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Sialic acid linked indocyanine green Sia-ICG as well as preparation method and application thereof

A synthesis method and complete reaction technology, applied in the field of biomedicine and disease treatment, can solve the problems of biosafety disputes of nanocarriers, and achieve the effects of enhanced biocompatibility, excellent tumor targeting, and good in vitro performance.

Pending Publication Date: 2022-04-15
SHANDONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the biological safety of nanocarriers is still controversial, and their efficacy is usually limited by the physicochemical properties of nanoparticles, such as particle size and charge and surface modification, etc.

Method used

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  • Sialic acid linked indocyanine green Sia-ICG as well as preparation method and application thereof
  • Sialic acid linked indocyanine green Sia-ICG as well as preparation method and application thereof
  • Sialic acid linked indocyanine green Sia-ICG as well as preparation method and application thereof

Examples

Experimental program
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preparation example Construction

[0043] In yet another specific embodiment of the present invention, the synthesis method includes:

[0044] (1) Dissolve compound 1 in methanol, add CF 3 After COOH, stir until the reaction solution becomes clear, remove the solvent, and dry to obtain compound 2 (methyl sialate);

[0045] Preferably, compound 1 (sialic acid), methanol, CF 3 The mass volume ratio of COOH is: 20~30g: 300~600mL: 3~15mL;

[0046] (2) Compound 2 was dissolved in pyridine, p-toluenesulfonyl chloride was added under ice-bath conditions, and after slowly rising to room temperature, the reaction was carried out overnight; pyridine was removed, and compound 3 was obtained after purification. The structure of compound 3 was as follows:

[0047]

[0048] In yet another specific embodiment of the present invention, the molar volume ratio of compound 2 (methyl sialate), p-toluenesulfonyl chloride and pyridine is 3.0-4.5 mmol: 4.0-6.8 mmol: 7.5-16 mL;

[0049] (3) After dissolving the product obtained in...

Embodiment 1

[0087] The structural formula of the near-infrared dye-coupled sialic acid compound is:

[0088]

[0089] The preparation method of above-mentioned Sia-ICG compound, its reaction scheme is as follows:

[0090]

[0091] Specifically include the following steps:

[0092] (1) Dissolve sialic acid (30g) in methanol (600mL), add CF 3 After COOH (15 mL), stir at room temperature until the reaction solution becomes clear. After the reaction is complete, concentrate under reduced pressure to remove the solvent, and dry in an oven at 42°C to obtain methyl sialate (compound 2).

[0093] (2) Compound 2 (10g, 30.93mmol, 1eq) was dissolved in pyridine (100mL), p-toluenesulfonyl chloride (8.85g, 46.40mmol, 1.5eq) was added under ice-cooling conditions, warmed to room temperature, and stirred overnight. Concentrate under reduced pressure to remove most of pyridine, and purify by silica gel column chromatography (EtOAc:MeOH=20:1).

[0094] (3) After dissolving the product (5g, 10.47m...

Embodiment 2

[0103] The antitumor effect of the present invention is proved by the following specific experiments, taking the compound Sia-ICG prepared in Example 1 as an example:

[0104] Hemolytic Ability of Compound Sia-ICG

[0105] The mouse whole blood was centrifuged, washed with PBS, red blood cells were taken and diluted, and different concentrations of free ICG and Sia-ICG were added. Negative control group: PBS, positive control group: red blood cell lysate. Incubate for 1 h in a sterile incubator containing 5% carbon dioxide. After centrifugation, the supernatant was collected, and the absorbance was measured at 541 nm.

[0106] Cytotoxicity assay (MTT) of compound Sia-ICG

[0107] 5000 / well of 4T1 tumor cells were added to a 96-well plate, and after all of them adhered to the wall, different concentrations of ICG (control group) and Sia-ICG (experimental group) were added. After incubating for 24 hours in a sterile constant temperature incubator containing 5% carbon dioxide,...

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Abstract

The invention provides sialic acid linked indocyanine green Sia-ICG as well as a preparation method and application thereof, and belongs to the technical field of biological medicines and disease treatment. According to the invention, indocyanine green and N-acetylneuraminic acid are coupled through a Sia-C9 site to synthesize Sia-ICG (indocyanine green). The Sia-ICG shows good in-vitro performance, which is specifically reflected in that the stability is enhanced, the non-specific binding with serum protein is reduced, the biocompatibility is enhanced and the like. In addition, compared with ICG, the Sia-ICG has excellent tumor targeting performance, and the circulation time of the Sia-ICG in the body is long. What's more important is that effective photo-thermal and photodynamic anti-tumor treatment effects are generated through combination of Sia-ICG and near-infrared laser irradiation. Therefore, the Sia-ICG is a new generation of anticancer diagnosis and treatment agent with great attraction, can be applied to clinical diagnosis and treatment of human tumors, and has good practical application value.

Description

technical field [0001] The invention belongs to the technical field of biomedicine and disease treatment, and specifically relates to a sialic acid-linked indocyanine green Sia-ICG and its preparation method and application. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] In 2020, there will be as many as 19.3 million new cancer cases worldwide, and nearly 10 million cancer deaths. It is estimated that by 2040, there will be 28.4 million new cancer cases worldwide, a 47% increase from 2020. Therefore, it is urgent to develop effective cancer treatments and provide affordable cancer treatments to a wider population. In recent decades, phototherapy technologies such as ph...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H13/04C07H1/00A61K31/7056A61P35/00A61K47/54A61K41/00
CPCY02P20/55
Inventor 吴选俊董会玲
Owner SHANDONG UNIV
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