Tumor-targeting near-infrared fluorescent probe and preparation method thereof

A technology of tumor-targeting and fluorescent probes, which is applied in the field of tumor-targeting near-infrared fluorescent probes and its preparation, can solve problems such as lack of selectivity, unfavorable detection and analysis, and inability to achieve specific labeling of target proteins. The effect of improving specificity and sensitivity

Inactive Publication Date: 2018-10-02
WUHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, cyanine dyes are non-specific fluorescent probes, and their fluorescent labeling is only realized by reacting with some active groups, which lacks specific selectivity and is not conducive to detection and analysis.
Especially in the complex human body, it is impossible to achieve specific labeling of the target protein. Therefore, it is necessary to develop specific small molecule fluorescent probes with small molecular weight, good membrane permeability, low background noise and easy preparation to meet the requirements of detection and analysis. actual needs

Method used

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  • Tumor-targeting near-infrared fluorescent probe and preparation method thereof
  • Tumor-targeting near-infrared fluorescent probe and preparation method thereof
  • Tumor-targeting near-infrared fluorescent probe and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Example 1: Synthesis of 1-(4-sulfobutyl)-2,3,3-trimethyl-3H-indole

[0022] Take 4.8 g of 2,3,3-trimethyl-3H-indole and 13.6 g of 1,4-butane sultone, add 40 ml of 1,2-dichlorobenzene, and heat to 120°C under nitrogen to react 8 hours, then cooled to room temperature, added 200 ml of acetone to precipitate, filtered, added an appropriate amount of methanol, and then added isopropanol to precipitate to obtain 1-(4-sulfobutyl)-2,3,3-trimethyl-3H- indole.

Embodiment 2

[0023] Example 2: Synthesis of 5-carboxy-1-(4-sulfobutyl)-2,3,3-trimethyl-3H-indole

[0024] Take 4.56 grams of hydrazinobenzoic acid, 5 grams of sodium acetate and 3.7 grams of methyl isopropyl ketone, dissolve them in 30 milliliters of glacial acetic acid, stir and react at room temperature for 1 hour, then heat to 50 ° C for 4.5 hours, and cool to room temperature. Remove the solvent by rotary evaporation under reduced pressure, wash with 20 ml of water and 2 ml of methanol, dissolve the precipitate in 20 ml of 1,2-dichlorobenzene, add 4.3 g of 1,4-butane sultone, resuspend, and heat to React at 180°C for 5 hours, then cool to room temperature, filter, wash with an appropriate amount of acetone, and dry to obtain 5-carboxy-1-(4-sulfobutyl)-2,3,3-trimethyl-3H-indole.

Embodiment 3

[0025] Example 3: Synthesis of 5-carboxylic acid-1,1'-bis-(4-sulfobutyl) sodium indole dicarbocyanine (IDCC)

[0026] Weigh 1 g of 1-(4-sulfobutyl)-2,3,3-trimethyl-3H-indole and 0.78 g of malondialdehyde bisphenylimide monohydrochloride, dissolve in 12 ml of anhydrous acetic acid , heated to 120°C and stirred for 30 minutes, cooled to room temperature and added 1.2 grams of 5-carboxy-1-(4-sulfobutyl)-2,3,3-trimethyl-3H-indole and 1 gram of acetic acid sodium, plus 12 ml of anhydrous acetic acid, heated to 120 ° C and stirred, cooled to room temperature, extracted with 150 ml of ether, filtered, purified by reverse chromatography, and freeze-dried to obtain 5-carboxylic acid-1,1'-bis -(4-sulfobutyl)indole dicarbocyanine sodium.

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Abstract

The invention provides a tumor-targeting near-infrared fluorescent probe and a preparation method thereof, and is characterized in that the fluorescent probe comprises a cyanine fluorescent dye part and a targeting carrier part; the cyanine fluorescent dye part and the targeting carrier part are coupled by covalent bonds, wherein, the cyanine fluorescent dye part comprises IDCC and ITCC, and the targeting carrier part comprises EBP molecules. After entering a body, the tumor-targeting near-infrared fluorescent probe reaches tumor tissue and is bonded with EGFR of cells, and exhibits a strong effect of targeted fluorescent labeling, thereby not only improving the specificity and the sensitivity of tumor fluorescence imaging significantly, but also providing important information for the evaluation of molecular typing and molecular targeted drug efficacy of tumors, and having strong practicality for guiding and monitoring the application of molecular targeted drugs.

Description

technical field [0001] The invention relates to the field of medical imaging, in particular to a tumor-targeting near-infrared fluorescent probe and a preparation method thereof. Background technique [0002] Fluorescence analysis is a method of qualitative and quantitative analysis that uses the characteristics of certain substances that can produce fluorescence under light irradiation. Now, this analytical method has been widely used in analytical chemistry, especially in the fields of biology and medicine. However, most biomolecules themselves have no fluorescence or weak fluorescence, and the detection sensitivity is low. In order to detect them with high sensitivity, people use fluorescent probes to label or derivatize the analytes to generate covalent or fluorescent molecules with high fluorescence intensity. For non-covalently bound substances, the detection limit can be greatly reduced by fluorescence detection. Since fluorescent probes are fluorophores designed to...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07K14/71C09K11/06G01N33/574
CPCG01N33/57492C09K11/06C07K14/71C09K2211/1466
Inventor 艾时斌黄泽波刘鑫刘永梅陈飞陈晶
Owner WUHAN UNIV
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