CN109701069A - A kind of antibacterial tissue adhesive and preparation method thereof - Google Patents
A kind of antibacterial tissue adhesive and preparation method thereof Download PDFInfo
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- CN109701069A CN109701069A CN201910087144.8A CN201910087144A CN109701069A CN 109701069 A CN109701069 A CN 109701069A CN 201910087144 A CN201910087144 A CN 201910087144A CN 109701069 A CN109701069 A CN 109701069A
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- antibacterial
- tissue adhesive
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Abstract
The invention discloses a kind of antibacterial tissue adhesive, the high molecular polymer by functional modification and the antibacterial agent with amino are formed.Antibacterial tissue adhesive can be realized the quick-binding closing of wound, it is closed suitable for skin incision, is suitable for soft tissue injury and bonds, can be realized the quick-binding closing of wound, and compared with commercially available tissue medical glue, have the effect of obviously there is promotion wound healing.
Description
Technical field
The invention belongs to biomedical materials field, it is related to a kind of antibacterial tissue adhesive and preparation method thereof.
Background technique
As medical tissue adhesive has the closed effect of quick-binding to biological tissue of human body, wound can be partially replaced
Suture, can be applied to the various surface of a wound, comprising: skin incision closure, soft tissue injury bonding, bone and cartilage bonding, vascular closure
Hemostasis etc..Currently, commercialized medical tissue adhesive is mainly based on cyano-acrylate binder, due to cyanoacrylate
The characteristic of esters of gallic acid adhesive makes bonded part really up to the mark after solidification, and elasticity not enough, and is easy the disadvantages of causing inflammation, and
It is not ideal medical tissue adhesive.Therefore, the improvement of cyano-acrylate binder causes extensive research, such as
CN103272263B discloses the method reduced by the method for blending to tissue irritation.But it is possible to quick-binding, matching
Tissue, good drawing force and the new type bonding agent with excellent biological safety are urgently developed.
Factors, the wound infections such as wound climate pollution, the decline of patient's autoimmunity become the disaster in clinical care
Topic causes wound infection and not only impacts to post-operative recovery, the life of patient but will be threatened when critical.Currently, medical tissue
Adhesive does not have the function of antibacterial also, is easy to that bacterium infection occurs during the surface of a wound bonds and heals, causes inflammation,
Influence healing.Therefore, the new medical tissue adhesive with antibacterial functions becomes the urgent need of clinical application.
Therefore, a kind of good biocompatibility is developed, quick-binding and antibacterial can be capable of under tissue wet environment
Medical tissue adhesive is particularly important.
Summary of the invention
In view of this, the present invention provides a kind of antibacterial tissue adhesive and preparation method thereof.The present invention specifically provide as
Under technical solution:
1, a kind of antibacterial tissue adhesive, the high molecular polymer by functional modification and the antibacterial agent group with amino
At.
Further, the molar ratio of the high molecular polymer of the functional modification and antibacterial agent is 0.05~20:1, described
The molar ratio of functionalization group and high molecular polymer chain link on the high molecular polymer of functional modification is 0.05~1:1,
The molecular weight of the high molecular polymer of the functional modification is 5kDa~2000kDa.
Further, the functional modification includes active fat modification, polyphenol modification, oxidative modification, halogenated modification.
Further, the high molecular polymer of the functional modification includes the natural polysaccharide of functional modification, described natural
Polysaccharide includes starch, cellulose, chondroitin sulfate, sodium alginate, hyaluronic acid, glucan, polyamino acid, bovine serum albumin
And its their derivative.
Further, the high molecular polymer of the functional modification includes the polylactic acid of functional modification, polycaprolactone, gathers
Acid anhydrides, polyoxyethylene, polyglycolic acid, polyethylene glycol, polyvinyl alcohol, polyphosphate, polyorthoester, polyaminoacid and its they
Derivative.
