CN109021242A - A kind of PCE polymer and preparation method thereof and the method for preparing antibacterial nano fiber material using it - Google Patents
A kind of PCE polymer and preparation method thereof and the method for preparing antibacterial nano fiber material using it Download PDFInfo
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- CN109021242A CN109021242A CN201810637474.5A CN201810637474A CN109021242A CN 109021242 A CN109021242 A CN 109021242A CN 201810637474 A CN201810637474 A CN 201810637474A CN 109021242 A CN109021242 A CN 109021242A
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- 229920000642 polymer Polymers 0.000 title claims abstract description 71
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 56
- 239000002121 nanofiber Substances 0.000 title claims abstract description 56
- 239000000463 material Substances 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims description 17
- 241000894006 Bacteria Species 0.000 claims abstract description 51
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims abstract description 48
- 230000029663 wound healing Effects 0.000 claims abstract description 45
- 230000001684 chronic effect Effects 0.000 claims abstract description 42
- 229920002521 macromolecule Polymers 0.000 claims abstract description 42
- 229920000728 polyester Polymers 0.000 claims abstract description 41
- 239000003814 drug Substances 0.000 claims abstract description 38
- 229940079593 drug Drugs 0.000 claims abstract description 37
- 230000015572 biosynthetic process Effects 0.000 claims abstract description 25
- 238000003786 synthesis reaction Methods 0.000 claims abstract description 25
- 238000010041 electrostatic spinning Methods 0.000 claims abstract description 13
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 11
- KDXKERNSBIXSRK-RXMQYKEDSA-N D-lysine Chemical compound NCCCC[C@@H](N)C(O)=O KDXKERNSBIXSRK-RXMQYKEDSA-N 0.000 claims abstract description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 54
- 238000003756 stirring Methods 0.000 claims description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 17
- 239000000178 monomer Substances 0.000 claims description 17
- 239000008367 deionised water Substances 0.000 claims description 14
- 229910021641 deionized water Inorganic materials 0.000 claims description 14
- 238000004108 freeze drying Methods 0.000 claims description 14
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 claims description 13
- 239000000047 product Substances 0.000 claims description 10
- 229920001345 ε-poly-D-lysine Polymers 0.000 claims description 10
- 230000003115 biocidal effect Effects 0.000 claims description 8
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical class CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 238000000502 dialysis Methods 0.000 claims description 8
- 230000004927 fusion Effects 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 239000012299 nitrogen atmosphere Substances 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 229920001432 poly(L-lactide) Polymers 0.000 claims description 3
- 229920001606 poly(lactic acid-co-glycolic acid) Polymers 0.000 claims description 3
- 229920001610 polycaprolactone Polymers 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- 238000009987 spinning Methods 0.000 claims description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims 1
- 229910021529 ammonia Inorganic materials 0.000 claims 1
- 238000002242 deionisation method Methods 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 abstract description 38
- 208000015181 infectious disease Diseases 0.000 abstract description 35
- 229960005082 etohexadiol Drugs 0.000 abstract description 9
- 230000000845 anti-microbial effect Effects 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 230000010148 water-pollination Effects 0.000 abstract description 3
- 230000001737 promoting effect Effects 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 150000003457 sulfones Chemical class 0.000 description 5
- 241000191967 Staphylococcus aureus Species 0.000 description 4
- 230000003013 cytotoxicity Effects 0.000 description 4
- 231100000135 cytotoxicity Toxicity 0.000 description 4
- 230000002194 synthesizing effect Effects 0.000 description 4
- 235000005979 Citrus limon Nutrition 0.000 description 3
- 244000131522 Citrus pyriformis Species 0.000 description 3
- 206010018910 Haemolysis Diseases 0.000 description 3
- 208000028990 Skin injury Diseases 0.000 description 3
- 206010052428 Wound Diseases 0.000 description 3
- 208000027418 Wounds and injury Diseases 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 239000012620 biological material Substances 0.000 description 3
- 230000008588 hemolysis Effects 0.000 description 3
- 239000012528 membrane Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 238000001523 electrospinning Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 230000035876 healing Effects 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- DWNBOPVKNPVNQG-LURJTMIESA-N (2s)-4-hydroxy-2-(propylamino)butanoic acid Chemical compound CCCN[C@H](C(O)=O)CCO DWNBOPVKNPVNQG-LURJTMIESA-N 0.000 description 1
- 229920001730 Moisture cure polyurethane Polymers 0.000 description 1
