Preparation method and application of heptamethine indocyanine dye

A technology for heptamethine indocyanine and indocyanine, which is applied in the field of polymethine indocyanine dyes and their preparation, can solve the problems of high price, high consumption of organic solvents, low purity and the like, and achieves improved preparation efficiency , No need for noble metal catalysis, the effect of large single reaction volume

Active Publication Date: 2020-09-15
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
View PDF6 Cites 3 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the heptamethine indole cyanine sold in the market is only a new indocyanine green (IR-820), and the purity is low (80%), and the price is high (1324 yuan/g)
At the same time, the production and purification ...

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
  • Preparation method and application of heptamethine indocyanine dye
  • Preparation method and application of heptamethine indocyanine dye
  • Preparation method and application of heptamethine indocyanine dye

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0136] As mentioned above, the present application relates to a preparation method of heptamethine indole cyanine dye, comprising the following steps: reacting 2,3,3-trimethylindole derivatives with nucleophilic substitution compounds to obtain organic ammonium salts; The organic ammonium salt and cycloalkene derivatives are mixed in a green organic solvent for reaction, after the reaction, an organic precipitant is added to the product to cool and stand overnight to obtain the heptamethine indole cyanine dye. The method has the advantages of short synthesis route, simple process, no catalyst, high yield, simple purification method, high atom utilization rate and less organic solvent consumption, which greatly improves the preparation efficiency of this type of dye, and can realize low-cost mass production. It is of great significance in the production and application research of heptamethine indole cyanine dyes.

[0137] In addition, according to the preparation method of the...

Embodiment 1

[0144] Example 1 Synthesis of compound 53

[0145] Compound 53 was synthesized according to the following route:

[0146]

[0147] 1) Synthesis of 2,3,3-trimethyl-1-(butane)-indole

[0148] Add 2,3,3-trimethylindole and 4-bromobutane in a molar ratio of 1:1.5 into the reactor, seal it and pump it to 10Pa, heat it to 110°C and stir it for 8 hours, cool it to room temperature and pump it The resulting product was filtered and directly carried out to the next reaction.

[0149] 2) Synthesis and purification of compound 53

[0150] Add 2-chloro-1-formyl-3-hydroxyl in a molar ratio of 1:2.5 to the 2,3,3-trimethyl-1-(butane)-indole obtained in step 1) into the reactor After completely dissolving methylenecyclopentene with methanol, heat it to 75°C for 24 hours under closed conditions and then cool down to room temperature. Put the reaction system in a refrigerator at 4°C and let it stand for 24 hours. filtered, and then vacuum-dried the obtained solid to obtain the product comp...

Embodiment 2

[0152] Example 2 Synthesis of compound 26

[0153] Compound 26 was synthesized according to the following route:

[0154]

[0155] 1) Synthesis of 2,3,3-trimethyl-1-(p-methylbenzoic acid)-indole

[0156] Add 2,3,3-trimethylindole and p-bromomethylbenzoic acid with a molar ratio of 1:1.5 into the reactor, pump it to 10Pa after sealing, heat to 110°C and stir for 12 hours, cool to room temperature The obtained product was suction filtered, and the next step reaction was carried out directly.

[0157] 2) Synthesis and purification of compound 26

[0158] Add 2,3,3-trimethyl-1-(p-methylbenzoic acid)-indole molar ratio of 1:2.5 2-chloro-1-formyl- 3-Hydroxymethylenecyclohexene, after being completely dissolved in methanol, heated to 75°C for 24 hours under closed conditions, then cooled to room temperature, put the reaction system in a refrigerator at 4°C for 24 hours, then added petroleum ether to stand After suction filtration, the obtained solid was vacuum-dried to obtain ...

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 preparation method and application of a heptamethine indocyanine dye, and belongs to the field of polymethine indocyanine dyes and preparation thereof. The method comprises the following steps: 1) carrying out a heating reaction on raw materials containing a 2,3,3-trimethylindole derivative and a nucleophilic substituted compound under a vacuum condition to obtain an organic ammonium salt; and 2) carrying out a heating reaction on a solution containing the organic ammonium salt obtained in the step 1) and a cycloalkene derivative under a closed condition. According tothe invention, the structural formula of the heptamethine indocyanine dye is represented by a formula (I); the dye has near-infrared light absorption and fluorescence development performances and canbe used as a probe auxiliary agent; and the method is short in synthetic route, green in solvent, simple in process, free of noble metal catalysis, large in single reaction amount, high in product yield and purity, high in universality and capable of being used for synthesizing products of various structure types.

Description

technical field [0001] The application relates to a preparation method of heptamethine indole cyanine dye and the application of the dye, and belongs to the field of polymethine indole cyanine dye and its preparation. Background technique [0002] The indocyanine green in the heptamethine cyanine dye is the only near-infrared dye approved by the US Food and Drug Administration for clinical photothermal therapy, and its derivative new indocyanine green belongs to the heptamethine indocyanine dye kind of. This type of dye has a strong absorption effect in the near-infrared region around 808nm, which can be used as a complement to other medical diagnosis and treatment methods (such as MRI, PET, SPECT, ultrasound echo scanning technology, radiography and tomography) Imaging technology, also used as a photosensitizer for photothermal therapy, has important research and application value in life science and biomedical research. [0003] Heptamethine indole cyanine dyes have mult...

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
IPC IPC(8): C09B23/08C09K11/06G01N21/64
CPCC09B23/086C09K11/06G01N21/6458C09K2211/1029C09K2211/1007
Inventor 李娟袁博蒋振奇吴爱国
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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