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Zinc-aluminum ion recognition fluorescent probe as well as preparation method and application thereof

A technology of ion recognition and fluorescent probes, applied in the field of fluorescent probes, can solve problems affecting the accuracy of detection results, fluorescence quenching, etc., and achieve the effects of improving diagnostic accuracy, easy cell uptake, and low cytotoxicity

Active Publication Date: 2021-09-17
RUIJIN HOSPITAL AFFILIATED TO SHANGHAI JIAO TONG UNIV SCHOOL OF MEDICINE
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, most of these probes have the aggregation fluorescence quenching (ACQ) effect, that is, the fluorescence is quenched in the solid state and in the aggregated state, which affects the accuracy of the detection results.

Method used

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  • Zinc-aluminum ion recognition fluorescent probe as well as preparation method and application thereof
  • Zinc-aluminum ion recognition fluorescent probe as well as preparation method and application thereof
  • Zinc-aluminum ion recognition fluorescent probe as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Example 1: Synthesis and characterization of fluorescent probes

[0034] The synthesis of ligand fluorescent probe HL is as follows: figure 1 shown. It is obtained by a simple condensation reaction of 3,4,5-tribenzyloxybenzohydrazide and salicylaldehyde. 3,4,5-tribenzyloxybenzohydrazide is prepared in two steps using methyl gallate as the initial raw material. First, methyl gallate and benzyl chloride are used as an acid-binding agent in potassium carbonate. Substitution to methyl 3,4,5-tribenzyloxybenzoate followed by hydrazinolysis of methyl 3,4,5-tribenzyloxybenzoate to 3,4,5-tribenzyloxybenzoyl Hydrazine, and at the same time, the ligand fluorescent probe was characterized by NMR and other means to confirm that we had obtained a very pure product, and the fluorescent probe NMR characterization was as follows: figure 2 shown.

[0035] Synthesis of ethyl 3,4,5-tribenzyloxybenzoate (corresponding to a)

[0036] Ethyl 3,4,5-trihydroxybenzoate (4.6 g, 0.025 mole) a...

Embodiment 2

[0041] Example 2: Research on Spectral Behavior and Specificity of Fluorescent Probe HL in Response to Zinc and Aluminum Ions

[0042] A 2 mM methanol solution of the fluorescent probe was prepared, and then diluted 100 times to obtain a HL methanol solution with a concentration of 20 μM. Various metal ion aqueous solutions with a concentration of 20 μM were obtained by using different metal nitrate configurations. The aqueous solution of metal ions was added dropwise to the 20 μM HL methanol solution, and the changes in the ultraviolet absorption spectrum and fluorescence emission spectrum of the fluorescent probe methanol solution were recorded. After the titration is completed, continue to drop 20 μM zinc and aluminum ion aqueous solution in the above mixed solution, and further record the change of the fluorescence spectrum. At the same time, the HL solution with a concentration of 20 μM was added with constant concentrations of zinc and aluminum ion aqueous solutions, an...

Embodiment 3

[0043] Example 3: Responsive imaging and monitoring of zinc and aluminum ions in cells

[0044] PC-3 prostate cancer was divided into 2 groups and spread in 12-well cell culture plate at a cell density of 80,000 cells per well, and adhered to the wall overnight. After the cells adhered to the wall, the old medium was removed, and one group was added with pure fresh medium for culture, and the other group was added with fresh medium of 20 μM zinc ions and aluminum ions respectively, and then continued to incubate for 30 minutes. After the incubation is complete, remove the medium, wash the cells twice with fresh medium, add 20 μM fluorescent probe medium solution (DMSO is the most co-solvent, the concentration is less than 1 / 1000) to the cells in the two groups, and incubate the cells again After 30 minutes, the culture medium was removed, and the cells were washed twice with PBS, and the cells were observed with a fluorescence microscope. The results were as follows: Figure ...

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Abstract

The invention provides a zinc-aluminum ion recognition fluorescent probe as well as a preparation method and application thereof. The molecule of the fluorescent probe contains a Schiff base structure and three benzyl groups. The zinc-aluminum ion fluorescent probe provided by the invention has the characteristics of double mechanisms, double response, high sensitivity, high specificity, no influence of other metal ions, easiness in cellular uptake, low cytotoxicity and the like. The probe is applied to peripheral blood of a prostate cancer patient, the zinc content in serum can be quantitatively detected, and valuable information is provided for diagnosis of a suspected prostate cancer patient. The probe is combined with prostate cancer serum PSA detection, so that the diagnosis accuracy of prostate cancer can be effectively improved, puncture diagnosis requirements of patients with serum PSA in a gray range are avoided, and excessive diagnosis and excessive treatment are avoided.

Description

technical field [0001] The invention relates to the technical field of fluorescent probes, in particular to a zinc-aluminum ion-recognizing fluorescent probe and a preparation method and application thereof. Background technique [0002] Prostate cancer is the cancer with the highest prevalence rate in men, and the incidence rate has a clear trend of younger in recent years. In a normal prostate gland, the glandular cell structure is complete, the glandular function is normal, and the PSA level in the serum is generally lower than 1ng / mL. However, when prostate cancer occurs, the morphology and structure of prostate cells and tissues are destroyed, causing the antigens on the cell surface to leak into the serum, and the serum PSA level increases. Therefore, patients with prostate cancer generally have higher serum PSA levels than normal patients. Although serum PSA content is considered to be an important diagnostic biomarker for prostate cancer, since some benign prostati...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C251/86C07C249/16C07C241/04C07C243/38C09K11/06G01N21/64
CPCC07C251/86C07C249/16C07C241/04C09K11/06G01N21/6428G01N21/6486C09K2211/1007C07C243/38
Inventor 李培勇芦鑫淼秦敬灿朱新远
Owner RUIJIN HOSPITAL AFFILIATED TO SHANGHAI JIAO TONG UNIV SCHOOL OF MEDICINE
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