CN112868668B - Fe3O4-DA-AMP nano composite antibacterial material and preparation method and application thereof - Google Patents
Fe3O4-DA-AMP nano composite antibacterial material and preparation method and application thereof Download PDFInfo
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- CN112868668B CN112868668B CN202110294503.4A CN202110294503A CN112868668B CN 112868668 B CN112868668 B CN 112868668B CN 202110294503 A CN202110294503 A CN 202110294503A CN 112868668 B CN112868668 B CN 112868668B
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- adipic acid
- antibacterial material
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/16—Heavy metals; Compounds thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/44—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a nitrogen atom attached to the same carbon skeleton by a single or double bond, this nitrogen atom not being a member of a derivative or of a thio analogue of a carboxylic group, e.g. amino-carboxylic acids
- A01N37/46—N-acyl derivatives
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- 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
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- 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
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- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01G—COMPOUNDS CONTAINING METALS NOT COVERED BY SUBCLASSES C01D OR C01F
- C01G49/00—Compounds of iron
- C01G49/02—Oxides; Hydroxides
- C01G49/08—Ferroso-ferric oxide (Fe3O4)
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K17/00—Carrier-bound or immobilised peptides; Preparation thereof
- C07K17/14—Peptides being immobilised on, or in, an inorganic carrier
Abstract
The invention belongs to the technical field of metal nano materials, and particularly discloses Fe3O4-DA-AMP nano composite antibacterial material and preparation method and application thereof. The DA-labeled antibacterial peptide (DA-adipic acid-GKRWWKWWRR) is connected to Fe through a coordination bond between Fe and phenolic hydroxyl groups of DA3O4Above, adipic acid acts as a linker molecule. Preparation of the resulting Fe3O4-DA-AMP nano composite antibacterial material with excellent antibacterial property and Fe3O4Has good biocompatibility, small interference to normal physiological activities of body cells, low toxicity and high safety.
Description
Technical Field
The invention belongs to the technical field of metal nano materials, and particularly relates to Fe3O4-DA-AMP nano composite antibacterial material and preparation method and application thereof.
Background
With the development of science and technology and the improvement of living standard, the environmental sanitation requirements of people on living, working and living are increasingly improved, so that the rapid development of antibacterial technology and antibacterial materials is promoted, and the nano antibacterial material is an important one of the antibacterial materials. The nano antibacterial material is a novel material with antibacterial property, has the advantages of large specific surface area, high reactivity and the like, and can keep the growth and reproduction of microorganisms including bacteria, fungi, yeasts, algae, viruses and the like at a low level, thereby greatly improving the antibacterial property of the material. In recent years, a large number of drug-resistant bacteria and multi-drug-resistant bacteria have been continuously developed. The spontaneous drug-resistant mutation of bacteria, the screening of antibiotics and the environmental adaptability of pathogenic bacteria are the basis for the generation of clinical drug-resistant bacteria and multi-drug-resistant bacteria. The antibacterial peptides (AMPs) have incomparable advantages of the traditional antibiotics, have unique antibacterial mechanism and quick bactericidal action, are not easy to cause drug resistance of bacteria, and are a class of antibacterial drugs with great potential.
The existing nano composite antibacterial material has certain cytotoxicity and high preparation cost (such as gold nanoparticles, silver nanoparticles and the like).
The magnetic nano material is a powder material with a spinel structure, and has four basic nano size effects as common nano materials. The magnetic nano material has good biocompatibility, can be biodegraded, has no potential cytotoxicity to human bodies, and simultaneously shows some interesting characteristics: superparamagnetism, high saturation magnetic field, low Curie temperature and unique physicochemical properties, and the surface is easy to modify biological functional groups, so the magnetic resonance imaging detection magnetic resonance imaging detection magnetic resonance imaging detection magnetic resonance imaging.
Disclosure of Invention
The invention aims to provide Fe3O4the-DA-AMP composite nano antibacterial material has a good antibacterial effect and has wide application prospects in the fields of bacteriostasis and sterilization.
The specific technical scheme of the invention is as follows:
the nano composite antibacterial material provided by the invention is made of Fe3O4Magnetic nanoparticles and DA-modified antibacterial peptide, wherein DA-labeled antibacterial peptide (DA-adipic acid-GKRWWKWWRR) is connected to Fe through coordination bond between Fe and phenolic hydroxyl group of DA3O4Above, adipic acid acts as a linker molecule.
Wherein, Fe3O4Magnetic nanoparticles of FeCl2And FeCl3Coprecipitating to obtain the product with particle size of 143nm and potential of-7.5 mV.
