Cyanine-based organic compound, intermediate and application thereof

An organic compound and compound technology, applied in the field of fluorescent probes, can solve the problems of in situ and real-time detection of organisms, and achieve the effects of short response time, reduced interference and high sensitivity

Inactive Publication Date: 2018-06-08
YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, most of these methods require sample pretreatment and large detecti...

Method used

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  • Cyanine-based organic compound, intermediate and application thereof
  • Cyanine-based organic compound, intermediate and application thereof
  • Cyanine-based organic compound, intermediate and application thereof

Examples

Experimental program
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Embodiment 1

[0033] 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 p-methylaminonitrobenzene (0.06 g, 0.4 mmol) in a 20 ml anhydrous DMF round-bottomed flask, add 0.0167 g of sodium hydride at room temperature, and stir for 15 minutes under the protection of argon. Then, cyanine fluorophore (0.255 g, 0.4 mmol) was added to the above solution and reacted at room temperature for 1 hour. Wash with excess saturated potassium iodide solution, extract with dichloromethane after washing, and rotary evaporate to obtain crude product. The crude product was purified by column chromatography, and the eluent was selected as dichloromethane:methanol=1:4 to obtain compound II...

Embodiment 2

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

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

[0044] Add different concentrations of O to each 10ml colorimetric tube 2 ·- (0-10 μM), the volume was adjusted to 10 ml with 10 mM HEPES (pH 7.4), and finally the compound of formula I was added (final concentration 10 μM). Shake the solution well, and after equilibrating at 25°C for 15 minutes, pipette 1ml of the solution into a fluorescent dish to measure the fluorescence spectrum. Fluorescence spectra were measured at 700-...

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Abstract

The invention relates to a fluorescence probe, in particular to a cyanine-based organic compound, an intermediate and application thereof. The structural formula of the cyanine-based organic compoundis as shown in FORMULA I. The compound is used as the fluorescence probe for detecting O2.- and H2Sn. According to the fluorescence probe disclosed by the invention, under the existence of O2.- and H2Sn, a corresponding fluorescence emission wavelength and corresponding intensity changes, so as to detect O2.- and H2Sn; furthermore, the interference of external detection conditions can be greatly reduced, and the detection precision is improved. The compound used as the fluorescence probe can be used for detecting O2.- and H2Sn levels inside and outside cells and transducing cell signals for deeply researching O2.- and H2Sn, and particularly has an important biomedical significance in researches on physiological and pathological effects of H2Sn in living cells.

Description

technical field [0001] The invention relates to a fluorescent probe, specifically a cyanine-based organic compound, an intermediate and its application. Background technique [0002] There are a variety of endogenous active species in organisms, including active oxygen species, active sulfur species, active nitrogen species, etc. Superoxide anion (O 2 ·- ) is the most important kind of reactive oxygen species present in cells, which plays an important role in different physiological and pathological processes. Reactive sulfur species (Reactive Sulfur Species, RSS) is a general term for a class of sulfur-containing molecules in organisms, and is one of the most important endogenous active species in organisms. Reactive sulfur species play crucial roles in regulating redox homeostasis in living organisms as well as other processes such as health and disease. Sulfane sulfur is a kind of active sulfur species, which refers to the form of 6 valence electrons (S 0 ) ionized s...

Claims

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Application Information

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IPC IPC(8): C07D209/14C09K11/06C09B23/06G01N21/64
CPCC07D209/14C09B23/0091C09B23/06C09K11/06C09K2211/1007C09K2211/1029G01N21/643G01N21/6486
Inventor 陈令新高敏王猛于法标
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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