A cyanine-based organic compound and its application

A technology of organic compounds and cyanines, applied in the field of fluorescent probes, can solve the problems of damaging biological samples, high detection limits, and inability to detect cysteine, so as to improve detection accuracy and reduce interference

Active Publication Date: 2016-06-01
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 type of fluorescent probe responds slowly to cysteine ​​and has a high detection limit, so it cannot be used for rapid detection of cysteine.
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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  • A cyanine-based organic compound and its application
  • A cyanine-based organic compound and its application
  • A cyanine-based organic compound and its application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020] The structural formula of cyanine-based organic compounds is:

[0021]

[0022] The compound of formula I is combined with cysteine ​​in the water body to be measured, the simulated physiological environment, or the inside and outside of the organism to obtain the compound of the structure formula II, which leads to the change of the fluorescence intensity and wavelength of the compound of formula I, as well as the change of ultraviolet absorption, and then uses The compound of formula I can detect cysteine ​​qualitatively and quantitatively.

[0023]

[0024] Preparation of organic compound of formula I based on cyanine:

[0025] (1) Preparation of Compound 1

[0026] Dissolve 20-50mL of DMF in a graduated cylinder in 20-40mL of dichloromethane, pour it into a 250mL three-neck flask (stir with a magnet), and cool in an ice-water bath. Dissolve 20-40mL of phosphorus oxychloride into 20-40mL of dichloromethane, pour it into a constant pressure funnel, add dropwis...

Embodiment 2

[0043] The prepared formula one compound is used as a probe in the water system, simulated physiological environment and intracellular detection of cysteine, simulated physiological conditions, the following experiments are carried out under pH7-8 conditions (HEPES buffer solution, The concentration is 1-30mM), and the probe concentration is 0.5-10μM.

[0044] The pH effect of the probes prepared above on response to cysteine:

[0045] The pH gradient was controlled with HEPES buffer solution. Add 0.8-1mL of 1-10mM HEPES with different pH gradients into a 1.5ml colorimetric tube, then add 1-10μL of 100μM probe, shake the solution, and equilibrate at 25-40℃ for 10-30min, then add the above mixed working solution Fluorescence spectra were measured in fluorescent dishes. Fluorescence intensity changes with pH as figure 1 shown. Depend on figure 1 It is shown that the fluorescence intensity does not change significantly in the range of pH 4.0-8.0, that is, in the system of pH...

Embodiment 3

[0047] Probe selectivity for cysteine

[0048] pH was controlled with HEPES buffer solution. Take multiple 1.5ml colorimetric tubes, add 0.9-1mL 1-10mM HEPES, pH7-8 to the colorimetric tubes, then add 1-10μL 100μM probe, and then add the analytes such as figure 2 As shown, the working solution of the analyte is as follows: blank (no amino acid), cysteine, homocysteine, glutathione, tryptophan, glycine, threonine, proline, arginine , serine, methionine, valine, the final concentration of cysteine ​​and homocysteine ​​is 20 μM, and the final concentration of others is 2 mM. Shake the solution evenly, and after equilibrating at 25-40°C for 10-30 minutes, pour the working solution in each colorimetric tube into a fluorescent dish to measure the fluorescence spectrum. The selectivity of the probe for cysteine ​​as figure 2 shown. It can be seen from the figure that the probe has good selectivity to cysteine, and after interacting with cysteine, the fluorescence excited at 720...

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PUM

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Abstract

The invention relates to a fluorescence probe, and particularly relates to a cyanin-based organic compound and an application thereof. A structural formula of the cyanin-based organic compound is as shown in the formula I in the specification. According to the compound serving as a cysteine fluorescent probe, the corresponding fluorescence intensity obviously changes under the existence of cysteine, the compound can be applied to cysteine detection, the interference of an external detection condition can be greatly reduced, and the detection accuracy is improved. According to the compound serving as the cysteine fluorescent probe, ultraviolet absorption obviously changes under the existence of cysteine, and the compound serving as the cysteine fluorescent probe can be simultaneously used for detection by using an ultraviolet spectrophotometer and naked eyes. The compound can be applied to detection of cysteine levels inside and outside a cell as the fluorescent probe, and the compound has important biomedical significance on intensive study of dynamics mechanism of the processes of cysteine generation, transportation and accumulation inside a living body, particularly study of physiological action of cysteine in mitochondria.

Description

technical field [0001] The invention relates to a fluorescent probe, specifically a cyanine-based organic compound and its application. Background technique [0002] Cysteine ​​is a thiol-containing amino acid and one of the important physiologically active substances. As the substrate of reduced glutathione, it can increase the production of glutathione, thereby protecting the stability of the cell membrane and reducing the damage of myocardial cells in ischemia-reperfusion. L-cysteine ​​participates in the reduction of cells and the phospholipid metabolism in the liver, and has the functions of protecting liver cells and promoting liver function. In addition, L-cysteine ​​also stimulates the differentiation of pre-T lymphocytes into mature lymphocytes and increases the body's resistance to certain toxins. Changes in the content of cysteine ​​in organisms and metabolic disorders can lead to the occurrence of some diseases. By measuring the content of cysteine ​​in organis...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/12C09B23/10C09K11/06G01N21/64G01N33/52
CPCC07D209/12C09B23/107C09K11/06C09K2211/1007C09K2211/1029G01N21/6428
Inventor 陈令新殷堃于法标张卫卫陈浩刘萍
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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