The DA modified antibacterial peptide DA-adipic acid-GKRWWKWWRR is prepared by a solid phase synthesis method, namely, after a monomer amino acid protected by Fmoc on a solid phase resin is deprotected, an amino group is exposed, and a peptide bond is formed with a carboxyl group of the amino acid in a solution through a condensation reaction, so that the amino acid is connected to the resin, and a peptide chain is extended from a C end to an N end until the required peptide chain is synthesized. The specific operation is shown in the examples.
The DA-modified antimicrobial peptide (DA-AMP) was purified by HPLC.
DA-labeled antibacterial peptide (DA-adipate-GKRWWKWWRRC) was attached to Fe through a coordination bond between Fe and the phenolic hydroxyl group of DA.
Fe3O4-DA-AMP nano composite antibacterial materialThe particle size of the material is 170nm, and the potential is 14 mV.
Fe3O4The preparation method of the-DA-AMP nano composite antibacterial material comprises the following steps:
1) synthesis of Fe3O4；
2) Synthesizing DA-adipic acid-GKRWWKWWRR;
3) synthesis of Fe3O4-DA-AMP
Ligand exchange reaction of DA-AMP to obtain DA-AMP and Fe3O4And (4) combining.
Fe3O4the-DA-AMP nano composite antibacterial material is used for preparing a magnetic nano antibacterial probe for bacteriostasis and sterilization and can be used for in-vitro blood disinfection.
Compared with the prior art, the invention has the following beneficial effects:
fe prepared by the method of the invention3O4the-DA-AMP nano composite antibacterial material has higher antibacterial activity and can be widely applied to the fields of bacteriostasis and sterilization; the preparation process disclosed by the invention is simple, wide in raw material source, mild in reaction condition, easy to synthesize and suitable for popularization and use.
Description of the drawings:
FIG. 1 is Fe3O4-a particle size map of DA;
FIG. 2 is Fe3O4-a particle size diagram of the DA-AMP nanocomposite antibacterial material;
FIG. 3 is Fe3O4-DA and Fe3O4-potentiometric diagram of the DA-AMP nanocomposite antibacterial material;
FIG. 4 is an HPLC chart of DA-adipic acid-GKRWWKWWRRC;
FIG. 5 is a mass spectrum of DA-adipic acid-GKRWWKWWRRC;
FIG. 6 is Fe3O4-DA-AMP、Fe3O4And an antimicrobial profile of AMP;
FIG. 7 is Fe3O4MIC determination of DA-AMP bacterial plating patterns;
FIG. 8 is Fe3O4MIC quantification map of DA-AMP.
Detailed Description
The present invention will be described in detail with reference to examples, but the present invention is not limited to these examples.
Example 1
1、Fe3O4Synthesis of-DA-AMP nano composite antibacterial material
1)Fe3O4Synthesis of (2)
FeCl is added2And FeCl3(molar ratio 1: 2) in ultrapure water by addition of NH4Preparation of OA-Fe by OH coprecipitation3O4And (3) nanoparticles.
In a 500mL round bottom flask, 0.86g FeCl2And 2.35g FeCl3Dissolved in 40mL of deionized water. Then, 3.75mL of 25% NH was added rapidly with vigorous stirring4And (5) OH. While the temperature of the solution was further raised to 80 ℃, 0.3mL of Oleic Acid (OA) was injected. After mixing for 1 hour, 30mL of toluene and excess NaCl were added to the solution with vigorous stirring to obtain OA-Fe dispersed in the toluene phase3O4And (3) nanoparticles. The toluene phase was separated and 30mL acetone was added and the hydrophobic Fe was collected by magnetic separation3O4And (3) nanoparticles. Collecting Fe3O4The nanoparticles were dried under vacuum at 40 ℃ overnight and then dispersed in toluene at a concentration of 10 mg/mL.
Note: all glassware was cleaned and the water was ultrapure water.
2) Synthesis of DA-adipic acid-GKRWWKWWRR
The polypeptide is obtained by a solid phase polypeptide synthesis technology based on 2-Chlorotrityl Chloride resin with Fmoc protective groups.
Respectively weighing amino acid, HBTU and HOBT in an amount which is 5 times of the molar weight of the resin, dissolving the amino acid, HBTU and HOBT in DMF, and adding DIEA for coupling for 30 min. The Fmoc protecting group was then removed by reaction with 20% piperidine for 30min and the procedure was repeated until the desired peptide chain was synthesized (GKRWWKWWRR). Respectively weighing adipic acid, HBTU and HOBT in an amount which is 5 times of the molar weight of resin (the resin for synthesizing the polypeptide) and dissolving the adipic acid, HBTU and HOBT in DMF, adding DIEA for coupling for 30min, and reacting twice. The DA modification was consistent with adipic acid. Finally, the labeled polypeptide is cleaved from the resin with a cleavage solution, purified by HPLC, the molecular weight is determined by LC-MS, and the purification and mass spectra are shown in FIG. 4 and FIG. 5.
