Excited state intramolecular proton transfer regulation based fluorescence probe, and synthetic method and applications thereof

A fluorescent probe and proton transfer technology, applied in the field of fluorescent probes and their synthesis, can solve the problems of fluorescence enhancement and quenching, and achieve the effect of simple raw materials, avoiding the influence of external factors, and simple separation and purification process of products

Active Publication Date: 2013-10-02
BOHAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these methods generally show fluorescence enhancement or quenching at the original

Method used

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  • Excited state intramolecular proton transfer regulation based fluorescence probe, and synthetic method and applications thereof
  • Excited state intramolecular proton transfer regulation based fluorescence probe, and synthetic method and applications thereof
  • Excited state intramolecular proton transfer regulation based fluorescence probe, and synthetic method and applications thereof

Examples

Experimental program
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Effect test

Embodiment 1

[0041] (1) Synthetic relay recognition Zn 2+ and S 2- The reaction formula of the ratiometric fluorescent probe:

[0042]

[0043] (2) Synthetic relay recognition of Zn 2+ and S 2- The specific steps of the ratiometric fluorescent probe:

[0044] Weigh 300mg of the intermediate N -(2-(1 H-Benzimidazolyl)phenyl)-2-chloroacetamide (compound 1) and 170mg 2-aminomethylpyridine, dissolved in 10ml N,N - In dimethylformamide (DMF), stir the reaction at room temperature for 5 hours, add 200ml of distilled water to dilute, adjust the pH value to 7.5 with dilute hydrochloric acid, collect the resulting precipitate by filtration, and recrystallize with acetonitrile to obtain a fluorescent probe N -(2-(1H-Benzimidazolyl)phenyl)-2-(2-aminomethylpyridyl)acetamide (compound L), yield 65%.

Embodiment 2

[0046] Weigh 400mg of the intermediate N -(2-(1H-Benzimidazolyl)phenyl)-2-chloroacetamide (compound 1) and 300mg 2-aminomethylpyridine, dissolved in 13ml N,N - In dimethylformamide (DMF), stir the reaction at room temperature for 8 hours, add 200ml of distilled water to dilute, adjust the pH value to 7 with dilute hydrochloric acid, collect the resulting precipitate by filtration, and recrystallize with acetonitrile to obtain a fluorescent probe N -(2-(1H-Benzimidazolyl)phenyl)-2-(2-aminomethylpyridyl)acetamide, the yield was 71%.

Embodiment 3

[0048] Weigh 500mg of the intermediate N -(2-(1H-Benzimidazolyl)phenyl)-2-chloroacetamide (compound 1) and 560mg of 2-aminomethylpyridine, dissolved in 15ml of DMF, stirred at room temperature for 10h, Add 250ml of distilled water for dilution, adjust the pH value to 6.5 with dilute hydrochloric acid, collect the resulting precipitate by filtration, and recrystallize with acetonitrile to obtain a fluorescent probe N -(2-(1H-Benzimidazolyl)phenyl)-2-(2-aminomethylpyridyl)acetamide, the yield was 76%.

[0049] The fluorescent probe of embodiment 1~embodiment 3 N -(2-(1 H Basic data for -benzoimidazolyl)phenyl)-2-(2-aminomethylpyridyl)acetamide:

[0050] Melting point: 179℃~180℃;

[0051] 1 H NMR (400 MHz, DMSO- d 6 ) δ 13.39 (s, 1H), 13.05 (s, 1H), 8.81 (d, J = 8.3 Hz, 1H), 8.51 (d, J = 3.3 Hz, 1H), 8.06 (d, J = 7.7 Hz, 1H), 7.63 (t, J = 7.3 Hz, 1H), 7.54-7.46 (m, 3H), 7.35 (s, 1H), 7.35 –7.25 (m, 3H), 7.14 (s, 1H), 3.97 (s, 2H), 3.45 (s, 2H). (eg figure 1 )....

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Abstract

The invention discloses an excited state intramolecular proton transfer regulation based fluorescence probe, and a synthetic method and applications thereof. The structural formula of the fluorescence probe is shown in the patent specification of the invention. Specific synthetic steps are as following: DMF is taken as a solvent; molar ratio of N-(2-(1H-benzimidazolyl)phenyl)-2-chloroacetamide to picolylamine, which are used as raw materials, is 1:1.5-1.3; the mixture is stirred at room temperature for 5 to 10 h; the mixture is diluted with distilled water, pH value of the mixture is adjusted to 6.5 to 7.5 with dilute hydrochloric acid, the mixture is filtered, produced sediment is collected and is recrystallized with acetonitrile, so that the fluorescence probe N-(2-(1H-benzimidazolyl)phenyl)-2-(2- picolylamine)acetamide is obtained. Advantages are that: synthesis is simple; water solubility is high; the fluorescence probe is friendly to the environment, and can be used for monitoring, analyzing and tracking Zn<2+> and S<2-> in water environment system and biological cell system; sensitivity is high, and anti-interference capability is excellent.

Description

technical field [0001] The invention relates to a fluorescent probe based on the regulation of proton transfer in excited state intramolecules, its synthesis method and application. Background technique [0002] The content of zinc ions in the human body is second only to iron ions, and it is an essential nutrient for the human body. It plays a very important role in many physiological and pathological processes of organisms. It is not only the main component of dozens of enzymes in the human body, but also an essential trace element for human brain development; at the same time, zinc can also affect the proliferation and activity of lymphocytes. Lack of zinc can cause abnormal taste and smell, hepatosplenomegaly, enteropathic acrodermatitis, etc., while excessive zinc can cause prostate cancer, diabetes and brain diseases. Since zinc plays a very important role in human growth and development, the identification and detection of zinc ions are of great significance to biolo...

Claims

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Application Information

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IPC IPC(8): C09K11/06C07D401/12G01N21/64
Inventor 汤立军钟克利侯淑华彭亚晶蔡明君
Owner BOHAI UNIV
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