- 206010072170 Skin wound Diseases 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 206010048038 Wound infection Diseases 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical class ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000005213 imbibition Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 210000002429 large intestine Anatomy 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000002070 nanowire Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000008439 repair process Effects 0.000 description 1
- 230000037380 skin damage Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 238000012719 thermal polymerization Methods 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G81/00—Macromolecular compounds obtained by interreacting polymers in the absence of monomers, e.g. block polymers
-
- 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
- A61L15/26—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
-
- 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
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F1/00—General methods for the manufacture of artificial filaments or the like
- D01F1/02—Addition of substances to the spinning solution or to the melt
- D01F1/10—Other agents for modifying properties
- D01F1/103—Agents inhibiting growth of microorganisms
-
- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/88—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds
- D01F6/92—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from mixtures of polycondensation products as major constituent with other polymers or low-molecular-weight compounds of polyesters
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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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- 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
- A61L2300/412—Tissue-regenerating or healing or proliferative agents
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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
- A61L2400/00—Materials characterised by their function or physical properties
- A61L2400/12—Nanosized materials, e.g. nanofibres, nanoparticles, nanowires, nanotubes; Nanostructured surfaces
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Abstract
The invention discloses a kind of antibacterial nano fiber materials of Promote Chronic Ischemic Wound Healing and preparation method thereof for drug-resistant bacteria infection, and by citric acid and 1,8- ethohexadiol obtains PC prepolymer by melt polymerization；Then poly-D-lysine (EPL) is grafted on PC and obtains PCE polymer；PCE polymer and synthesis polyester macromolecule PE are prepared into nano-fiber material by electrostatic spinning under the conditions of 18Kv.Synthesis polyester macromolecule PE-PCE polymer nanofiber material prepared by the present invention has good biocompatibility, preferable mechanical property and hydrophily, excellent anti-microbial property, simultaneously, synthesis polyester macromolecule PE-PCE polymer nanofiber material also shows the effect for preferably promoting Promote Chronic Ischemic Wound Healing in animal experiments, therefore the nano-fiber material has good application prospect.
Description
Technical field
The invention belongs to degradable biological medical field of material technology, and in particular to a kind of PCE polymer and its preparation side
Method and the method for preparing antibacterial nano fiber material using it.
Background technique
The chronic skin injury due to caused by bacterium infection has become the threat of major medical in recent years, especially drug-resistant bacteria
Caused wound infection typically results in skin trauma and is difficult to heal, and few drugs can effectively treat wound caused by drug-fast bacteria
Infection.Conventional antibacterial biological material includes inorganic nano material and organic cationic polymer, but these anti-biotic materials
Biocompatibility and the poor requirement for not being able to satisfy wound healing of blood compatibility.It is same in order to effectively treat drug-fast bacteria infection
When promote wound healing, develop the antibacterial nano fiber material with biocompatibility, effectively antagonize drug-resistant bacteria and have imitative
Raw structure and good mechanical property are necessary and urgent.
Most develop currently, polyesters biomaterial is become with its good mechanical property and excellent biocompatibility
One of biomaterial of potentiality.PC is formed by citric acid and 1,8- ethohexadiol by dehydration condensation, has synthon
The advantages such as the good, excellent in mechanical performance of nontoxic, biocompatibility, and still have unreacted carboxylic acid group can be in PC polymer
Modified again, but PC does not have apparent bacteriostasis property, this make its as promote the application of Promote Chronic Ischemic Wound Healing material by
Great limitation is arrived, if it is possible to by further modifying PC, in the item for keeping its good biocompatibility and mechanical property
It is improved its antibacterial under part, the application in body will be greatly improved.
Summary of the invention
It is an object of the invention to overcome the above-mentioned prior art, a kind of PCE polymer and preparation method thereof is provided
With the method for preparing antibacterial nano fiber material using it, this method simple process, nano fibrous membrane obtained has good
Antibacterial effect, biocompatibility and promotion Promote Chronic Ischemic Wound Healing effect.
