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Application of morpholine-pyridine-merocyanine derivative as hydrogen sulfide fluorescent probe

A technology of fluorescent probes and derivatives, applied in fluorescence/phosphorescence, luminescent materials, organic chemistry, etc., can solve the problems of limited practical application, not many hydrogen sulfide fluorescent probes, and inability to recognize hydrogen sulfide, and achieve wide application value , the effect of easy availability of raw materials, simple synthesis and post-processing methods

Pending Publication Date: 2021-06-25
HENAN POLYTECHNIC UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of the existing fluorescent probes for hydrogen sulfide require organic co-solvents (>10%), and cannot recognize hydrogen sulfide in pure aqueous phase, which limits its further practical application.
Moreover, there are not many reports on lysosome-targeted hydrogen sulfide fluorescent probes today.

Method used

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  • Application of morpholine-pyridine-merocyanine derivative as hydrogen sulfide fluorescent probe
  • Application of morpholine-pyridine-merocyanine derivative as hydrogen sulfide fluorescent probe
  • Application of morpholine-pyridine-merocyanine derivative as hydrogen sulfide fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation method of the morpholine-pyridine-merocyanine derivative fluorescent probe of this embodiment is as follows:

[0030]4.41 g, 4-[2-(6-hydroxy-2-naphthyl)-vinyl]-1-[2-(4-morpholinoethyl)]-pyridine bromide (10 mmol) and 2.23 g 2,4-Dinitrofluorobenzene (12 mmol) was dissolved in 0.2L of acetonitrile, then 2.77 g of anhydrous potassium carbonate (20 mmol) was added, and the reaction was stirred at room temperature for 3-4 h. After the reaction was completed, the reaction liquid was rotary evaporated. The obtained solid was washed with ethyl acetate, and then recrystallized with absolute ethanol to obtain the fluorescent probe of the morpholine-pyridine-merocyanine derivative. The yield of the target product was 67%.

[0031] Adopt nuclear magnetic resonance instrument to carry out nuclear magnetic resonance analysis to the morpholine-pyridine-merocyanine derivative that makes, the result is as follows:

[0032] 1 H NMR (400 MHz, D 2 O), δ (ppm): 8.97 (s, ...

Embodiment 2

[0036] Morpholine-pyridine-merocyanine derivatives on HS − Determination of optical properties of

[0037] The morpholine-pyridine-merocyanine derivatives prepared in the above example 1 were used as fluorescent probes in HEPES buffer solution (0.05 mol / L, pH=5) to prepare a molar concentration of 1×10 -5 mol / L solution, respectively, at a molar concentration of 3×10 -5 mol / L anion (OAc − 、Br − , Cl − , ClO − , I − , F − , PPi, H 2 PO 4 − 、HPO 4 − 、PO 4 3− 、HS − 、HSO 3 − 、HSO 4 − , SO 4 2 − , S 2 o 3 2− , S 2− and SO 3 2− ) or amino acid (Ala, Hcy, Cys) solution, add the same amount of the above fluorescent probe solution, and use the fluorescence spectrometer to analyze (excitation wavelength is 370 nm), the obtained fluorescence spectrum is shown in Figure 4 . pass Figure 4 It can be seen that the morpholine-pyridine-merocyanine derivatives prepared by the present invention are only suitable for HS as probes − With obvious response, the cha...

Embodiment 3

[0040] Fluorescent Probes of Morpholine-Pyridine-Merocyanine Derivatives in Intracellular HS − detection experiment

[0041] 1 x 10 for HeLa cells -5 mol / L of the morpholine-pyridine-merocyanine derivative fluorescent probe prepared in Example 1 above and the commercial lysosome localization dye LysoTracker Blue were co-incubated at 37°C for 30 minutes to obtain the fluorescence imaging image of HeLa cells , specifically as Figure 6 As shown, where: where: a is the fluorescence imaging image of the blue channel; b is the fluorescence imaging image of the green channel; c is the superimposed picture of the blue channel and the green channel; d is the intensity correlation map of the blue channel and the green channel; f Overlay of blue and green channel intensity distributions across a single HeLa region. From Figure 6 It can be seen that the fluorescence of the green channel of the probe in HeLa cells is basically consistent with the fluorescence of the blue channel of ...

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Abstract

The invention provides an application of a morpholine-pyridine-merocyanine derivative fluorescent probe as a hydrogen sulfide fluorescent probe. The chemical structural formula of a morpholine-pyridine-merocyanine derivative is shown in the specification. The morpholine-pyridine-merocyanine derivative fluorescent probe disclosed by the invention can selectively act with hydrogen sulfide under physiological conditions; the fluorescent color of a solution is changed from green to orange yellow, a typical ratio fluorescence signal is presented, and the fluorescent probe is particularly applied to convenient detection of hydrogen sulfide in cytolysosome as a fluorescent probe.

Description

technical field [0001] The invention belongs to the field of organic synthesis, and specifically relates to morpholine-pyridine-merocyanine derivatives and their preparation methods and applications. Background technique [0002] Hydrogen sulfide (H 2 S) is a well-known colorless, highly toxic acid gas, H 2 S is both a reactive sulfur (RSS) and a reducing agent. Therefore, the H in the organism 2 The imbalance of S level will cause damage to the body, causing Alzheimer's disease, gastric mucosal injury, stroke, diabetes, Down's syndrome, liver cirrhosis and cancer and other diseases. In addition, H 2 S also plays an important role in the regulation of the nervous, respiratory, gastrointestinal and endocrine systems, and even low concentrations of exogenous hydrogen sulfide can affect the eyes as well as the respiratory and central nervous systems. Therefore, it is possible to accurately, rapidly and reliably detect H 2 S concentration variation is very necessary. [0...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09K11/06G01N21/64C07D213/30
CPCC09K11/06C07D213/30G01N21/6428G01N21/643C09K2211/1029C09K2211/1044C09K2211/1007C09K2211/1011C09K2211/1014
Inventor 韩学锋吴伟娜郭芳芳宋雨飞刘爽爽王元
Owner HENAN POLYTECHNIC UNIV
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