CN108929439A - Multifunctional polymer and its preparation method and application - Google Patents
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Abstract
The invention belongs to macromolecule polymer material field, it is related to a kind of multifunctional polymer and its preparation method and application.Using antibacterial oligomer and polypeptide as raw material, the antibacterial oligomer and the polypeptide react the multifunctional polymer in the presence of condensing agent and inert gas, obtain multifunctional polymer.Multifunctional polymer of the invention has the characteristics that efficient, stable, broad-spectrum antiseptic；Also there is low or no cytotoxicity, have the corresponding biological function of polypeptide；The preparation process of multifunctional polymer provided by the present invention is simple, mild condition；Type, the number of access polypeptide can be controlled according to application demand by preparing multifunctional polymer, to realize the purpose controling effectively to multifunctional polymer antibiotic property and bioactivity；Avoid the generation of the relevant bacterium infection of bio-medical material；Improve the service life and application range of polymer.
Description
Technical field
The invention belongs to macromolecule polymer material field, it is related to a kind of multifunctional polymer and preparation method thereof and answers
With.
Background technique
With the development of science and technology and the raising of human living standard, people are proposed many to the various aspects of life
New demand.By taking medical domain as an example, the appearance of a large amount of artificial organs, joint prosthesis and Thermosensitive Material Used for Controlled Releasing of Medicine etc., so that raw
Object medical material gradually enters into the visual field of people, has welcome the high speed development of a new round.And so-called bio-medical material, refer to one
Class can be used for diagnosing, treat, repairing or replacing human body damaged tissues or organ, or even promote the hi tech and new material of its function,
It can be natural material, be also possible to artificial synthesized, or both compound.Bio-medical material is answered medical domain
With, not only significantly reduce the death rate caused by the major diseases such as cardiovascular disease, cancer, wound, saved necessarily count it is critical
The life of patient, and the general level of the health and quality of life of the mankind are greatly improved, therefore have a very important significance.
However, bio-medical material is in actual application, but also there is problems, for example, with bio-medical material
Expect that relevant bacterium infection problem is causing the concern of people.Although in clinical practice, all implant devices and operation
Medical instrument can all be handled using preceding by a series of very strict sterilizations, but these measures can not disappear completely
A possibility that except patient by bacterium infection, therefore once infection occurs, and generally requires to depend on antibiotic even multiple for a long time
Operation can cure, and this can not only bring the economic pressures having to patient, can also cause to the mind & body of patient
Greatly injury, therefore research and develop itself bio-medical material with anti-infective function with what important clinical meaning and extensively
Wealthy application prospect.
Currently, the research and development for the bio-medical material itself with anti-infective function achieve greater advance both at home and abroad,
It mainly passes through the physical methods such as blending and antibacterial agent or antiseptic elements is added in material matrix, or is changed by various surfaces
Property technology make material surface formed the coating containing antibacterial agent；Make antibacterial group and matrix by way of chemical graft or block
Material is connected；Simultaneously using physics and chemical method preparation antibiotic property bio-medical material etc..However, which kind of side either used
All there is preparation process complexity in method, product is not easy to control, and material has the problems such as suitable cytotoxicity.
Therefore, try to explore new preparation method exploitation and prepare ontology with good anti-microbial property and biocompatibility,
And the bio-medical material that product property control effectively can be had a very important significance.
Summary of the invention
In view of this, having the purpose of the present invention is to provide a kind of multifunctional polymer and its preparation method and application
Efficiently, stablize, broad-spectrum antiseptic the features such as, and can by adjust polymer material in polypeptide containing amount and type to the antibacterial of material
Performance and bioactivity control effectively, and can apply in terms of bio-medical material.
To achieve the above object, the technical scheme is that：
A kind of multifunctional polymer, the multifunctional polymer are made using antibacterial oligomer and polypeptide as raw material；It is described anti-
Bacterium oligomer is as shown in formula I or formula II or formula III, and the polypeptide is as shown in formula IV；
In formula IV, " n " is the quantity of amino in polypeptide；" m " is the quantity of hydroxyl in polypeptide；" x " is carboxyl in polypeptide
Quantity, different polypeptides, numerical value is different, n >=0, m >=0, x >=0.
The multifunctional polymer includes the backbone structure with good anti-microbial property；It can reduce Materials Cell toxicity simultaneously
Play the polypeptide of its special biological；And containing amount and type material can be resisted by adjusting polypeptide in polymer material
Bacterium performance and bioactivity control effectively.
Further, the molar ratio of the polypeptide and the antibacterial oligomer is 0.01-30:1.
