Near-infrared fluorescent molecular probe and synthesis method and application thereof

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 low quantum yield, instability, leakage, etc., to enhance molecular fluorescence intensity, increase Large conjugated system, the effect of increasing the stock displacement

Active Publication Date: 2017-03-15
SOUTHEAST UNIV
View PDF4 Cites 3 Cited by
  • 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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Near-infrared fluorescent molecular probe and synthesis method and application thereof
  • Near-infrared fluorescent molecular probe and synthesis method and application thereof
  • Near-infrared fluorescent molecular probe and synthesis method and application thereof

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-2-hydroxymethyl Cyclohexene and 30ml of n-butanol: mixed solvent of toluene (v / v) = 7:3 were added to a 100ml reaction flask, and under the protection of argon, the reaction was heated at reflux at 75°C for 5h. At room temperature, after concentration under reduced pressure, add methyl tert-butyl ether of 3 times the volume of the concentrated reaction solution, filter, and separate and purify the filter cake with column chromatography (silica gel column, the specification of silica gel is 200-300 mesh), and the eluent is A mixed solution of dichloromethane and...

Embodiment 2

[0041](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.

[0042] (2) Take 2.76mmol 1-m-fluorobenzyl-2,3,3-trimethyl-3H-indoline-5-sulfonic acid, 1.38mmol 2-chloro-1-formyl-2-hydroxymethyl Cyclohexene and 20ml of pyridine were added to a 100ml reaction bottle, and under the protection of argon, heated to reflux at 75°C for 8 hours. After the reaction was completed, the temperature was lowered to room temperature, concentrated under reduced pressure, and then added 4 times the volume of the concentrated reaction solution MTBE was filtered, and the filter cake was separated and purified by column chromatography (silica gel column, the specification...

Embodiment 3

[0046] (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.

[0047] (2) Take 2.76mmol 1-m-fluorobenzyl-2,3,3-trimethyl-3H-indoline-5-sulfonic acid, 1.38mmol 2-chloro-1-formyl-2-hydroxymethyl Cyclohexene, 2.76mmol of anhydrous sodium acetate and 20ml of absolute ethanol were added to a 100ml reaction bottle, under the protection of argon, heated at reflux at 75°C for 4h, after the reaction was completed, lowered to room temperature, and concentrated under reduced pressure Add methyl tert-butyl ether of 5 times the volume of the concentrated reaction solution, filter, and the filter cake is separated and purified by column chromatography (silic...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

PUM

No PUM Login to view more

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

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to view more

Application Information

Patent Timeline
no application Login to view more
Patent Type & Authority Applications(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
Who we serve
  • R&D Engineer
  • R&D Manager
  • IP Professional
Why Eureka
  • Industry Leading Data Capabilities
  • Powerful AI technology
  • Patent DNA Extraction
Social media
Try Eureka
PatSnap group products

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic.

© 2024 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap