CN114539434A - Dopamine-tyrosine-trehalose polymer and preparation method and application thereof - Google Patents
Dopamine-tyrosine-trehalose polymer and preparation method and application thereof Download PDFInfo
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- CN114539434A CN114539434A CN202111660472.6A CN202111660472A CN114539434A CN 114539434 A CN114539434 A CN 114539434A CN 202111660472 A CN202111660472 A CN 202111660472A CN 114539434 A CN114539434 A CN 114539434A
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/006—Heteroglycans, i.e. polysaccharides having more than one sugar residue in the main chain in either alternating or less regular sequence; Gellans; Succinoglycans; Arabinogalactans; Tragacanth or gum tragacanth or traganth from Astragalus; Gum Karaya from Sterculia urens; Gum Ghatti from Anogeissus latifolia; Derivatives thereof
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/28—Polysaccharides or their derivatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/44—Medicaments
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/46—Deodorants or malodour counteractants, e.g. to inhibit the formation of ammonia or bacteria
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/42—Use of materials characterised by their function or physical properties
- A61L15/62—Compostable, hydrosoluble or hydrodegradable materials
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L2300/00—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices
- A61L2300/40—Biologically active materials used in bandages, wound dressings, absorbent pads or medical devices characterised by a specific therapeutic activity or mode of action
- A61L2300/404—Biocides, antimicrobial agents, antiseptic agents
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
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Abstract
The invention discloses a dopamine-tyrosine-trehalose polymer and a preparation method and application thereof. The preparation method comprises the steps of condensing trehalose solution and epichlorohydrin; condensing tyrosine with the product; then mixing with dopamine, and adding an initiator, a cross-linking agent and a catalyst; and (5) freeze-drying to obtain a final product. The invention also discloses the antibacterial action, toxicological property and biodegradability of the polymer.
Description
Technical Field
The invention relates to the field of medicines, and particularly relates to a dopamine-tyrosine-trehalose polymer and a preparation method and application thereof.
Background
Dressing with good biocompatibility and biodegradability is widely applied to the medical field at present, and the dressing with antibacterial function modification can prevent the breeding of harmful microorganisms and has traditional Chinese medicine significance for controlling the spread of germs. Therefore, researches on antibacterial agents and antibacterial functional materials have been receiving general attention from researchers.
Dopamine can be oxidized and polymerized into polydopamine, the polydopamine has rich o-phenylenediquinone groups, and the polydopamine can generate Michael addition with functional molecules containing amino groups or sulfydryl groups and the like, so that other molecules are coupled to form a net structure, and the protective and antibacterial functions are achieved.
The common dressing has the antibacterial function that the disinfectant is soaked on the surface of the dressing to achieve the disinfection effect, or the iodine disinfectant is used in combination with the disinfectant and antibiotics, but the biocompatibility and the degradability of the disinfectant are all insufficient.
Disclosure of Invention
The dressing prepared by oxidative crosslinking polymerization of dopamine-tyrosine-trehalose has good antibacterial function, good biocompatibility and good biodegradability, and can be applied to surgical operations, burns and superficial wound care, disinfection and protection.
The purpose of the invention can be realized by the following technical scheme:
a preparation method of a dopamine-tyrosine-trehalose polymer comprises the following steps:
the first step is as follows: mixing trehalose and an ethanol solution, swelling overnight, cooling the swelled trehalose solution to 0-5 ℃, firstly adding an acidic catalyst and a solvent a, then slowly adding epoxy chloropropane, heating to reflux after the addition is finished, reacting for 1-3 h, cooling, and performing rotary evaporation to obtain an intermediate I;
the second step is that: dissolving the intermediate I in a solvent b, adding tyrosine, heating and refluxing, reacting for more than 8 hours, cooling, and performing rotary evaporation to obtain an intermediate II;
the third step: and dissolving the intermediate II in a solvent, sequentially adding dopamine hydrochloride, an initiator, a cross-linking agent and a catalyst, reacting for 7-8 hours, adding distilled water, centrifuging, removing supernatant, repeating for three to four times, collecting the lower layer, and freeze-drying to obtain the dopamine-tyrosine-trehalose polymer.
