CN108525002B - Injectable biological glue with high adhesion performance and preparation method and application thereof - Google Patents
Injectable biological glue with high adhesion performance and preparation method and application thereof Download PDFInfo
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- CN108525002B CN108525002B CN201710115561.XA CN201710115561A CN108525002B CN 108525002 B CN108525002 B CN 108525002B CN 201710115561 A CN201710115561 A CN 201710115561A CN 108525002 B CN108525002 B CN 108525002B
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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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/04—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials
- A61L24/046—Surgical adhesives or cements; Adhesives for colostomy devices containing macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/30—Macromolecular organic or inorganic compounds, e.g. inorganic polyphosphates
- A61K47/34—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyesters, polyamino acids, polysiloxanes, polyphosphazines, copolymers of polyalkylene glycol or poloxamers
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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
- A61L24/00—Surgical adhesives or cements; Adhesives for colostomy devices
- A61L24/001—Use of materials characterised by their function or physical properties
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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
- A61L2400/06—Flowable or injectable implant compositions
Abstract
The invention discloses an injectable biological glue with high adhesive property, and a preparation method and application thereof. The injectable biological glue is formed by the interaction of polyethylene glycol derivatives (polyethylene glycol succinimidyl ester) and tannic acid through hydrogen bonds. The preparation method of the injectable biological glue comprises the following steps: (1) preparing a solution 1 of polyethylene glycol derivatives; (2) preparing a solution 2 of tannic acid; (3) and mixing the solution 1 and the solution 2, and centrifuging to obtain a precipitate. The injectable biological glue with high adhesive property has potential application in the following fields: surgical wound adhesion; a drug delivery system; medical built-in articles; surface coating of medical implant. The invention has the following beneficial effects: the invention adopts two groups of substances of PEG derivatives and tannic acid to form injectable biological glue through the interaction of physical action (hydrogen bond); the adhesive has higher adhesive capacity; can be used through a single-tube injector, and is more convenient to use.
Description
Technical Field
The invention relates to biological glue, in particular to injectable biological glue with high adhesion property.
Background
The problem of surgical wound closure has become more and more of a concern. Conventional methods generally employ suture stitching. However, suture suturing introduces new suture wounds, causes secondary damage to the wounds during the suture removal process, and is prone to infection.
Biological glues have been developed to replace sutures in surgery. Biological glues generally fall into two broad categories: natural and synthetic biological glues. The natural biological glue is represented by fibrin glue, is generally weak in strength, and is easy to cause the problem of cross infection of blood diseases such as AIDS. The synthesized glue mainly uses the derivative of cyanoacrylate, has higher strength, but has poor biocompatibility and toxic degradation products.
Some new biological glues, such as two-component biological glues (Coseal and Duraseal) based on PEG, and biological glues based on PEG and chitosan, are also continuously developed. The biological glue has strong adhesion performance and good biocompatibility, but the biological glue is usually double-component biological glue, a double-injector is required to be used when the biological glue is used, equipment is large, the operation is complex, and particularly, the operation of tissue adhesion in certain deep layers is difficult. Meanwhile, most of the glues are crosslinked by chemical action, if cracking occurs in use, irreversible damage to chemical bonds is caused, the glues lose the effect, and the glues are usually cleaned and coated with new biological glue, so that the operation time and the cost are greatly improved.
Disclosure of Invention
The invention aims to provide an injectable biological glue with high adhesive property, and a preparation method and application thereof.
The injectable biological glue provided by the invention is formed by the interaction of polyethylene glycol derivatives and tannic acid through hydrogen bonds;
the polyethylene glycol derivative is polyethylene glycol succinimidyl ester.
The polyethylene glycol derivative may be any one of formula I, formula II, formula III, and formula IV:
in the formula, n is a natural number between 2 and 10000, and can be 14 to 56, 14, 28 or 56;
the group R is a formula a or a formula b, in the formula a and the formula b, M represents a nitrogen atom, a carbon atom, an oxygen atom, a sulfur atom, a phosphorus atom or a benzene ring, preferably an oxygen atom, a nitrogen atom or a sulfur atom, and is connected to the polyethylene glycol end, and Z is an integer between 0 and 5, such as 0, 2 or 3;
radical R1、R2、R3、R4、R5、R6、R7、R8、R9、R10、R11、R12、R13、R14、R15And R16Each independently represents a hydrogen atom, a hydroxyl group, an alkyl group having 1 to 10 carbon atoms (preferably a methyl group), an aryl group or a sulfonic acid group.
