A kind of near-infrared fluorescent molecular probe and its synthesis method and application

A technology of fluorescent molecular probes and synthesis methods, applied in cell imaging, the field of preparation of molecular probes, can solve problems such as instability, leakage, low quantum yield, etc., to achieve increased conjugated systems, The effect of increasing the stock displacement and enhancing the fluorescence intensity of molecules

Active Publication Date: 2019-05-28
SOUTHEAST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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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 kind of near-infrared fluorescent molecular probe and its synthesis method and application
  • A kind of near-infrared fluorescent molecular probe and its synthesis method and application
  • A kind of near-infrared fluorescent molecular probe and its synthesis method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0036] (1) Add 4.47mmol 2,3,3-trimethyl-3H-indoline-5-potassium sulfonate, 5.81mmol m-fluorobenzyl bromide and 12ml toluene in batches to a 50ml one-necked flask, under the protection of argon 1.31g of 1-m-fluorobenzyl-2,3,3-trimethyl-3H-indoline-5-sulfonic acid, It is a pink solid with a yield of 84.4%.

[0037] (2) Take 2.76mmol 1-m-fluorobenzyl-2,3,3-trimethyl-3H-indoline-5-sulfonic acid, 1.38mmol 2-chloro-1-formyl-3-hydroxymethylene Cyclohexene and 30ml of n-butanol: mixed solvent of toluene (v / v) = 7:3 was added in a 100ml reaction flask, under the protection of argon, heated at reflux at 75°C for 5h, the reaction was completed, and the to room temperature, concentrated under reduced pressure, then added methyl tert-butyl ether of 3 times the volume of the concentrated reaction solution, filtered, and the filter cake was separated and purified by column chromatography (silica gel column, the specification of silica gel is 200-300 mesh), and the eluent It is a mixed solu...

Embodiment 2

[0042](1) Add 4.47mmol 2,3,3-trimethyl-3H-indoline-5-potassium sulfonate, 8.94mmol m-fluorobenzyl bromide and 24ml toluene in batches to a 50ml single-necked flask, under the protection of argon at 90°C for 16 h, cooled to room temperature, filtered, washed with toluene, and dried in vacuo to obtain 1.21 g of 1-m-fluorobenzyl-2,3,3-trimethyl-3H-indoline-5-sulfonic acid, It is a pink solid.

[0043] (2) Take 2.76mmol 1-m-fluorobenzyl-2,3,3-trimethyl-3H-indoline-5-sulfonic acid, 1.38mmol 2-chloro-1-formyl-3-hydroxymethylene Cyclohexene and 20ml of pyridine were added to a 100ml reaction flask, under the protection of argon, heated to reflux at 75°C for 8h, after the reaction was completed, lowered to room temperature, concentrated under reduced pressure and added 4 times the volume of the concentrated reaction solution The methyl tert-butyl ether, filter, filter cake is separated and purified by column chromatography (silica gel column, the specification of silica gel is 200-30...

Embodiment 3

[0047] (1) Add 4.47mmol 2,3,3-trimethyl-3H-indoline-5-potassium sulfonate, 11.62mmol m-fluorobenzyl bromide and 24ml toluene in batches to a 50ml one-necked flask, under the protection of nitrogen , reacted at 90°C for 15h, lowered to room temperature, filtered, washed with toluene, and dried in vacuo to obtain 1.28g of 1-m-fluorobenzyl-2,3,3-trimethyl-3H-indoline-5-sulfonic acid, as pink solid.

[0048] (2) Take 2.76mmol 1-m-fluorobenzyl-2,3,3-trimethyl-3H-indoline-5-sulfonic acid, 1.38mmol 2-chloro-1-formyl-3-hydroxymethylene Cyclohexene, 2.76mmol of anhydrous sodium acetate and 20ml of absolute ethanol were added to a 100ml reaction flask, under the protection of argon, heated at reflux at 75°C for 4h, the reaction was completed, cooled to room temperature, concentrated under reduced pressure After adding concentrated methyl tert-butyl ether of 5 times the volume of the reaction solution, filter, and the filter cake is separated and purified by column chromatography (silic...

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Abstract

The invention discloses a near-infrared fluorescent molecular probe and a synthesis method and application thereof. The structure of the near-infrared fluorescent molecular probe is represented by a formula (II) shown in the description. The synthesis method comprises the steps: subjecting 2,3,3-trimethyl-3H-indolin-5-sulfonate to a reaction with meta-fluorobenzyl bromide in an organic solvent under the protection of inert gas, so as to obtain a compound represented by a formula (I) shown in the description; subjecting the compound represented by the formula (I) to a reaction with 2-chloro-1-formyl-2-hydroxymethylcyclohexene in an organic solvent under the protection of inert gas, thereby obtaining the compound represented by the formula (II). The invention further discloses application of the near-infrared fluorescent molecular probe in living cell imaging. According to the near-infrared fluorescent molecular probe with a novel structure, disclosed by the invention, the fluorescence intensity can be enhanced, and the cell imaging effect is improved.

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] With the rapid development of life science research, fluorescent molecular probes have become more and more widely used in cellular immunology, molecular biology, molecular genetics, etc., and have become one of the important tools for life science research. The emission wavelength of the near-infrared fluorescent probe is 650-900nm. Compared with fluorescent molecular probes in the ultraviolet or visible light region, it has the advantages of low background fluorescence interference, strong tissue penetration and no photodamage to biological organisms. Therefore, the development of water-soluble near-infrared fluorescent probes with good biocompatibility, high quantum yield, and good c...

Claims

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Application Information

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