CN114788786B - Zwitterionic polymer/amorphous calcium phosphate nano-composite and preparation method and application thereof - Google Patents

Zwitterionic polymer/amorphous calcium phosphate nano-composite and preparation method and application thereof Download PDF

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CN114788786B
CN114788786B CN202110925067.6A CN202110925067A CN114788786B CN 114788786 B CN114788786 B CN 114788786B CN 202110925067 A CN202110925067 A CN 202110925067A CN 114788786 B CN114788786 B CN 114788786B
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zwitterionic polymer
phosphate
amorphous calcium
calcium phosphate
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CN114788786A (en
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刘文广
杨建海
魏祥雨
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Tianjin University
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    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
    • A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/15—Compositions characterised by their physical properties
    • A61K6/17—Particle size
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/20—Protective coatings for natural or artificial teeth, e.g. sealings, dye coatings or varnish
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
    • A61K6/69—Medicaments
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K6/00—Preparations for dentistry
    • A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
    • A61K6/831—Preparations for artificial teeth, for filling teeth or for capping teeth comprising non-metallic elements or compounds thereof, e.g. carbon
    • A61K6/838—Phosphorus compounds, e.g. apatite
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00—Nanotechnology for materials or surface science, e.g. nanocomposites
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B82—NANOTECHNOLOGY
    • B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00—Manufacture or treatment of nanostructures

Abstract

The invention provides a zwitterionic polymer/amorphous calcium phosphate nano-composite, which is prepared by dissolving a zwitterionic polymer in a calcium chloride aqueous solution, and uniformly stirring and mixing the solution A; dissolving phosphate in water, and stirring to obtain solution B; adding the solution B into the solution A, and stirring for 5-30min at a rotation speed of 400-600rpm to fully react the solution B, thus obtaining the zwitterionic polymer/amorphous calcium phosphate nano-composite. The compound has good biocompatibility, can promote enamel remineralization and dentin tubule occlusion in saliva environment, and can inhibit caries bacteria adhesion and bacterial biofilm formation, thereby realizing blocking caries process, remineralizing demineralized dental hard tissue.