In the technical scheme of the invention, the concentration of the trehalose solution in the first step is 0.1-1 g/mL, and the ethanol solution is prepared by mixing the following components in a mass ratio of 8: 1-3 of a mixture of ethanol and water.
In the technical scheme of the invention, the acidic catalyst in the first step is any one of glacial acetic acid, concentrated sulfuric acid and p-toluenesulfonic acid; the mass ratio of the trehalose to the acidic catalyst is 5: 0.1 to 1.
In the technical scheme of the invention, the mass-volume ratio of trehalose to epichlorohydrin is 1-10 g: 5-15 mL.
In the technical scheme of the invention, the solvent a in the first step is toluene; in the second step, the solvent b is one of acetonitrile, DMF and DMSO.
In the technical scheme of the invention, in the second step, the mass ratio of trehalose to tyrosine is 1-5: 1 to 5.
In the technical scheme of the invention, the initiator in the third step is potassium persulfate, ammonium persulfate and sodium persulfate, the cross-linking agent is methyl acrylate, and the catalyst is triethylene diamine.
In the technical scheme of the invention, the mass ratio of trehalose to dopamine hydrochloride to initiator to cross-linking agent to catalyst is 3-8: 3-8: 0.5-1.5: 3-8: 0.5 to 1.5.
The dopamine-tyrosine-trehalose polymer is prepared by the method.
The technical scheme of the invention is as follows: the dopamine-tyrosine-trehalose polymer prepared by the preparation method is applied to the preparation of the dressing with the antibacterial function.
The invention has the beneficial effects that:
1. the dressing prepared by oxidative crosslinking polymerization of dopamine-tyrosine-trehalose has good antibacterial property and film forming property.
2. The polymer prepared by the invention has excellent antibacterial property.
3. The polymer prepared by the invention has good biocompatibility.
Detailed Description
The invention is further illustrated by the following examples, without limiting the scope of the invention:
example 1
Dissolving 5g of trehalose in 10mL of 80% ethanol solution, swelling at room temperature overnight, cooling to 2 ℃, adding glacial acetic acid 0.5g, adding 50mL of toluene, stirring, dropwise adding 10mL of epichlorohydrin, after dropwise adding, heating to reflux, reacting for 2h, cooling, and performing rotary evaporation to dryness to obtain 6.2g of yellow oily matter.
The yellow oil is dissolved in 50mL acetonitrile, 5g tyrosine is added, the mixture is heated and refluxed, the reaction is carried out for 8h, the mixture is cooled and is rotated and evaporated to dryness, and 15g yellow white viscous substance is obtained.
Dissolving 15g of the yellow-white sticky matter in 50mL of water, adding 5g of dopamine hydrochloride, dropwise adding 20g of a 5% solution of potassium persulfate, keeping stirring at room temperature overnight after dropwise adding, dropwise adding 5g of methyl acrylate, adding 0.5g of triethylene diamine after dropwise adding, heating, refluxing and stirring for 7h, cooling to room temperature, adding 50mL of water, centrifuging, discarding a supernatant, repeating for 3 times, collecting a lower-layer white sticky matter, and freeze-drying to obtain 3g of a white porous polymer.
Example 2
Dissolving 5g of trehalose in 10mL of 80% ethanol solution, swelling at room temperature overnight, cooling to 3 ℃, adding 1g of concentrated sulfuric acid, adding 50mL of toluene, stirring, dropwise adding 10mL of epichlorohydrin, after the dropwise addition is finished, heating to reflux, reacting for 2h, cooling, and performing rotary evaporation to dryness to obtain 6.2g of yellow oily matter.