Further, polypeptide shown in formula IV is or mixtures thereof biologically active polypeptide, artificial synthetic polypeptide.
As a preference, the polypeptide includes 24 peptide of Mechano growth factor (MGF-Ct24E) and RGD peptide.
The second object of the present invention is to provide the preparation method of multifunctional polymer described in one kind, and the antibacterial is oligomeric
Object and the polypeptide react in the presence of condensing agent and inert gas, obtain multifunctional polymer.
Preparation method simple process provided by the present invention, mild condition；Polymer can be regulated and controled according to practical application request
Anti-microbial property and bioactivity；It overcomes traditional small molecule antibacterial agent or existing defect in the process is used alone in polypeptide；It keeps away
The generation of the relevant bacterium infection of bio-medical material is exempted from；Improve the service life and application range of polymer.
Inert gas environment is remained in reaction system during the preparation process；The experimental provision used in preparation process,
Raw materials and reagents first pass through dehydration in advance.
Further, the condensing agent is that n-hydroxysuccinimide and 1- (3- dimethylamino-propyl) -3- ethyl carbon two are sub-
Amine hydrochlorate or dicyclohexylcarbodiimide.
The inert gas includes helium, argon gas, xenon.
Further, it is 7- that tertiary amines organic base is added after condensing agent activates and adjusts reaction system pH for the antibacterial oligomer
9, polypeptides reactive is added in the presence of an inert gas and obtains multifunctional polymer.
The preparation method further includes step：Gained is slowly dropped to double steamings containing the crude product solution of multifunctional polymer
It in water, and is transferred into bag filter, is freeze-dried after dialysing 24-72 hours in distilled water to constant weight, much function
It can polymeric articles.
Further, the time of the activation is 0.5-2h；The temperature that polypeptides reactive is added is 20-50 DEG C, and the reaction time is
6-24h。
A kind of specific preparation method of multifunctional polymer, includes the following steps：
1) constituent of multifunctional polymer is chosen according to a certain percentage：Antibacterial oligomer, polypeptide；
2) appropriate antibacterial oligomer is dissolved in dimethyl sulfoxide, under inert gas protection, sequentially adds N- hydroxyl amber
Amber acid imide and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride or dicyclohexylcarbodiimide, at room temperature
Activation antibacterial oligomer 0.5-2 hours；
3) it is 7-9 that tertiary amines organic base, which is added, and adjusts the pH of reaction system；
It 4) is 0.01-30 according to the molar ratio of polypeptide and antibacterial oligomer:1, under inert gas shielding, at 20-50 DEG C
Reaction 6-24 hours, obtains multifunctional polymer.
The dimethyl sulfoxide can be replaced with the high polar solvent such as formamide.
The multifunctional polymer is white, is dissolved in the high polar solvent such as dimethyl sulfoxide, water, does not dissolve in anhydrous second
The low polar solvent such as alcohol, toluene.
Further, the preparation method of the antibacterial oligomer is：It is with or mixtures thereof diamines and ethylene diamine tetra-acetic anhydride
Raw material reacts 10~48h at 25 DEG C~45 DEG C in inert gas, antibacterial oligomer is made.
Resulting antibacterial oligomer precipitates in dehydrated alcohol or methanol, and is dried under vacuum to constant weight.
Further, the molar ratio of or mixtures thereof diamines and ethylene diamine tetra-acetic anhydride is 0.5-2:1；The diamines is fat
Race's diamines or aromatic diamine.
The object of the invention is also to provide application of the multifunctional polymer described in one kind in terms of bio-medical material.
Multifunctional polymer of the invention has the characteristics that efficient, stable, broad-spectrum antiseptic, has low or no cytotoxicity,
It can be used as bio-medical material to be used to diagnosing, treat, repair or replacing human body damaged tissues or organ, or even promote its function
Hi tech and new material.Bio-medical material not only significantly reduces cardiovascular disease, cancer, wound in the application of medical domain
Etc. the death rate caused by major diseases, saved ten million and counted the life of urgent patient, and greatly improved the health of the mankind
Horizontal and quality of life, therefore have a very important significance.
The beneficial effects of the present invention are：
1) multifunctional polymer provided by the present invention has the characteristics that efficient, stable, broad-spectrum antiseptic；
2) multifunctional polymer provided by the present invention has low or no cytotoxicity, has the corresponding biological function of polypeptide
The characteristics of；
3) preparation process of multifunctional polymer provided by the present invention is simple, mild condition；
4) multifunctional polymer provided by the present invention can control type, the number of access polypeptide according to application demand,
It is control effectively according to practical application request to multifunctional polymer antibiotic property and bioactivity to realize；Overcome tradition
Small molecule antibacterial agent or polypeptide existing defect during being used alone；Avoid the relevant bacterium infection of bio-medical material
Occur；Improve the service life and application range of polymer.