The polyethylene glycol derivative can be any one of the following 1) to 8):
1) shown as formula I, wherein R is formula a, in the formula a, Z is 2, M is oxygen atom, n is 56, R1、R2、R3And R4Are each a hydrogen atom;
2) as shown in formula II, wherein R is formula b, in the formula b, Z is 0-1, M is oxygen atom, n is 56, R1、R2、R3And R4Are each a hydrogen atom, R5、R6、R7And R8Are all hydroxyl;
3) as shown in formula II, wherein R is formula b, in the formula b, Z is 0, M is oxygen atom, n is 56, R1、R2、R3And R4Are each a hydrogen atom, R5、R6、R7And R8Are all hydroxyl;
4) as shown in formula II, wherein R is formula b, in the formula b, Z is 1, M is oxygen atom, n is 56, R1、R2、R3And R4Are each a hydrogen atom, R5、R6、R7And R8Are all hydroxyl;
5) shown as formula III, wherein R is formula a, in the formula a, Z is 3, M is nitrogen atom, n is 28, R1、R2、R3And R4Are each a hydrogen atom, R5、R6、R7And R8Are each methyl, R9、R10、R11And R12Are all benzene rings;
6) the formula IV is shown in the specification, wherein R is a formula b, in the formula b, Z is 2-3, M is a sulfur atom, n is 14-16, R1、R3、R7And R10Are all sulfonic acid groups, R2、R4、R5、R6、R8、R9、R11、R12、R13、R14、R15And R16Are each a hydrogen atom;
7) shown as a formula IV, wherein R is a formula b, in the formula b, Z is 2, M is sulfur atom, n is 14, R1、R3、R7And R10Are all sulfonic acid groups, R2、R4、R5、R6、R8、R9、R11、R12、R13、R14、R15And R16Are each a hydrogen atom;
8) shown as a formula IV, wherein R is a formula b, in the formula b, Z is 3, M is a sulfur atom, n is 16, R1、R3、R7And R10Are all sulfonic acid groups, R2、R4、R5、R6、R8、R9、R11、R12、R13、R14、R15And R16Are all hydrogen atoms.
In the injectable biological glue, the mass ratio of the polyethylene glycol derivative to the tannic acid can be 1: 0.001 to 1000, specifically 1: 0.4-4, 1: 0.4-1, 1: 0.4-0.5, 1: 0.4, 1: 0.5, 1: 1 or 1: 4.
the invention further provides a preparation method of the injectable biological glue, which comprises the following steps:
(1) preparing a solution 1 of the polyethylene glycol derivative;
(2) preparing a solution 2 of the tannic acid;
(3) and mixing the solution 1 and the solution 2, and centrifuging to obtain a precipitate, namely the biological glue.
In the preparation method, in the step (1), the mass-volume concentration of the polyethylene glycol derivative in the solution 1 may be 0.01-10000 mg/ml, specifically 400-600 mg/ml, 400mg/ml, 500mg/ml or 600 mg/ml;
the solvent of the solution 1 can be secondary water, ultrapure water, physiological saline or phosphate buffer solution with pH of 7.4.
In the preparation method, in the step (2), the mass-volume concentration of the tannic acid in the solution 2 can be 0.01-10000 mg/ml, specifically 400-600 mg/ml, 400mg/ml, 500mg/ml or 600 mg/ml;
the solvent of the solution 1 is secondary water, ultrapure water, physiological saline or phosphate buffer solution with pH of 7.4.
In the above preparation method, in the step (3), the volume ratio of the solution 1 to the solution 2 may be 1: 0.001 to 1000, specifically 1: 0.4-4, 1: 0.4-1, 1: 0.4-0.5, 1: 0.4, 1: 0.5, 1: 1 or 1: 4;
the centrifugation speed can be 100-20000 r/min, and the time can be 1-60 min, such as centrifugation for 5min under 3000 r/min.
The injectable biological glue with high adhesive property has potential application in the following fields:
(1) surgical wound adhesion;
(2) a drug delivery system;
(3) medical built-in articles;
(4) surface coating of medical implant.
Compared with the prior art, the invention has the following beneficial effects:
(1) the invention adopts two FDA approved substances of PEG derivatives and tannic acid, and has good biocompatibility.
(2) The PEG derivative and the tannic acid interact with each other through physical action (namely hydrogen bond) to form the injectable biological glue.
(3) The biological glue has high adhesion capability.
