CN117229430A - Active short peptide modified chitin and preparation method thereof - Google Patents
Active short peptide modified chitin and preparation method thereof Download PDFInfo
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- CN117229430A CN117229430A CN202311197709.0A CN202311197709A CN117229430A CN 117229430 A CN117229430 A CN 117229430A CN 202311197709 A CN202311197709 A CN 202311197709A CN 117229430 A CN117229430 A CN 117229430A
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- 102000004196 processed proteins & peptides Human genes 0.000 claims description 7
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- 239000000463 material Substances 0.000 abstract description 40
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- 238000011069 regeneration method Methods 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 3
- 230000007547 defect Effects 0.000 abstract description 2
- 238000011161 development Methods 0.000 abstract description 2
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- 239000007924 injection Substances 0.000 abstract description 2
- 230000035876 healing Effects 0.000 abstract 1
- 231100000241 scar Toxicity 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 23
- 229920001661 Chitosan Polymers 0.000 description 18
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 11
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 8
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- 230000004048 modification Effects 0.000 description 4
- 238000012986 modification Methods 0.000 description 4
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- 229920000642 polymer Polymers 0.000 description 4
- 230000006196 deacetylation Effects 0.000 description 3
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- 239000011259 mixed solution Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 2
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- OVRNDRQMDRJTHS-FMDGEEDCSA-N N-acetyl-beta-D-glucosamine Chemical group CC(=O)N[C@H]1[C@H](O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-FMDGEEDCSA-N 0.000 description 2
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- ACBQROXDOHKANW-UHFFFAOYSA-N bis(4-nitrophenyl) carbonate Chemical compound C1=CC([N+](=O)[O-])=CC=C1OC(=O)OC1=CC=C([N+]([O-])=O)C=C1 ACBQROXDOHKANW-UHFFFAOYSA-N 0.000 description 2
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- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
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- DUKURNFHYQXCJG-UHFFFAOYSA-N Lewis A pentasaccharide Natural products OC1C(O)C(O)C(C)OC1OC1C(OC2C(C(O)C(O)C(CO)O2)O)C(NC(C)=O)C(OC2C(C(OC3C(OC(O)C(O)C3O)CO)OC(CO)C2O)O)OC1CO DUKURNFHYQXCJG-UHFFFAOYSA-N 0.000 description 1
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Abstract
The application discloses a preparation method of active short peptide modified chitin. The chitin material with the function of promoting tissue regeneration and promoting scar healing is prepared by taking chitin as a main chain and taking high-activity short peptide as a bioactive grafting group and grafting and modifying. Chitin derivative materials of different uses are prepared by using chitin or derivatives thereof of different molecular weights as a main chain. The technical scheme provided by the application endows the chitin with bioactivity functions such as tissue regeneration promotion and the like, expands the application range of the chitin, and provides materials and ideas for further development and utilization of the chitin; and overcomes the defect that the injection type chitin is used as a material with a physical filling function and has a single function, and adds biological functions of promoting cell regeneration, tissue repair and the like to the chitin material.
Description
Technical Field
The application belongs to the technical field of biomedical materials, and in particular relates to an active short peptide modified chitin and a preparation method thereof.
Background
Chitin (chitin), the second most bioactive polysaccharide in nature. The chitin has a chemical structure very similar to that of plant cellulose, belongs to a polymer of six-carbon sugar, and is formed by linking 1000-3000 acetylglucosamine residues through beta-1, 4-glucoside bonds, and has a molecular weight of more than 100 ten thousand. Chitin is a renewable resource, and the use of chitin to fully utilize and impart high added value is a research hotspot for a large number of scientific researchers in recent years. Chitin is not readily soluble in water, dilute acids, bases, ethanol and other organic solvents, so that its range of use is limited. The chitin is subjected to deacetylation purification by a chemical method to obtain a polymer formed by polymerizing two monomers of acetylglucosamine and glucosamine, and when the deacetylation degree of the polymer reaches more than 55%, the polymer is called chitosan, and the chitosan is the only basic cationic polysaccharide in the nature at present and has the effects of resisting bacteria and viruses. In addition, the water solubility of chitin can be enhanced by carboxymethylation of chitin to form carboxymethyl chitin. These chitin derivatives are widely used as tissue fillers, joint lubricants and functional moisturizing components in medical, cosmetic and food fields, forming an industry of a certain scale.