Description

Zwitterionic polymer/amorphous calcium phosphate nano-composite and preparation method and application thereof
Technical Field
The invention relates to the technical field of biological materials, in particular to a zwitterionic polymer/amorphous calcium phosphate nano-composite.
Background
Caries is a bacterial biofilm-dependent disease in which cariogenic bacteria (such as Streptococcus mutans) metabolize carbohydrates by fermentation, and the pH value within the plaque biofilm @<5.5 Acid is produced, demineralization of the hard tissues of the teeth (enamel and dentin) occurs. It has been found that the combined action of bacteriostasis and remineralization can simultaneously prevent cariogenic processes and prevent new caries. Amorphous Calcium Phosphate (ACP) nanoparticles are capable of releaseAmplified amount of Ca 2+ And PO (PO) 4 3- Ions have great potential in the treatment of enamel demineralization. Spherical ACP nanoparticles can be deposited into chains and then converted to Hydroxyapatite (HA) to form enamel. ACP, however, is an unstable substance that readily reacts with atmospheric water in solution or in the dry state, rapidly converts to thermodynamically more stable calcium phosphate, and cannot maintain supersaturated Ca for remineralization 2+ 、PO 4 3- An ionic environment. Studies have shown that amelogenin (Amel) can stabilize ACP to form Amel/ACP particles and direct particle alignment, fusion and conversion to HA crystals. Inspired by the ability of the amelogenin to stabilize ACP, researchers speculate that the presence of macromolecules can act as stabilizers to directly isolate supersaturated calcium and phosphorus ions in solution from the precipitate, acting to stabilize the calcium/phosphorus ions. Thus, amorphous Calcium Phosphate (ACP) can be stabilized by forming a nanocomposite, remineralizing demineralized enamel with matrix-stabilized ACP nanoparticles. However, the use of these nanocomposites ignores the bacterial challenges of the presence of cariogenic bacterial biofilms in the actual caries-demineralization areas and the continued presence in the oral cavity.
Disclosure of Invention
The invention overcomes the defects in the prior art, and the application of the traditional nano-composite ignores the existence of a cariogenic bacterial biomembrane in an actual caries demineralization area and the bacterial challenges continuously existing in an oral cavity, and provides the zwitterionic polymer/amorphous calcium phosphate nano-composite which has good biocompatibility, can promote enamel remineralization and dentinal tubule occlusion in a saliva environment, and can inhibit caries bacterial adhesion and bacterial biomembrane formation, thereby realizing blocking of caries progress and remineralization of demineralized dental hard tissues.
The aim of the invention is achieved by the following technical scheme.
The zwitterionic polymer/amorphous calcium phosphate nano-composite and the preparation method thereof are carried out according to the following steps:
step 1, dissolving a zwitterionic polymer in a calcium chloride aqueous solution, and stirring and mixing uniformly to obtain a solution A, wherein the chemical structure of the zwitterionic polymer is as follows:
in the above chemical formula, R is H or CH 3 ，R 1 Is O or NH, n is 1, 2 or 3, M is 1 or 2, the concentration of the calcium chloride aqueous solution is 0.01-0.1M, and the concentration of the zwitterionic polymer in the solution A is 1-10wt%;
step 2, dissolving phosphate in water, stirring and dissolving to obtain a solution B, wherein the phosphate adopts one of disodium hydrogen phosphate, dipotassium hydrogen phosphate, sodium dihydrogen phosphate and potassium dihydrogen phosphate, and the concentration of the phosphate aqueous solution is 0.01-0.1M;
and 3, adding the solution B prepared in the step 2 into the solution A prepared in the step 1, and stirring for 5-30min at the rotation speed of 400-600rpm to fully react the solution to obtain the zwitterionic polymer/amorphous calcium phosphate nano-composite (PCBA/ACP).
In step 1, the concentration of the aqueous solution of calcium chloride was 0.02M, and in solution A, the concentration of the zwitterionic polymer was 6wt%.
In step 1, the zwitterionic polymer was a carboxylic acid betaine Polymer (PCBA) having the following chemical structure:
in step 2, dipotassium hydrogen phosphate is used as phosphate, and the concentration of the phosphate aqueous solution is 0.06M.
In step 3, stirring is carried out at 500rpm for 10min.
The beneficial effects of the invention are as follows: the invention provides a novel bionic Amorphous Calcium Phosphate (ACP) nano-composite which is synthesized by adopting a zwitterionic polymer with good biocompatibility to stabilize Amorphous Calcium Phosphate (ACP) nano-particles, and the chelation of carboxyl groups rich on side chains of the zwitterionic polymer to the Amorphous Calcium Phosphate (ACP) nano-particles can stabilize Amorphous Calcium Phosphate (ACP) nano-particles in solution, and simultaneously charged quaternary ammonium salt groups can be used as nucleation sites to mediate the transformation of the Amorphous Calcium Phosphate (ACP) nano-particles to oriented apatite crystals, so that effective in-vitro mineralization is realized, meanwhile, the inherent super-hydrophilic property of the zwitterionic polymer can endow the Amorphous Calcium Phosphate (ACP) nano-composite with antibacterial property against bacterial adhesion and bacterial biofilm formation in an acidic environment caused by bacterial biofilm, so that the zwitterionic polymer/amorphous calcium phosphate nano-composite is a very promising tooth remineralizing nano-material with double effects on caries prevention: 1) An antimicrobial film; 2) Promoting enamel remineralization and dentinal tubule occlusion.
Drawings
FIG. 1 is a transmission electron microscope image of a zwitterionic polymer/amorphous calcium phosphate nanocomposite (PCBA/ACP) solution prepared in example 1, with diffraction rings in the upper right hand corner, (a) 1 day, (b) 2 days, (c) 3 days, (d) 4 days, (e) 5 days, and (f) 7 days;
