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A Class of Dual Responsive Fluorescent Dye Molecules

A fluorescent dye, dual-response technology, applied in the field of organic fluorescent dyes, can solve problems such as the inability to achieve dual-line detection of NTR and NADH

Active Publication Date: 2022-06-28
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In recent years, many small molecule fluorescent probes for the detection of NTR and NADH have been developed, but none of them can achieve dual-line detection of NTR and NADH

Method used

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  • A Class of Dual Responsive Fluorescent Dye Molecules
  • A Class of Dual Responsive Fluorescent Dye Molecules
  • A Class of Dual Responsive Fluorescent Dye Molecules

Examples

Experimental program
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preparation example Construction

[0052] On the other hand, the present invention also describes the preparation method of the above-mentioned fluorescent dye, comprising the following steps:

[0053] In the presence of a catalyst, compounds a and b are reacted in a molar ratio of 1:1-1:10 to prepare a compound of formula I;

[0054]

[0055] The reaction temperature is 0-200 ° C, the reaction time is 1-32 hours, and the reaction solvent is selected from ethanol, glacial acetic acid, ethylene glycol monomethyl ether, methanol, dichloromethane, acetone, glycerol, ethyl acetate, N-N- 2 methylformamide or a mixture thereof; the reaction catalyst is selected from piperazine, piperidine, potassium hydroxide, sodium hydroxide, pyridine, sodium methoxide, methanol-potassium hydroxide, potassium carbonate, triethylamine and 4-dimethylamino Pyridine.

[0056] The molar ratio of catalyst to reactant is 1:0.05-1:0.2.

[0057] In the specific embodiment, the reaction temperature of the step is preferably 30-180°C, mo...

Embodiment 1

[0067] The synthetic route of dye compound 1-1 is as follows:

[0068]

[0069] (1) Synthesis of Dye Compound 1-1

[0070] With 5mmol of a-1 (synthetic method reference: Kawaguchi, Hirobumi; Hamasaki, Ichiya; Inagaki, Yoshio.Stilbene derivative and electrophotographic photoreceptorusing it May6,1998JP 10114728) and 6.25mmol of b-1 (synthetic method reference: Venis, Michael A. and Thomas, Emrys W. Synthesis and auxin activity of 5-substituted 1-naphthaleneacetic acids. Phytochemistry, 1990, 29, 381-383) was added to a round bottom flask containing 6 mL of absolute ethanol and piperidine was added for catalysis. The reaction was heated to 100°C for 3 hours, then heated to 120°C for 5 hours, and then stopped. The solvent was removed by spin drying in vacuo, and treated with column chromatography (petroleum ether: dichloromethane, 1:1, v / v) to obtain orange-red compound 1-1 in a yield of 50%.

[0071] (2) Characterization of Dye Compound 1-1

[0072] 1 H NMR(600MHz, CDCl3)...

Embodiment 2

[0073] Example 2: Absorption spectrum detection test of dye compound 1-1

[0074] Draw 3 μL of the 6 mmol / L dye mother liquor configured with DMSO and add it to a four-way cuvette containing 3 mL of high-purity water, measure its absorption spectrum, and collect the absorbance value at the wavelength of 230-800 nm. The wavelength corresponding to the maximum absorbance value is its absorption wavelength. The result is as figure 2 shown.

[0075] The instruments used in this example were an Agilent 8453 UV spectrophotometer.

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Abstract

A class of dual-response fluorescent dye molecules has a structure of general formula I. The molecule has a dual-line response characteristic to nitroreductase (NTR) and nicotinamide adenine dinucleotide (NADH) in vivo. Specific detection can be performed for both enzyme levels. At the same time, this kind of probe has good water solubility, good photostability, low phototoxicity, photobleaching and excellent biological toxicity. It has a good application prospect in biological detection.

Description

technical field [0001] The invention relates to the design and synthesis of an organic dye molecule for detecting nitroreductase in vivo and its application in biological analysis, in particular to p-nitroreductase (NTR) and reduced coenzyme nicotinamide adenine dinucleotide (NADH) Organic fluorescent dyes with dual responses. Background technique [0002] The phenomenon of cellular hypoxia is caused by insufficient oxygen supply in cells, and a series of diseases, such as cardiac ischemia, stroke, and inflammation, can be triggered by hypoxia. In addition, hypoxia is also a common phenomenon in the growth of malignant tumors. Malignant tumors are not easily cured due to the easy metastasis of tumor cells, and at the same time, they will increase the resistance to chemotherapy and radiotherapy, thereby reducing the therapeutic effect. Therefore, exploring cellular hypoxia and developing detection methods for cellular hypoxia is of great significance for disease diagnosis, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C211/59C07C209/68C07F9/50C09K11/06C09B57/00G01N21/33G01N21/64
CPCC07C211/59C07F9/5022C09K11/06C09B57/00G01N21/643G01N21/33C09K2211/1007C09K2211/1011C09K2211/1014G01N2021/6439G01N2021/6417
Inventor 仉华杨怡婷申聪聪苏莉陈粤华刘俊维
Owner HENAN NORMAL UNIV
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