Specific embodiment
It detailed description of a preferred embodiment of the present invention will be given below.The reality of actual conditions is not specified in preferred embodiment
Proved recipe method, usually according to normal condition, illustrated embodiment are but not to be to preferably be illustrated to the contents of the present invention
The contents of the present invention are only limitted to illustrated embodiment.So those skilled in the art are according to foregoing invention content to embodiment party
Case carries out nonessential modifications and adaptations, still falls within protection scope of the present invention.
Embodiment 1
The antibacterial oligomer for weighing 0.001mol is added in the round-bottomed flask of 50ml, adds 10ml dimethyl sulfoxide,
Under inert gas protection, 0.5h~1h is stirred at 40 DEG C, is mixed them thoroughly.Then, after reducing temperature to room temperature, successively
Appropriate n-hydroxysuccinimide and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added, activates at room temperature
Antibacterial oligomer 0.5-2 hours.Then, appropriate triethylamine is added to adjust after reaction system is pH7-9, then weighs 0.00001mol
It after 24 peptide of Mechano growth factor (MGF-Ct24E) is dissolved in 2ml dimethyl sulfoxide, is slowly dropped into above-mentioned reaction system, at 20-50 DEG C
Reaction 6-24 hours, obtains multifunctional polymer.
Embodiment 2
The antibacterial oligomer for weighing 0.001mol is added in the round-bottomed flask of 50ml, adds 10ml dimethyl sulfoxide,
Under inert gas protection, 0.5h~1h is stirred at 40 DEG C, is mixed them thoroughly.Then, after reducing temperature to room temperature, successively
Appropriate n-hydroxysuccinimide and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added, activates at room temperature
Antibacterial oligomer 0.5-2 hours.Then, appropriate triethylamine is added to adjust after reaction system is pH7-9, then weighs 0.0001mol
It after 24 peptide of Mechano growth factor (MGF-Ct24E) is dissolved in 2ml dimethyl sulfoxide, is slowly dropped into above-mentioned reaction system, at 20-50 DEG C
Reaction 6-24 hours, obtains multifunctional polymer.
Embodiment 3
The antibacterial oligomer for weighing 0.001mol is added in the round-bottomed flask of 50ml, adds 10ml dimethyl sulfoxide,
Under inert gas protection, 0.5h~1h is stirred at 40 DEG C, is mixed them thoroughly.Then, after reducing temperature to room temperature, successively
Appropriate n-hydroxysuccinimide and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added, activates at room temperature
Antibacterial oligomer 0.5-2 hours.Then, appropriate triethylamine is added to adjust after reaction system is pH7-9, then weighs 0.001mol power
After 4 peptide of growth factor-2 (MGF-Ct24E) is dissolved in 2ml dimethyl sulfoxide, it is slowly dropped into above-mentioned reaction system, it is anti-at 20-50 DEG C
It answers 6-24 hours, obtains multifunctional polymer.
Embodiment 4
The antibacterial oligomer for weighing 0.001mol is added in the round-bottomed flask of 50ml, adds 10ml dimethyl sulfoxide,
Under inert gas protection, 0.5h~1h is stirred at 40 DEG C, is mixed them thoroughly.Then, after reducing temperature to room temperature, successively
Appropriate n-hydroxysuccinimide and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added, activates at room temperature
Antibacterial oligomer 0.5-2 hours.Then, appropriate triethylamine is added to adjust after reaction system is pH7-9, then weighs 0.01mol power
After 4 peptide of growth factor-2 (MGF-Ct24E) is dissolved in 5ml dimethyl sulfoxide, it is slowly dropped into above-mentioned reaction system, it is anti-at 20-50 DEG C
It answers 6-24 hours, obtains multifunctional polymer.
Embodiment 5
The antibacterial oligomer for weighing 0.001mol is added in the round-bottomed flask of 50ml, adds 10ml dimethyl sulfoxide,
Under inert gas protection, 0.5h~1h is stirred at 40 DEG C, is mixed them thoroughly.Then, after reducing temperature to room temperature, successively
Appropriate n-hydroxysuccinimide and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added, activates at room temperature
Antibacterial oligomer 0.5-2 hours.Then, appropriate triethylamine is added to adjust after reaction system is pH7-9, then weighs 0.03mol power
It after 4 peptide of growth factor-2 (MGF-Ct24E) is dissolved in 10ml dimethyl sulfoxide, is slowly dropped into above-mentioned reaction system, at 20-50 DEG C
Reaction 6-24 hours, obtains multifunctional polymer.
