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A kind of organic compound and application thereof based on cyanine

A technology of organic compounds and free radicals, applied in the field of near-infrared fluorescent probes, can solve problems such as damage to biological samples, slow response, inability to effectively avoid biological autofluorescence interference, etc., to reduce interference and improve detection accuracy.

Active Publication Date: 2019-02-19
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 fluorescent probes are 2 ·- Slow response, high detection limit, cannot be used for fast detection of O 2 ·-
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 kind of organic compound and application thereof based on cyanine
  • A kind of organic compound and application thereof based on cyanine
  • A kind of organic compound and application thereof based on cyanine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] The structural formula of cyanine-based organic compounds is:

[0032]

[0033] The compound of formula I and the O in the water body to be determined, the simulated physiological environment or the organism 2 ·- Combining, the compound of structural formula II structure is obtained, which leads to the change of the fluorescence intensity and wavelength of the compound of formula I, and the change of ultraviolet absorption, and then utilizes the compound of formula I in O 2 ·- The compound of formula II can be formed under O 2 ·- Perform qualitative and quantitative testing.

[0034]

[0035] Preparation of organic compound of formula I based on cyanine:

[0036] (1) Preparation of Compound 1

[0037] Under nitrogen protection, (4-bromobutyl)triphenylphosphine bromide (14.35g, 30mmol) and sodium azide (3.9g, 60mmol) were dissolved in 50mL DMF. Stir overnight at 90°C. The color of the solution ranges from colorless to light yellow to red. The reaction flas...

Embodiment 2

[0049] The compound shown in the prepared formula I is used as a probe in water system, simulated physiological environment and intracellular for O 2 ·- The detection of simulating physiological conditions, the following experiments were all carried out under the condition of pH=7.4 (HEPES buffer solution, the concentration was 40mM), and the probe concentration was 10μM.

[0050] The compound shown in the above-mentioned preparation gained formula I to O 2 ·- UV response of:

[0051] pH was controlled with HEPES buffer solution. Add 10μM formula I compound to each 10mL colorimetric tube, then add 40mM HEPES with different pH, and then add 10μM O 2 ·- , dilute to 10ml with ultrapure water, shake the solution evenly, and after equilibrating for 10 minutes, add the above-mentioned working solution into a cuvette to measure the ultraviolet absorption spectrum. The UV absorption spectrum was used to detect O 2 ·- before and after changes such as figure 1 As shown, the com...

Embodiment 3

[0054] The compound shown in formula I is pair O 2 ·- Fluorescent response of:

[0055] pH was controlled with HEPES buffer solution. Add 10μM compound formula 1 to each 10ml colorimetric tube, then add 40mM HEPES of different pH, and then add 10μM O 2 ·- , dilute to 10ml with ultrapure water, shake the solution evenly, and after equilibrating for 10 minutes, add the above working solution into a fluorescent dish to measure the fluorescence spectrum. Fluorescence spectroscopy in the detection of O 2 - before and after changes such as figure 2 shown. The compound shown in formula I can be used to realize O in vivo 2 - detection.

[0056] Depend on figure 2 means with O 2 ·- The change of the fluorescence intensity of the system with the change of concentration indicates that with the change of O 2 - With the increase of the concentration, the fluorescence intensity in the 630-830nm band of the system is obviously enhanced, and the fluorescence intensity in the ...

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Abstract

The invention relates to a near-infrared fluorescent probe for detecting a superoxide anion free radical (O2<.>), in particular to a cyanine-based organic compound and application thereof. The compound is shown as a structural formula I and is taken as the O2<.> fluorescent probe. The compound used as the O2<.> fluorescent probe has the benefits that under the existence of O2<.>, a corresponding fluorescence wavelength obviously displaces, and the compound can be used for O2<.> detection and can greatly reduce the interference from external detection conditions, so that the detection precision is improved; under the existence of the O2<.>, the ultraviolet absorption is also changed obviously, and an ultraviolet spectrophotometer and naked eyes can be simultaneously used for detection; the compound can be used for detection on intracellular and extracellular O2<.> levels and has important biomedical significances in deeply studying a dynamic mechanism on production, conveyance and accumulation of the O2<.> in organisms and particularly in studying a physiological role of the O2<.> in mitochondria.

Description

technical field [0001] The present invention relates to detecting superoxide anion free radical (O 2 ·- ), specifically a cyanine-based organic compound and its application. Background technique [0002] superoxide anion radical (O 2 ·- ) is an important active oxygen free radical in cells, mainly produced in mitochondria. o 2 ·- It is an important cell signaling molecule involved in various physiological and pathological processes, including innate immunity and metabolic homeostasis. O in vivo 2 ·- Changes in the content and metabolic disorders can lead to the occurrence of some diseases. exception generation O 2 ·- May cause oxidative damage to biomolecules. Its secondary products, such as hydrogen peroxide, hydroxyl radicals, peroxynitrosyl ions, and hypochlorous acid are also involved in signal transduction and various pathological processes, including pulmonary arterial hypertension, cardiomyopathy, atherosclerosis sclerosis, ischemia-reperfusion injury, di...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F9/6558C09K11/06G01N21/33G01N21/64
CPCC07F9/65583C09K11/06C09K2211/1029C09K2211/1059C09K2211/1096G01N21/33G01N21/6428
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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