Synthesis method for ether amination cyclodextrin derivatives

A synthesis method and technology of cyclodextrin, which is applied in the field of synthesis of ether aminated cyclodextrin derivatives, can solve the problems of not increasing the inclusion ratio of biologically active molecules, not improving biologically active substances, and requiring a large amount, so as to achieve improved stability performance, reduce usage, and increase package capacity

Active Publication Date: 2018-09-28
JIANGNAN UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, in order to improve the water solubility of cyclodextrin and thus increase the solubility of cyclodextrin in water, there are mainly hydroxypropyl cyclodextrin, carboxymethyl cyclodextrin, hydroxyethyl cyclodextrin, etc., these cyclodextrin derivatives Can increase the inclusion amount of small molecular bioactive molecules, but cannot increase the inclusion ratio of bioactive molecules
Some scholars and experts have clarified that cyclodextrin or cyclodextrin derivatives have good inclusion ability with antioxidant drugs and improve their antioxidant properties. Such as vitamin A, E, resveratrol, etc.), the inclusion ability requires multiple inclusion complex hosts to include a guest molecule
This will lead to the encapsulation of few biologically active molecules requiring a large amount of cyclodextrin, and the application of this inclusion compound in organisms will bring certain side effects

Method used

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  • Synthesis method for ether amination cyclodextrin derivatives
  • Synthesis method for ether amination cyclodextrin derivatives
  • Synthesis method for ether amination cyclodextrin derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] 1. Synthesis of mono-6-deoxy-polyetheramine D400 cyclodextrin (β-CD-6-D400)

[0026] Dissolve β-cyclodextrin (β-CD) (17.0g, 15.0mmol) in 200mL of 1% NaOH solution, and add 15mL of p-toluenesulfonyl chloride (4.0g, 22.5mmol) dropwise at 0°C ) in acetonitrile solution, stirred and reacted at 25°C for 2h, then filtered, adjusted to pH 2 with hydrochloric acid, kept at 4°C for 14h, a large amount of precipitate precipitated out, filtered, and the solid was recrystallized 3 times to obtain a white solid, which was vacuum-dried at 40°C for 5h. Obtain β-CD-6-OTs for future use.

[0027] Mix β-CD-6-OTs (0.50g, 0.39mmol) and polyetheramine D400 (1.2g, 3.00mmol), add 10mL of DMF solvent to dissolve completely, use 1mol / L hydrochloric acid solution to adjust the pH of the system to 5.5, 60 ℃ reaction 24h. The reaction solution was concentrated and dialyzed in water at 40° C. for 2 days using a dialysis bag with a molecular weight cut-off of 1500, then concentrated and separated ...

Embodiment 2

[0034] 1. Synthesis of mono-6-deoxy-polyetheramine D2000 cyclodextrin (β-CD-6-D2000)

[0035] Mix β-CD-6-OTs (0.50g, 0.39mmol) and polyetheramine D2000 (1.6g, 0.80mmol), add 10mL of DMF solvent to dissolve completely, and use 1mol / L hydrochloric acid solution to adjust the pH of the system to 6.5, 100 ℃ reaction 2h. The reaction solution was concentrated and dialyzed in water at 40° C. for 2 days using a dialysis bag with a molecular weight cut off of 3500. Then concentrate and separate with a silica gel column to obtain β-CD-6-D2000 white powder. The elution used is gradient elution, and the gradient elution agent is composed of n-butanol, ethanol, water, and ammonia water in a certain proportion, and the proportion is 6:2:2:1 in terms of volume ratio. β-CD-6-D2000, 1 H NMR (400MHz, DMSO-d 6 ) δ = 5.60-5.75 (m, 14H), 4.82 (s, 7H), 4.36 (s, 6H), 3.00-3.40 (m, 37H), 1.54-0.79 (m, 6H). MALDI-TOF-MS: calculated m / z [M+H 2 O] 3134.6; measured value, 3134.7 [M+H 2 O].

[00...

Embodiment 3

[0039] Determination of DPPH free radical scavenging rate of cyclodextrin and ether aminated cyclodextrin VE inclusion compound: Take 0.5, 1.0, 1.5, 2.0, 2.5mL of VE inclusion compound samples (1.00mM) respectively and place them in the colorimetric Then take 1.82mg DPPH and dilute it in a 100mL volumetric flask, configure 0.46mM ethanol solution, then pipette 5mL DPPH and dissolve it in the above colorimetric tube, then dilute to 10mL, dissolve evenly, and let it stand for 30min , Obtained the scavenging rate of DPPH free radicals of clathrate samples with different concentrations, and tested the ultraviolet-visible spectrum (U-3900, Hitachi, Japan), and calculated the scavenging rate.

[0040] figure 1 The scavenging efficiency of host-guest inclusion complexes β-CD-VE, β-CD-6-D400-VE, β-CD-6-D2000-VE at different concentrations on DPPH·free radicals. Depend on figure 1 It can be seen that when the concentration of the clathrate is 0.35mM, it has the highest scavenging rat...

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Abstract

The invention provides a synthesis method for ether amination cyclodextrin derivatives. The method comprises the steps that mono-6-tosyl cyclodextrin and polyether amine are mixed on the basis that the mole ratio is 1:(2-8), a DMF solvent is added for complete dissolution, pH is regulated through a hydrochloric acid solution to 5.5-6.5, a reaction is performed at the temperature of 60-100 DEG C for 2-24 h, the obtained reaction mixed solution is subjected to concentration and dialysis, and column chromatography elution is performed to obtain purified mono-6-deoxo-polyether amine cyclodextrin.The prepared mono-6-deoxo-polyether amine cyclodextrin can achieve complete molecule clathration on biological activity molecules which are large in molecular weight, complex in molecule structure andlikely to oxide and deteriorate in the environment, and therefore the stability of biological activity molecules under the natural environment is greatly improved. The synthesized ether amination cyclodextrin is expected to be widely applied to the fields of food, cosmetics and biological medical treatment.

Description

technical field [0001] The invention belongs to the technical field of preparation of cyclodextrin derivatives, in particular to a synthesis method of ether aminated cyclodextrin derivatives. Background technique [0002] Cyclodextrin is a general term for a series of cyclic oligosaccharides produced by amylose under the action of cyclodextrin glucosyltransferase produced by Bacillus. Cyclodextrin has a special molecular structure with a hydrophilic outer wall and a hydrophobic inner cavity, and has a good encapsulation effect on small molecular compounds. However, due to poor solubility of the cyclodextrin itself, and the inability to achieve complete inclusion of complex biologically active molecules, Therefore restricting its wide application. The cavity depth of cyclodextrin is only about 0.79nm, so some macromolecular bioactive substances cannot be completely included, and two or more cyclodextrin molecules are required for effective inclusion. [0003] At present, in...

Claims

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Application Information

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IPC IPC(8): C08B37/16C08G81/00
CPCC08B37/0012C08G81/00
Inventor 杨成张冬梅
Owner JIANGNAN UNIV
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