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Multifunctional imaging probe for detecting copper ions and synthesis method of multifunctional imaging probe

An imaging probe and multi-functional technology, applied in chemical instruments and methods, measuring devices, and nuclear magnetic resonance analysis, etc., can solve the problems of restricted fluorescence imaging and limited tissue penetration, so as to make up for low sensitivity and avoid tissue damage. The effect of poor penetration

Inactive Publication Date: 2017-04-19
DALIAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application of fluorescence imaging in living organisms is limited by its limited tissue penetration, and only good in vitro imaging can be achieved.

Method used

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  • Multifunctional imaging probe for detecting copper ions and synthesis method of multifunctional imaging probe
  • Multifunctional imaging probe for detecting copper ions and synthesis method of multifunctional imaging probe
  • Multifunctional imaging probe for detecting copper ions and synthesis method of multifunctional imaging probe

Examples

Experimental program
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Effect test

Embodiment 1

[0021]

[0022] a Dissolve 2 grams of compound 1 (7-N, N-dimethylamino-2-oxo-2H-3-coumaric acid ethyl ester) in 25 ml of ethanol, and add 10 times the molar amount of hydrazine hydrate to the solution , stirred at room temperature, reacted for four hours, and filtered to obtain a yellow solid with a yield of 80%, HRMS 275.1270.

[0023]

[0024] b Dissolve all the yellow solids obtained in step a in 10 ml of DMF solution, add 0.5 times the molar amount of DTPA, heat and reflux in an oil bath at 100 degrees for six hours, and distill DMF under reduced pressure to obtain a yellow solid with a yield of 80 %, HRMS907.3712.

[0025]

[0026] c Dissolve the yellow solid obtained in step b and an equimolar amount of gadolinium nitrate in methanol, stir at room temperature for 24 hours, and dry under reduced pressure to obtain the target product with a yield of 95%, HRMS 1060.2718.

Embodiment 2

[0028]

[0029] In the step of Example 1c, europium nitrate is used instead of gadolinium nitrate, and the rest are the same as example 1, HRMS 1057,2689.

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Abstract

The invention belongs to the field of biological detection and particularly relates to a kind of multifunctional imaging molecular probes detecting copper ions by using fluorescent imaging and magnetic resonance imaging. The probe has the following structural general formula (please see the formula in the specification). The probe is synthesized based on fluorescein and DTPA, firstly, coumarin serves as a raw material, the coumarin and ten-fold hydrazine hydrate are subjected to a stirring reaction in ethanol, and yellow solids are obtained; and then in a dimethylformamide solution, the yellow solids and diethylenetriamine pentaacetic acid dianhydride are further subjected to a heating reaction, drying under reduced pressure is performed, an obtained product and gadolinium nitrate or europium nitrate are stirred in a methanol solution at room temperature to stay overnight, and drying under reduced pressure is performed so that a target product can be obtained. Probe molecules have good chemical and light stability and sensitivity, the probe molecules have high selectivity on the copper ions and are not interfered by metal ions in other living organisms, high-sensitivity fluorescent imaging and high-spatial-resolution magnetic resonance imaging of the copper ions can be achieved, and advantages of two kinds of imaging manners are complemented.

Description

technical field [0001] The invention belongs to the field of biological detection, and in particular relates to a class of multifunctional imaging molecular probes for detecting copper ions by fluorescence imaging and magnetic resonance imaging. Background technique [0002] Copper is a basic trace element and an essential nutrient element in organisms, and plays an important role in the basic physiological processes of organisms. Too much or too little copper ions will lead to growth and metabolic disorders, and may even cause serious diseases such as Wilson's disease, Menkes' syndrome, ALS and Alzheimer's. But so far, the mechanism of uptake and storage of copper ions is still difficult to explain clearly, especially with regard to the process of metabolism and regulation. In order to study these physiological processes, it is urgent to design and synthesize highly selective copper ion molecular probes. [0003] Fluorescent bioimaging provides a simple and minimally dama...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D311/16C09K11/06G01N21/64G01N24/08
CPCC07D311/16C09K11/06C09K2211/182G01N21/6428G01N24/08
Inventor 张晓琳
Owner DALIAN UNIV
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