3)Fe3O4Synthesis of-DA-AMP
Ligand exchange reaction of DA-AMP to obtain DA-AMP and Fe3O4And (4) combining.
5mg of DA-AMP was dissolved in an aqueous solution at pH 4.0, and then 500. mu.L of OA-Fe was added3O4Toluene solution and shaking for 10 minutes to facilitate ligand exchange. Acetone was added in excess and precipitation of the dispersed particles was observed by the addition of a magnet. The obtained precipitate can be easily dispersed in water to form a stable colloid. The subsequent precipitation-dispersion process was repeated 3 times, washing off the free DA-AMP.
Control group DA-Fe3O4The synthesis method is the same as that of Fe3O4Synthesis of-DA-AMP, as shown in detail below:
DA was weighed out and dissolved in water at pH 4.0, and OA-Fe was added3O4Shaking the toluene solution promoted the binding of the two.
2、Fe3O4Characterization of-DA-AMP nanocomposite antibacterial Material
1)Fe3O4Determination experiment of hydrated particle size and Zeta potential of-DA-AMP nano composite antibacterial material
20 mu L of synthesized DA-Fe is taken respectively3O4、Fe3O4DA-AMP, diluted to 2mL with deionized water. Of these, 1mL was used for measuring the hydrated particle size and 1mL was used for measuring the Zeta potential. Each set of samples was assayed in triplicate and monitored for changes throughout the process. The effect is shown in figure 1 and figure 2.
According to the determination of DA-Fe3O4、Fe3O4The change of the hydrated particle size and the Zeta potential of DA-AMP was used to determine whether each step was successful. As can be seen from the graph, from the original DA-Fe3O4Nanoparticles to final Fe3O4The hydrated particle size of the-DA-AMP nanoprobe is increased, which proves the successful coupling of DA-AMP. FIG. 3 shows the variation of Zeta potentialThe change also proves Fe3O4The nanoparticles have DA-AMP attached.
3、Fe3O4Antibacterial performance test of-DA-AMP nano composite antibacterial material
1)Fe3O4Antibacterial Effect of-DA-AMP against Staphylococcus aureus
To explore Fe3O4Effect of-DA-AMP nanocomposite antibacterial Material on bacterial growth, 100. mu.L of S.aureus cultured overnight was aspirated, added to 5mL of TSB medium, and cultured at 37 ℃ for 6 hours at a bacterial concentration of 108And (4) CFU. Diluting the bacterial liquid by 50 times, and then respectively taking 250 mu L of Fe3O4-DA-AMP、DA-Fe3O4DA-AMP and 1mL of diluted bacterial solution were mixed, and co-cultured at 37 ℃ and 180rpm for 1 hour. The coculture solution was taken out and diluted 20000 times, 70. mu.L of the coculture solution was added to the TSA solid medium, spread uniformly by an applicator, placed in an incubator upside down, and cultured at 37 ℃ for 16 hours. The plates were removed and colonies counted and plotted using origin software.
According to Fe3O4-DA-AMP nano composite antibacterial material and Fe3O4Comparison of the antibacterial effect with DA-AMP shows that Fe is present3O4the-DA-AMP showed a significant antibacterial effect (FIG. 6).
2)Fe3O4MIC assay of-DA-AMP against Staphylococcus aureus
To explore Fe3O4MIC of-DA-AMP nanoprobe to Staphylococcus aureus, 100. mu.L of overnight-cultured S.aureus bacteria were aspirated, added to 5mL of TSB medium, and cultured at 37 ℃ for 6h at a bacterial concentration of 108And (4) CFU. Diluting the bacterial liquid by 50 times, and then respectively taking Fe with different concentrations3O4250 mu L of-DA-AMP nanoprobe was mixed with 1mL of diluted bacterial solution, and co-cultured at 180rpm and 37 ℃ for 1 hour. The coculture solution was taken out and diluted 20000 times, 70. mu.L of the coculture solution was added to the TSA solid medium, spread uniformly by an applicator, placed in an incubator upside down, and cultured at 37 ℃ for 16 hours. The plates were removed and colonies counted and plotted using origin software.
According to different concentrations of Fe3O4Antibacterial effect of-DA-AMP nanoprobeAs can be seen, Fe3O4MIC of-DA-AMP nanoprobe50About 0.35mM (FIGS. 7, 8).
