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Method for photochemical cross-linking cell adhesion peptides on chitosan hydroxyl

A chitosan hydroxyl and adhesive technology, which is applied in the field of biomedical material chitosan modification, can solve the difficult problems of amino protection and deprotection process chemical toxicity, and achieve mild reaction conditions, stable state, easy saved effect

Active Publication Date: 2010-06-23
ZHANGJIAGANG IND TECH RES INST CO LTD DALIAN INST OF CHEM PHYSICS CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, if the amino group is to be retained, it is difficult to avoid the cumbersome amino protection and deprotection process using the amino protecting agent phthalic anhydride, benzyl chloroformate, benzaldehyde, 4-methyl-2-pentanone, and chemical toxicity

Method used

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  • Method for photochemical cross-linking cell adhesion peptides on chitosan hydroxyl
  • Method for photochemical cross-linking cell adhesion peptides on chitosan hydroxyl
  • Method for photochemical cross-linking cell adhesion peptides on chitosan hydroxyl

Examples

Experimental program
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Effect test

Embodiment 1

[0027]1. At room temperature, 1 g of chitosan (Mw=148kDa, DD=80%) was dissolved in 100 mL of acetic acid aqueous solution with a molar concentration of 0.05M, and the pH of the solution was adjusted to pH4.5 to form a transparent 1% (w / v ) chitosan solution;

[0028] 2. The ratio of sulfo-SANPAH and GRGDY is 1:1, respectively added to water, the final concentration of photosensitive cross-linking agent is 2M, GRGDY and sulfo-SANPAH are reacted at room temperature for 120 minutes in the dark to form GRGDY-SANPAH and its precursors. The mixture of reacted raw materials;

[0029] 3. The ratio of sulfo-SANPAH and GRGDY is 1:1, respectively added to water, the final concentration of photosensitive cross-linking agent is 2M, and GRGDY and sulfo-SANPAH are mixed at room temperature in the dark;

[0030] 4. Add chitosan solution to GRGDY-SANPAH and its raw material mixture according to the ratio of photosensitive cross-linking agent to glucosamine residues in chitosan at 1:2, mix wel...

Embodiment 2

[0035] 1. At room temperature, dissolve 3g of chitosan (Mw=90kDa, DD=90%) in 100mL of 0.05M acetic acid aqueous solution, and adjust the pH of the solution to pH4.5 to form a transparent 3% (w / v ) chitosan solution;

[0036] 2. The ratio of sulfo-SANPAH and GRGDY is 1:2, respectively added to the same volume of ethanol and water, and then mixed, the final concentration of photosensitive cross-linking agent is 1mM, GRGDY and sulfo-SANPAH react at room temperature for 60 minutes in the dark , to form a mixture of GRGDY-SANPAH and its unreacted raw materials;

[0037] 3. According to the material ratio of the photosensitive cross-linking agent and the glucosamine residue in the chitosan as 1:5, add the chitosan solution to the above reaction mixture, mix well, and expose to UV light for 45min.

[0038] 4. The above-mentioned reaction mixture solution is added to a dialysis bag with a molecular weight cut-off (MWCO) of 14kDa, and the dialyzed aqueous solution does not detect chan...

Embodiment 3

[0041] 1. At room temperature, dissolve 1g chitosan (Mw=50kDa, DD=80%) in 100mL molar concentration 0.1M acetic acid aqueous solution, adjust the pH of the solution to pH6.0 to form a transparent 1% (w / v ) chitosan solution;

[0042] 2. Weigh the photosensitive cross-linking agent sulfo-SANPAH (measured according to the ratio of the photosensitive cross-linking agent to the glucosamine residue in chitosan is 1:50), add it to ethanol, and then add it to the photosensitive cross-linking agent solution. The aqueous solution of GRGDY with the ratio of sulfo-SANPAH to GRGDY was 1:50, and the final concentration of the photosensitive cross-linking agent was 1 μM. The reaction was performed in the dark for 90 min at room temperature to form a mixed solution of GRGDY-SANPAH and unreacted raw materials;

[0043] 3. According to the material ratio of the photosensitive crosslinking agent and the glucosamine residue in the chitosan as 1:50, add the chitosan solution to the above reactio...

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Abstract

The invention relates to a method for photochemical cross-linking cell adhesion peptides on chitosan hydroxyl, namely a group selectively grafts the cell adhesion peptides on chitosan molecules. In particular, bifunctional photosensitive crosslinker sulfo-SANPAH is utilized to modify hydrophilic polypeptide GRGDY containing cell adhesion factors RGD on the chitosan hydroxyl to increase the water solubility and the targeting of a material, while amidogen is retained and tedious amino protection, a deprotection process and chemical toxicity caused by the same are avoided. The method adopts UV-activated photochemical cross-linking and has the advantages of mild reaction conditions and fast reaction rate, and the feature group of the crosslinker is beneficial to judging the conducting of grafting reaction. The targeted adhesion chitosan material synthesized by the method is suitable for preparing DNA and small RNA (siRNA, microRNA, shRNA, and the like.) targeted delivery systems, cell adhesion cultures, microencapsulated tissue cells for transplant, scaffolds for tissue engineering, and the like applied in the biomedical field under physiological conditions.

Description

technical field [0001] The present invention relates to the modification of biomedical material chitosan, in particular to a method for photochemically cross-linking cell-adhesive peptides selectively on the hydroxyl groups of chitosan using photosensitive cross-linking agent groups. Background technique [0002] Chitin, the second largest renewable resource on earth, known as the "sixth element of life", its deacetylated product, chitosan (CTS), is the only basic polysaccharide among the natural polysaccharides composed of glucosamine and acetylglucosamine. It has the characteristics of good biocompatibility, biological activity, safety (non-toxic, degradable), etc., and has been widely used as tissue engineering scaffolds, wound dressings, hemostatic materials, drug sustained-release agents, etc. Aiming at the poor hydrophilicity of chitosan (dissolving only in acidic conditions) and slow degradation rate, the C 2 -NH 2 , C 3 -OH, C 6 The reactivity of the -OH group (w...

Claims

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Application Information

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IPC IPC(8): C08B37/08
Inventor 马小军杨艳刘袖洞于炜婷
Owner ZHANGJIAGANG IND TECH RES INST CO LTD DALIAN INST OF CHEM PHYSICS CHINESE ACADEMY OF SCI
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