Embodiment 6
The antibacterial oligomer for weighing 0.001mol is added in the round-bottomed flask of 50ml, adds 10ml dimethyl sulfoxide,
Under inert gas protection, 0.5h~1h is stirred at 40 DEG C, is mixed them thoroughly.Then, after reducing temperature to room temperature, successively
Appropriate n-hydroxysuccinimide and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added, activates at room temperature
Antibacterial oligomer 0.5-2 hours.Then, appropriate triethylamine is added to adjust after reaction system is pH7-9, then weighs 0.00001mol
It after RGD peptide is dissolved in 2ml dimethyl sulfoxide, is slowly dropped into above-mentioned reaction system, reacts 6-24 hours, obtain more at 20-50 DEG C
Functional polymer.
Embodiment 7
The antibacterial oligomer for weighing 0.001mol is added in the round-bottomed flask of 50ml, adds 10ml dimethyl sulfoxide,
Under inert gas protection, 0.5h~1h is stirred at 40 DEG C, is mixed them thoroughly.Then, after reducing temperature to room temperature, successively
Appropriate n-hydroxysuccinimide and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added, activates at room temperature
Antibacterial oligomer 0.5-2 hours.Then, appropriate triethylamine is added to adjust after reaction system is pH7-9, then weighs 0.0001mol
It after RGD peptide is dissolved in 2ml dimethyl sulfoxide, is slowly dropped into above-mentioned reaction system, reacts 6-24 hours, obtain more at 20-50 DEG C
Functional polymer.
Embodiment 8
The antibacterial oligomer for weighing 0.001mol is added in the round-bottomed flask of 50ml, adds 10ml dimethyl sulfoxide,
Under inert gas protection, 0.5h~1h is stirred at 40 DEG C, is mixed them thoroughly.Then, after reducing temperature to room temperature, successively
Appropriate n-hydroxysuccinimide and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added, activates at room temperature
Antibacterial oligomer 0.5-2 hours.Then, appropriate triethylamine is added to adjust after reaction system is pH7-9, then weighs 0.001mol
It after RGD peptide is dissolved in 2ml dimethyl sulfoxide, is slowly dropped into above-mentioned reaction system, reacts 6-24 hours, obtain more at 20-50 DEG C
Functional polymer.
Embodiment 9
The antibacterial oligomer for weighing 0.001mol is added in the round-bottomed flask of 50ml, adds 10ml dimethyl sulfoxide,
Under inert gas protection, 0.5h~1h is stirred at 40 DEG C, is mixed them thoroughly.Then, after reducing temperature to room temperature, successively
Appropriate n-hydroxysuccinimide and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added, activates at room temperature
Antibacterial oligomer 0.5-2 hours.Then, appropriate triethylamine is added to adjust after reaction system is pH7-9, then weighs 0.01mol
It after RGD peptide is dissolved in 5ml methyl sulfoxide, is slowly dropped into above-mentioned reaction system, is reacted 6-24 hours at 20-50 DEG C, obtain more function
It can polymer.
Embodiment 10
The antibacterial oligomer for weighing 0.001mol is added in the round-bottomed flask of 50ml, adds 10ml dimethyl sulfoxide,
Under inert gas protection, 0.5h~1h is stirred at 40 DEG C, is mixed them thoroughly.Then, after reducing temperature to room temperature, successively
Appropriate n-hydroxysuccinimide and 1- (3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride is added, activates at room temperature
Antibacterial oligomer 0.5-2 hours.Then, appropriate triethylamine is added to adjust after reaction system is pH7-9, then weighs 0.03mol
It after RGD peptide is dissolved in 10ml dimethyl sulfoxide, is slowly dropped into above-mentioned reaction system, reacts 6-24 hours, obtain more at 20-50 DEG C
Functional polymer.
Embodiment 11
Multifunctional polymer obtained by Examples 1 to 5 is dissolved in distilled water by the concentration of 6mg/ml, it is sufficiently molten to it
It takes 5 μ l on the circle scraps of paper after solution respectively, after dry at room temperature, sterilizing, places it in and be inoculated with consolidating for staphylococcus aureus
It is cultivated 24 hours at 37 DEG C in body culture medium, then its antibacterial circle diameter is detected with vernier caliper, to obtain multifunctional polymeric
Killing effect of the object to microorganism.
The experimental results showed that：Present invention multifunctional polymer obtained is to gram-positive bacterium, such as golden yellow grape
Coccus has good killing effect.
