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

A chitosan hydroxyl and adhesion technology, applied in the field of modification of biomedical material chitosan, can solve the problems of difficult amino protection and chemical toxicity during deprotection, and achieve mild reaction conditions, fast reaction rate, steady state effect

Active Publication Date: 2012-12-05
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
Comparison scheme
Effect test

Embodiment 1

[0027]1. At room temperature, dissolve 1 g of chitosan (Mw=148kDa, DD=80%) in 100 mL of aqueous acetic acid with a molar concentration of 0.05 M, adjust the pH of the solution to pH 4.5, and form a transparent 1% (w / v ) chitosan solution;

[0028] 2. Add sulfo-SANPAH and GRGDY to water at a ratio of 1:1 according to the amount of substances. The final concentration of photosensitive cross-linking agent is 2M. GRGDY and sulfo-SANPAH react at room temperature in the dark for 120 minutes to form GRGDY-SANPAH and its untreated The mixed solution of raw materials for the reaction;

[0029] 3. The ratio of sulfo-SANPAH and GRGDY is 1:1 according to the amount of substances, respectively added to water, the final concentration of photosensitive crosslinking 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 glu...

Embodiment 2

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

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

[0037] 3. Measure according to the ratio of photosensitive cross-linking agent and glucosamine residue in chitosan as 1:5, add chitosan solution to the above reaction mixture, mix well, and irradiate with UV for 45 minutes.

[0038] 4. Add the above reaction mixture solution into a dialysis bag with a molecular weight cut-off (MWCO) of 14kDa, and dialyze until the dialyzed aqueous solution cannot detect any ch...

Embodiment 3

[0041] 1. At room temperature, dissolve 1 g of chitosan (Mw=50kDa, DD=80%) in 100 mL of aqueous acetic acid with a molar concentration of 0.1 M, adjust the pH of the solution to pH 6.0, and form a transparent 1% (w / v ) chitosan solution;

[0042] 2. Take by weighing photosensitive crosslinking agent sulfo-SANPAH (according to photosensitive crosslinking agent and chitosan, the ratio of substance amount of glucosamine residue is 1:50 metering), join in the ethanol, add to photosensitive crosslinking agent solution subsequently Add sulfo-SANPAH to GRGDY aqueous solution with a ratio of 1:50 of sulfo-SANPAH to GRGDY, and the final concentration of photosensitive cross-linking agent is 1 μM. React in the dark for 90 minutes at room temperature to form a mixture of GRGDY-SANPAH and unreacted raw materials;

[0043] 3. Measure according to the ratio of photosensitive cross-linking agent and glucosamine residue in chitosan as 1:50, add chitosan solution to the above reaction mixture...

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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 chitosan, a biomedical material, in particular to a method for selectively photochemically crosslinking cell-adhesive peptides on chitosan hydroxyl groups using photosensitive crosslinker groups. Background technique [0002] Chitin, the second largest renewable resource on the earth known as the "sixth element of life", and its deacetylated product chitosan (CTS) is the only alkaline polysaccharide among natural polysaccharides composed of glucosamine and acetylglucosamine. It has good biocompatibility, bioactivity, safety (non-toxic, degradable) and other characteristics, and has been widely used as tissue engineering scaffolds, wound dressings, hemostatic materials, drug sustained release agents, etc. In view of the poor hydrophilicity of chitosan (dissolved only under acidic conditions) and slow degradation rate, the C 2 -NH 2 、C 3 -OH,C 6 The reactivity of the -OH group (where C 2 -NH 2 It...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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