FIG. 2 is a laser confocal microscope image and stereoscopic 3D image of an enamel specimen surface biofilm after treatment with a zwitterionic polymer/amorphous calcium phosphate nanocomposite (PCBA/ACP) solution prepared in example 1, a blank enamel specimen, a carboxylic acid betaine Polymer (PCBA) and a zwitterionic polymer/amorphous calcium phosphate nanocomposite (PCBA/ACP);
FIG. 3 is a scanning electron microscope image of enamel remineralization and dentinal tubule occlusion after treatment with the zwitterionic polymer/amorphous calcium phosphate nanocomposite (PCBA/ACP) solution prepared in example 1, wherein A and B are untreated acid etched enamel and dentin; c and D are zwitterionic polymer/amorphous calcium phosphate nanocomposite (pcba/ACP) treated acid etched enamel and dentin.
Detailed Description
The technical scheme of the invention is further described by specific examples.
Example 1
A method for preparing a zwitterionic polymer/amorphous calcium phosphate nanocomposite (pcba/ACP) according to the following steps:
s1: 0.6g of a zwitterionic polymer carboxylic acid type betaine Polymer (PCBA) is dissolved in 10mL of 0.2M calcium chloride aqueous solution, and the solution A is obtained by stirring for 10min at a rotation speed of 500 rpm;
s2: weighing 20.88mg of dipotassium hydrogen phosphate and dissolving in 10mL of deionized water to obtain a solution B;
s3: solution B was slowly added to solution A and stirred at 500rpm for 10min to allow sufficient reaction to give zwitterionic polymer/amorphous calcium phosphate nanocomposite (PCBA/ACP).
To further investigate the properties of the resulting zwitterionic polymer/amorphous calcium phosphate nanocomposite (PCBA/ACP) prepared in example 1, a corresponding experimental verification was made in this example:
as shown in fig. 1, which shows a transmission electron microscope image of a material solution, the upper right corner shows a diffraction ring, and it can be seen from the image that the zwitterionic polymer/amorphous calcium phosphate nanocomposite (pcba/ACP) solution was able to stabilize for 1 day without any aggregation or particle size increase, and in the next two days, although there was a small aggregation, the nanoparticles were still amorphous, and on days 4 and 5, the nanoparticles were significantly aggregated, indicating that the stabilization effect of the zwitterionic polymer/amorphous calcium phosphate nanocomposite (pcba/ACP) on the Amorphous Calcium Phosphate (ACP) nanoparticles had been significantly reduced, but the SAED image of the nanoparticles did not show a significant crystal structure, and after 7 days, the spherical particles had disappeared, converted to a needle-like structure, and in this experiment, the carboxylic acid betaine polymer (aa) could stabilize the Amorphous Calcium Phosphate (ACP) nanoparticles in the solution for at least 1 day, and as a nucleation inhibitor, aggregate the Amorphous Calcium Phosphate (ACP) nanoparticles into large particles for a prolonged period of time, which could be beneficial to the rapid transition of Amorphous Calcium Phosphate (ACP) to the amorphous calcium phosphate particles to the hydroxyapatite region before the amorphous calcium phosphate particles were rapidly mineralized.
As shown in fig. 2, which is a confocal laser image of bacterial biofilm on the enamel surface, it can be seen that the surface of enamel without any treatment forms a dense bacterial biofilm, the bacteria are active bacteria, while the bacteria in the bacterial biofilm on the enamel surface treated with the zwitterionic polymer/amorphous calcium phosphate nanocomposite (pcba/ACP) are dead bacteria, indicating that the zwitterionic polymer/amorphous calcium phosphate nanocomposite (pcba/ACP) can kill the bacteria in the bacterial biofilm.
As shown in fig. 3, which is a scanning electron microscope image of enamel remineralization and dentinal tubule occlusion, it can be seen that the acid etched enamel surface forms a uniform mineral layer after treatment with a zwitterionic polymer/amorphous calcium phosphate nanocomposite (pcba/ACP), and the dentinal tubules are almost completely closed, indicating that the material is capable of remineralizing dental hard tissue.
Example 2
The preparation method of the zwitterionic polymer/amorphous calcium phosphate nano-composite comprises the following steps:
s1: 1.0g of a zwitterionic polymer carboxylic acid type betaine Polymer (PCBA) is dissolved in 10mL of 0.2M calcium chloride aqueous solution, and the solution A is obtained by stirring for 10min at a rotation speed of 500 rpm;
s2: 41.76mg of dipotassium hydrogen phosphate is weighed and dissolved in 10mL of deionized water to obtain solution B;
s3: solution B was slowly added to solution A and stirred at 500rpm for 10min to allow sufficient reaction to give zwitterionic polymer/amorphous calcium phosphate nanocomposite (PCBA/ACP).
Example 3
The preparation method of the zwitterionic polymer/amorphous calcium phosphate nano-composite comprises the following steps:
s1: 1.0g of a zwitterionic polymer carboxylic acid type betaine Polymer (PCBA) is dissolved in 10mL of 0.3M calcium chloride aqueous solution, and the solution A is obtained by stirring for 10min at a rotation speed of 500 rpm;
s2: 41.76mg of dipotassium hydrogen phosphate is weighed and dissolved in 10mL of deionized water to obtain solution B;
s3: solution B was slowly added to solution A and stirred at 500rpm for 10min to allow sufficient reaction to give zwitterionic polymer/amorphous calcium phosphate nanocomposite (PCBA/ACP).
Example 4
The preparation method of the zwitterionic polymer/amorphous calcium phosphate nano-composite comprises the following steps:
s1: 0.6g of a zwitterionic polymer carboxylic acid type betaine Polymer (PCBA) is dissolved in 10mL of 0.4M calcium chloride aqueous solution, and the solution A is obtained by stirring for 10min at a rotation speed of 500 rpm;
s2: 41.76mg of dipotassium hydrogen phosphate is weighed and dissolved in 10mL of deionized water to obtain solution B;
s3: solution B was slowly added to solution A and stirred at 500rpm for 10min to allow sufficient reaction to give zwitterionic polymer/amorphous calcium phosphate nanocomposite (PCBA/ACP).
The foregoing has described exemplary embodiments of the invention, it being understood that any simple variations, modifications, or other equivalent arrangements which would not unduly obscure the invention may be made by those skilled in the art without departing from the spirit of the invention.

