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Imidazo [1,2-a] pyridine mercuric ion rate-type fluorescent probe and application thereof

A fluorescent probe, imidazolo technology, applied in the field of organic small molecule fluorescent probes

Inactive Publication Date: 2018-11-27
TAISHAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, its application in the field of fluorescent probes has rarely been reported.

Method used

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  • Imidazo [1,2-a] pyridine mercuric ion rate-type fluorescent probe and application thereof
  • Imidazo [1,2-a] pyridine mercuric ion rate-type fluorescent probe and application thereof
  • Imidazo [1,2-a] pyridine mercuric ion rate-type fluorescent probe and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Embodiment 1: The synthesis scheme of the compound of formula (1) is shown in the following formula:

[0015]

[0016] Concrete synthetic steps are as follows:

[0017] In a 50 mL round bottom flask, add 0.216 g (0.30 mmol) 2-(4-methoxyphenyl) imidazo[1,2-a]pyridine rhodamine hydrazide derivative, 0.32 g (2.4 mmol) iso Phenyl thiocyanate, 20 mL N,N-dimethylformamide, react at room temperature for 12 hours. After the reaction was detected by TLC, 100 mL of dichloromethane was added, washed three times with 30 mL of water, the dichloromethane layer was dried over anhydrous sodium sulfate, concentrated, and column chromatography gave 0.13 g of a purple solid, with a yield of 67%.

[0018] Melting point determination: mp:201-203℃

[0019] H NMR spectrum test 1 H NMR (400 MHz, DMSO): δ 11.32 (s, 1H) 8.57 (d, J = 6.8Hz, 1H), 8.39 (s, 1H), 7.92 (d, J = 8.6 Hz, 2H), 7.82 – 7.75 (m, 1H), 7.70 (d, J = 8.5 Hz, 2H) 7.65 (s, 1H), 7.55 – 7.44 (m, 2H), 7.43 (d, J = 8.4Hz, 2H), ...

Embodiment 2

[0021] To formula (1) compound (10 -6 M) PBS / EtOH (9 / 1, v / v, pH=7.50) buffer solution were added 7 equivalents of Mg 2+ , Ca 2+ , Al 3+ , S n 2+ , Pb 2+ , Cr 3+ , Mn 2+ , Fe 3+ , Fe 2+ , Na + , K + , Cu 2+ , Co 2+ , Ni 2+ ,Zn 2+ , Cd 2+ , Ag + , HCO 3 - , Ac - , NO 2 - , F - , NO 3 - , Br - , I - After measuring the change in the ratio of the fluorescence emission intensity at 436nm and 590nm, it was found that: the compound of formula (1) is 2+ Has better fluorescence selectivity, adding 7 equivalents of Hg 2+ After that, the fluorescence intensity of compound 1 at 436nm was significantly reduced, and at the same time, the fluorescence intensity at 590nm was significantly enhanced, I590 / I 436 = 8.6, such as figure 1 , figure 2 shown.

Embodiment 3

[0023] Respectively in formula (1) compound (10 -6 M) and 7 equivalents of Mg 2+ , Ca 2+ , Al 3+ , S n 2+ , Pb 2+ , Cr 3+ , Mn 2+ , Fe 3 + , Fe 2+ , Na + , K + , Cu 2+ , Co 2+ , Ni 2+ , Zn 2+ , Cd 2+ , Ag + , HCO 3 - , Ac - , NO 2 - , F - , NO 3 - , Br - , I - In different anion and cation solutions, add 7 equivalents of Hg 2+ After measuring the change in the ratio of fluorescence emission intensity at 436nm and 590nm, it was found that the compound of formula (1) has strong anti-interference ability to other ions, such as image 3 shown.

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Abstract

The invention discloses a 2-(4-methoxy phenyl) imidazo [1,2-a] pyridine rhodamine hydrazide derivative Hg2+ rate-type fluorescent probe. The probe is a 2-(4-methoxy phenyl) imidazo [1,2-a] pyridine rhodamine hydrazide derivative substituted by phenyl isothiocyanate, and the chemical structural formula of the derivative is shown in the formula (1). The fluorescent probe has good fluorescent selectivity, high sensitivity and high capacity of resisting interference of other ions on Hg2+ in a PBS / EtOH (9 / 1, v / v, pH=7.50) buffer solution and is wide in application prospect.

Description

technical field [0001] The invention relates to the field of organic small molecule fluorescent probes, in particular to a Hg 2+ Synthesis and application of ratiometric fluorescent probe 2-(4-methoxyphenyl)imidazo[1,2-a]pyridine rhodamine hydrazide derivatives. Background technique [0002] Mercury is a highly toxic heavy metal that seriously harms human health. Elemental Hg and Hg in the environment 2＋ It can be converted into methylmercury by microorganisms, and further absorbed by the human body through the food chain, thus causing huge damage to the human brain, kidneys and endocrine system. Therefore, it is of great significance to identify and detect mercury ions in the field of life sciences and environmental monitoring. [0003] Imidazo[1,2-a]pyridines are widely used in the field of medicinal chemistry and are the main components of some important drugs, such as zolimidine, saripidem, Zolpidem and soraprazan. In addition, such derivatives also have biological a...

Claims

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Application Information

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IPC IPC(8): C07D519/00C09K11/06G01N21/64
CPCC07D519/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1088G01N21/643
Inventor 段桂运夏成才李彦忠
Owner TAISHAN MEDICAL UNIV