In order to achieve the above objectives, the present invention is achieved by the following scheme:
A kind of PCE polymer, structural formula are as follows:
A kind of preparation method of PCE polymer, comprising the following steps:
1) taking molar ratio is the citric acid and 1 of 1:1, and 8 butanediols carry out high-temperature fusion polymerization reaction, to reaction monomers lemon
Acid and 1,8 butanediols are cooled to 140 DEG C after all melting in 160 DEG C of oil baths, react 1 hour under vacuum conditions, and reaction produces
Object was through deionized water dialysis 48 hours, freeze-drying；
2) the poly- citrate PC of 0.5mmol is dissolved completely in the dimethyl sulfoxide of 10mL；Add 2.5mmol's
EDC is stirred evenly；The NHS of 1mmol is then added, stirs evenly；Antibiotic active molecular is added, is stirred evenly；Product is being gone
It dialyses 48 hours in ionized water, to remove the poly-D-lysine and catalyst EDC and NHS that do not react, is freeze-dried
To PCE polymer.
A further improvement of the present invention lies in that:
Citric acid and 1,8 butanediols carry out high-temperature fusion polymerization reaction in the round-bottomed flask of 50mL in step 1).
High-temperature fusion polymerization reaction be heated in nitrogen atmosphere 160 DEG C to monomer melt after be cooled to 140 DEG C, vacuum item
It is reacted 1 hour under part.
Antibiotic active molecular is ε-poly-D-lysine EPL, ε-poly-D-lysine EPL and poly- citrate PC in step 2)
Molar ratio is (0.1~10): 1.
In step 2), be added EDC after, 25 DEG C at a temperature of stir 30min；Be added NHS after, 25 DEG C at a temperature of
Stir 12h；Be added antibiotic active molecular after, 25 DEG C at a temperature of stir 72h.
A method of antibacterial nano fiber material is prepared using PCE polymer, comprising the following steps:
The mixture of PCE polymer and synthesis polyester macromolecule synthesis polyester macromolecule PE composition is added to the two of 2mL
In the mixed liquor of chloromethanes and dimethyl sulfoxide, electrostatic spinning is carried out under 18Kv voltage, is obtained for drug-resistant bacteria infection
The antibacterial nano fiber material of Promote Chronic Ischemic Wound Healing.
Itself further improvement is that
The mass ratio of PCE polymer and mixture is (0.1~0.5): 1.
The spinning solution solvent used when electrostatic spinning is the mixed liquor of methylene chloride and dimethyl sulfoxide, methylene chloride and mixed
The volume ratio for closing liquid is (0.7~0.9): 1.
Synthesizing polyester macromolecule PE is one or more of PCL, PLLA and PLGA mixture.
Compared with prior art, the invention has the following advantages:
The present invention is poor for antimicrobial agent, wound healing effect is unable to present in existing antibacterial nano fiber material
The disadvantages of, a kind of preparation method of the antibacterial nano fiber material of Promote Chronic Ischemic Wound Healing for drug-resistant bacteria infection is provided,
The technology, for monomer, obtains flexible poly- lemon by thermal polymerization with human body natural bioactive substances citric acid, 1,8- ethohexadiol
Lemon acid esters macromolecule prepolymer (PC)；Poly-D-lysine (EPL) with antibacterial activity is grafted with the prepolymer, obtained tool
It is obtained after flexible and excellent antibacterial performance polymer PC E polymer and synthesis polyester macromolecule PE mixed high-voltage electrospinning
The antibacterial nano fiber material of the final Promote Chronic Ischemic Wound Healing that can be used for drug-resistant bacteria infection.Preparation method letter of the invention
It is single, easy to operate, cost of material is lower.The results show: this method chronic wound obtained for drug-resistant bacteria infection
The antibacterial nano fiber material of healing has good elasticity and biocompatibility, can effectively kill including drug-fast bacteria
Various bacteria, and certain effect is shown in terms of wound healing.