Further, the high molecular polymer of functional modification includes the glucan of tannic acid modification, and succinimide rouge is repaired
The sodium alginate of decorations, the amine-modified hyaluronic acid of DOPA, vinyl benzyl chloride/polyvinyl alcohol copolymer, bar amine hydrochlorate modification
Bovine serum albumin(BSA), polyvinyl salicylide/ethylene glycol copolymer.
Further, the antibacterial agent with amino is streptomysin, gentamicin, tobramycin, amikacin, how to replace rice
One in star, ε-poly-D-lysine, polyaminopropyl biguanide, hexamethylene or polyhexamethylene list guanidine hydrochloride
Kind is several.
Further, the antibacterial tissue adhesive is 10~40 seconds to the bonding time of organism, and overlap joint-shear tension is held
Load intensity is 11.8~14.57KPa, and tissue peeling force is 10.5~13.1N/m, and tensile strength is 24.9~32.3KPa.
Further, there is bacteriostasis to escherichia coli, staphylococcus aureus and Candida albicans.
2, a kind of preparation method of antibacterial tissue adhesive, by the high molecular polymer of functional modification and with amino
Antibacterial agent be directly blended or be blended to obtain in water.
The beneficial effects of the present invention are: it is seeped using the high molecular polymer of functionalization and with amino antibacterial agent in wound
At liquid occur reaction and generate adhesive effect.Based on unused functional modification group, bond properties is controllable, and the present invention is anti-
Hyphostroma adhesive (curing time 10s~40s) has more compared to cyanoacrylate acids medical adhesive (curing time 180s)
The fast tissue adhesion time.The overlap joint of antibacterial tissue adhesive-shear tension 11.8~14.57KPa of bearing strength, can be realized
The quick-binding of wound is closed, and is suitable for skin incision and is closed.The T- removing of antibacterial tissue adhesive stretches bearing strength 10.5
~13.1N/m is suitable for soft tissue injury and bonds.Its tensile strength tensile strength of antibacterial tissue adhesive be 24.9~
32.3KPa can be realized the quick-binding closing of wound.Antibacterial tissue adhesive glue and commercially available tissue medical glue, blank group phase
Than, hence it is evident that there is the effect for promoting wound healing.
Different with traditional adhesive, in antimicrobial adhesive of the invention, amino antibacterial agent is to constitute adhesive skeleton
One of component, amino antibacterial agent also can reach the purpose of antibacterial while generating adhesive effect.It is compared with commercial binder,
Adhesive provided by the present invention has common escherichia coli, staphylococcus aureus and Candida albicans good anti-
Bacterium effect, the minimum inhibitory concentration to above-mentioned three kinds of strains be respectively 64 μ of μ g/ml~128 g/ml, 64 μ g/ml, 32 μ g/ml~
256μg/ml.It can be reduced during the surface of a wound bonds and heals and bacterium infection occurs, accelerate the healing of the surface of a wound.
Therefore, antimicrobial adhesive preparation method provided by the present invention is simple, good to organism bonding effect while having
Good antibacterial effect can be applied to the surface of a wound of infection and prevent the generation of trauma surface infestation, these features are viscous for the antibacterial
The clinical application of mixture provides sound assurance.
Detailed description of the invention
In order to keep the purpose of the present invention, technical scheme and beneficial effects clearer, the present invention provides following attached drawing:
Fig. 1 is the minimum inhibitory concentration figure of embodiment 1.
Fig. 2 is the minimum inhibitory concentration figure of embodiment 2.
Fig. 3 is the minimum inhibitory concentration figure of embodiment 3.
Fig. 4 is the minimum inhibitory concentration figure of commercially available cyanoacrylate adhesive.
Fig. 5 is the anti-microbial property figure of 4,5 and 6 pairs of escherichia coli of embodiment, staphylococcus aureus, Candida albicans.
Fig. 6 is S. aureus Inoculate in the antibacterial situation comparison diagram of SD rat wound.
Fig. 7 is the promoting healing rate comparison diagram for SD rat wound.
Specific embodiment
With reference to the accompanying drawing, a preferred embodiment of the present invention will be described in detail.
