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Pyrido benzimidazole mercury ion ratio fluorescence probe, and applications thereof

A ratiometric fluorescent probe, benzimidazole technology, applied in fluorescence/phosphorescence, luminescent materials, material analysis by optical means, etc., can solve the problem of less ratiometric fluorescent probes

Inactive Publication Date: 2018-06-29
TAISHAN MEDICAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, at present, almost all mercury ion probes are single-signal enhancement or decrease probes, and there are few ratiometric fluorescent probes with two or more signal response changes.

Method used

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  • Pyrido benzimidazole mercury ion ratio fluorescence probe, and applications thereof
  • Pyrido benzimidazole mercury ion ratio fluorescence probe, and applications thereof
  • Pyrido benzimidazole mercury ion ratio fluorescence probe, and applications thereof

Examples

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] Add 20 mL of dichloromethane, 0.272 g (1.0 mmol) of 4-phenylpyridobenzimidazole-3-carbaldehyde, 0.530 g (5.0 mmol) of mercaptopropionic acid, and 0.5 mL of boron trifluoride in a 50 mL round-bottom flask Diethyl ether solution, reacted at room temperature for 12 hours. After the reaction was detected by TLC, it was concentrated, and column chromatography gave 0.262 g off-white solid with a yield of 56.2%.

Embodiment 2

[0019] To formula (1) compound (10 -5 M) PBS buffer solution (pH = 7.40) were added 10 equivalents of Mg 2+ , Ca 2+ , Al 3+ ,Sn 2+ , Pb 2+ ,Cr 3+ , Mn 2+ , Fe 3+ ,Co 2+ , Ni 2+ ,Zn 2+ ,Cd 2+ ,Pd 2+ ,Hg 2+ and Ag + After measuring the change in the ratio of the fluorescence emission intensity at 440nm and 518nm, it was found that: the compound of formula (1) is 2+ Has better fluorescence selectivity, adding 10 equivalents of Hg 2+ After that, the fluorescence intensity of compound 1 at 440nm was significantly reduced, and at the same time, the fluorescence intensity at 518nm was significantly enhanced, I 518 / I 440 =5.0, such as figure 1 , figure 2 shown.

Embodiment 3

[0021] Respectively in formula (1) compound (10 -5 M) and 10 equivalents of Mg 2+ , Ca 2+ , Al 3+ ,Sn 2+ , Pb 2+ ,Cr 3+ , Mn 2+ , Fe 3+ ,Co 2 + , Ni 2+ ,Zn 2+ ,Cd 2+ ,Pd 2+ ,Hg 2+ and Ag + In the solution of different metal ions, add 10 equivalents of Hg 2+ After measuring the change in the ratio of fluorescence emission intensity at 440nm and 518nm, 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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PUM

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Abstract

The invention discloses a pyrido benzimidazole derivative Hg <2+> ratio fluorescence probe. The pyrido benzimidazole derivative Hg <2+> ratio fluorescence probe is pyrido benzimidazole substituted mercaptopropanoic acid, and the chemical structure is represented by formula I. The pyrido benzimidazole derivative Hg <2+> ratio fluorescence probe possesses excellent fluorescence selectivity, relatively high sensitivity, and relative high capacity in resisting influences of other ions in PBS buffer solution (pH=7.40) on Hg <2+>, and the application prospect is promising.

Description

technical field [0001] The invention relates to the field of organic small molecule fluorescent probes, in particular to a Hg 2+ Ratiometric fluorescent probe pyridobenzimidazole substituted mercaptopropionic acid and its application. Background technique [0002] Although pyrido[1,2-a]benzimidazoles were discovered in the 1930s, scientists have not paid enough attention to them. It was not until the 1990s that such compounds were found to have good pharmacological activities, and people gradually deepened their research on them, and successively found that they have anti-anxiety, antibacterial, anti-tumor, anti-cancer and other activities. However, due to limited synthesis methods, there are few reports on its application in the field of fluorescent probes. [0003] Hg 2+ It is the most dangerous and common heavy metal pollutant. It easily enters the human food chain through biofilms such as skin, respiratory tract, and gastrointestinal tract tissues. After entering the ...

Claims

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Application Information

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IPC IPC(8): C07D471/04C09K11/06G01N21/64
CPCC07D471/04C09K11/06C09K2211/1007C09K2211/1029C09K2211/1044G01N21/643
Inventor 吴守林巩学勇葛燕青
Owner TAISHAN MEDICAL UNIV