Mono-6-(biotinamide)-6-deoxy-β-cyclodextrin and its preparation method and application

A technology based on biotinamide and cyclodextrin, which is applied in the direction of drug combination, ketone active ingredients, antineoplastic drugs, etc., can solve the problems affecting the delivery of curcumin, improve the antitumor efficiency, expand the hydrophobic cavity, reduce the side effects

Active Publication Date: 2021-03-30
CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although these drug carriers can effectively solve the solubility of curcumin and inhibit its degradation, these large-sized drug carriers will affect the delivery of curcumin in cells

Method used

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  • Mono-6-(biotinamide)-6-deoxy-β-cyclodextrin and its preparation method and application
  • Mono-6-(biotinamide)-6-deoxy-β-cyclodextrin and its preparation method and application
  • Mono-6-(biotinamide)-6-deoxy-β-cyclodextrin and its preparation method and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Example 1 Preparation of single (6-oxo-6-p-toluenesulfonyl)-β-cyclodextrin (2)

[0042] β-cyclodextrin (1) (9.99g, 88mmol) was dissolved in 220ml of water, added finely ground Ts 2 O (4.26g, 13mmol) crystallized and stirred in an ice bath for 2h. 10% NaOH aqueous solution was added dropwise to the reaction solution, stirred for 20 min and then filtered. use NH 4 Cl adjusted the pH value of the filtrate to neutral, and a large amount of white solids were precipitated. They were refrigerated overnight in the refrigerator, and 2.97 g of white solids were obtained by filtration, with a yield of 26.1%. ESI / MS(m / z):1290.30[M+H] + .

Embodiment 2

[0043] Example 2 Preparation of mono-(6-azido-6-deoxy)-β-cyclodextrin (3)

[0044] 6-Oxygen-6-p-toluenesulfonyl)-β-cyclodextrin (2) (1.34g, 1mmol) and sodium azide

[0045] (0.82g, 12.3mmol) was dissolved in 13.5ml of distilled water, and the reaction was stirred in an oil bath at 80°C (reflux by condensation). After 5 hours, it was taken out from the eggplant-shaped bottle and cooled to room temperature, and filtered to obtain a white solid powder (1.02 g, 83%). ESI-MS(m / s): 1187.40[M+H] + .

Embodiment 3

[0046] Example 3 Preparation of mono-(6-amino-6-deoxy)-β-cyclodextrin (4)

[0047] Mono-(6-azido-6-deoxy)-β-cyclodextrin (3) (1.21g, 1mmol) was dissolved in 5ml DMF and added to a 50ml eggplant-shaped bottle, and three Phenylphosphonium (0.58g, 2.2mmol). Then 3.5ml of concentrated ammonia water was added dropwise, and a white solid powder (0.81g, 70%) was obtained by filtration. ESI-MS(m / s): 1135.20[M+H] + .

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Abstract

The invention discloses mono-6-(biotinacylamino)-6-deoxygenated-beta-cyclodextrin and a preparation method and an application thereof. The invention firstly discloses mono-6-(biotinacylamino)-6-deoxygenated-beta-cyclodextrin which is prepared by connecting biotin to cyclodextrin by taking imine as a connecting arm. The mono-6-(biotinacylamino)-6-deoxygenated-beta-cyclodextrin can be taken as a drug carrier for transporting an anti-tumor drug curcumin in a targeted manner. The invention further discloses a supermolecular clathrate compound formed by mono-6-(biotinacylamino)-6-deoxygenated-beta-cyclodextrin and curcumin. The supermolecular clathrate compound not only can improve the water solubility of curcumin and enhance the stability of the curcumin, but also can convey the curcumin to tumor cells in a targeted manner, so that the supermolecular clathrate compound shows more excellent anti-tumor activity. The supermolecular clathrate compound has an important application prospect in preparing the anti-tumor drugs.

Description

technical field [0001] The present invention relates to a compound obtained by modifying β-cyclodextrin with biotin, and also relates to a preparation method of the compound. The present invention further relates to a supramolecular clathrate formed by the compound and curcumin and its incorporation into Application in the preparation of antitumor drugs. Background technique [0002] Curcumin (English name curcumin) is a polyphenolic compound extracted from the rhizomes of turmeric plants in the ginger family. It has anti-tumor, anti-inflammatory, anti-oxidation, anti-bacterial, anti-atherosclerosis, and treatment of Alzheimer's disease Wide range of pharmacological activities. In terms of anti-tumor, curcumin can exert its anti-tumor effect by inducing apoptosis of various cancer cells, arresting cell cycle, inhibiting tumor angiogenesis and other pathways, and has shown good safety in both in vivo and in vitro experiments. Therefore, the application of curcumin in anti-t...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C08B37/16A61K31/12A61P35/00
CPCA61K31/12C08B37/0012C08B37/0015
Inventor 李莉刘海清郭建鹏王毅王玉记赵明
Owner CAPITAL UNIVERSITY OF MEDICAL SCIENCES
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