Embodiment 1
The preparation of natural polymers base tissue adhesive: 3g tannic acid is modified glucan (structural formula are as follows:
, molecular weight=60~80KDa, x=300~500, y=30~50) mixed with 1.2g streptomysin after obtain polysaccharide-based
Tissue adhesive 1.
Embodiment 2
The preparation of natural polymers base tissue adhesive: by the sodium alginate (knot of 1g succinimide fat modification
Structure formula are as follows:, molecular weight=1800~2000kDa, x=10000~12000, y=500~600) and the mixing of 0.2g gentamicin
Obtain polysaccharide-based tissue adhesive 2.
Embodiment 3
The preparation of polysaccharide-based tissue adhesive: by the amine-modified hyaluronic acid of 1g DOPA (structural formula is,
, molecular weight=800~1000kDa, x=400~500, y=40~50), 20 μ L H2O2With 0.02g amikacin
It is dissolved in 10mL deionized water, general purification, polysaccharide-based tissue adhesive 3 is obtained after freeze-drying.
Embodiment 4
The preparation of synthesising macromolecule copolymer base tissue adhesive: by 3g vinyl benzyl chloride/polyvinyl alcohol copolymer (structure
Formula are as follows:
, molecular weight=5~8kDa, x=25~50, y=25~50) and it is dissolved in after 10mL deionized water with 2g tobramycin
To antibacterial tissue adhesive 4.
Embodiment 5
The preparation of synthesising macromolecule copolymer base tissue adhesive: the bovine serum albumin(BSA) that 1g dopamine hydrochloride is modified
(BSA-CA-DOPA, molecular formula are as follows:,
, molecular weight=60~70kDa, degree of substitution=35%), 20 μ L H2O2It is dissolved in 100m g polyaminopropyl biguanide
In 10mL deionized water, antibacterial tissue adhesive 5 is obtained.
Embodiment 6
The preparation of synthesising macromolecule copolymer base tissue adhesive: by 3g polyvinyl salicylide/ethylene glycol copolymer,
Its structure are as follows:, molecular weight=20~25kDa, x=15~18, y=40~50, z=8~10), 1g Netilmicin is dissolved in 10mL
In deionization, antibacterial tissue adhesive 6 is obtained.
Embodiment 7
In order to prove beneficial effects of the present invention, to embodiment 1-6 obtained in embodiment and commercially available cyanoacrylate acids
Medical adhesive has carried out the adhesive test of fresh porcine skin, and specific test situation is as follows:
Each by Examples 1 to 6 sample is applied between the fresh pigskin of two panels, and contact area is 2.5x 1cm2,
The pigskin of bonding was placed on the fixture of universal testing machine in every 10 seconds, so that crosshead loads sample with the speed of 5mm/min
To destruction, its overlap joint-shear tension bearing strength is tested, the record organization peeling force in tester for elongation obtains the number of table 1
According to；Each by Examples 1 to 6 sample is applied between the fresh pigskin of two panels, and contact area is 2.5x 15cm2, every 10
The pigskin of bonding is placed on the fixture of universal testing machine by the second, so that crosshead is loaded onto sample with the speed of 250mm/min
It destroys, tests its T- removing and stretch bearing strength, the record organization peeling force in tester for elongation obtains the data of table 2；It will be real
Each for applying 1~6 sample of example is applied between the fresh pigskin of two panels, and contact area is 2.5x 2.5cm2, will glue within every 10 seconds
The pigskin of conjunction is placed on mold and then is put on the fixture of universal testing machine, so that crosshead is with the speed of 2mm/min to sample
It is loaded onto destruction, tests its tensile strength, the record organization peeling force in tester for elongation obtains the data of table 1~3.
Table 1
Table 2
Table 3
From 1 data comparison of table it can be seen that embodiment 1-6 (tissue adhesion time 10s~40s) is compared to alpha-cyanoacrylate
Class medical adhesive (tissue adhesion time 600s, about 10min) has faster tissue adhesion time, and its overlap joint-shear tension
Bearing strength (11.8~14.57N/m) is greater than cyanoacrylate acids adhesive (only 11.4N/m), therefore can be good at reality
The quick-binding closing of existing wound, is suitable for skin incision and is closed.