However, most of chitin utilization is focused on the use of raw materials with unchanged chemical properties, the chitin is modified by a green biological method, the unique biological function is given to the chitin, the application in the medical field is expanded, and the important research direction for improving the added value of chitin materials is provided. The high-activity short peptide (bioactivator ShortPeptides, BSP) is a small molecular peptide chain which can simulate the physiological function of active protein in vivo and has no immunogenicity, and can realize the high expression of active ingredients in unit density so as to achieve specific purposes, such as antibiosis, tissue regeneration promotion, immunoregulation and the like. The BSP synthesis path is clear, has the advantages of rich active sites, stable conformation, easy synthesis, convenient preservation and the like, and is a research and industry hotspot in the field of the current international functional biological materials. At present, the related technology of modifying chitin and derivatives thereof by adopting materials with biological activity functions to obtain novel chitin materials is not reported yet.
Disclosure of Invention
The application aims to increase the biological functions of chitin materials, expand the application range of the chitin materials and provide chitin materials with excellent performance.
Based on the above-mentioned objects, the present application addresses this need in the art by providing an active short peptide modified chitin and a method for preparing the same.
In one aspect, the application relates to an active short peptide modified chitin, which takes chitin as a main chain, takes active short peptide as a bioactive grafting group and grafts on the main chain; wherein the chitin comprises chitin and derivatives of chitin, and the number of repeating units of the chitin monomer is 1-7000.
As a further improvement of the embodiment of the application, the active short peptide comprises a short peptide with an amino acid sequence of RXDX, LDXPX, KLDAPTX, KYILXWXPKNX, WTPPXAQITXYXLTXXLTXX, PHXXN, XXXDXP, XDXIHXL, KPDXXXYTITX, ATXTTITIX, XPPXXAXXT, WQPPXAXI, YXKPXXPPXXXXPXPXPXX, KNNQKXXPLIXXKKT, wherein X is E or G or V or S or R or none.
As a further improvement of the embodiment of the application, the molecular weight of the chitin main chain is 1K-1000kDa.
As a further improvement of the embodiments of the present application, the grafting sites between the backbone and the bioactive grafting groups include amino sites and hydroxyl sites.
As a further improvement of the embodiments of the present application, the active short peptide and the chitin main chain are directly covalently bound or bound by a short peptide linker or physically mixed.
As a further improvement of the embodiments of the present application, the short peptide linker is WLC, WGRGDSP or GWGLGPAGK or CCRR.
The application also provides the active short peptide modified chitin prepared by the preparation method.
On the other hand, the application also provides application of the active short peptide modified chitin as a physical filler.
Compared with the prior art, the application has the beneficial effects that:
the active modified chitin provided by the application is grafted on the surface of chitin by utilizing BSP with a bioactive function, so that the bioactive functions of promoting tissue regeneration and the like of the chitin are endowed, the application range of the chitin is enlarged, and materials and ideas are provided for further development and utilization of the chitin;
the chitin material with good biocompatibility and cell regeneration promoting function is obtained after the chitin material with different molecular weights is used as a main chain for modification, the technical scheme provided by the application overcomes the defect that the injection type chitin as a material with a physical filling function has too single function, and biological functions of promoting cell regeneration, tissue repair and the like are added to the chitin material.
Drawings
FIG. 1 shows the results of the culture of fibroblasts with the modified chitin material and the normal chitin material provided in the examples of the present application; wherein A is the culture result of common chitin material, and B is the culture result of activated short peptide modified chitosan on fibroblasts.
FIG. 2 shows the percutaneous absorption of modified chitin materials and common chitin materials provided by the examples of the application; wherein A is the percutaneous absorption result of common chitin material, and B is the percutaneous absorption result of modified chitin material.
Detailed Description
The technical aspects of the present application will be described with reference to examples for making the present application more understandable, but the present application is not limited to the following examples.
The experimental methods and the detection methods in the following embodiments are all conventional methods unless otherwise specified; the medicaments and materials are commercially available unless specified; the index data are all conventional measurement methods unless specified.