Detailed description of the invention
Fig. 1 is the 1H-NMR map of PCE polymer obtained；
Fig. 2 is that the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing produced by the present invention for drug-resistant bacteria infection (closes
At polyester macromolecule PE-PCE polymer) scanning electron microscopic picture；
Fig. 3 is that the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing produced by the present invention for drug-resistant bacteria infection (closes
At polyester macromolecule PE-PCE polymer) mechanical property；
Fig. 4 is that the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing produced by the present invention for drug-resistant bacteria infection (closes
At polyester macromolecule PE-PCE polymer) hydrophily；
Fig. 5 is that the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing produced by the present invention for drug-resistant bacteria infection (closes
At polyester macromolecule PE-PCE polymer) anti-microbial property；
Fig. 6 is that the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing produced by the present invention for drug-resistant bacteria infection (closes
At polyester macromolecule PE-PCE polymer) cytotoxicity (A in Fig. 7) and hemolysis (B in Fig. 7)；
Fig. 7 is that the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing produced by the present invention for drug-resistant bacteria infection (closes
At polyester macromolecule PE-PCE polymer) skin injury healing properties.
Specific embodiment
The invention will be described in further detail with reference to the accompanying drawing:
Referring to Fig. 1, the structural formula of PCE polymer prepared by the present invention are as follows:
Preparation method includes the following steps:
1) molar ratio is taken to carry out high-temperature fusion polymerization in the round-bottomed flask of 50mL for the citric acid of 1:1 and 1,8 butanediols
Reaction, high-temperature fusion polymerization reaction carry out under vacuum conditions；To reaction monomers citric acid and 1,8 butanediols in 160 DEG C of oil baths
140 DEG C are cooled to after middle all meltings, is reacted 1 hour under vacuum conditions, reaction product is cold through deionized water dialysis 48 hours
It is lyophilized dry；
2) the poly- citrate PC of 0.5mmol is dissolved completely in the dimethyl sulfoxide of 10mL；Add 2.5mmol's
EDC, 25 DEG C at a temperature of stir 30min；Then be added 1mmol NHS, 25 DEG C at a temperature of stir 12h；It adds anti-
Bacterium bioactive molecule, 25 DEG C at a temperature of stir 72h；Antibiotic active molecular is ε-poly-D-lysine EPL, ε-poly-D-lysine
The molar ratio of EPL and poly- citrate PC is (0.1~10): 1；Product is dialysed 48 hours in deionized water, is not sent out with removing
The poly-D-lysine and catalyst EDC and NHS of raw reaction, freeze-drying obtain PCE polymer.
Further, the method that the present invention prepares antibacterial nano fiber material is based on above-mentioned steps, further includes following step
It is rapid:
3) mixture of PCE polymer and synthesis polyester macromolecule PE composition is added to the methylene chloride and diformazan of 2mL
In the mixed liquor of base sulfoxide, electrostatic spinning is carried out under 18Kv voltage, obtains the Promote Chronic Ischemic Wound Healing infected for drug-resistant bacteria
Antibacterial nano fiber material.The mass ratio of PCE polymer and mixture is (0.1~0.5): 1.It is used when electrostatic spinning
Spinning solution solvent is the mixed liquor of methylene chloride and dimethyl sulfoxide, the volume ratio of methylene chloride and mixed liquor be (0.7~
0.9):1.Synthesizing polyester macromolecule PE is one or more of PCL, PLLA and PLGA mixture.
The antibacterial nano fiber of Promote Chronic Ischemic Wound Healing prepared by the present invention for drug-resistant bacteria infection.Poly- citrate is pre-
Polymers (PC) is because have good elasticity, good biocompatibility to have been widely used for field of biomedicine.However PC
Prepolymer does not have apparent antibacterial effect that it is caused to be restricted as the application of promotion Promote Chronic Ischemic Wound Healing material；Poly relies
Propylhomoserin (EPL) is a kind of antibacterial agent of poly- polypeptide, has excellent broad spectrum antibacterial performance, but its cytotoxicity is larger.With
After EPL modifies PC, the anti-microbial property of polymer can be greatlyd improve, polymer still has good biofacies at the same time
Capacitive and elasticity.Therefore, in the present invention, poly- citrate (PC) is modified using EPL, obtained product PCE polymerization
Object mixes electrospinning with synthesis Polymer Synthesizing polyester macromolecule PE, and finally obtained nano fibrous membrane not only has good life
Object compatibility and excellent fungistatic effect, and can have certain elasticity, gas permeability and dilution properties, it is a kind of for resistance to
The antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing of medicine bacterium infection.
