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Fluorescent probe for selectively detecting zinc ions in cells, synthesizing method thereof and application thereof

A technology of fluorescent probes and zinc ions, applied in measuring devices, material analysis through optical means, instruments, etc., can solve the problems that chemical sensing molecules are rarely reported, and achieve simple structure, high efficiency, and simple synthesis method Effect

Inactive Publication Date: 2009-12-30
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Due to their large molar extinction coefficient and high fluorescence quantum yield, coumarin compounds have been used as fluorescent markers in biotechnology to some extent, but they are used as chemical sensing molecules directly used to identify specific objects. Examples are rarely reported

Method used

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  • Fluorescent probe for selectively detecting zinc ions in cells, synthesizing method thereof and application thereof
  • Fluorescent probe for selectively detecting zinc ions in cells, synthesizing method thereof and application thereof
  • Fluorescent probe for selectively detecting zinc ions in cells, synthesizing method thereof and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 5.4g of 7-N, N-dimethylcoumarin-3-methylketone was dissolved in 10ml of dimethyl sulfoxide, and a solution of 4g of 2-hydrazinopyridine dissolved in 100ml of ethanol was slowly added dropwise under reflux. After reflux and stirring for 3 hours, the reaction was filtered to remove dimethyl sulfoxide and ethanol solvent, and the orange blocky crystal (I-1) was obtained after vacuum drying.

[0040] EI-MS, m / e, 350.1[M+1] + .λ ab. max / nm=470nm, Φ=0.08.

[0041]

[0042] Structure of fluorescent probe (I-1)

[0043] The fluorescent probe (I-1) was added to various metal ion aqueous solutions respectively, by Figure 1a , 1b can be seen that the fluorescent probe (I-1) on the zinc ion Zn 2+ There is a very specific fluorescent enhanced recognition effect.

[0044] Fluorescent probes for zinc ions Zn 2+ For selective recognition see figure 2 From the photo, it can be seen that the fluorescence is greatly enhanced after adding zinc ions, but the change is not...

Embodiment 2

[0048] 5.6g 7-N, N-dimethylcoumarin-3-methyl ketone was dissolved in 10ml tetrahydrofuran, and slowly added dropwise a solution of 7g 2-hydrazino-4-methoxypyridine dissolved in 100ml acetonitrile under reflux . After stirring and reacting under reflux for 5 hours, the mixture was filtered to remove tetrahydrofuran and acetonitrile solvent, and dried in vacuo to obtain orange blocky crystals (I-2).

[0049] EI-MS, m / e, 380.1[M+1] + .λ ab. max / nm=470nm, Φ=0.08.

[0050]

[0051] Structure of fluorescent probe (I-2)

Embodiment 3

[0053] 5.4g of 7-N, N-dimethylcoumarin 4-ethyl-3-aldehyde was dissolved in 10ml of ethanol, and a solution of 4g of 2-hydrazinopyridine dissolved in 200ml of ethanol was slowly added dropwise under reflux. After reflux and stirring for 5 hours, the reaction was filtered, the ethanol solvent was removed, and the orange block crystal (I-3) was obtained after vacuum drying.

[0054] EI-MS, m / e, 363.1[M+1] + .λ ab. max / nm=478nm, Φ=0.12.

[0055]

[0056] Structure of fluorescent probe (I-3)

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Abstract

The invention relates to a fluorescent probe for selectively detecting zinc ions in cells, a synthesizing method thereof and application thereof. The fluorescent probe has good selectivity for the zinc ions in vitro, and can be used for quick imaging of the zinc ions in the cells. The synthesizing method comprises the following steps: dissolving a coumarin-3-carbonyl compound with R1, R2, R3, R4 and R5 substituted groups into a drying organic solvent, slowing dropping 2-hydrazopyridine with R6 substituted group into the solution under refluxing and stirring, filtering the mixture after refluxing and stirring reaction, and removing the organic solvent to obtain the fluorescent probe (1) for selectively detecting the zinc ions in the cells. The fluorescent probe can be used for analysis detection and fluorescent imaging detection for the zinc ions in biological living cells and living tissues and detection for the zinc ions in pathological tissues in clinical medicine.

Description

technical field [0001] The invention relates to a fluorescent probe for selectively detecting intracellular zinc ions, a synthesis method and application thereof. Background technique [0002] Zinc is one of the essential trace elements for the human body, and its content in the human body is second only to iron. Most of the zinc ions in organisms are bound to proteins, and it acts as a cofactor in metalloproteins to regulate the activity of proteins or enzymes. In addition, zinc ions also have a neuromodulatory function. Zinc ions can enter cells through potential-regulated ion channels, and affect gene expression by changing the conformation of chromatin or blocking DNA synthesis through metalloproteins (zinc finger proteins). Zinc deficiency can cause nerve growth and development to be hindered, and it will lead to stunted development of sexual organs, manifested as hypoplasia of the prostate and seminal vesicles, decreased sperm, and reduced sexual physiological functio...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/12G01N21/00
Inventor 汪鹏飞盛瑞隆张洪艳刘卫敏
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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