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Application of 1,4-dihydropyridine derivative as NO fluorescent probe

A technology of dihydropyridine and fluorescent probes, which can be used in fluorescence/phosphorescence, organic chemistry, material excitation analysis, etc., and can solve problems such as insufficient specificity and limited use

Active Publication Date: 2013-05-01
NAT INST FOR FOOD & DRUG CONTROL
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

O-phenylenediamines, the most widely used and concerned fluorescent molecular probes for NO, still have many phenomena such as the sensitivity being affected by the pH of the medium and the existence of autoxidation due to their own structural characteristics and mechanism of action. Issues such as insufficient specificity limit its use

Method used

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  • Application of 1,4-dihydropyridine derivative as NO fluorescent probe
  • Application of 1,4-dihydropyridine derivative as NO fluorescent probe
  • Application of 1,4-dihydropyridine derivative as NO fluorescent probe

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Example 1 Synthesis of Coumarin Derivatives Based on Hantzsch Lipid Synthesis

[0025] 1. Synthesis of 1b (7-hydroxy-4-methyl-2H-chromen-2-one)

[0026]

[0027] 11g (100mmol) resorcinol, 13mL (100mmol) ethyl acetoacetate, 52mL H 3 PO 4 Add it into a round-bottomed flask, stir at room temperature for 12 hours, the solution turns into a yellow paste, pour the yellow paste into a large amount of water, and filter with suction to obtain a milky white solid. Recrystallization from ethyl acetate / petroleum ether afforded a pure white solid. 1 H NMR (400Hz CDCl 3 )δppm: 10.50(s,1H),7.60(d,1H,J=8.7Hz),6.82(q,1H,J=2.3Hz),6.70(d,1H,J=2.3Hz),6.12(d, 1H,J=0.9Hz),2.36(d,3H,J=0.9Hz).

[0028] 2. Synthesis of 1c (7-methoxy-4-methyl-2H-chromen-2-one7-methoxy-4-methylcoumarin)

[0029]

[0030] Dissolve 3.5g (22mmol) 1b with 30mL acetone, add 6.03g (43.2mmol) K 2 CO 3 , stirred for 10min, then added 3.12g (22mmol) CH 3 1, reflux reaction 6h, stop heating, heat filtration....

Embodiment 2

[0040] Example 2. Research on UV and Fluorescent Properties of Coumarin Derivatives and Fluorescent Probes

[0041] 1. The ultraviolet and fluorescent properties of coumarin derivatives:

[0042] Such as figure 1 Shown, the solvent is ethanol, the ultraviolet absorption spectrum of 4-methylcoumarin 1c ( figure 1 a,c=1.0×10 -4 mol L -1 ,ε=1.81×10 4 ) and 4-methylcoumarin 1c ( figure 1 b, c=1.0×10 -6 mol L -1 ,λ ex =323nm,λ em =384nm) fluorescence spectrum.

[0043] Such as figure 2 Shown, the UV absorption spectrum of 4-formyl coumarin 1d ( figure 2 a,c=1.0×10 -4 mol L -1 ,ε=2.22×10 4 ) and the fluorescence spectrum of 4-formylcoumarin 1d ( figure 2 b, c=1.0×10 -6 mol L -1 ,λ ex =324nm,λ em =389nm), the solvents are ethanol.

[0044] Such as figure 1 , figure 2 As shown, the different substituents on the 4th position of 7-methoxy-coumarin have no significant effect on its own fluorescence properties.

[0045] 2. The ultraviolet and fluorescent propert...

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Abstract

The invention relates to the field of probes, in particular to an application of a 1,4-dihydropyridine derivative as a NO fluorescent probe. According to the invention, based on the specific effect of the 1,4-dihydropyridine derivative and nitric oxide, (aromatization, resulting in the changes of electronic structure distribution and molecular conformation in the probes) features of corresponding pyridine derivatives are produced, to realize the response of the fluorescent probe to nitric oxide. Based on the changes of the fluorescence in nature before and after the detection (changes in fluorescence emission intensity, fluorescence emission wavelength, fluorescence emission service life and the like), the detection for the nitric oxide is realized.

Description

technical field [0001] The invention relates to the field of molecular probes, in particular to the use of 1,4-dihydropyridine derivatives as NO fluorescent probes. Background technique [0002] As an important messenger molecule and neuromodulator in organisms, nitric oxide molecule (NO) participates in the regulation of the physiological functions of multiple systems. There is already evidence that nitric oxide is also associated with diseases such as diabetes, Parkinson's disease and Alzheimer's disease. Therefore, NO-donating drugs have attracted extensive attention as potential cardiovascular, anti-tumor, novel anti-inflammatory and anti-Alzheimer's disease drugs. However, NO, as a gas free radical, is extremely unstable in the living body, so the method of detecting NO in the living body has always been a hot spot and difficulty in related research. [0003] "Fluorescent probe" generally refers to a compound that can selectively interact with other specific substance...

Claims

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Application Information

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IPC IPC(8): C07D405/04G01N21/64
Inventor 黄海伟龚兵李敏峰何兰宁保明
Owner NAT INST FOR FOOD & DRUG CONTROL
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