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Beta-cyclodextrin based star-shaped polymer and preparation method thereof

A cyclodextrin and polymer technology, applied in the field of star polymer and its preparation, can solve the problems of low solubility, liver toxicity and the like

Inactive Publication Date: 2017-01-11
HEFEI UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, β-CD has certain limitations in practical application, such as low solubility in water and possible liver toxicity.

Method used

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  • Beta-cyclodextrin based star-shaped polymer and preparation method thereof
  • Beta-cyclodextrin based star-shaped polymer and preparation method thereof
  • Beta-cyclodextrin based star-shaped polymer and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] 1. Preparation of intermediate β-CD-6-OTs

[0040] Add β-cyclodextrin (5.0g, 4.4mmol), sodium hydroxide (1.8g, 45mmol) and 100mL distilled water into a 250mL round-bottomed flask, and stir until completely dissolved; Sulfonyl chloride (TsCl, 1.68g, 8.8mmol), stirred and reacted for 5h, filtered, the filtrate was adjusted to pH 6-7 with 1.0mol / L hydrochloric acid, and then crystallized in ice water; filtered, the filter cake was washed twice with distilled water, The intermediate β-CD-6-OTs (1.07g, 18.9%) was obtained after drying (vacuum drying). 1 H-NMR (DMSO-d 6 , 400MHz, δ): 7.67(d, J=7.5Hz, 2H), 7.36(s, 2H), 4.77(dd, J=42.5, 15.0Hz, 7H), 4.37(s, 7H), 4.29(d, J = 15.2Hz, 7H), 4.17 (dd, J = 14.4, 8.9Hz, 14H), 3.81-3.00 (m, 34H), 2.38 (s, 3H).

[0041] 2. Initiator β-CD-6-NH 2 preparation of

[0042]Accurately weigh β-CD-6-OTs (0.98g, 0.82mmol) and dissolve in 10mL ethylenediamine, 2 protection, stirring and reacting at 70°C for 10 h; after the reaction, under st...

Embodiment 2

[0048] 1. Preparation of intermediate β-CD-6-OTs

[0049] Take a 250mL single-necked round bottom flask, first add β-cyclodextrin (10g, 8.8mmol), then inject 100mL of 1mol / L NaOH solution, and ultrasonically shake until completely dissolved. Cool the reaction solution in an ice-water bath for 30 min, add p-toluenesulfonyl chloride (TsCl, 3.80 g, 20.0 mmol) dropwise, and react for 5 h under magnetic stirring conditions; / L of hydrochloric acid to adjust the pH to 6-7, cooling and crystallizing in ice water, washing the filter cake obtained after filtration with ethanol and water successively, and drying to obtain the target β-CD-6-OTs (1.42g, yield 12.5%).

[0050] 2. Initiator β-CD-6-NH 2 preparation of

[0051] Accurately weigh β-CD-6-OTs (1.20g, 1.0mmol) and dissolve in 15mL ethylenediamine, 2 protection, stirring and reacting at 70°C for 10 h; after the reaction, under stirring, the reaction liquid was added dropwise to excess ethanol, and the crude product (white preci...

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Abstract

The invention discloses a beta-cyclodextrin based star-shaped polymer and a preparation method thereof. The structural formula of the beta-cyclodextrin based star-shaped polymer is as shown in the specification, wherein x and y respectively represent degree of polymerization of monomers and each range from 30 to 80. Beta-cyclodextrin with polypeptide branch can form clathrate compound with related molecular drug to improve solubility and bioavailability of the molecular drug. As polypeptide with good biocompatibility and biodegradability cannot accumulate in the body, the material itself or degradation products have no toxic or side effect to the body.

Description

[0001] 1. Technical field [0002] The invention relates to a star polymer and a preparation method thereof, in particular to a star polymer based on β-cyclodextrin and a preparation method thereof. [0003] 2. Background technology [0004] β-Cyclodextrin (β-Cyclodextrin, β-CD) is a D-glucose oligomeric ring formed by amylose under the action of cyclodextrin glucosyltransferase and linked by α-1,4 glycosidic bonds. Its structure resembles a truncated conical cavity, with hydrophilic hydroxyl groups on the outside and hydrophobic cavities on the inside. The interior of the cavity can use hydrophobic interactions, hydrogen bonds, van der Waals forces and other non-bonding interactions to recognize guest molecules of appropriate size and shape, such as hydrophobic small molecules (such as anticancer, antiviral drugs, etc.), proteins, oligonucleotides, etc. Form host-guest inclusion complexes, enhance the reactivity and solubility of guest molecules. β-CD is widely used in medic...

Claims

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Application Information

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IPC IPC(8): C08B37/16A61K47/40A61K47/69
CPCC08B37/0015
Inventor 杨庆华郑磊陈庚柳杰王强盛
Owner HEFEI UNIV OF TECH
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