A switch type zinc ion fluorescent probe and its preparation method and application

A fluorescent probe, zinc ion technology, applied in fluorescence/phosphorescence, chemical instruments and methods, luminescent materials, etc., can solve the problems of lack of comprehensive characteristics of prostate cancer, unable to meet the needs of early diagnosis of prostate cancer, etc., and achieve simple post-processing The effect of convenience, easy product and high reaction yield

Active Publication Date: 2019-01-22
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the reported fluorescent probes for zinc ions cannot meet the needs of early diagnosis of prostate cancer.
Although two fluorescent probes have been reported for the detection of zinc ions in prostate cancer cells in recent years, they still lack the comprehensive characteristics suitable for the diagnosis of prostate cancer, including specific binding selectivity for zinc ions, high sensitivity, dynamic Physical detection requirements such as wide range, fast response, high fluorescence signal-to-noise ratio, quantitative detection, and biocompatibility

Method used

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  • A switch type zinc ion fluorescent probe and its preparation method and application
  • A switch type zinc ion fluorescent probe and its preparation method and application
  • A switch type zinc ion fluorescent probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] 1. Synthesis of intermediate N-(6-picoline)-2,2-dimethylpentanamide

[0050]

[0051] Add 7g (64.73mmol) of 2-amino-6-picoline, 10.8mL (7.86g, 77.68mmol) of triethylamine, and 20mL of dichloromethane into a 100mL two-necked flask, stir in an ice-water bath, and add 8.72 within 40 minutes mL (8.6g, 71.2mmol) of pivaloyl chloride was dissolved in 20mL of dichloromethane, reacted in an ice-water bath for 1 hour after the addition, and then reacted at room temperature for 3 hours. After TLC detection confirmed that the reaction was completed, the reaction solution was poured into a separatory funnel, washed with saturated sodium bicarbonate and saturated brine, and the organic phase was dried with magnesium sulfate and then spin-dried. 1 H NMR (400MHz, CDCl 3 )δ8.50(s,1H),8.13(d,J=8.4Hz,1H),7.65(t,J=7.9Hz,1H),6.92(d,J=7.5Hz,1H),2.50(s, 4H), 1.34(s, 9H).

[0052] 2. Synthesis of intermediate N-(6-bromomethylpyridine)-2,2-dimethylpentanamide

[0053]

[0054] Add 1....

Embodiment 2

[0068] Fluorescent probe 1 prepared in embodiment 1 is to the absorption titration of zinc ion

[0069] 0.0073g of Probe 1 was dissolved in 5mL DMSO to prepare a 2mM stock solution. Make a 10μM solution with HEPES (pH=7.4), gradually add 2mM Zn(ClO 4 ) 2 solution. Test for changes in its absorption. The result is as image 3 shown.

Embodiment 3

[0071] Fluorescence response titration of fluorescent probe 1 prepared in Example 1 to zinc ions

[0072] 0.0073g of Probe 1 was dissolved in 5mL DMSO to prepare the mother solution. Make a 10μM solution with HEPES (pH=7.4), gradually add 2mM Zn(ClO 4 ) 2 solution. Test for its fluorescence change. (The excitation wavelength is 510nm, the slit [5,5].) The results are as follows Figure 4 shown.

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Abstract

The invention provides a switch-type zinc ion fluorescent probe and its preparation method and application. Sensitivity, the fluorescence of the probe is enhanced by 96 times after the probe is combined with zinc ions through the rhodamine switch ring. The preparation method of the probe is simple and suitable for scale-up synthesis and practical application. It can be used for the detection of intracellular zinc ions in the field of chemical analysis and detection, and has broad application prospects for the detection of zinc ions in other biological samples.

Description

technical field [0001] The invention belongs to the field of chemical analysis and detection, and in particular relates to a switch-type zinc ion fluorescent probe, its preparation method and application. Background technique [0002] Zinc is an important trace element, the content in the human body is second only to iron. Zinc is not only an important part of various proteins, DNA, RNA and ribosomes in the body, but also participates in the composition of more than 3,000 transcription factors. At the same time, zinc ions are the active centers of many enzymes and directly participate in various physiological processes in the human body. A healthy prostate is rich in zinc, the highest of all soft tissues in the body. The concentration of zinc ions in the precancerous glands of the prostate is significantly reduced, and this loss of zinc ions continues to occur during the pathological changes of prostate cancer. The study found that the decrease in zinc ion concentration wa...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D491/107C09K11/06G01N21/64
CPCC07D491/107C09K11/06C09K2211/1029C09K2211/1088G01N21/6428
Inventor 徐兆超尹文婷乔庆龙
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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