Claims (7)

1. A zwitterionic polymer/amorphous calcium phosphate nanocomposite characterized by: the method comprises the following steps of:
step 1, dissolving a zwitterionic polymer in a calcium chloride aqueous solution, and stirring and mixing uniformly to obtain a solution A, wherein the zwitterionic polymer adopts a carboxylic acid type betaine polymer, and the chemical structure of the zwitterionic polymer is as follows:
the concentration of the calcium chloride aqueous solution is 0.01-0.1M, and the concentration of the zwitterionic polymer in the solution A is 1-10wt%;
step 2, dissolving phosphate in water, stirring and dissolving to obtain a solution B, wherein the phosphate adopts one of disodium hydrogen phosphate, dipotassium hydrogen phosphate, sodium dihydrogen phosphate and potassium dihydrogen phosphate, and the concentration of the phosphate aqueous solution is 0.01-0.1M;
and 3, adding the solution B prepared in the step 2 into the solution A prepared in the step 1, and stirring for 5-30min at the rotation speed of 400-600rpm to fully react the solution B to obtain the zwitterionic polymer/amorphous calcium phosphate nano-composite.
2. The zwitterionic polymer/amorphous calcium phosphate nanocomposite according to claim 1, characterized in that: in step 1, the concentration of the aqueous solution of calcium chloride was 0.02M, and in solution A, the concentration of the zwitterionic polymer was 6wt%.
3. The zwitterionic polymer/amorphous calcium phosphate nanocomposite according to claim 1, characterized in that: in step 2, dipotassium hydrogen phosphate is used as phosphate, and the concentration of the phosphate aqueous solution is 0.06M.
4. A method for preparing a zwitterionic polymer/amorphous calcium phosphate nanocomposite, characterized by: the method comprises the following steps of:
step 1, dissolving a zwitterionic polymer in a calcium chloride aqueous solution, and stirring and mixing uniformly to obtain a solution A, wherein the zwitterionic polymer adopts a carboxylic acid type betaine polymer, and the chemical structure of the zwitterionic polymer is as follows:
the concentration of the calcium chloride aqueous solution is 0.01-0.1M, and the concentration of the zwitterionic polymer in the solution A is 1-10wt%;
step 2, dissolving phosphate in water, stirring and dissolving to obtain a solution B, wherein the phosphate adopts one of disodium hydrogen phosphate, dipotassium hydrogen phosphate, sodium dihydrogen phosphate and potassium dihydrogen phosphate, and the concentration of the phosphate aqueous solution is 0.01-0.1M;
and 3, adding the solution B prepared in the step 2 into the solution A prepared in the step 1, and stirring for 5-30min at the rotation speed of 400-600rpm to fully react the solution B to obtain the zwitterionic polymer/amorphous calcium phosphate nano-composite.
5. The method for preparing the zwitterionic polymer/amorphous calcium phosphate nanocomposite according to claim 4, wherein: in step 1, the concentration of the aqueous solution of calcium chloride was 0.02M, and in solution A, the concentration of the zwitterionic polymer was 6wt%.
6. The method for preparing the zwitterionic polymer/amorphous calcium phosphate nanocomposite according to claim 4, wherein: in step 2, dipotassium hydrogen phosphate is used as phosphate, and the concentration of the phosphate aqueous solution is 0.06M.
7. The method for preparing the zwitterionic polymer/amorphous calcium phosphate nanocomposite according to claim 4, wherein: in step 3, stirring is carried out at 500rpm for 10min.
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JP4673310B2 (en) * 2004-08-11 2011-04-20 クラレメディカル株式会社 Dental polymerizable composition
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