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Dual-response fluorescent dye molecules

A fluorescent dye, dual-response technology, applied in the field of organic fluorescent dyes, can solve the problems of inability to achieve dual-line detection of NTR and NADH, and achieve the effects of low/non-toxic, high selective recognition, and suitable water solubility

Active Publication Date: 2020-02-25
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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  • Dual-response fluorescent dye molecules

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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, compound a and b react according to a molar ratio of 1:1-1:10 to prepare a compound of general 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 its mixture; 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] Wherein the molar ratio of catalyst to reactant is 1:0.05-1:0.2.

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

Embodiment 1

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

[0068]

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

[0070] 5mmol of a-1 (synthesis method reference: Kawaguchi, Hirobumi; Hamasaki, Ichiya; Inagaki, Yoshio. Stilbene derivative and electrophotographic photoreceptorusing it May6, 1998JP 10114728) and 6.25mmol of b-1 (synthesis method reference: Venis, Michael A. and Thomas, Emrys W. Synthesis and auxin activity of 5-substituted 1-naphthalene acetic acids. Phytochemistry, 1990, 29, 381-383) were added to a round bottom flask containing 6 mL of absolute ethanol, and then 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 vacuum spin-drying, followed by column chromatography (petroleum ether:dichloromethane, 1:1, v / v) to obtain orange-red compound 1-1 with a yield of 50%.

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

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

Embodiment 2

[0073] Embodiment 2: Absorption Spectrum Detection Test of Dye Compound 1-1

[0074] Take 3μL of 6mmol / L dye mother solution prepared with DMSO and add it to a four-way cuvette containing 3mL of high-purity water, measure its absorption spectrum, collect the absorbance value at a wavelength of 230-800nm, and 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 are Agilent 8453 UV spectrophotometers.

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Abstract

Dual-response fluorescent dye molecules having structures shown as a general formula I are provided. The molecules have dual-response characteristics to nitroreductase (NTR) and nicotinamide adenine dinucleotide (NADH) in vivo. Specific detection of the levels of the two enzymes can be performed. At the same time, probes of this type have good water solubility, good photostability, low phototoxicity, photobleaching and excellent biological toxicity. The dual-response fluorescent dye molecules have good application prospects in biological detection.

Description

technical field [0001] The present invention relates to the design, synthesis and application in biological analysis of an organic dye molecule for detecting nitroreductase in vivo, especially for nitroreductase (NTR) and reduced coenzyme nicotinamide adenine dinucleotide (NADH) is an organic fluorescent dye with dual responses. Background technique [0002] The phenomenon of cellular hypoxia is caused by insufficient supply of oxygen in cells, which can lead to a series of diseases, such as cardiac ischemia, stroke and inflammation. In addition, the hypoxic state is also a common phenomenon in the growth of malignant tumors. Malignant tumors are difficult to cure because of the easy metastasis of tumor cells, and at the same time, it will increase the resistance to chemotherapy and radiotherapy, thereby reducing the therapeutic effect. Therefore, exploring cell hypoxia and developing detection methods for cell hypoxia are of great significance for researches such as disea...

Claims

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Application Information

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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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