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A kind of quinoline-substituted coumarin derivative, its preparation method and its application in ratio-type pH fluorescent probe

A technology of coumarin derivatives and fluorescent probes, which is applied in the field of analytical chemistry, can solve the problems of external environment, probe load and retention, etc. , accurate results

Active Publication Date: 2020-04-24
CHINA THREE GORGES UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But at the same time, the accuracy of the results is easily affected by factors such as external environment, detection substrate and photobleaching, probe loading and retention.

Method used

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  • A kind of quinoline-substituted coumarin derivative, its preparation method and its application in ratio-type pH fluorescent probe
  • A kind of quinoline-substituted coumarin derivative, its preparation method and its application in ratio-type pH fluorescent probe
  • A kind of quinoline-substituted coumarin derivative, its preparation method and its application in ratio-type pH fluorescent probe

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Experimental program
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Embodiment 1

[0025] Synthesis of embodiment 1pH fluorescent probe 3-[2-[8-carboxyquinolin-2-yl]vinyl]-7-diethylaminocoumarin

[0026] This embodiment provides a synthetic method for 3-[2-[8-carboxyquinolin-2-yl]vinyl]-7-diethylaminocoumarin, the main steps of which are as follows:

[0027] Add successively 0.3745g (2.0026mmoS) 2-methyl-8-carboxyquinoline, 0.5904g (2.4000mmoS), 2.00mL acetic acid, 0.6991g sodium acetate, 2.88mL acetic anhydride in the 50mL two-necked bottle, stir and reflux for 6 hours, After cooling, a red solid precipitated out, which was filtered by suction and washed with ethanol to obtain 0.6657 g of the product, with a yield of 80.40%. 1 H NMR (400MHz, CDCS 3 )δ8.72 (m, J=7.3,1.4Hz,1H),8.29(d,J=8.7Hz,1H),8.01(m,J=8.1,1.3Hz,1H),7.86(s,1H), 7.80(d,J=16.1Hz,1H),7.72(d,J=8.7Hz,1H),7.67–7.62(m,1H),7.61(d,J=2.7Hz,1H),7.36(d,J =8.9Hz, 1H), 6.63(m, J=8.9, 2.4Hz, 1H), 6.48(d, J=2.2Hz, 1H), 3.45(dd, J=7.1Hz, 4H), 1.70(s, 1H ),1.24(t,J=7.1Hz,6H).

[0028] image 3 For the ...

Embodiment 2

[0030] The preparation of embodiment 2 test solution

[0031] (1) The preparation procedure of the stock solution: in a 10mL sample bottle, prepare 10 mL of the stock solution with chloroform -3 mol / L stock solution for use. Prepare V (methanol): V (PBS buffer solution) = 9:1 with different pH values ​​(4.92, 5.33, 5.48, 5.71, 5.96, 6.19, 6.64, 7.07, 7.46, 7.70, 7.75, 7.98, 8.67, 8.74, 9.01 , 10.65, 11.03, 11.39, 11.65) of the buffer solution was monitored with a magnetic pH meter.

[0032] (2) Test of the fluorescence emission spectrum of the probe against pH changes: take 2 mL of different pH values ​​(4.92, 5.33, 5.48, 5.71, 5.96, 6.19, 6.64, 7.07, 7.46, 7.70, 7.75, 7.98, 8.67, 8.74, 9.01 , 10.65, 11.03, 11.39, 11.65) buffer solution, adding 20 μL of the stock solution configured in Example 2 (1) for fluorescence spectrum testing.

[0033] (3) Probe S to OH -Selectivity experiment: get 14 parts of 2mL pH=3.15 buffer solution, each add 20 μL of the stock solution prepare...

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Abstract

The invention belongs to the technical field of analytical chemistry and particularly relates to a quinoline substituted coumarin derivative and a preparation method and application thereof. The quinoline substituted coumarin derivative of 7-diethylin-3-(2-(8-carboxyl quinoline)-2-yl)vinyl) coumarin is prepared from raw materials of 2-methy-8-carboxyl quinoline and 3-formyl-7-diethylin coumarin and by condensation. The coumarin derivative S disclosed by the invention is a rate type pH fluorescent probe, the probe S can respond pH within a range of 5 to 8 and has a good linear relationship, a relative standard deviation is 0.9983, and a pKa value is 8.65. The probe further has better optical chemical stability and quick OH- response, and OH- response of the probe is not interfered with by other anions; furthermore, the probe has good reversibility.

Description

technical field [0001] The invention belongs to the technical field of analytical chemistry, and in particular relates to a double bond-containing olefin, a coumarin derivative, a quinoline derivative and a preparation method and application thereof. Background technique [0002] In the field of environmental detection and biology, pH value is an important indicator parameter. Intracellular pH plays a crucial role in many cellular biological processes, and abnormal pH changes can lead to cell dysfunction, mutations in growth and division, and may also trigger diseases such as cancer and Alzheimer's syndrome. Therefore, it is of great theoretical and practical significance to study the change of intracellular pH. [0003] The glass electrode method is a common method for measuring pH value, but it is not suitable for the determination of living body or extreme pH value due to its defects such as electrochemical interference or mechanical damage. Fluorescent probe detection ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D405/06C09K11/06G01N21/64
CPCC07D405/06C09K11/06C09K2211/1029C09K2211/1088G01N21/6428G01N21/643
Inventor 但飞君韩雅莲刘瑶唐倩
Owner CHINA THREE GORGES UNIV
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