Cyanine-based organic compounds and intermediates thereof, and application of cyanine-based organic compounds and intermediates thereof

A technology of organic compounds and fluorescent probes, applied in the field of fluorescent probes, can solve the problems of complex operation methods and large instruments, and achieve the effects of wide application range, reduced interference, and short response time

Active Publication Date: 2017-11-28
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, most of these methods require pretreatment of samples, complicated operations and large instruments.

Method used

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  • Cyanine-based organic compounds and intermediates thereof, and application of cyanine-based organic compounds and intermediates thereof
  • Cyanine-based organic compounds and intermediates thereof, and application of cyanine-based organic compounds and intermediates thereof
  • Cyanine-based organic compounds and intermediates thereof, and application of cyanine-based organic compounds and intermediates thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1. Preparation of cyanine-based organic compounds:

specific Embodiment

[0030] The cyanine fluorophore shown in compound I is commercially available, and then different detection groups are modified at the corresponding positions of the fluorophore to obtain the corresponding cyanine compound. Specific examples are as follows:

[0031] (1) Preparation of compound II

[0032] Cyanine fluorophore (0.255g, 0.4mmol) was dissolved in 20ml of methanol, Na 2 S (0.03g, 0.4mmol) was dissolved in 1ml of water, and at room temperature, 1ml of Na 2S solution was added dropwise to a round bottom flask, and refluxed for 30 min under the protection of argon. Wash with excess saturated potassium iodide solution, then extract with dichloromethane, and spin evaporate to obtain a crude product. The crude product was purified by column chromatography using ethyl acetate and methanol (6:1 / v / v) as the eluent to obtain 0.146 g (0.229 mmol) of compound II as a green solid with a yield of 57.3%.

[0033] Compound II: 1 H NMR (500MHz, CDCl 3 -D 1 )δ(ppm):0.937-0.982...

Embodiment 2

[0040] The prepared compound I was used as a probe in water system, simulated physiological environment and intracellular for O 2 ·- and Hg 2+ 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.

[0041] The compound I prepared above is used as a probe pair O 2 ·- the response to:

[0042] pH was controlled with HEPES buffer solution. Add 10 μM compound I to each 10ml colorimetric tube, and then add 0-10 μM different concentrations of O 2 ·- , then dilute to 10ml with 10mM HEPES, shake the solution evenly, and after equilibrating for 10min, pour the working solution in each colorimetric tube into a fluorescent dish to measure the fluorescence spectrum. Fluorescence intensity was measured at 755-845nm (see figure 1 ),Such as figure 1 shown. The above compound I can be used to realize the O in vivo 2 ·- detection,...

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Abstract

The invention relates to fluorescent probes used for detecting superoxide anions (O2.<->) and bivalent mercury ions (Hg<2+>), in particular to fluorophore derivatives and application thereof. For example, the cyanine fluorophore derivatives have a chemical structure as shown in a structural formula I, and the cyanine compounds are taken as fluorescent probes for the O2.<-> and the Hg<2+>. The fluorescent probes provided by the invention have the corresponding fluorescence emission wavelength and intensity change in the presence of the O2.<-> and the Hg<2+>, can be used for detecting the O2.<-> and the Hg<2+>, can greatly reduce the interference of external detection conditions, and is high in detection signal-to-noise ratio and good in sensitivity and selectivity. As the fluorescent probes, the compounds can be used for detecting the levels of the O2.<-> and the Hg<2+> in complex biological samples and have important biomedical significance for the study of cell signal transduction of the O2.<-> and the Hg<2+>. The structural formula I is described in the description.

Description

technical field [0001] The invention relates to a fluorescent probe, in particular to a cyanine-based organic compound, an intermediate and an application thereof. Background technique [0002] Mercury is ubiquitous in nature, mainly in three forms: elemental mercury, inorganic mercury, and organic mercury compounds. When inorganic mercury enters the body, it becomes Hg 2+ , which accumulates the most in the kidneys, up to 90%. Therefore, when heavy metals enter the human body, the kidney is the main accumulation organ, and the structure and function of the kidney are also damaged, thus showing some clinical signs of mercury poisoning-related nephropathy. The pathogenesis of mercury poisoning is complex, for example, mercury can combine with sulfhydryl groups on the cell membrane, causing changes in membrane permeability; mercury can combine with metallothionein in the human body, and can replace metal molecules in certain enzymes to change its activity; Intoxication can ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/10C09K11/06G01N21/64
CPCC07D209/10C09K11/06C09K2211/1029G01N21/6428G01N21/6486
Inventor 陈令新王悦于法标高敏
Owner YANTAI INST OF COASTAL ZONE RES CHINESE ACAD OF SCI
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