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Heptamethine indocyanine dye as well as preparation method and application thereof

A technology of heptamethine indocyanine and indocyanine, which is applied in the field of heptamethine indocyanine dye and its preparation, can solve the problems of limited wide application, poor photostability, low photothermal conversion efficiency, etc., and achieves many chemical sites. , The effect of improving photothermal stability and clarifying biodegradation pathways

Active Publication Date: 2021-10-01
YANSHAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, indocyanine green (ICG) has poor photostability and low photothermal conversion efficiency, which limits its wide application.

Method used

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  • Heptamethine indocyanine dye as well as preparation method and application thereof
  • Heptamethine indocyanine dye as well as preparation method and application thereof
  • Heptamethine indocyanine dye as well as preparation method and application thereof

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preparation example Construction

[0076] The invention provides the preparation method of above-mentioned heptamethine indocyanine dye, comprises the following steps:

[0077] ①When R 1 for When, the preparation method of described heptamethine indocyanine dye comprises the following steps:

[0078] A compound having a structure shown in formula a is reacted with a compound having a structure shown in formula b to obtain a compound having a structure shown in formula c;

[0079]

[0080] A compound having a structure shown in formula c undergoes a nucleophilic substitution reaction with a nucleophile to obtain a heptamethine indocyanine dye;

[0081] The nucleophile has a structure shown in formula d-1, formula d-2 or formula d-3;

[0082]

[0083] In the present invention, the preparation method of the compound having the structure shown in formula a preferably includes the following steps:

[0084] Phosphorus oxychloride is mixed with N'N-dimethylformamide to obtain Vilsmeier-Haack weak nucleophil...

Embodiment 1

[0133] (1) Preparation of compound (compound 1) shown in formula a

[0134] Add 1 mL of POCl to 1.2 mL of anhydrous DMF at 2 °C 3 After reacting for 30min, add 0.5mL cyclohexanone, heat and reflux for 1h; then cool to 20°C, add 2.9mL aniline / ethanol mixture dropwise, the molar ratio of aniline and ethanol in the mixture is 1:1; after stirring for 1.5 hours, pour into concentrated HCl, recrystallized in an ice-water bath, filtered, washed, and vacuum-dried to obtain 1.044 g of compound 1 with a yield of 61%.

[0135] LCMS(ESI+): Calculated [M+H] + 323.1, measured to 323.1.

[0136] Synthetic route is as shown in formula D:

[0137]

[0138] (2) Preparation of compound (compound 2) shown in formula b

[0139] Toluene, 1.3g 1,1,2-trimethyl-1H-benzo[e]indole and 1.1mL 1,3-propane sultone were heated to reflux for 18 hours; cooled to room temperature, the obtained blue crystals were filtered , washed with diethyl ether, the product was recrystallized with methanol and dieth...

Embodiment 2

[0154] Weigh 200 mg heptamethine indole cyanine dye Cy1, add 10 mL of a mixture of trifluoroacetic acid (TFA) and water, stir at room temperature for 4 hours, evaporate the solvent to dryness, add ethyl acetate and stir, filter and dry under vacuum The crude product was obtained, and then separated and purified by column chromatography to obtain the heptamethine indocyanine dye Cy2.

[0155] LCMS(ESI+): Calculated [M+H] + 886.3; 886.3 detected.

[0156] The synthetic route is shown in formula H:

[0157]

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Abstract

The invention provides a heptamethine indocyanine dye as well as a preparation method and an application thereof, and belongs to the technical field of fine chemical engineering. The heptamethine indocyanine dye provided by the invention has a structure as shown in a formula 1, has strong near-infrared absorption in a near-infrared region, and has good light stability and photo-thermal conversion efficiency, and the photo-thermal conversion rate and photo-thermal stability of the heptamethine indocyanine dye are obviously improved compared with indocyanine green. Meanwhile, the heptamethine indocyanine dye provided by the invention has a good fluorescence property. The heptamethine indocyanine dye disclosed by the invention belongs to small organic molecules, has low cytotoxicity and multiple chemical sites, and is easy to further design and synthesize functional molecules; and has good biocompatibility, is easy to remove in a living body, has a clear biodegradation pathway, and can be applied to the fields of biomarkers, optical imaging, photo-thermal imaging, photo-acoustic imaging, photodynamic therapy and photo-thermal therapy.

Description

technical field [0001] The invention relates to the technical field of fine chemicals, in particular to a heptamethine indocyanine dye and a preparation method and application thereof. Background technique [0002] Photothermal material is a kind of light energy that is absorbed by the surface localized plasmon resonance effect and converted into kinetic energy of electron or hole resonance, or energy generated by electronic transition, and the vibration energy scattered by the lattice is transmitted to the surrounding environment so that the environment A material whose temperature increases has been extensively studied in the field of photothermal therapy. [0003] An ideal near-infrared photothermal material should have strong near-infrared absorption and good stability, and can effectively convert the absorbed near-infrared light energy into heat energy, that is, have a high photothermal conversion efficiency. Near-infrared photothermal materials are divided into inorga...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C09B23/08C09K11/06G01N21/64A61K49/00A61K41/00
CPCC09B23/086C09B23/0066C09K11/06A61K49/0032A61K41/008G01N21/6428C09K2211/1007C09K2211/1029
Inventor 杨靓月郭英杰王兴宗李响晋腾达唐煜文
Owner YANSHAN UNIV
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