Heptamethane sulfonic indocyanine dye, preparation method and application thereof

A technology for heptamethinesulfonic acid-based indocyanines and dyes, which is applied in the directions of methine/polymethine-based dyes, organic dyes, chemical instruments and methods, and can solve the problems of high price, high consumption of organic solvents, low purity, etc question

Inactive Publication Date: 2020-09-15
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • 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 process of its different derivatives requires a lot of condition screening and consumes a lot of organic solvents, and most of the selected solvents are highly toxic solvents, such as o-dichlorobenzene, toluene, benzene, etc.

Method used

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  • Heptamethane sulfonic indocyanine dye, preparation method and application thereof
  • Heptamethane sulfonic indocyanine dye, preparation method and application thereof
  • Heptamethane sulfonic indocyanine dye, preparation method and application thereof

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preparation example Construction

[0143] As mentioned above, the present application relates to a preparation method of heptamethinesulfonate indole cyanine dye, comprising the following steps: 2,3,3-trimethyl-sulfonate indole derivative and nucleophilic substitution The compound is reacted to obtain an organic ammonium salt; the organic ammonium salt and cycloalkene derivatives are mixed in an environment-friendly organic solvent for reaction, and after the reaction, an organic precipitant is added to the product to cool and stand overnight to obtain the heptamethinesulfonyl indole Cyanine dyes. The method has the advantages of short synthesis route, simple process, no catalyst, high yield, simple purification method, high atom utilization rate and less consumption of organic solvents, can greatly improve the preparation efficiency of such dyes, and realize low-cost mass production , It is of great significance in the production and application research of heptamethinesulfonate indole cyanine dyes.

[0144] ...

Embodiment 1

[0151] Example 1 Synthesis of 2,3,3-trimethyl-4-sulfonic indole

[0152] Dissolve p-sulfophenylhydrazine, 3-methyl-2-butanone, and anhydrous sodium acetate at a molar ratio of 1:1.1:1.5 in acetic acid, and react under reflux and stirring for 8 hours. The reaction solvent was removed by rotary evaporation, and then a mixed solution of water and methanol with a volume ratio of 9:1 was added to dissolve the remaining substances. The resultant was filtered, and then exposed to crystallization at room temperature for 48 hours to obtain crystal 2,3,3-trimethyl-4-sulfonylindole.

Embodiment 2

[0153] Embodiment 2 synthetic compound 53

[0154] Compound 53 was synthesized according to the following route:

[0155]

[0156] 1) Synthesis of 2,3,3-trimethyl-1-(butane)-sulfonyl indole

[0157] In the reactor, add 2,3,3-trimethyl-sulfonyl indole and 4-bromobutane obtained in Example 1 with a molar ratio of 1:1.5, and vacuumize the reactor to 10Pa after sealing . The reaction system was heated to 110° C. and stirred for 8 hours, then cooled to room temperature. The obtained product was filtered with suction and used directly for the next reaction.

[0158] 2) Synthesis and purification of compound 53

[0159] Add 2,3,3-trimethyl-1-(butane)-sulfonylindole molar ratio of 1:2.5 2-chloro-1-formyl- 3-Hydroxymethylenecyclopentene. After completely dissolving with methanol, the reaction system was heated to 75° C. for 24 hours under closed conditions, then cooled to room temperature, and placed in a 4° C. refrigerator for 24 hours. Petroleum ether was added, then allowe...

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Abstract

The invention discloses a heptamethine sulfonic indocyanine dye, a preparation method and application thereof, and belongs to the field of polymethine indocyanine dyes and preparation thereof, whereinthe structural formula of the heptamethane sulfonic indocyanine dye is represented by a formula (I), and the dye has near-infrared light absorption and fluorescence development performance and can beapplied to probe aids. The preparation method of the dye comprises the following steps: 1) carrying out a heating reaction on raw materials containing a 2,3,3-trimethyl-sulfonic indole derivative anda 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 inthe step (1) and a cycloalkene derivative under a closed condition. The method has the advantages of short synthesis route, environment-friendly solvent, simple process, avoidance of noble metal catalysis, high yield, high purity and the like, is high in applicability, and can be used for synthesizing products of various structure types.

Description

technical field [0001] The application relates to a heptamethinesulfonate indole cyanine dye, its preparation method and application, 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 diagnostic 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 multiple modifiable s...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/08C07D209/10C09K11/06G01N21/64A61K49/00
CPCA61K49/0032C07D209/10C09B23/0066C09B23/08C09K11/06C09K2211/1007C09K2211/1029G01N21/643
Inventor 李娟袁博吴爱国蒋振奇
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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