Pyrazolo[1,5-a]pyridine-substituted rhodamine hydrazide cu2+ ratiometric fluorescent probes and their applications

A technology of pyridine rhodamine hydrazide and rhodamine hydrazide, which is applied in the field of organic small molecule fluorescent probes, and can solve the problems of fewer ratiometric fluorescent probes and single signal enhancement or weakening

Inactive Publication Date: 2019-06-21
TAISHAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although a variety of Cu 2+ Fluorescent probes have been reported, but most of the current fluorescent probes are almost all single signal enhancement or weakening fluorescent probes, and there are few ratiometric fluorescent probes with two or more signal changes.

Method used

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  • Pyrazolo[1,5-a]pyridine-substituted rhodamine hydrazide cu2+ ratiometric fluorescent probes and their applications
  • Pyrazolo[1,5-a]pyridine-substituted rhodamine hydrazide cu2+ ratiometric fluorescent probes and their applications
  • Pyrazolo[1,5-a]pyridine-substituted rhodamine hydrazide cu2+ ratiometric fluorescent probes and their applications

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0015] Embodiment 1: The synthesis scheme of the compound of formula (1) is shown in the following formula:

[0016]

[0017] Concrete synthetic steps are as follows:

[0018] In a 50 mL round bottom flask, add 0.16 g (0.30 mmol) rhodamine hydrazide, 0.08 g (0.30 mmol) 2-phenylpyrazolo[1,5-a]pyridine-5-carboxylic acid, 0.07 g (0.36 mmol) EDC, 0.04g (0.36 mmol) DMAP, 20 mL dichloromethane, 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 sodium sulfate, concentrated, and column chromatography gave 0.13 g of a white solid with a yield of 65%.

Embodiment 2

[0020] To formula (1) compound (10 -6 M) HEPES / CH 3 Add 1 equivalent of Mg to CN(8 / 2, v / v, pH=7.30) buffer solution 2+ , Ca 2+ , Al 3+ , Pb 2+ , Cr 3+ , Mn 2+ , Fe 3+ , Na + , Fe 2+ , Co 2+ , Ni 2+ , Zn 2+ , S n 2+ ,Cd 2+ , Pd 2+ , Hg 2+ and Ag + After measuring the change in the ratio of fluorescence emission intensity at 445nm and 570nm, it was found that: the compound of formula (1) has 2+ It has better fluorescence selectivity, adding 1 equivalent of Cu 2+ After that, the fluorescence intensity of the probe at 445nm decreased significantly, and at the same time, the fluorescence intensity at 570nm increased significantly, I 570 / I 445 = 0.6, such as figure 1 , figure 2 shown.

Embodiment 3

[0022] Respectively in formula (1) compound (10 -6 M) and 1 equivalent of Mg 2+ , Ca 2+ , Al 3+ , Pb 2+ , Cr 3+ , Mn 2+ , Fe 3+ , Na + , Fe 2+ , Co 2+ , Ni 2+ , Zn 2+ , S n 2+ , Cd 2+ , Pd 2+ , Hg 2+ and Ag + Add 1 equivalent of Hg to the solution of different metal ions 2+ After measuring the change in the ratio of fluorescence emission intensity at 445nm and 570nm, 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 Cu<2+> ratio type fluorescent probe of 2-phenylpyrazolo[1,5-a]pyridine rhodamine hydrazide derivative, which is prepared from 2-phenylpyrazolo[1, 5-a]pyridine rhodamine hydrazide with the chemical structural formula being shown in formula (1). The fluorescent probe has better fluorescence selectivity and higher sensitivity to Cu<2+> in HEPES / CH3CN (8 / 2, v / v, pH=7.30), andcompared with existing probes, the fluorescent probe provided by the invention has the remarkable advantages of short reaction time, no background interference and the like, and thus has broad application prospects.

Description

technical field [0001] The invention relates to the field of organic small molecule fluorescent probes, in particular to a novel Cu 2+ Synthesis and application of ratiometric fluorescent probe 2-phenylpyrazolo[1,5-a]pyridine substituted rhodamine hydrazide. Background technique [0002] As a heavy metal element, copper is an essential trace element for living organisms and is closely related to human health. However, when the copper content in the body is too high, it will cause a burden to the liver and other organs, and the metabolism will be disordered, causing liver ascites, cirrhosis and other diseases. At present, in the fields of machinery manufacturing, construction industry, medical treatment, etc., the excessive use and improper treatment of copper materials have caused it to become one of the heavy metal pollutants, and the control and monitoring of Cu in water 2+ content has become a hot issue of concern. [0003] Due to the advantages of good selectivity, hi...

Claims

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Application Information

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Patent Type & AuthorityPatents(China)
IPC IPC(8): C07D519/00C09K11/06G01N21/64
CPCC07D519/00C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044C09K2211/1088G01N21/6428
Inventor葛燕青吉瑞雪徐志扬刘爱坤
OwnerTAISHAN MEDICAL UNIV