In order to increase the biological functions of the chitin material and expand the application range of the chitin material, and provide the chitin material with excellent performance, the embodiment provides a preparation method of the active short peptide modified chitin, which comprises the following steps: chitin is taken as a main chain, and active short peptide is taken as a bioactive grafting group and grafted on the main chain; wherein the chitin comprises chitin and derivatives of chitin, and the number of repeating units of the chitin monomer is 1-7000.
After chitin materials with different molecular weights are used as main chains for modification, the chitin materials with good biocompatibility and cell regeneration promoting function are obtained.
According to the preparation method of the active short peptide modified chitin, the grafting sites between the main chain and the bioactive grafting groups comprise amino sites and hydroxyl sites, the reactions of the different sites are different, the types of the generated groups are different, and the preparation method provides possibility for further expansion of the functions of the material.
In the test of modifying chitin or chitin derivatives, the chitin or chitin derivatives are heated in a water bath, and then the chitin or chitin derivatives heated in the water bath are added into dimethyl sulfoxide according to the following adding proportion: chitin or chitin derivative, dimethyl sulfoxide, in g/mL
=1:5-5000. The amount of dimethyl sulfoxide determines the concentration of the product, and products with different concentrations have different functions.
The application also provides a preparation experiment of the active short peptide modified chitin and the derivatives thereof.
Example 1
The embodiment provides a preparation method of active short peptide modified chitin and derivatives thereof.
The chitosan, dimethyl sulfoxide (DMSO), aniline and phosphate-DMSO buffer system described in this example were prepared from Sigma-Aldrich, polypeptides REDG and WGRGDSP (linker) were prepared from Hangzhou peptide Biotechnology, inc., bis (p-nitrophenyl) carbonate (4-NPBC) was prepared from TCI, and diethyl ether was obtained from national pharmaceutical Chemicals, inc.
Heating chitosan with molecular weight of about 500kDa to 80deg.C in water bath, maintaining at that temperature for 1 hr, and adding chitosan into DMSO with pH of 6.8 at 37deg.C at ratio of 1:5 for reaction for 1 hr in terms of g/mL; according to the mass ratio of the polypeptide REDG to the chitosan=2:1, grafting the polypeptide REDG to the amino group of the chitosan after the reaction with DMSO through WGRGDSP (linker), adding 2% cetyltrimethylammonium bromide (CTA) to react with the hydroxyl group of the primary alcohol at the 6 position of the chitosan for 1h to obtain modified chitosan, mixing and dissolving the modified chitosan and di (p-nitrophenyl) carbonate (4-NPBC) in a phosphate-DMSO buffer system with pH=8.0, reacting for 2h, mixing with aniline, reacting for 48h at the temperature of 60 ℃, precipitating with diethyl ether after the reaction is finished, and washing the product to obtain the high molecular weight chitosan material with the function of promoting the biological activity of tissue repair.
The example also provides a biological activity test of the chitosan material: the cells were cultured in a dish containing the chitosan and the normal chitosan provided in this example for 24 hours, respectively, using the normal chitosan as a control group, and the attachment and proliferation of the cells were observed, and the results are shown in FIG. 1. As can be seen from a and B in fig. 1, compared with the control group, the activated short peptide modified chitosan provided in this embodiment adheres well to the fibroblasts and effectively promotes proliferation of the fibroblasts, and has better biocompatibility and higher bioactivity.
Example 2
The embodiment provides a preparation method of active short peptide modified chitin.
This example relates to the reagent source as in example 1.
Heating carboxymethyl chitin with molecular weight of about 80kDa to 80 ℃, adding the carboxymethyl chitin heated by the water bath into phosphate-DMSO with a polar solvent of pH=4.6 according to g/mL ratio of 1:5 and stirring for 1 hour, and adding the mixed solution into DMSO containing carbodiimide and 1-hydroxybenzotriazole (HOBt) with a pH of 6.8 according to the ratio of the substances of carboxymethyl chitin to DMSO=1:4 (prepared according to the ratio of the substances of 1:3:6) for 1 hour under the temperature condition of 37 ℃; grafting polypeptide REDG to active 6-hydroxyl of carboxymethyl chitin in the mixture through GWGLGPAGK (linker) to obtain modified carboxymethyl chitin; the modified carboxymethyl chitin is dissolved in a mixed solution with pH=6.0 and containing lipophilic groups such as palmitic acid, the dissolution ratio is calculated in mg/mL, the mixed solution of the modified carboxymethyl chitin and the palmitic acid=1:3, and the mixture is stirred for 24 hours to fully react, so that the carboxymethyl chitin material with medium molecular weight and the function of promoting tissue repair bioactivity is obtained.