In order to better understand the present invention, the present invention is described in detail With reference to embodiment, but this hair
Bright content is not limited solely to the following examples.
Embodiment 1
1) 50mL the preparation of PC prepolymer: is added according to molar ratio 1:1 in citric acid and 1,8- ethohexadiol that gross weight is 5g
In round-bottomed flask, be heated in nitrogen atmosphere 160 DEG C to monomer melt after be cooled to 140 DEG C rapidly, reacted under vacuum condition
1 hour.Reaction product is after deionized water dialysis 48 hours, and freeze-drying is in case subsequent experimental uses.
2) preparation of PCE polymer: the weighed poly- citrate PC of 0.5mmol is dissolved completely in 10mL dimethyl sulfoxide
In；Add the EDC of 2.5mmol, 25 DEG C of stirring 30min；The NHS, 25 DEG C of stirring 12h of 1mmol is then added；It adds
0.5mmol ε-poly-D-lysine EPL, 25 DEG C of stirring 72h；Product is dialysed 48 hours in deionized water, is not occurred instead with removing
The monomer and catalyst EDC and NHS answered, freeze-drying obtain PCE polymer.
3) preparation for the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing of drug-resistant bacteria infection: by PCE polymer
Methylene chloride and the dimethyl Asia of 2mL are dissolved in synthesis polyester macromolecule PE (mass ratio of PCE and mixture is 0.1:1)
In the mixed liquor of sulfone (volume ratio of methylene chloride and mixed liquor is 0.8:1), electrostatic spinning is carried out under 18Kv voltage, is obtained
The antibacterial nano fiber material of Promote Chronic Ischemic Wound Healing for drug-resistant bacteria infection.
Embodiment 2
1) 50mL the preparation of PC prepolymer: is added according to molar ratio 1:1 in citric acid and 1,8- ethohexadiol that gross weight is 5g
In round-bottomed flask, be heated in nitrogen atmosphere 160 DEG C to monomer melt after be cooled to 140 DEG C rapidly, react 1 under vacuum condition
Hour.Reaction product is after deionized water dialysis 48 hours, and freeze-drying is in case subsequent experimental uses.
2) preparation of PCE polymer: the weighed poly- citrate PC of 0.5mmol is dissolved completely in 10mL dimethyl sulfoxide
In；Add the EDC of 2.5mmol, 25 DEG C of stirring 30min；The NHS, 25 DEG C of stirring 12h of 1mmol is then added；It adds
0.5mmol ε-poly-D-lysine EPL, 25 DEG C of stirring 72h；Product is dialysed 48 hours in deionized water, is not occurred instead with removing
The monomer and catalyst EDC and NHS answered, freeze-drying obtain PCE polymer.
3) preparation for the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing of drug-resistant bacteria infection: by PCE polymer
Methylene chloride and the dimethyl Asia of 2mL are dissolved in synthesis polyester macromolecule PE (mass ratio of PCE and mixture is 0.3:1)
In the mixed liquor of sulfone (volume ratio of methylene chloride and mixed liquor is 0.8:1), electrostatic spinning is carried out under 18Kv voltage, is obtained
The antibacterial nano fiber material of Promote Chronic Ischemic Wound Healing for drug-resistant bacteria infection.
Embodiment 3
1) 50mL the preparation of PC prepolymer: is added according to molar ratio 1:1 in citric acid and 1,8- ethohexadiol that gross weight is 5g
In round-bottomed flask, be heated in nitrogen atmosphere 160 DEG C to monomer melt after be cooled to 140 DEG C rapidly, reacted under vacuum condition
1 hour.Reaction product is after deionized water dialysis 48 hours, and freeze-drying is in case subsequent experimental uses.
2) preparation of PCE polymer: the weighed poly- citrate PC of 0.5mmol is dissolved completely in 10mL dimethyl sulfoxide
In；Add the EDC of 2.5mmol, 25 DEG C of stirring 30min；The NHS, 25 DEG C of stirring 12h of 1mmol is then added；It adds
0.5mmol ε-poly-D-lysine EPL, 25 DEG C of stirring 72h；Product is dialysed 48 hours in deionized water, is not occurred instead with removing
The monomer and catalyst EDC and NHS answered, freeze-drying obtain PCE polymer.