The yellow oil is dissolved in 50ml DMF, 5g tyrosine is added, the heating reflux is carried out, the reaction is carried out for 9h, the cooling and the rotary evaporation to dryness are carried out, and 15g brown viscous substance is obtained.
Dissolving 15g of the yellow-white sticky matter in 50mL of water, adding 5g of dopamine hydrochloride, dropwise adding 20g of 5% solution of ammonium persulfate, keeping stirring at room temperature overnight after dropwise adding, dropwise adding 5g of methyl acrylate, adding 0.5g of triethylene diamine after dropwise adding, heating, refluxing and stirring for 7.5h, cooling to room temperature, adding 50mL of water, centrifuging, discarding supernatant, repeating for 4 times, collecting lower-layer white sticky matter, and freeze-drying to obtain 2g of white porous polymer.
Example 3
Dissolving 5g of trehalose in 10mL of 80% ethanol solution, swelling at room temperature overnight, cooling to 5 ℃, adding 0.2g of p-toluenesulfonic acid, adding 50mL of toluene, stirring, dropwise adding 10mL of epichlorohydrin, heating to reflux after dropwise addition is completed, reacting for 2h, cooling, and performing rotary evaporation to dryness to obtain 6.2g of yellow oily matter.
The yellow oil was dissolved in 50ml of ldmso, 5g of tyrosine was added, heated to reflux, reacted for 10h, cooled and rotary evaporated to dryness to give 8g of brown viscous material.
Dissolving 15g of the yellow-white sticky matter in 50mL of water, adding 5g of dopamine hydrochloride, dropwise adding 20g of a 5% solution of sodium persulfate, keeping stirring at room temperature overnight after dropwise adding, dropwise adding 5g of methyl acrylate, adding 0.5g of triethylene diamine after dropwise adding, heating, refluxing and stirring for 8 hours, cooling to room temperature, adding 50mL of water, centrifuging, discarding a supernatant, repeating for 3 times, collecting a lower-layer white sticky matter, and freeze-drying to obtain 2.8g of a white porous polymer.
And (3) sterilization experiment:
the polymers of the examples were formulated into 1% solutions and subjected to sterilization tests according to the "Disinfection specifications" as follows
Table 1 example 1 results of sterilization experiments
Table 2 example 2 results of sterilization experiments
Table 3 example 3 results of sterilization experiments
As can be seen from tables 1-3, the high molecular polymer prepared by the present invention has 100% of sterilization rate on Escherichia coli, Staphylococcus aureus and Candida albicans.
And (3) toxicological experiments:
two toxicological experiments were carried out on the silicone blood-sucking sponges obtained in examples 1 to 3. The experiment refers to the skin irritation test and skin allergy test of the second part of the 2002 edition of Disinfection technical Specification. The results are shown in the following table:
table 4 skin irritation test results
And (4) conclusion: as is clear from Table 4, the high molecular weight polymer obtained by the present invention is non-irritating.
TABLE 5 skin allergy test
And (4) conclusion: as is clear from Table 5, the high molecular weight polymer obtained by the present invention had a skin sensitization rate of 0 and was not allergenic.
Claims (10)
1. A preparation method of a dopamine-tyrosine-trehalose polymer is characterized by comprising the following steps: the method comprises the following steps:
the first step is as follows: mixing trehalose and an ethanol solution, swelling overnight, cooling the swelled trehalose solution to 0-5 ℃, firstly adding an acidic catalyst and a solvent a, then slowly adding epoxy chloropropane, heating to reflux after the addition is finished, reacting for 1-3 h, cooling, and performing rotary evaporation to obtain an intermediate I;
the second step is that: dissolving the intermediate I in a solvent b, adding tyrosine, heating and refluxing, reacting for more than 8 hours, cooling, and performing rotary evaporation to obtain an intermediate II;
the third step: and dissolving the intermediate II in a solvent, sequentially adding dopamine hydrochloride, an initiator, a cross-linking agent and a catalyst, reacting for 7-8 hours, adding distilled water, centrifuging, removing a supernatant, repeating for three to four times, collecting a lower layer, and freeze-drying to obtain the dopamine-tyrosine-trehalose polymer.