(4) The biological glue can be used through a single-tube injector, and is more convenient to use.
Drawings
Fig. 1 is a comparative schematic diagram of the adhesion strength and fibrin glue of the biogel prepared in example 1 of the present invention.
Detailed Description
The experimental procedures used in the following examples are all conventional procedures unless otherwise specified.
Materials, reagents and the like used in the following examples are commercially available unless otherwise specified.
The adhesion properties in the following examples were measured as follows:
the method for bonding and stretching the pigskin comprises the following steps: directly coating the biological glue on two pieces of pigskin by using an injector, wherein the coating area is 1cm multiplied by 1cm, overlapping the coating positions, pressing the pigskin for 30s by using a force of 30 newtons, and measuring the shear strength when the two pieces of pigskin are separated by using a universal tensile machine, namely the adhesive strength.
Examples 1,
Weighing 5000mg of two-arm polyethylene glycol succinimide (shown as formula I, R is a formula a, Z is 2, M is oxygen atom, n is 56, and R1、R2、R3And R4Both hydrogen atoms) was dissolved in 10mL of a PBS buffer solution having a pH of 7.4 (mass-volume concentration of 500mg/mL), 5000mg of tannic acid was weighed and dissolved in 10mL of a PBS solution having a pH of 7.4 (mass-volume concentration of 500mg/mL), and the two solutions were mixed at a volume ratio of 1: 1 (the mass ratio of the two-arm polyethylene glycol succinimide to the tannic acid is 1: 1), centrifuging for 5min at the speed of 3000r/min, pouring out the supernatant, and obtaining the precipitate, namely the biological glue. The biogenic glue is placed in a syringe and left for further use.
The measurement shows that the biological glue prepared by the embodiment has the adhesion performance of 249kPa, has higher adhesion capacity, and is far better than the commercial fibrin glue (15.2kPa), as shown in figure 1.
After the biological glue is adopted to firmly bond the two pigskins, the two pigskins are manually separated, then the two pigskins are combined together, after 2min, the adhesion strength is measured again, the adhesion strength can be recovered to 135kPa, and is still superior to commercially available fibrin glue, which shows that the biological glue has the capability of repeatedly bonding for many times, even if a wound is cracked again due to external force in the using process, the wound can be directly closed, and the biological glue can firmly bond the wound again after a period of time.
Examples 2,
Weighing 4000mg of four-arm polyethylene glycol succinimide (shown as formula II, R is formula b, Z is 0, M is oxygen atom, n is 56, and R is1、R2、R3And R4Is a hydrogen atom, R5、R6、R7And R8All hydroxyl groups) was dissolved in 10mL of a PBS buffer solution having a pH of 7.4 (mass-volume concentration of 400mg/mL), 4000mg of tannic acid was weighed and dissolved in 10mL of a PBS solution having a pH of 7.4 (mass-volume concentration of 400mg/mL),the two solutions are mixed according to the volume ratio of 2: 1 (the mass ratio of the four-arm polyethylene glycol succinimide to the tannic acid is 2: 1), centrifuging for 5min at the speed of 3000r/min, pouring out the supernatant, and obtaining the precipitate, namely the biological glue. The biogenic glue is placed in a syringe and left for further use.
Through measurement, the biological glue prepared by the embodiment has the adhesion performance of 265kPa, has higher adhesion capability, and is far better than the commercial fibrin glue (15.2 kPa).
After the biological glue is adopted to firmly bond the two pigskins, the two pigskins are manually separated, then the two pigskins are combined together, after 2min, the adhesion strength is measured again, the adhesion strength can be recovered to 150Pa, and the adhesive strength is still superior to that of the commercially available fibrin glue, so that the biological glue has the capability of repeatedly bonding for multiple times, even if the wound is cracked again due to external force in the using process, the wound can be directly closed, and the wound can be firmly bonded again by the biological glue after a period of time.
Examples 3,
Weighing 4000mg of six-arm polyethylene glycol succinimide (shown as formula III, R is a formula a, Z is 3, M is nitrogen atom, n is 28, and R is1、R2、R3And R4Are each a hydrogen atom, R5、R6、R7And R8Are each methyl, R9、R10、R11And R12Both benzene rings) was dissolved in 10mL of a PBS buffer solution (mass-volume concentration of 400mg/mL) having a pH of 7.4, 4000mg of tannic acid was weighed and dissolved in 10mL of a PBS solution (mass-volume concentration of 400mg/mL) having a pH of 7.4, and the two solutions were mixed in a volume ratio of 1: 4 (the mass ratio of the six-arm polyethylene glycol succinimide to the tannic acid is 1: 4), centrifuging for 5min at the speed of 3000r/min, and pouring out the supernatant to obtain a precipitate, namely the biological glue. The biogenic glue is placed in a syringe and left for further use.