From 2 data comparison of table it can be seen that embodiment 1-6 (tissue adhesion time 10s~40s) is compared to alpha-cyanoacrylate
Class medical adhesive has faster tissue adhesion time (tissue adhesion time 600s, about 10min), and its T- removing stretches carrying by force
It spends (24.4~32.3KPa) and is greater than cyanoacrylate acids adhesive (only 24KPa), be suitable for soft tissue injury and bond.
From 3 data comparison of table it can be seen that embodiment 1-6 (tissue adhesion time 10s~40s) is compared to alpha-cyanoacrylate
Class medical adhesive (tissue adhesion time 600s, about 10min) has the faster tissue adhesion time, and its tensile strength (24.4~
32.3KPa) it is greater than cyanoacrylate acids adhesive (24KPa), can be realized the quick-binding closing of wound, be more applicable for bone
It is bonded with cartilage.
Embodiment 8
In order to prove beneficial effects of the present invention, embodiment 1-6 and commercially available cyanoacrylate acids medical adhesive are resisted
Bacterium contrast test, specific test situation are as follows:
The anti-microbial property of antibacterial tissue adhesive is by minimum inhibitory concentration (minimum inhibitory
Concentration, MIC) and inhibition zone method characterized, MIC is one of antibacterial activity size for measuring antibacterials
Index refers to the lowest concentration of drug that can inhibit growth of pathogenic bacteria in culture medium after cultivating bacterium 24 hours in vitro.Inhibition zone method
It is called diffusion method, is to spread to be suppressed surrounding bacterial growth and formed transparent in agar plate using drug to be measured
Circle, i.e. inhibition zone, a kind of method of drug inhibitory potency to be measured is determined according to inhibition zone size.
1, the measurement of minimum inhibitory concentration
(1) prepared by antibacterial tissue adhesion developing agent storage liquid
Antibacterial tissue adhesive is diluted in sterile water, the stoste of 2560 μ g/ml is made.
(2) prepared by culture medium
Use ordinary nutritional broth bouillon, sand Bao Shi agar medium, LB broth bouillon, potato dextrose agar
Culture medium, Czapek's medium, helicobacter pylori agar medium
(3) MIC plate makes
The antibacterial tissue adhesion developing agent storage liquid of various concentration after doubling dilution is added separately to 96 hole polystyrenes of sterilizing
In plate, the 1st to the 10th hole adds antibacterial tissue adhesion developing agent storage liquid, every 70 μ L of hole, antibacterial tissue adhesive concentration is respectively 1024,
512,256,128,64,32,8,4,2,1 μ g/mL, the 11st, 12 holes antibacterial agent is not added as positive control.
(4) prepared by inoculum
Concentration is equivalent to bacteria suspension of 0.5 Maxwell than turbid standard, after the dilution of LB meat soup 1: 1000, to every Kong Zhongjia 70
μl.At this point, the 1st hole to the 10th hole drug concentration is respectively 1024,512,256,128,64,32,8,4,2,1 μ g/mL, after sealing
Set judging result after 37 DEG C of shaking tables are incubated for for 24 hours.
(5) result judges
Under the premise of bacterium obviously grows in Positive control wells, OD600 is measured by microplate reader, with complete in aperture
The minimum concentration for inhibiting bacterial growth is MIC, obtains Fig. 1, Fig. 2 and Fig. 3, Fig. 4.
From Fig. 1 data comparison it can be seen that embodiment 1 is to escherichia coli, staphylococcus aureus, Candida albicans
MIC is respectively 64 μ g/ml, 64 μ g/ml, 32 μ g/ml.
From Fig. 2 data comparison it can be seen that embodiment 2 is to escherichia coli, staphylococcus aureus, Candida albicans
MIC is respectively 128 μ g/ml, 64 μ g/ml, 256 μ g/ml.
