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A heptamethine near-infrared fluorescent molecular probe and its preparation method and application

A technology of fluorescent molecular probe, heptamethine, which is applied in the preparation of the molecular probe and the application field of cell imaging, can solve problems such as instability, low quantum yield, leakage, etc., and achieve enhanced molecular fluorescence intensity, High sensitivity, increase the effect of stock displacement

Active Publication Date: 2019-05-31
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the application of ICG also has certain limitations such as low quantum yield, photoinstability in vivo, and leakage in blood vessels, etc.

Method used

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  • A heptamethine near-infrared fluorescent molecular probe and its preparation method and application
  • A heptamethine near-infrared fluorescent molecular probe and its preparation method and application
  • A heptamethine near-infrared fluorescent molecular probe and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0037] Add 3.21mmol of compound 1 (2,3,3-trimethyl-3H-indoline-5-sulfonate potassium), 4.17mmol of compound 2 (p-nitrobenzyl bromide) and 10ml of toluene in batches to a 50ml one-necked flask , under the protection of argon, reacted at 90°C for 16h, cooled to room temperature, filtered, washed with toluene, and dried in vacuo to obtain 0.94g brownish red solid (compound 3, 1-p-nitrobenzyl-2,3,3-tri Methyl-3H-indoline-5-sulfonic acid), yield 78.3%.

[0038] Take 1.98mmol of compound 3 and 0.99mmol of compound 4 (2-chloro-1-formyl-3-hydroxymethylenecyclohexene) into a 100ml reaction flask, add 30ml of n-butanol:toluene=7:3 In the mixed solvent, under the protection of argon, heat and reflux at 75°C for 6 hours. The solution turns from light red to deep red, and finally a large number of green components appear. After cooling down to room temperature, add 3 times the volume of the concentrated reaction solution after concentrating under reduced pressure. Diethyl ether was filter...

Embodiment 2

[0044] Add 3.21mmol of compound 1 (2,3,3-trimethyl-3H-indoline-5-sulfonate potassium), 8.34mmol of compound 2 (p-nitrobenzyl bromide) and 10ml of toluene in batches to a 50ml one-necked flask , under the protection of argon, reacted at 90 ° C for 15 h, cooled to room temperature, filtered, washed with toluene, and dried in vacuo to obtain 0.92 g of a brownish red solid (compound 3, 1-p-nitrobenzyl-2,3,3-tri methyl-3H-indoline-5-sulfonic acid).

[0045] Take 1.98mmol of compound 3 and 0.99mmol of compound 4 (2-chloro-1-formyl-3-hydroxymethylenecyclohexene) and add it to a 100ml reaction flask, add 30ml of absolute ethanol solvent, and then add 1.98mmol of Anhydrous sodium acetate was used as a catalyst, under the protection of argon, reflux reaction at 75°C for 4 hours, the reaction solution was brown, lowered to room temperature, concentrated under reduced pressure, added ether with 4 times the volume of the concentrated reaction solution, filtered, and used for filter cake Sep...

Embodiment 3

[0049] Add 3.21mmol compound 1 (2,3,3-trimethyl-3H-indoline-5-potassium sulfonate), 12.51mmol compound 2 (p-nitrobenzyl bromide) and 15ml toluene in batches to a 50ml one-necked flask , under the protection of argon, reacted at 85°C for 36h, cooled to room temperature, filtered, washed with toluene, and dried in vacuo to obtain 0.88g brownish red solid (compound 3, 1-p-nitrobenzyl-2,3,3-tri methyl-3H-indoline-5-sulfonic acid).

[0050] Get 1.98mmol of compound 3 and 0.99mmol of compound 4 (2-chloro-1-formyl-3-hydroxymethylenecyclohexene) and join in a 100ml reaction flask, add 30ml of pyridine as a reaction solvent, under the protection of argon reflux at 75°C for 8 hours, lower to room temperature, concentrate under reduced pressure, add 5 times the volume of diethyl ether of the concentrated reaction solution, filter, and separate the filter cake by column chromatography (silica gel column, the specification of silica gel is 200-300 mesh) For purification, the eluent was a ...

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Abstract

The invention discloses a heptamethine cyanine near-infrared fluorescent molecular probe and a preparation method and application thereof. The structure of the near-infrared fluorescent molecular probe is as shown in the formula (V). The preparation method includes the following steps: allowing 2,3,3-trimethyl-3H-indoline-5-sulfonate to react with p-nitrobenzylbromide in an organic solvent under the protection of inert gases to obtain a compound shown in the formula (III); allowing the compound shown in the formula (III) to react with 2-chlorine-1-formyl-2-hydroxymethyl cyclohexene in an organic solvent under the protection of inert gases to obtain a compound shown in the formula (V). The invention further discloses the application of the near-infrared fluorescent molecular probe in living cell imaging. The near-infrared fluorescent molecular probe is novel in structure, can enhance the fluorescence intensity and improves the cell imaging effect.

Description

technical field [0001] The invention belongs to the field of biochemical detection, and in particular relates to a new near-infrared fluorescent molecular probe, and also relates to a preparation method of the molecular probe and its application in cell imaging. Background technique [0002] Near-infrared (NIR) fluorescence imaging technology has a wide range of applications in cell biology, pharmacology, and disease diagnosis. As a non-invasive diagnostic technology, near-infrared fluorescence imaging technology has the advantages of non-radiation, non-destructive, real-time and on-site detection of biological information. Many organisms and their tissues emit fluorescence under the excitation of visible light, which seriously interferes with the fluorescence detection and imaging of biological samples. The maximum absorption wavelength and emission wavelength of near-infrared fluorescent probes are 600-900nm, which can avoid background interference. Therefore, near-infrar...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/10C09K11/06G01N21/64
CPCC07D209/10C09K11/06C09K2211/1007C09K2211/1029G01N21/6428G01N21/6486
Inventor 吉民王影邢静蔡进陈峻青
Owner SOUTHEAST UNIV
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