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Amino-acid modified chitin nucleophic NO donor and its synthesis method

A synthesis method and amino acid technology, applied in the field of medical engineering, can solve the problems of poor biocompatibility, low loading level, and poor biocompatibility of modified chitosan, so as to promote wound healing, prevent restenosis, improve Effect of antithrombotic properties

Inactive Publication Date: 2006-11-29
SHANGHAI JIAO TONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that the biocompatibility of the base material used is not good, and due to the water solubility of the base material, films and coatings with good mechanical properties cannot be prepared.
The disadvantage is that the biocompatibility of modified chitosan is poor, and the loading degree of NO is low.

Method used

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  • Amino-acid modified chitin nucleophic NO donor and its synthesis method
  • Amino-acid modified chitin nucleophic NO donor and its synthesis method
  • Amino-acid modified chitin nucleophic NO donor and its synthesis method

Examples

Experimental program
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Effect test

Embodiment 1

[0028] Example 1: Introduction of glycine at the C6 site

[0029] Preparation of carboxymethyl chitosan

[0030] Add 15g of chitosan and 200ml of isopropanol into a three-neck bottle, stir to disperse chitosan evenly in isopropanol, divide 50ml of 10mol / L NaOH solution into 5 parts, add one part every 30min, and stir at room temperature After 1 hour, a slurry of the reactant was obtained. Dissolve 24g of solid chloroacetic acid in 70ml of isopropanol and add it to the reactant slurry in 4 portions. After the addition, the reactant was heated to 70° C. with a water bath, and the reflux condensing device was turned on under temperature control, and stirred for 2 hours. After stopping, adjust the pH value to 7-8 with glacial acetic acid, and a large amount of light yellow flocculent precipitates precipitated. Vacuum filtration gave a yellow solid, which was washed with methanol three times, and the obtained yellow solid was vacuum-dried for 1 day at 60°C.

[0031] Activation o...

Embodiment 2

[0036] Example 2: Introduction of lysine at the C6 site

[0037] Take by weighing 1: 1 lysine and the activated carboxymethyl chitosan in embodiment 1 and add the NaHCO of 0.05mol / L 3 In the buffer solution, a pale yellow solution was obtained after stirring for 1 day. After the resulting solution was concentrated, it was dialyzed for three days and freeze-dried to obtain a white fibrous substance.

[0038] Lysine modified chitosan FTIR: 1730cm -1 (-COOH), 1630cm -1 and 1514cm -1 (NH 3 + ), 1415cm -1 (-CH 2 and -CH 3 ), 2928cm -1 (-CH 2 ). 1 H NMR: 4.33(8H), 3.41(9H), 1.05(10H), 0.88(11H), 2.35(12H), 3.60(13H).

Embodiment 3

[0039] Example 3: Introduction of amino acids at the C2 site

[0040] Because there are also carboxyl groups in amino acids, first activate the carboxyl groups in amino acids, and then combine with -NH at the 2nd carbon position in chitosan 2 reaction. Dissolve amino acid in 100ml of water alcohol (2:1), add N-hydroxysuccinimide (NHS), stir for 1 hour, add dicyclohexylcarbodiimide (DCC) alcohol solution, and react at room temperature for 24 hours. In the above reaction system, the molar ratio of amino acid:NHS:DCC is 1:1.5:1. Take a quantitative amount of chitosan (amino acid: chitosan molar ratio 1:1) dissolved in 0.1M acetic acid solution, add dropwise to the above solution under stirring, react at room temperature for 24 hours, concentrate the resulting solution, dialyze for three days, freeze-dry A white fibrous substance was obtained.

[0041] FTIR: 1650cm -1 (amide I), 1560cm -1 (Amide II), 1310cm -1 (amide III); 1 H NMR: 3.53 (8H)

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Abstract

A nucleophilic NO donor is prepared from chitosan through modifying by amino acid to increase its nucleophilic sites (NH groups), and reacting on NO. It has different NO releasing speeds and half-life, low cytotoxicity and generation of cancergenic ammonium nitrite.

Description

technical field [0001] The invention relates to a medicine in the technical field of medical engineering and a synthesis method thereof, in particular to an amino acid modified chitosan nucleophilic NO donor and a synthesis method thereof. Background technique [0002] In the last decade, foreign pairs based on [N(O)NO] - A great deal of research has been done on the controlled-release materials of NO donors with functional groups. The initial research focused on dispersing the ionic nucleophilic NO donor NONOate in various hydrophobic polymers to enhance the hemocompatibility of these materials through the release of NO. Although these studies have been fairly successful, it has been found that hydrophilic NO donors leach from the polymer to form carcinogenic N-nitrosamine species in the blood. To apply this kind of material in clinic, the following points must also be considered: biocompatibility and biodegradability as polymer matrix materials. Cytotoxicity and biocomp...

Claims

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Application Information

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IPC IPC(8): A61K47/48A61K47/36C08B37/00A61P9/00A61P7/02A61P11/00A61P17/02A61K47/61
Inventor 万锕俊高群
Owner SHANGHAI JIAO TONG UNIV
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