3) preparation for the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing of drug-resistant bacteria infection: by PCE polymer
Methylene chloride and the dimethyl Asia of 2mL are dissolved in synthesis polyester macromolecule PE (mass ratio of PCE and mixture is 0.5:1)
In the mixed liquor of sulfone (volume ratio of methylene chloride and mixed liquor is 0.8:1), electrostatic spinning is carried out under 18Kv voltage, is obtained
The antibacterial nano fiber material of Promote Chronic Ischemic Wound Healing for drug-resistant bacteria infection.
Embodiment 4
1) 50mL the preparation of PC prepolymer: is added according to molar ratio 1:1 in citric acid and 1,8- ethohexadiol that gross weight is 5g
In round-bottomed flask, be heated in nitrogen atmosphere 160 DEG C to monomer melt after be cooled to 140 DEG C rapidly, reacted under vacuum condition
1 hour.Reaction product is after deionized water dialysis 48 hours, and freeze-drying is in case subsequent experimental uses.
2) preparation of PCE polymer: the weighed poly- citrate PC of 0.5mmol is dissolved completely in 10mL dimethyl sulfoxide
In；Add the EDC of 2.5mmol, 25 DEG C of stirring 30min；The NHS, 25 DEG C of stirring 12h of 1mmol is then added；It adds
0.05mmol ε-poly-D-lysine EPL, 25 DEG C of stirring 72h；Product is dialysed 48 hours in deionized water, is not occurred instead with removing
The monomer and catalyst EDC and NHS answered, freeze-drying obtain PCE polymer.
3) preparation for the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing of drug-resistant bacteria infection: by PCE polymer
Methylene chloride and the dimethyl Asia of 2mL are dissolved in synthesis polyester macromolecule PE (mass ratio of PCE and mixture is 0.3:1)
In the mixed liquor of sulfone (volume ratio of methylene chloride and mixed liquor is 0.7:1), electrostatic spinning is carried out under 18Kv voltage, is obtained
The antibacterial nano fiber material of Promote Chronic Ischemic Wound Healing for drug-resistant bacteria infection.
Embodiment 5
1) 50mL the preparation of PC prepolymer: is added according to molar ratio 1:1 in citric acid and 1,8- ethohexadiol that gross weight is 5g
In round-bottomed flask, be heated in nitrogen atmosphere 160 DEG C to monomer melt after be cooled to 140 DEG C rapidly, reacted under vacuum condition
1 hour.Reaction product is after deionized water dialysis 48 hours, and freeze-drying is in case subsequent experimental uses.
2) preparation of PCE polymer: the weighed poly- citrate PC of 0.5mmol is dissolved completely in 10mL dimethyl sulfoxide
In；Add the EDC of 2.5mmol, 25 DEG C of stirring 30min；The NHS, 25 DEG C of stirring 12h of 1mmol is then added；It adds
5mmol ε-poly-D-lysine EPL, 25 DEG C of stirring 72h；Product is dialysed 48 hours in deionized water, is not reacted with removing
Monomer and catalyst EDC and NHS, freeze-drying obtain PCE polymer.
3) preparation for the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing of drug-resistant bacteria infection: by PCE polymer
Methylene chloride and the dimethyl Asia of 2mL are dissolved in synthesis polyester macromolecule PE (mass ratio of PCE and mixture is 0.3:1)
In the mixed liquor of sulfone (volume ratio of methylene chloride and mixed liquor is 0.9:1), electrostatic spinning is carried out under 18Kv voltage, is obtained
The antibacterial nano fiber material of Promote Chronic Ischemic Wound Healing for drug-resistant bacteria infection.
For the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing of drug-resistant bacteria infection, (synthesis is poly- prepared by the present invention
Ester macromolecule PE-PCE polymer nanofibre film) it can effectively inhibit various bacteria (large intestine bar including drug-resistant bacteria
Bacterium/staphylococcus aureus/resistant Staphylococcus aureus), and have the water absorbing properties of preferable elasticity, appropriateness, it is same with this
Shi Hecheng polyester macromolecule PE-PCE polymer nanofibre film also shows good biocompatibility and promotes chronic wound
The performance that face is repaired, below with reference to experimental data detailed analysis.
