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Heptamethine carboxyl indocyanine dye, preparation method and application thereof

A technology of heptamethine carboxyl and indole cyanine, applied in the direction of methine/polymethine dyes, organic dyes, chemical instruments and methods, etc., can solve the problems of large consumption of organic solvents, high price, low purity, etc.

Pending 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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  • Heptamethine carboxyl indocyanine dye, preparation method and application thereof
  • Heptamethine carboxyl indocyanine dye, preparation method and application thereof
  • Heptamethine carboxyl indocyanine dye, preparation method and application thereof

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preparation example Construction

[0148] As mentioned above, the present application relates to a preparation method of heptamethine carboxy indole cyanine dye, comprising the following steps: reacting 2,3,3-trimethyl-carboxy indole derivatives with nucleophilic substitution compounds to obtain organic Ammonium salt: mix organic ammonium salt and cycloalkene derivatives in an environment-friendly organic solvent for reaction, add an organic precipitant to the product after cooling and let it stand overnight to obtain the heptamethene carboxyindole 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 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 heptamethine carboxyindole cyanine dyes.

[0149] In addition, the preparation method of t...

Embodiment 1

[0156] Example 1 Synthesis of 2,3,3-trimethyl-4-carboxyindole

[0157] Dissolve p-carboxyphenylhydrazine, 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-carboxyindole.

Embodiment 2

[0158] Embodiment 2 synthetic compound 53

[0159] Compound 53 was synthesized according to the following route:

[0160]

[0161] 1) Synthesis of 2,3,3-trimethyl-1-(butane)-carboxyindole

[0162] The 2,3,3-trimethyl-carboxyindole and 4-bromobutane obtained in Example 1 were added into the reactor at a molar ratio of 1:1.5, and the reactor was sealed and then evacuated to 10 Pa. 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.

[0163] 2) Synthesis and purification of compound 53

[0164] Add 2-chloro-1-formyl-3 to the reactor in a molar ratio of 1:2.5 to 2,3,3-trimethyl-1-(butane)-carboxyindole obtained in step 1) -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 ...

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Abstract

The invention discloses a heptamethine carboxyl 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 heptamethine carboxyl indocyanine dye is represented by a formula (I), and the dye has near-infrared light absorption and fluorescence development properties, and can beused as a probe auxiliary agent. 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-carboxyl indole 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. 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 heptamethine carboxy indole cyanine dye and its preparation method and application, belonging 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
CPCA61K49/0032C07D209/10C09B23/0066C09B23/08C09K11/06C09K2211/1007C09K2211/1029G01N21/643A61K49/00C07D209/60C09B23/10G01N21/64
Inventor 吴爱国蒋振奇袁博李娟
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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