Conjugate containing alpha-galactosylceramide analogue and carbohydrate antigen as well as preparation method and application of conjugate

A galactosylceramide and conjugate technology, applied in the field of anti-tumor sugar vaccine development, can solve the problems of uncertain glycoprotein vaccine coupling site, complex composition, unstable coupling rate and the like, and achieve high yield , easy operation, mild reaction conditions

Active Publication Date: 2020-10-13
GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, glycoprotein vaccines still have disadvantages such as uncertain coupling sites, unstable coupling rates, and complex components.

Method used

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  • Conjugate containing alpha-galactosylceramide analogue and carbohydrate antigen as well as preparation method and application of conjugate
  • Conjugate containing alpha-galactosylceramide analogue and carbohydrate antigen as well as preparation method and application of conjugate
  • Conjugate containing alpha-galactosylceramide analogue and carbohydrate antigen as well as preparation method and application of conjugate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0075] This example is a conjugate containing an α-galactosylceramide analogue and a carbohydrate antigen provided by the present invention, and its structural formula is shown in the following formula (III):

[0076]

[0077] The preparation method of the above-mentioned conjugate containing α-galactosylceramide analogue and carbohydrate antigen comprises the following steps:

[0078] (1) Compound 1 and Compound 2 are dissolved in an organic solvent, and a condensing agent is added to react to obtain Compound 3; the reaction formula to obtain Compound 3 is shown in the following formula:

[0079]

[0080] The specific operation of step (1) is: dichloromethane solution (80.0mL) dissolves (compound 1) Fmoc-L-threonine (4.5g, 13.1mmol) and (compound 2) 2-[2-(2-propane Alkynyloxy)ethoxy]ethylamine (2.2g, 15.7mmol), N,N'-dicyclohexylcarbodiimide (3.0g, 14.4mmol) and 1-hydroxybenzotriazole ( 0.7g, 1.3mol), remove the ice bath, return to room temperature, stir and react at ro...

experiment example 1

[0106] In this experimental example 1, mice were immunized with the conjugate (fully synthetic sugar vaccine) prepared in Example 1, and its immune effect was preliminarily evaluated by ELSA experiment, and the antibody serum was proved to be able to specifically recognize by fluorescence activated cell sorting (FACS). Tumor cells (MCF-7), and antibody-mediated complementation-dependent cytotoxicity (CDC) experiments showed that antibody serum has the ability to kill tumor cells mediated by complement.

[0107] 1. ELISA immunoassay

[0108] 1) Immunization of mice:

[0109] Take 6 C57BL / 6 mice aged 6-8 weeks. After the sugar vaccine was prepared into liposomes, the immune test was carried out by subcutaneous injection in mice. One initial immunization and three booster immunization schemes were used to inject the prepared vaccines on days 0, 14, 21, and 28 respectively. The injection volume is 0.1mL; on the 38th day, 0.1mL to 0.2mL of blood is collected from each mouse, plac...

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Abstract

The invention relates to a conjugate containing an alpha-galactosylceramide analogue and a carbohydrate antigen as well as a preparation method and application of the conjugate, and belongs to the technical field of anti-tumor carbohydrate vaccine development. The invention provides the conjugate containing the alpha-galactosylceramide analogue and the carbohydrate antigen. The conjugate is a compound as shown in a general formula (I) or an isomer, a pharmaceutically acceptable salt, a hydrate or a solvent compound of the compound as shown in the general formula (I). The conjugate can generateimmunoreaction with higher titer aiming at tumor carbohydrate antigen Tn specificity, achieves the purpose of killing tumor cells, generates an anti-tumor effect, and is expected to become a new generation of anti-tumor drugs, wherein the n is an integer from 2 to 6, the m is an integer from 9 to 25, and the R is selected from any substituent group in -CH3.

Description

technical field [0001] The invention relates to a conjugate containing an α-galactosylceramide analogue and a sugar antigen, a preparation method and application thereof, and belongs to the technical field of anti-tumor sugar vaccine development. Background technique [0002] Cancer prevention and treatment has become an important public health problem in our country, seriously threatening people's lives. An effective cancer prevention and treatment method is urgently needed. Tumor vaccines are considered to be the fourth treatment after surgery, chemotherapy and radiation, and have shown good prospects for clinical application. Tumor carbohydrate vaccines targeting tumor-associated carbohydrate antigens (TACAs) abnormally expressed on the surface of tumor cells have the advantages of high specificity, less side effects, and better efficacy. Among them, the Thomsennouveau (Tn) antigen is abnormally overexpressed on the surface of malignant tumor cells such as breast cancer,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A61K39/39A61K39/385A61K39/00A61P35/00A61P35/02C07H19/056C07H1/00
CPCA61K39/39A61K39/385A61K39/001172A61P35/00A61P35/02C07H19/056C07H1/00A61K2039/6018A61K2039/55511Y02P20/55
Inventor 廖国超刘中秋杨德盈练庆海高玲强吴鹏苏诗薇曾莉茗
Owner GUANGZHOU UNIVERSITY OF CHINESE MEDICINE
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