Fig. 1 is the 1H-NMR figure of the polymer PC E polymer of the Promote Chronic Ischemic Wound Healing obtained for drug-resistant bacteria infection
Spectrum, from figure 1 it appears that methylene (- CH2) proton peak on 1,8- ethohexadiol is located at 1.2,1.5,3.9 Hes
4.1ppm belongs to the methene proton of citric acid positioned at the multiplet of 2.6-3.0ppm, and at 8.57ppm proton peak (-
CONH- appearance) illustrates that EPL is successfully grafted on PC prepolymer and forms new PCE polymer.
Fig. 2 is that the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing produced by the present invention for drug-resistant bacteria infection is being swept
Retouch the pattern under Electronic Speculum.Wherein A is pure PE nanofiber, and B is PE-10%PCE nanofiber, and C is PE-30%PCE Nanowire
Dimension, D are PE-50%PCE nanofiber.
Fig. 3 is the power of the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing produced by the present invention for drug-resistant bacteria infection
Learn performance.From figure 3, it can be seen that synthesis polyester macromolecule PE-PCE polymer antibacterial nano fiber shows preferable drawing
Stretch performance and lower Young's modulus.Wherein A is stress-strain diagram, and B is Young's modulus, and C is elongation at break, and D is to stretch
Intensity.
Fig. 4 is the parent of the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing produced by the present invention for drug-resistant bacteria infection
It is aqueous., it can be seen that synthesis polyester macromolecule PE-PCE polymer antibacterial nano fiber shows preferable hydrophily.Its
Middle A is water contact angle picture, and B is corresponding statistical data, and C is water absorption rate.
Fig. 5 is the anti-of the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing produced by the present invention for drug-resistant bacteria infection
Bacterium performance.As can be seen that being directed to three kinds of different bacterium (staphylococcus aureus, Escherichia coli and resistant S grape balls
Bacterium), synthesize polyester macromolecule PE-30%PCE polymer and synthesis polyester macromolecule PE-50%PCE polymer all present it is excellent
Different antibacterial effect, bacteriostasis rate are up to 99% or more.Wherein A is S. aureus colonies number, and B is E. coli clones
Number, C are resistant Staphylococcus aureus clump count.
Fig. 6 is the antibacterial nano fiber material pair of the Promote Chronic Ischemic Wound Healing produced by the present invention for drug-resistant bacteria infection
L929 cytotoxicity (A) and haemolysis property (B).A shows to synthesize polyester macromolecule PE-10%PCE polymer and synthesis in Fig. 6
Polyester macromolecule PE-30%PCE polymer is extremely low to L929 cytotoxicity.B shows to synthesize polyester macromolecule PE-10% in Fig. 6
The hemolysis rate of PCE polymer and synthesis polyester macromolecule PE-30%PCE polymer is 5% hereinafter, this illustrates to synthesize polyester height
Molecule PE-10%PCE polymer and the biocompatibility for synthesizing polyester macromolecule PE-30%PCE polymer are preferable.
Fig. 7 is the antibacterial nano fiber material of the Promote Chronic Ischemic Wound Healing produced by the present invention for drug-resistant bacteria infection small
The intracorporal skin injury repair ability test of mouse.A shows lower synthesis polyester macromolecule PE-30% at the same time in Fig. 7
The area of the mouse skin wound healing of PCE polymer treatment is greater than other groups of mouse, and B shows to synthesize polyester macromolecule in Fig. 7
The time of the mouse skin damage recovery from illness of PE-30%PCE polymer treatment is most short.As can be seen that synthesis polyester macromolecule PE-
30%PCE polymer antibacterial nano fiber material has certain facilitation to wound healing.
The antibacterial nano fiber material of the prepared Promote Chronic Ischemic Wound Healing for drug-resistant bacteria infection (closes in the present invention
At polyester macromolecule PE-PCE polymer), preparation process is simple, the various bacteria including drug-fast bacteria can be effectively killed,
And there are good mechanical property and water imbibition, there is good biocompatibility, meanwhile, synthesis polyester macromolecule PE-PCE polymerization
Object antibacterial nano fiber material can promote Promote Chronic Ischemic Wound Healing to a certain extent, therefore the material has good application prospect.