From Fig. 3 data comparison it can be seen that embodiment 3 is to escherichia coli, staphylococcus aureus, Candida albicans
MIC is respectively 64 μ g/ml, 64 μ g/ml, 32 μ g/ml.
From Fig. 4 data it can be seen that commercially available cyanoacrylate adhesive to escherichia coli, staphylococcus aureus,
Candida albicans are almost without antibacterial action.
4 performance comparison of table
From 4 data comparison of table it can be seen that compared Examples 1 to 3 and commercially available cyanoacrylate tissue adhesion doctor
With glue for the MIC of escherichia coli, staphylococcus aureus and Candida albicans.MIC is that bacterium is enabled to stop development and division
Minimum antimicrobial agent concentration, this concentration is lower, illustrates that antibacterial ability is stronger.Illustrate Examples 1 to 3 to escherichia coli, gold
Staphylococcus aureus, Candida albicans inhibition zone it is obvious that having strong antibacterial action.And commercially available cyanoacrylate group
Bonding medical adhesive is knitted to escherichia coli, staphylococcus aureus, Candida albicans almost without antibacterial action.
2, inhibition zone method
(1) main vessel and articles
Culture dish (diameter 90mm), punch (aperture 6mm), Oxford cup (internal diameter 6mm), stainless pipe (outer diameter 6mm),
Filter paper, triangular flask (250mL).
(2) culture medium
Fluid nutrient medium: peptone 10g/L, yeast powder 5g/L, NaCl 10g/L, pH 7.8.
Plating medium: peptone 10g/L, yeast powder 5g/L, NaCl 10g/L, agar powder 20g/L, pH 7.8.
(3) method
The activation of strain and the preparation of bacterium solution: by the strain streak inoculation of freezen protective to plating medium, 37 DEG C of cultures
24h；Choose single colonie and be seeded to 100mL fluid nutrient medium, 37 DEG C, 150r/min shaking table culture stay overnight, bacterium solution is spare.
The preparation of test panel:
Pre-add bacterium solution pour plate method: injecting a certain amount of bacterium solution into the plating medium for having cooled to 50 DEG C or so,
It is uniformly mixed, one layer of culture medium is first spread in test panel, Oxford cup is placed on culture medium, (about 20mL/ is flat for pour plate
Plate), it is spare after horizontal rest solidification.
Three holes are made a call in each plate with Odontothrips loti, antibacterial tissue adhesive is placed in hole, culture for 24 hours, remains to see
It examines.
(4) result is judged
The inhibitory potency that embodiment 4,5,6 is determined according to inhibition zone size, obtains Fig. 5.
From Fig. 5 data comparison it can be seen that embodiment 4,5,6 pairs of escherichia coli, staphylococcus aureus, whites read ball
The inhibition zone of bacterium is it is obvious that have very strong antibacterial action.
Embodiment 9
Animal antibacterial tests performance --- in order to prove beneficial effects of the present invention, in embodiment 1 sample with it is commercially available
Cyanoacrylate acids medical adhesive has carried out contrast test, and specific test situation is as follows:
(1) storage of embodiment 1 preparation
Embodiment 1 is prepared remained with commercially available cyanoacrylate acids medical adhesive it is spare.
(2) mouse is used in test
SD rat: male mouse, growth cycle 4-6 weeks, growth was fast, and breeding performance is good, was mostly used for safety testing and nutrition
Research related with growth and development.The strain is sensitive to sex hormone, has stronger resistance to respiratory disease.It is widely used in medicine
Reason, toxicity, drug effect and GLP experiment.
(3) spare bacterium solution
The activation of strain and the preparation of bacterium solution: by the strain streak inoculation of freezen protective to plating medium, 37 DEG C of cultures
24h；Choose single colonie and be seeded to 100mL fluid nutrient medium, 37 DEG C, 150r/min shaking table culture stay overnight, concentration is equivalent to 0.5 Maxwell
It is more spare than the bacteria suspension bacterium solution of turbid standard.
(4) prepared by inoculum
Bacterium solution is separated out by bacterium solution in supercentrifuge, physiological saline is then added, so that bacterium solution dilutes 1000 times, is stayed
To spare.
