organic compounds and organisms, applied in the field of near-infrared fluorescent probes, can solve the problems of slow Sec response, damage to biological samples, and large photobleaching effect of organisms, so as to reduce interference and improve detection accuracy.

Inactive Publication Date: 2018-03-02
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, this kind of fluorescent probe responds slowly to Sec and has a high detection limit, so it cannot be used for rapid detection of Sec.
Moreover, the excitation and emission wavelength of this probe is in the ultraviolet region, which cannot effectively avoid the interference of biological autofluorescence. At the same time, ultraviolet light has a great photobleaching effect on organisms and is easy to damage biological samples.

Method used

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

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Preparation of organic compound of formula I based on cyanine:

[0030] Under nitrogen protection, a commercial cyanine dye (60 mg, 0.1 mmol) was dissolved in a mixture of triethylamine (0.1 mL) and anhydrous dichloromethane (5 mL), and 2,4-dinitro Sulfonyl chloride (0.3 mmol), and the resulting mixture was stirred at 50°C for 6 hours. Then, with 10 mL saturated NaHCO 3 Aqueous solution quenched the reaction. Ethyl acetate (50 mL) was added and neutralized with hydrochloric acid (150 mL, 1M), then washed with brine. Stand still after washing, collect the organic layer and dry it with anhydrous magnesium sulfate, and concentrate in vacuo to obtain the green viscous solid of formula I, and then pass through the gradient eluent CH 2 Cl 2 and CH 3 OH (100:0-85:15, v / v) by chromatography on silica gel (200-300 mesh).

[0031] 1 H NMR (400MHz, CD 3 OD)δ(ppm):8.57(s,1H),7.87-7.79(m,16H),7.75-7.70(m,9H),7.50-7.37(m,4H),7.17-7.12(m,1H), 7.09-7.01(m,3H),6.79-6.75(d,1H),5...

Embodiment 2

[0034] The compound shown in the prepared formula I was used as a probe to detect Sec in 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, concentration 40 mM), the probe concentration was 15 μM.

[0035] The ultraviolet response of the compound shown in formula I prepared above to Sec:

[0036] pH was controlled with HEPES buffer solution. Add 15μM compound of formula Ⅰ to each 10mL colorimetric tube, then add 40mM HEPES with different pH, then add 15μM Sec, dilute to 10ml with ultrapure water, shake the solution well, and after equilibrating for 10min, add the above working solution into the colorimetric tube The UV absorption spectrum was measured in a dish. The changes of the ultraviolet absorption spectrum before and after the detection of Sec are as follows: figure 1 As shown, the compound represented by formula I can b...

Embodiment 3

[0039] The fluorescence response of the compound shown in formula I to Sec:

[0040] pH was controlled with HEPES buffer solution. Add 15μM compound formula 1 to each 10ml colorimetric tube, then add 40mM HEPES with different pH, then add 15μM Sec, dilute to 10ml with ultra-pure water, shake the solution, after 10min equilibration, add the above working solution into the fluorescent dish Measure the fluorescence spectrum. The changes of fluorescence spectrum before and after detecting Sec are as follows: figure 2 shown. The compound represented by formula I can be used to realize Sec detection in vivo.

[0041] Depend on figure 2 Indicates the change of fluorescence intensity of the system with the change of Sec concentration, indicating that with the increase of Sec concentration, the fluorescence intensity of the system in the 630-830nm band is obviously enhanced, and the fluorescence intensity of the 780-810nm band is obviously weakened.

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Abstract

The invention relates to a near-infrared fluorescent probe for detecting selenocysteine (Sec), and concretely relates to an organic compound based on cyanine and an application thereof. A structural formula of the organic compound based on the cyanine is shown as a formula I, the structural formula of the compound is shown as the formula I in the specification, and the compound is taken as a fluorescent probe of Sec. The Sec fluorescent probe compound can generate obvious displacement of corresponding fluorescence wavelength under existence of Sec, which can be used for Sec detection, interference by external detection condition is greatly reduced, and detection precision is increased. Under existence of Sec, according to the Sec fluorescent probe compound, the ultraviolet absorption generates obvious change, and an ultraviolet spectrophotometer and naked eyes are simultaneously used for detection. The compound as the fluorescence probe can be used for detecting the Sec level inside and outside cells, and has important biomedical meaning on a deep research a dynamics mechanism of generation, conveying and accumulation of Sec in organism, especially the research of physiological effect of Sec in mitochondria.

Description

technical field [0001] The invention relates to a near-infrared fluorescent probe for detecting selenocysteine ​​(Sec), in particular to a cyanine-based organic compound and its application. Background technique [0002] Selenocysteine ​​(Sec) is one of the most basic active selenium species in cells and is an active component of selenoproteins. Sec is also an important cell signaling molecule involved in a variety of physiological and pathological processes, including innate immunity and metabolic homeostasis. Changes in the content of Sec in organisms and metabolic disorders can lead to some diseases. For example, the deficiency of Sec leads to poor immune function and high risk of cancer. However, excessive supplementation of Sec resulted in increased risk of type 2 diabetes and acute or chronic Se toxicity. By measuring the content of Sec in organisms, the diagnosis of some metabolic diseases can be realized. Therefore, it is of great significance to realize rapid an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/6558C09K11/06G01N21/64
CPCC07F9/65583C09K11/06C09K2211/1007C09K2211/1029C09K2211/1059G01N21/6428G01N21/6458
Inventor 陈令新韩潇玥于法标王蕊
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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