Through measurement, the biological glue prepared by the embodiment has the adhesion performance of 299kPa, has higher adhesion capacity, and is far better than the commercial fibrin glue (15.2 kPa).
After the biological glue is adopted to firmly bond the two pigskins, the two pigskins are manually separated, then the two pigskins are combined together, after 2min, the adhesion strength is measured again, the adhesion strength can be recovered to 170Pa, and the adhesive strength is still superior to that of the commercially available fibrin glue, so that the biological glue has the capability of repeatedly bonding for multiple times, even if the wound is cracked again due to external force in the using process, the wound can be directly closed, and the wound can be firmly bonded again by the biological glue after a period of time.
Examples 4,
Weighing 6000mg of eight-arm polyethylene glycol succinimide (shown as formula IV, R is formula b, Z is 2, M is sulfur atom, n is 14, and R is1、R3、R7And R10Are all sulfonic acid groups, R2、R4、R5、R6、R8、R9、R11、R12、R13、R14、R15And R16Both hydrogen atoms) was dissolved in 10mL of a PBS buffer solution having a pH of 7.4 (mass-volume concentration of 600mg/mL), 6000mg of tannic acid was weighed and dissolved in 10mL of a PBS solution having a pH of 7.4 (mass-volume concentration of 600mg/mL), and the two solutions were mixed in a volume ratio of 7: 3 (the mass ratio of the eight-arm polyethylene glycol succinimide to the tannic acid is 7: 3), centrifuging for 5min at the speed of 3000r/min, pouring out the supernatant, and obtaining the precipitate, namely the biological glue. The biogenic glue is placed in a syringe and left for further use.
The measurement shows that the biological glue prepared by the embodiment has the adhesion performance of 432kPa, has higher adhesion capacity, and is far better than the commercial fibrin glue (15.2 kPa).
After the biological glue is adopted to firmly bond the two pigskins, the two pigskins are manually separated, then the two pigskins are combined together, after 2min, the adhesion strength is measured again, the adhesion strength can be recovered to 245Pa, and the adhesive strength is still superior to that of the commercially available fibrin glue, so that the biological glue has the capability of repeatedly bonding for multiple times, even if the wound is cracked again due to external force in the using process, the wound can be directly closed, and the wound can be firmly bonded again by the biological glue after a period of time.
Examples 5,
Weighing 5000mg of eight-arm polyethylene glycol succinimide (shown as formula IV, R is formula b, Z is 3, M is sulfur atom, n is 16, and R is1、R3、R7And R10Are all sulfonic acid groups, R2、R4、R5、R6、R8、R9、R11、R12、R13、R14、R15And R16Both hydrogen atoms) was dissolved in 10mL of a PBS buffer solution having a pH of 7.4 (mass-volume concentration of 500mg/mL), 6000mg of tannic acid was weighed and dissolved in 10mL of a PBS solution having a pH of 7.4 (mass-volume concentration of 600mg/mL), and the two solutions were mixed in a volume ratio of 7: 3 (the mass ratio of the eight-arm polyethylene glycol succinimide to the tannic acid is 7: 3), adding 200mg of paclitaxel medicine into the mixture, centrifuging the mixture at the speed of 3000r/min for 5min, and pouring out the supernatant to obtain a precipitate, namely the paclitaxel-loaded biological glue. The biological glue loaded with the paclitaxel is put into an injector and can be injected into a human body to be used as a drug release system.
Examples 6,
Weighing 4000mg of four-arm polyethylene glycol succinimide (shown as formula II, R is formula b, Z is 1, M is oxygen atom, n is 56, and R is1、R2、R3And R4Is a hydrogen atom, R5、R6、R7And R8Both hydroxyl groups) was dissolved in 10mL of a PBS buffer solution having a pH of 7.4 (mass-volume concentration of 400mg/mL), 4000mg of tannic acid was weighed and dissolved in 10mL of a PBS solution having a pH of 7.4 (mass-volume concentration of 400mg/mL), and the two solutions were mixed in a volume ratio of 2: 1 (the mass ratio of the four-arm polyethylene glycol succinimide to the tannic acid is 2: 1), centrifuging for 5min at the speed of 3000r/min, pouring out the supernatant, and obtaining the precipitate, namely the biological glue. The biogenic glue is placed in a syringe and left for further use.