(5) zoopery
SD rat is divided into two groups, one group is used for embodiment 1, and another group is used for commercially available cyanoacrylate acids medical adhesive, often
After one mouse depilation, the wound for being about 2cm is respectively opened in backbone two sides, side is only inoculated with bacterium solution, and other do not deal with, separately
It is bonded after side inoculation bacterium solution with medical adhesive.
(6) result judges
Under the premise of bacterium obviously grows in positive control wound, its tissue is taken to do homogenized respectively, then every group
It takes 20 μ L slurries to be laid in solid medium tablets, cultivates 12h, observe the growing state of bacterium and the healing state of wound.Knot
Fruit is as shown in Fig. 6 and Fig. 7.
Fig. 6 be embodiment 1 and commercially available tissue adhesion medical adhesive for S. aureus Inoculate in the anti-of SD rat
Bacterium situation, Fig. 6 it can be seen that antibacterial tissue adhesive (embodiment 1) of the invention to the fungistatic effect of staphylococcus aureus
It is obvious that finding out almost without bacterium colony have strong antibacterial action from agar medium plate.And commercially available tissue adhesion medical adhesive
There is the formation of many bacterium colonies to staphylococcus aureus with blank group almost without antibacterial action.
From the wound healing rate comparison diagram that Fig. 7 is for SD rat, it will thus be seen that embodiment 1 and commercially available tissue medical glue,
Blank group is compared, and the wound healing ratio highest of embodiment 1 illustrates that obviously there is promotion wound in antibacterial tissue adhesive of the invention
The effect of healing.
Finally, it is stated that preferred embodiment above is only used to illustrate the technical scheme of the present invention and not to limit it, although logical
It crosses above preferred embodiment the present invention is described in detail, however, those skilled in the art should understand that, can be
Various changes are made to it in form and in details, without departing from claims of the present invention limited range.
Claims (10)
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| CN110774693A (en) * | 2019-10-21 | 2020-02-11 | 江阴金凤特种纺织品有限公司 | Antibacterial and antimicrobial SMMS composite non-woven fabric |
| CN110917391A (en) * | 2019-12-26 | 2020-03-27 | 广东泰宝医疗科技股份有限公司 | Polypeptide modified sodium alginate/PVA hydrogel dressing and preparation method thereof |
| CN114191621A (en) * | 2020-09-18 | 2022-03-18 | 西华师范大学 | Antibacterial and anti-adhesion medical polypropylene patch with multi-layer surface structure and preparation method and use thereof |
| CN114191621B (en) * | 2020-09-18 | 2022-08-19 | 西华师范大学 | Antibacterial anti-adhesion medical polypropylene patch with multilayer surface structure and preparation method and application thereof |
| CN114732936A (en) * | 2021-01-08 | 2022-07-12 | 陈娜 | High-air-permeability degradable drug-loaded skin wound dressing |
| CN114425103A (en) * | 2022-04-06 | 2022-05-03 | 中国科学院苏州纳米技术与纳米仿生研究所 | Bionic biogel and preparation method and application thereof |
| CN118834319A (en) * | 2024-08-01 | 2024-10-25 | 北京师范大学珠海校区 | Adhesion-adjustable quaternary ammonium salt polyvinyl alcohol, preparation method and application |
| CN118834319B (en) * | 2024-08-01 | 2025-03-25 | 北京师范大学珠海校区 | Quaternary ammonium salt polyvinyl alcohol with adjustable adhesion, preparation method and application |
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Effective date of registration: 20200110 Address after: 310000 room 1-709, Heda pharmaceutical Valley Center, No. 291, Fucheng Road, Xiasha street, Qiantang New District, Hangzhou City, Zhejiang Province Applicant after: Wendexilin (Hangzhou) Biotechnology Co.,Ltd. Address before: 100029 Beijing, North Third Ring Road, No. 15 East Road, Chaoyang District Applicant before: Beijing University of Chemical Technology |
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Application publication date: 20190503 |