It also have the advantage that
(1) prepolymer PC used in the present invention is a kind of degradable macromolecule, and monomer biocompatibility is good, cheap
It is easy to get, while also there is certain elasticity.
(2) access of poly-D-lysine of the present invention so that originally do not have anti-microbial property prepolymer PC shown it is excellent
Different broad spectrum antibacterial performance can effectively kill the various bacteria including drug-fast bacteria.
(3) antibacterial nanofiber membrane is prepared using electrostatic spinning technique in the present invention, manufactured tunica fibrosa has specific surface
The performances such as product is big, breathes freely, can promote Promote Chronic Ischemic Wound Healing.
The above content is merely illustrative of the invention's technical idea, and this does not limit the scope of protection of the present invention, all to press
According to technical idea proposed by the present invention, any changes made on the basis of the technical scheme each falls within claims of the present invention
Protection scope within.
Claims (10)
1. a kind of PCE polymer, which is characterized in that structural formula are as follows:
。
2. the preparation method of PCE polymer described in a kind of claim 1, which comprises the following steps:
1) taking molar ratio is the citric acid and 1 of 1:1, and 8 butanediols carry out high-temperature fusion polymerization reaction, to reaction monomers citric acid and
1,8 butanediol is cooled to 140 DEG C after all melting in 160 DEG C of oil baths, reacts 1 hour under vacuum conditions, reaction product warp
Deionized water dialysis 48 hours, freeze-drying；
2) the poly- citrate PC of 0.5mmol is dissolved completely in the dimethyl sulfoxide of 10mL；The EDC of 2.5mmol is added,
It stirs evenly；The NHS of 1mmol is then added, stirs evenly；Antibiotic active molecular is added, is stirred evenly；Product is in deionization
It dialyses 48 hours in water, to remove the poly-D-lysine and catalyst EDC and NHS that do not react, freeze-drying obtains PCE
Polymer.
3. preparation method according to claim 2, which is characterized in that citric acid and 1 in step 1), 8 butanediols are in 50mL
Round-bottomed flask in carry out high-temperature fusion polymerization reaction.
4. preparation method according to claim 2 or 3, which is characterized in that high-temperature fusion polymerization reaction is in nitrogen atmosphere
Be heated to 160 DEG C to monomer melt after be cooled to 140 DEG C, reacted 1 hour under vacuum condition.
5. preparation method according to claim 2, which is characterized in that antibiotic active molecular is that ε-poly relies ammonia in step 2)
The molar ratio of sour EPL, ε-poly-D-lysine EPL and poly- citrate PC are (0.1~10): 1.
6. preparation method according to claim 2 or 5, which is characterized in that in step 2), after EDC is added, in 25 DEG C of temperature
Degree is lower to stir 30min；Be added NHS after, 25 DEG C at a temperature of stir 12h；After antibiotic active molecular is added, in 25 DEG C of temperature
Lower stirring 72h.
7. a kind of PCE polymer using the preparation of claim 2-6 any one the method prepares antibacterial nano fiber material
Method, which comprises the following steps:
The mixture of PCE polymer and synthesis polyester macromolecule synthesis polyester macromolecule PE composition is added to the dichloromethane of 2mL
In the mixed liquor of alkane and dimethyl sulfoxide, electrostatic spinning is carried out under 18Kv voltage, obtains infecting for drug-resistant bacteria chronic
The antibacterial nano fiber material of wound healing.
8. the method according to the description of claim 7 is characterized in that the mass ratio of PCE polymer and mixture be (0.1~
0.5):1。
9. the method according to the description of claim 7 is characterized in that the spinning solution solvent used when electrostatic spinning is methylene chloride
With the mixed liquor of dimethyl sulfoxide, the volume ratio of methylene chloride and mixed liquor is (0.7~0.9): 1.
10. the method according to the description of claim 7 is characterized in that synthesis polyester macromolecule PE is in PCL, PLLA and PLGA
One or more of mixtures.
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| CN109731147A (en) * | 2018-12-24 | 2019-05-10 | 西安交通大学 | Multi-functional PCS Hybrid nanofibers bio-medical method for producing elastomers and application |
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