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A deoxyglucose-modified folic acid derivative and its synthesis and application

A technology of deoxyglucose and folic acid derivatives, applied in the field of biomedicine, can solve the problems of poor curative effect, easy to cause immune reaction, uneven particle size of liposomes, etc., and achieve the effect of correct structure

Active Publication Date: 2022-03-29
北京和益源生物技术有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there have been many reports on a variety of targeted antineoplastic drugs developed based on folic acid. The particle size of the liposomes prepared by the treatment strategy is not uniform, the efficiency of carrying anti-tumor drugs is low, the curative effect is poor, and the modified macromolecules are also likely to cause immune reactions in the body

Method used

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  • A deoxyglucose-modified folic acid derivative and its synthesis and application
  • A deoxyglucose-modified folic acid derivative and its synthesis and application
  • A deoxyglucose-modified folic acid derivative and its synthesis and application

Examples

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Embodiment 1

[0037]This example provides a deoxyglucose-modified folic acid derivative. The folic acid derivative (FA-2-DG) is formed by linking deoxyglucose and folic acid via aminoethanol, wherein the carboxyl group of folic acid is connected with the amino group of aminoethanol to form The amide bond, the hydroxyl group of aminoethanol and the hydroxyl group of deoxyglucose are connected to form a glycosidic bond. The chemical structural formula of the FA-2-DG is as figure 1 shown.

[0038] Deoxyglucose has multiple hydroxyl groups. During the reaction, the hydroxyl groups have high reactivity, so they need to be protected with acetyl groups before the reaction. The acetyl-protected reaction proceeds from deoxyglucose and acetic anhydride in anhydrous pyridine. The amino group of aminoethanol will also have relatively high reactivity during the reaction process, so aminoethanol is not used directly in the reaction process, but 2-bromoethanol is used to react with acetyl deoxyglucose f...

Embodiment 2

[0067] This embodiment provides a targeted anti-tumor nanoparticle, the nanoparticle is composed of the above-mentioned folic acid derivative and the anti-tumor drug cisplatin linked by coordination bonds. To prepare the complex of FA-2-DG and cisplatin, mix the aqueous solution of cisplatin and FA-2-DG of the same concentration and stir at room temperature. After two hours, cisplatin and FA-2-DG are formed as Figure 5 The coordination compound (FA-2-DG-Pt) shown. The mixed solution was injected into HPLC-MS analysis, and the formation of the complex was confirmed. For mass spectrometry results, see Figure 6 .

[0068] The morphological characterization techniques of atomic force microscopy, transmission electron microscopy and scanning electron microscopy all confirmed that FA-2-DG itself can self-assemble to form nanoparticles, and form a coordination bond with cisplatin, and obtain FA-2-DG-Pt after drug loading. It can also self-assemble into nanostructures.

[0069] ...

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Abstract

The invention discloses a deoxyglucose-modified folic acid derivative and its synthesis and application. The derivative is a novel compound formed by combining folic acid and deoxyglucose through chemical bonds——FA‑2‑DG . In the derivative, aminoethanol is used as a connecting arm between folic acid and deoxyglucose, the carboxyl of folic acid is connected with the amino group of aminoethanol to form an amide bond; the hydroxyl group of aminoethanol is connected with the hydroxyl group of deoxyglucose to form a glycoside bond. This connection method neither destroys the structure and function of folic acid and deoxyglucose itself, nor affects the recognition of folic acid by folate receptors. At the same time, the introduction of a connecting arm of two carbon atoms can also increase the distance between the two molecules of folic acid and deoxyglucose. The distance is more suitable for the hydrolysis of glycosidase to release deoxyglucose with anti-tumor activity. The derivative FA‑2‑DG can be used as a drug plastid to load drugs based on its structural features.

Description

technical field [0001] The invention belongs to the field of biomedicine, and in particular relates to a deoxyglucose-modified folic acid derivative and its synthesis and application. Background technique [0002] Malignant tumors are complex diseases that endanger human health today, and the number of human deaths every year is second only to cardiovascular and cerebrovascular diseases. Tumors with high expression of folate receptors have a higher incidence in women, and the development of targeted anti-tumor drugs based on folic acid recognition has always been one of the hot topics in the development of tumor drugs. At present, there have been many reports on a variety of targeted antineoplastic drugs developed based on folic acid. The particle size of the liposomes prepared by the treatment strategy is not uniform, the efficiency of carrying anti-tumor drugs is low, the curative effect is poor, and the modified macromolecules are also likely to cause immune reactions in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H15/04C07H1/00A61P35/00A61K47/54A61K47/69A61K33/243
CPCC07H15/04C07H1/00A61P35/00A61K47/549A61K47/6929A61K33/243
Inventor 金绍明葛绍阳刘治麟王鹏杰杜仲尧
Owner 北京和益源生物技术有限公司
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