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Cu < + > fluorescent probe based on axial coordination regulation and control of zinc porphyrin as well as preparation method and application of Cu < + > fluorescent probe

A fluorescent probe, zinc porphyrin technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of high toxicity, poor biocompatibility, poor cell membrane permeability, etc., and achieve good membrane permeability. , mild reaction conditions, excellent optical properties

Active Publication Date: 2022-01-25
ZHEJIANG UNIV CITY COLLEGE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is: improve the deficiencies of existing cuprous ion detection probes, and provide a method for preparing cuprous ion detection probes, the synthesis steps are simple, and the synthesized cuprous ion detection probes solve the problem of water solubility. and poor cell membrane permeability, high toxicity, poor biocompatibility and other issues

Method used

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  • Cu &lt; + &gt; fluorescent probe based on axial coordination regulation and control of zinc porphyrin as well as preparation method and application of Cu &lt; + &gt; fluorescent probe
  • Cu &lt; + &gt; fluorescent probe based on axial coordination regulation and control of zinc porphyrin as well as preparation method and application of Cu &lt; + &gt; fluorescent probe
  • Cu &lt; + &gt; fluorescent probe based on axial coordination regulation and control of zinc porphyrin as well as preparation method and application of Cu &lt; + &gt; fluorescent probe

Examples

Experimental program
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Embodiment 1

[0048] o-SNH 2 (60mg, 0.07mmol) was dissolved in 5mL DMF, and then bromoacetyl bromide (71mg, 0.35mmol) was dissolved in 1mL DMF, and sodium hydroxide (5mg, 0.125mmol) was dissolved in 1mL distilled water, and the three were mixed in 0 ℃ under ice bath for 1h, continue to react at room temperature (20°C) for 1h, collect the reaction liquid, dialyze it in a 1000kDa dialysis bag for 52h, freeze-dry for 14h to obtain 5-(2-bromoacetamidophenyl)-10,15,20 - Tris(4-sulfophenyl)porphyrin (o-SPBr), weight 53.1 mg, yield 77%.

[0049] Dissolve o-SPBr (50mg, 0.05mmol) and zinc acetate dihydrate (104.75mg, 0.5mmol) in 6mL of chloroform, heat the reaction solution to 60°C, reflux for 4 hours, collect the reaction solution in a 1000kDa dialysis bag After 48 hours of dialysis and freeze-drying for 24 hours, 5-(2-bromoacetamidophenyl)-10,15,20-tris(4-sulfophenyl)zinc porphyrin (o-ZSPBr) was obtained, weighing 49.8 mg, The yield was 95%.

[0050] After mixing commercially available 3-aminom...

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Abstract

The invention discloses a Cu < + > fluorescent probe based on axial coordination regulation of zinc porphyrin, and a preparation method and application of theCu < + > fluorescent probe. The method comprises the following steps: mixing 5-(2-bromoacetaminophenyl)-10, 15, 20-tris (4-sulfonyl phenyl) zinc porphyrin (o-ZSPBr), N-ethoxyethyl-3-alkyl pyridinamine derivative (N-EP), potassium carbonate and potassium iodide, dissolving the mixture in N, N '-dimethylformamide, and carrying out a heating reaction to obtain the final probe o-SZP. The probe is high in water solubility, obvious fluorescence enhancement can be displayed when Cu < + > is detected, the detection process is convenient, and a result is accurate. Interference of various metal ions is avoided. In combination with a laser confocal scanning microtechnique, fluorescence detection imaging of the probe on Cu < + > ions in living cells can be realized.

Description

technical field [0001] The invention relates to a zinc porphyrin derivative and a fluorescent sensor based on the derivative, in particular to a water-soluble cuprous ion using zinc porphyrin as a fluorescent chromophore, pyridine N and ether chain O as common signal recognition atoms (Cu + ) a preparation method of a fluorescent probe, and the application of the probe molecule in the detection of cuprous ions in aqueous solution and cells. Background technique [0002] Copper is an indispensable element in life. Cuprous ion is a cofactor of many redox enzymes, including cytochrome c oxidase, ceruloplasmin, tyrosinase, dopamine β-hydroxylase, lysyl oxidase, copper amine oxidase, etc., they Participate in the process of electron transfer / substrate oxidation, iron uptake, pigmentation, neurotransmitter synthesis and metabolism, epigenetic modification and antioxidant defense in organisms. These enzymes play a pivotal role in life activities. effect. The imbalance of cuprou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/22C09K11/06G01N21/64
CPCC07D487/22C09K11/06G01N21/6428G01N21/6458C09K2211/188C09K2211/1074C09K2211/1029G01N2021/6432G01N2021/6417
Inventor 吕媛媛陆慧珊易小琴唐烨娇
Owner ZHEJIANG UNIV CITY COLLEGE
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