2. The method according to claim 1, wherein the concentration of the trehalose solution in the first step is 0.1g to 1g/mL, and the ethanol solution is a solution of trehalose in a mass ratio of 8: 1-3 of a mixture of ethanol and water.
3. The preparation method according to claim 1, wherein the acidic catalyst in the first step is any one of glacial acetic acid, concentrated sulfuric acid and p-toluenesulfonic acid; the mass ratio of the trehalose to the acidic catalyst is 5: 0.1 to 1.
4. The preparation method according to claim 1, wherein the mass-to-volume ratio of trehalose to epichlorohydrin is 1-10 g: 5-15 mL.
5. The process according to claim 1, wherein the solvent a in the first step is toluene; in the second step, the solvent b is one of acetonitrile, DMF and DMSO.
6. The preparation method according to claim 1, wherein the mass ratio of trehalose to tyrosine in the second step is 1-5: 1 to 5.
7. The process according to claim 1, wherein the initiator in the third step is potassium persulfate, ammonium persulfate or sodium persulfate, the crosslinking agent is methyl acrylate, and the catalyst is triethylene diamine.
8. The preparation method according to claim 1, wherein the mass ratio of trehalose to dopamine hydrochloride to initiator to cross-linking agent to catalyst is 3-8: 3-8: 0.5-1.5: 3-8: 0.5 to 1.5.
9. A dopamine-tyrosine-trehalose polymer characterized by: the polymer is prepared by the method of claim 1.
10. The dopamine-tyrosine-trehalose polymer prepared by the preparation method of claim 1 is applied to the preparation of dressing with antibacterial function.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06279227A (en) * | 1993-02-01 | 1994-10-04 | Ichimaru Pharcos Co Ltd | Dermatic external preparation and cosmetic |
| US6287757B1 (en) * | 1998-08-24 | 2001-09-11 | Riken | Amino acid-trehalose composition |
| CN106581734A (en) * | 2016-11-22 | 2017-04-26 | 孙祎 | Preparation method of highly antibacterial alginate dressing |
| CN108359056A (en) * | 2018-03-06 | 2018-08-03 | 中国科学院理化技术研究所 | Self-healing hydrogel of cellulose-dopamine-polymer composite material and preparation method and application thereof |
| CN113631566A (en) * | 2019-02-08 | 2021-11-09 | 路博润先进材料公司 | Compounds useful for the treatment and/or care of the skin, hair, nails and/or mucous membranes |
| CN113735989A (en) * | 2021-10-11 | 2021-12-03 | 章毅 | Trehalose derivative and cryoprotectant and application thereof |
-
2021
- 2021-12-30 CN CN202111660472.6A patent/CN114539434A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH06279227A (en) * | 1993-02-01 | 1994-10-04 | Ichimaru Pharcos Co Ltd | Dermatic external preparation and cosmetic |
| US6287757B1 (en) * | 1998-08-24 | 2001-09-11 | Riken | Amino acid-trehalose composition |
| CN106581734A (en) * | 2016-11-22 | 2017-04-26 | 孙祎 | Preparation method of highly antibacterial alginate dressing |
| CN108359056A (en) * | 2018-03-06 | 2018-08-03 | 中国科学院理化技术研究所 | Self-healing hydrogel of cellulose-dopamine-polymer composite material and preparation method and application thereof |
| CN113631566A (en) * | 2019-02-08 | 2021-11-09 | 路博润先进材料公司 | Compounds useful for the treatment and/or care of the skin, hair, nails and/or mucous membranes |
| CN113735989A (en) * | 2021-10-11 | 2021-12-03 | 章毅 | Trehalose derivative and cryoprotectant and application thereof |
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Application publication date: 20220527 |