Example 3
The embodiment provides a preparation method of active short peptide modified chitin.
This example relates to the reagent source as in example 1.
Heating chitin with molecular weight of about 5kDa and deacetylation degree of above 55% to 80 deg.C in water bath, maintaining at the temperature for 1 hr, adding chitin heated in the water bath into DMSO (prepared according to the mass ratio of 1:1:3) containing carbodiimide and 1-hydroxybenzotriazole (HOBt) with pH of 6.8, and reacting for 1 hr; grafting polypeptide REDG to amino groups of the prepared chitin according to the mass ratio of the polypeptide REDG to chitin=2:1 through CCRR (linker), and modifying primary hydroxyl groups at 6 th position of a chitin main chain to obtain modified chitin; adding palmitic acid to modify-NH on chitin molecule 2 Esterification reaction with palmitic acid to generate ester, so that lipophilic groups are introduced, and the small molecular weight modified chitin material with the functions of transdermal absorption after being smeared and promoting tissue repair and bioactivity is obtained.
The embodiment also provides a biological activity test of the small molecular weight modified chitin material: the chitin material and the common carboxymethyl chitin provided in this embodiment are applied to the skin of the hand respectively by using the common chitosan as a control group, and the chitin material provided in this embodiment can be completely absorbed within 3 seconds after being applied (as shown in fig. 2B), but the common carboxymethyl chitin material is not completely absorbed within 3 minutes after being applied (as shown in fig. 2 a). As can be seen from fig. 2, compared with the control group, the chitin material provided in this embodiment has better biocompatibility.
The above-described embodiments are only preferred embodiments of the present application, and are not intended to be limiting in any way and in nature, and it should be noted that several modifications and additions may be made to those skilled in the art without departing from the application, which modifications and additions are also intended to be construed as within the scope of the application.
Claims (8)
1. A preparation method of active short peptide modified chitin is characterized in that chitin is taken as a main chain, and active short peptide is taken as a bioactive grafting group and grafted on the main chain; wherein the chitin comprises chitin and derivatives of chitin, and the number of repeating units of monomers in the chitin is 1-7000.
2. The method for preparing the chitin modified by the active short peptide according to claim 1, wherein the active short peptide comprises a polypeptide having an amino acid sequence of RXDX, LDXPX, KLDAPTX, KYILXWXPKNX, WTPPXAQITXYXLTXXLTXX, PHXXN, XXXDXP, XDXIHXL,
KPDXXXYTITX, ATETTITIXATXTTITIX, XPPXXAXXT, WQPPXAXI, YXKPXXPPXXXXPXPXPXX, KNNQKXXPLIXXKKT, wherein X is E or G or V or S or R or none.
3. The method for preparing the chitin modified by the active short peptide according to claim 1, wherein the molecular weight of the main chain is 1K-1000kDa.
4. The method of claim 1, wherein the grafting sites between the backbone and the bioactive grafting group comprise amino sites and hydroxyl sites.
5. The method for preparing the chitin modified by the active short peptide according to claim 1, wherein the bonding mode between the bioactive grafting group and the main chain is direct covalent bonding or physical mixing through a short peptide linker.
6. The method for preparing the active short peptide modified chitin according to claim 5, wherein the short peptide linker is WLC, WGRGDSP or GWGLGPAGK or CCRR.
7. An activated short peptide modified chitin prepared by the preparation method of any one of claims 1-6.
8. The use of the active oligopeptide-modified chitin of claim 7 as a physical filler.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202311197709.0A CN117229430A (en) | 2023-09-18 | 2023-09-18 | Active short peptide modified chitin and preparation method thereof |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202311197709.0A CN117229430A (en) | 2023-09-18 | 2023-09-18 | Active short peptide modified chitin and preparation method thereof |
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