The biological glue is coated on the surface of a PLGA stent for bone repair, so that the adhesion between the PLGA stent and the periphery of a placing position is enhanced, and the biological glue can be used as a surface coating of a medical implant.
Claims (7)
1. An injectable biological glue, which is characterized in that: the biological glue is formed by the interaction of polyethylene glycol derivatives and tannic acid through hydrogen bonds;
the polyethylene glycol derivative is polyethylene glycol succinimidyl ester, and is specifically any one of the following 1) -3):
1) as shown in formula II, wherein R is formula b, in the formula b, Z is 0-1, M is oxygen atom, n is 56, R1、R2、R3And R4Are each a hydrogen atom, R5、R6、R7And R8Are all hydroxyl;
2) shown as formula III, wherein R is formula a, in the formula a, Z is 3, M is nitrogen atom, n is 28, R1、R2、R3And R4Are each a hydrogen atom, R5、R6、R7And R8Are each methyl, R9、R10、R11And R12Are all benzene rings;
3) the formula IV is shown in the specification, wherein R is a formula b, in the formula b, Z is 2-3, M is a sulfur atom, n is 14-16, R1、R3、R7And R10Are all sulfonic acid groups, R2、R4、R5、R6、R8、R9、R11、R12、R13、R14、R15And R16Are each a hydrogen atom;
the mass ratio of the polyethylene glycol derivative to the tannic acid is 1: 0.001 to 1000.
2. The injectable biogenic glue according to claim 1, characterized in that: the polyethylene glycolThe structural formula of the derivative is shown as a formula II, wherein R is a formula b, in the formula b, Z is 0, M is oxygen atom, n is 56, R1、R2、R3And R4Are each a hydrogen atom, R5、R6、R7And R8Are all hydroxyl groups.
3. The injectable biogenic glue according to claim 1, characterized in that: the structural formula of the polyethylene glycol derivative is shown as a formula II, wherein R is a formula b, in the formula b, Z is 1, M is an oxygen atom, n is 56, and R1、R2、R3And R4Are each a hydrogen atom, R5、R6、R7And R8Are all hydroxyl groups.
4. The injectable biogenic glue according to claim 1, characterized in that: the structural formula of the polyethylene glycol derivative is shown as a formula IV, wherein R is a formula b, in the formula b, Z is 2, M is a sulfur atom, n is 14, R1、R3、R7And R10Are all sulfonic acid groups, R2、R4、R5、R6、R8、R9、R11、R12、R13、R14、R15And R16Are all hydrogen atoms.
5. The injectable biogenic glue according to claim 1, characterized in that: the structural formula of the polyethylene glycol derivative is shown as a formula IV, wherein R is a formula b, in the formula b, Z is 3, M is a sulfur atom, n is 16, R1、R3、R7And R10Are all sulfonic acid groups, R2、R4、R5、R6、R8、R9、R11、R12、R13、R14、R15And R16Are all hydrogen atoms.
6. Process for the preparation of the injectable biogenic glue according to any one of claims 1 to 5, comprising the following steps:
(1) preparing a solution 1 of the polyethylene glycol derivative;
the mass-volume concentration of the polyethylene glycol derivative in the solution 1 is 0.01-10000 mg/ml;
the solvent of the solution 1 is secondary water, ultrapure water, normal saline or phosphate buffer solution with pH of 7.4;
(2) preparing a solution 2 of the tannic acid;
the mass-volume concentration of the tannic acid in the solution 2 is 0.01-10000 mg/ml;
(3) mixing the solution 1 and the solution 2, and centrifuging to obtain a precipitate, namely the biological glue;
the volume ratio of the solution 1 to the solution 2 is 1: 0.001 to 1000;
the speed of centrifugation is 100-20000 r/min, and the time is 1-60 min.
7. Use of the injectable biogenic glue according to any one of claims 1 to 5 for the preparation of wound adhesives, drug delivery systems, medical implants or surface coatings for medical implants.
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| CN115814145A (en) * | 2022-04-14 | 2023-03-21 | 北京博辉瑞进生物科技有限公司 | Medical tissue glue for pancreas plugging and preparation method and application thereof |
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| KR101307367B1 (en) * | 2010-09-14 | 2013-09-25 | 주식회사 이노테라피 | Adhesive composition comprising tannin, polyethylene glycol, and water, low carbon alcohol or the mixture thereof |
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