Preparation method of near-infrared cyanine dye

A cyanine dye and near-infrared technology, which is applied in the field of preparation of near-infrared cyanine dyes, can solve the problems of reduced performance, limited practical application, poor photostability, etc., and achieves the effect of improving photostability

Active Publication Date: 2018-12-21
BEIJING TIANGANG AUX CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Heptamethine indocyanine dye is one of the cyanine dyes with longer absorption and emission wavelengths, and it has been reported that it can be used not only for tumor imaging, but also for photodynamic and photothermal therapy of tumors. However, due to its photostable The performance is poor, so that its performance gradually decreases during use, which greatly limits its practical application

Method used

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  • Preparation method of near-infrared cyanine dye
  • Preparation method of near-infrared cyanine dye
  • Preparation method of near-infrared cyanine dye

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Preparation of near-infrared cyanine dyes with good photostability, R 1 for hydrogen, R 2 is hydrogen, X - For iodide ion, n=1.

[0033] Synthesis of Compound A:

[0034]

[0035] Add N,N-dimethylformamide (14.62g, 200mmol) into a 250mL two-neck round-bottomed flask, cool in an ice-salt bath until the solution temperature is below 5°C, and add phosphorus oxychloride (15.33g, 100 mmol) was slowly added dropwise into a round bottom flask, and the temperature of the solution was controlled to maintain at 0-5°C. After stirring for 10 minutes, add cyclohexanone (9.81g, 100mmol) dropwise into the round bottom flask, control the temperature of the solution at 0-5°C, remove the ice bath and then stir for 10 minutes, then raise the temperature to 70°C for 2 hours . After the reaction solution was cooled to room temperature, it was slowly poured into 500 mL of ice-water mixture, and a yellow solid was precipitated, which was allowed to stand overnight. Suction filtration...

Embodiment 2

[0047] Preparation of near-infrared cyanine dyes with good photostability, R 1 for hydrogen, R 2 is methyl, X - For iodide ion, n=1.

[0048] Synthesis of Compound A:

[0049]

[0050] Add N,N-dimethylformamide (54.82g, 750mmol) into a 250mL two-necked round-bottomed flask, cool in an ice-salt bath until the solution temperature is below 5°C, and add phosphorus oxychloride (23.00g, 150 mmol) was slowly added dropwise into a round bottom flask, and the temperature of the solution was controlled to maintain at 0-5°C. After stirring for 15 minutes, add cyclohexanone (4.91g, 50mmol) dropwise into the round bottom flask, control the temperature of the solution at 0-5°C, remove the ice bath and stir for 15 minutes, then raise the temperature to 60°C for 6 hours . After the reaction solution was cooled to room temperature, it was slowly poured into 500 mL of ice-water mixture, and a yellow solid was precipitated, which was allowed to stand overnight. Suction filtration obtai...

Embodiment 3

[0062] Preparation of near-infrared cyanine dyes with good photostability, R 1 for hydrogen, R 2 is methoxy, X - For iodide ion, n=1.

[0063] Synthesis of Compound A:

[0064]

[0065] Add N,N-dimethylformamide (36.55g, 500mmol) into a 250mL two-necked round-bottomed flask, cool in an ice-salt bath until the solution temperature is below 5°C, and add phosphorus oxychloride (15.33g, 100 mmol) was slowly added dropwise into a round bottom flask, and the temperature of the solution was controlled to maintain at 0-5°C. After stirring for 20 minutes, add cyclohexanone (9.81g, 100mmol) dropwise into the round bottom flask, control the temperature of the solution at 0-5°C, remove the ice bath and stir for 30 minutes, then raise the temperature to 70°C for 8 hours . After the reaction solution was cooled to room temperature, it was slowly poured into 500 mL of ice-water mixture, and a yellow solid was precipitated, which was allowed to stand overnight. Suction filtration obt...

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Abstract

The invention discloses a preparation method and application of a near-infrared cyanine dye with high photo-stability. A structural formula of the dye is shown in the formula I as shown in the specification, wherein R1 is any of hydrogen, methyl and carboxyl, R2 is any of hydrogen, methyl and alkoxy, X<-> is any of an iodide ion and a bromide ion, n is any integer between 1 and 5. According to thedye, a hindered piperidine structure unit is introduced into a heptamethine indocyanine matrix through chemical bonding, so that the obtained dye is good in photo-stability and capable of absorptionand emission in a near-infrared region, has good photo-sensitive and photo-thermal properties, and further has good application prospects in fields such as textile coloring, near-infrared fluorescenceimaging, photo-dynamic therapy and photo-thermal therapy.

Description

technical field [0001] The invention relates to the technical field of organic dyes, in particular to a method for preparing a class of near-infrared cyanine dyes with good photostability. The near-infrared cyanine dyes are obtained by introducing hindered piperidine groups into traditional heptamethine indocyanine dyes. , significantly improved its light stability and improved its application performance. Background technique [0002] Since the discovery of cyanine dyes in 1865, these dyes have gradually occupied an important position in the application of photographic sensitization and other high-tech fields. It is different from traditional dyes, because of its poor photostability and prone to photobleaching, it cannot be used for dyeing fabrics. In the initial research, its main use was as a photosensitive material to expand the photosensitive range of silver halide and improve the photosensitivity. However, with the deepening of its research in recent years, it was fou...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/08C09K11/06A61K49/00A61K41/00A61P35/00
CPCA61K41/0052A61K41/0057A61K49/0032A61P35/00C09B23/086C09K11/06C09K2211/1007C09K2211/1029
Inventor 赵莉杨东升
Owner BEIJING TIANGANG AUX CO LTD
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