Embodiment 12
Antibiotic property polymer obtained by embodiment 6~10 is dissolved in distilled water by the concentration of 6mg/ml, sufficiently to it
It takes 5 μ l on the circle scraps of paper after dissolution respectively, after dry at room temperature, sterilizing, places it in and be inoculated with staphylococcus aureus
It is cultivated 24 hours at 37 DEG C in solid medium, then detects its antibacterial circle diameter with vernier caliper, so that it is poly- to obtain antibiotic property
Object is closed to the killing effect of microorganism.
The experimental results showed that：Present invention antibiotic property polymer obtained is to gram-positive bacterium, such as golden yellow grape
Coccus has good killing effect.
Embodiment 13
After weighing the progress sterilization treatment of multifunctional polymer obtained by Examples 1 to 5, according to the concentration of 20-25mg/ml
It is dissolved in cell culture fluid, after completely dissolution to it, takes 0.5ml in the 24 hole cells for being inoculated with a certain concentration mammalian cell
In culture plate, at 37 DEG C after stationary culture 24 hours, in microscopically observation cellular morphology, to obtain multifunctional polymer
Cell compatibility.
The experimental results showed that：Present invention multifunctional polymer obtained can significantly reduce the antibiotic property polymer
Cytotoxicity.
Embodiment 14
After weighing the progress sterilization treatment of multifunctional polymer obtained by embodiment 6~10, according to the dense of 20-25mg/ml
Degree is dissolved in cell culture fluid, after completely dissolution to it, takes 0.5ml thin in 24 holes for being inoculated with a certain concentration mammalian cell
In born of the same parents' culture plate, at 37 DEG C after stationary culture 24 hours, in microscopically observation cellular morphology, to obtain multifunctional polymer
Cell compatibility.
The experimental results showed that：Present invention multifunctional polymer obtained can significantly reduce the antibiotic property polymer
Cytotoxicity.
Finally, it is stated that the above examples are only used to illustrate the technical scheme of the present invention and are not limiting, although referring to compared with
Good embodiment describes the invention in detail, those skilled in the art should understand that, it can be to skill of the invention
Art scheme is modified or replaced equivalently, and without departing from the objective and range of technical solution of the present invention, should all be covered at this
In the scope of the claims of invention.
Claims (10)
1. multifunctional polymer, which is characterized in that the multifunctional polymer is made using antibacterial oligomer and polypeptide as raw material；Institute
Antibacterial oligomer is stated as shown in formula I or formula II or formula III, the polypeptide is as shown in formula IV；
In formula IV, " n " is the quantity of amino in polypeptide；" m " is the quantity of hydroxyl in polypeptide；" x " is the quantity of carboxyl in polypeptide,
Different polypeptides, numerical value is different, n >=0, m >=0, x >=0.
2. multifunctional polymer according to claim 1, which is characterized in that the polypeptide rubs with the antibacterial oligomer
You are than being 0.01-30:1.
3. multifunctional polymer according to claim 1, which is characterized in that polypeptide shown in formula IV is that bioactivity is more
Or mixtures thereof peptide, artificial synthetic polypeptide.
4. the preparation method of the described in any item multifunctional polymers of claim 1-3, which is characterized in that the antibacterial oligomer
It is reacted in the presence of condensing agent and inert gas with the polypeptide, obtains multifunctional polymer.
5. the preparation method according to claim 4, which is characterized in that the condensing agent is n-hydroxysuccinimide and 1-
(3- dimethylamino-propyl) -3- ethyl-carbodiimide hydrochloride or dicyclohexylcarbodiimide.
6. the preparation method according to claim 4, which is characterized in that the antibacterial oligomer is added after condensing agent activates
It is 7-9 that tertiary amines organic base, which adjusts reaction system pH, and polypeptides reactive is added in the presence of an inert gas and obtains multifunctional polymer.
7. preparation method according to claim 6, which is characterized in that the time of the activation is 0.5-2h；Polypeptide is added
The temperature of reaction is 20-50 DEG C, reaction time 6-24h.
8. the preparation method according to claim 4, which is characterized in that the preparation method of the antibacterial oligomer is：With two
Or mixtures thereof amine and ethylene diamine tetra-acetic anhydride are raw material, and at 25 DEG C~45 DEG C, 10~48h is reacted in inert gas, is made
Antibacterial oligomer.
9. preparation method according to claim 8, which is characterized in that or mixtures thereof diamines and ethylene diamine tetra-acetic anhydride
Molar ratio is 0.5-2:1；The diamines is aliphatic diamine or aromatic diamine.
10. application of the described in any item multifunctional polymers of claim 1-3 in terms of bio-medical material.
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