Claims (6)
1. Fe3O4-DA-AMP nanocomposite antimicrobial material, wherein said nanocomposite antimicrobial material is Fe3O4Magnetic nanoparticles and DA-modified antibacterial peptide DA-adipic acid-GKRWWKWWRR, wherein the DA-modified antibacterial peptide is connected to Fe through a coordination bond between the phenolic hydroxyl groups of Fe and DA3O4Above, adipic acid as the linker molecule;
the synthesis method of the DA-adipic acid-GKRWWKWWRR comprises the following steps: the polypeptide is obtained by solid phase polypeptide synthesis based on 2-Chlorotrityl Chloride resin with Fmoc protecting groups;
respectively weighing amino acid, HBTU and HOBT which are equivalent to 5 times of the molar weight of the resin, dissolving the amino acid, HBTU and HOBT in DMF, adding DIEA for coupling for 30min, then adding 20% piperidine for reaction for 30min to remove Fmoc protecting groups, and repeating the steps until the required peptide chain GKRWWKWWRR is synthesized; respectively weighing adipic acid, HBTU and HOBT which are equivalent to 5 times of the molar weight of the resin synthesized with the polypeptide, dissolving the adipic acid, HBTU and HOBT in DMF, adding DIEA for coupling for 30min, reacting twice, wherein the modification mode of DA is consistent with that of the adipic acid, and finally cracking the marked polypeptide from the resin by using a cutting fluid.
2. Fe of claim 13O4-DA-AMP nanocomposite antibacterial material, characterized in that said Fe3O4Magnetic nanoparticles of FeCl2And FeCl3Coprecipitating to obtain the product with particle size of 143nm and potential of-7.5 mV.
3. Fe of claim 13O4-DA-AMP nano composite antibacterial material, characterized in that, the DA modified antibacterial peptide DA-adipic acid-GKRWWKWWRR is prepared by solid phase synthesis method.
4. Fe of claim 13O4-DA-AMP nanocomposite antibacterial material, characterized in that said Fe3O4The particle size of the-DA-AMP nano composite antibacterial material is 170nm, and the potential is 14 mV.
5. Fe according to claim 13O4The preparation method of the-DA-AMP nano composite antibacterial material is characterized in that Fe3O4The preparation method of the-DA-AMP nano composite antibacterial material comprises the following steps:
1) synthesis of Fe3O4；
2) Synthesizing DA-adipic acid-GKRWWKWWRR;
3) synthesis of Fe3O4-DA-AMP
Ligand exchange reaction of DA-AMP to obtain DA-AMP and Fe3O4And (4) combining.
6. Fe according to claim 13O4-DA-AMP nanocomposite antibacterial material, use of said Fe3O4the-DA-AMP nano composite antibacterial material is used in the fields of bacteriostasis and sterilization.
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| ATE542920T1 (en) * | 2004-12-22 | 2012-02-15 | Ambrx Inc | MODIFIED HUMAN GROWTH HORMONE |
| CN102063991A (en) * | 2010-10-27 | 2011-05-18 | 高存元 | Production method of nano-magnetic fluid with special function |
| CN102034584A (en) * | 2010-10-28 | 2011-04-27 | 天津大学 | Magnetic poly-dopamine-iron oxide nanoparticles and preparation method thereof |
| CN102000658B (en) * | 2010-12-15 | 2013-04-03 | 成都西南交大科技园管理有限责任公司 | Polydopamine-based biofunction modification method |
| CN104258909A (en) * | 2014-08-01 | 2015-01-07 | 曲阜师范大学 | Fe3O4-poly-dopamine-Au nano-composite material as well as preparation method and application thereof |
| CN104575908A (en) * | 2015-01-30 | 2015-04-29 | 中山大学 | Dopamine modified magnetic nano-particle, method for preparing same and application of dopamine modified magnetic nano-particle |
| CN105154862B (en) * | 2015-09-09 | 2018-06-29 | 华南理工大学 | A kind of antibacterial processing method of surface of metal titanium |
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| CN105504018B (en) * | 2016-01-13 | 2019-01-04 | 郑州大学 | LAG-3 affinity peptide N13, preparation method and applications |
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| CN106282152A (en) * | 2016-08-08 | 2017-01-04 | 华南理工大学 | A kind of immobilized enzyme and the method being acylated by its catalysis dihydromyricetin |
| CN107456576B (en) * | 2017-07-31 | 2020-11-20 | 江苏大学 | Photothermal antibacterial agent polypeptide/Au/Fe3O4Preparation method and application of |
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| CN108376608B (en) * | 2018-02-10 | 2020-11-06 | 青岛大学 | Magnetic nano particle and application thereof in preparing magnetic solid phase carrier |
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| CN110669147A (en) * | 2019-10-24 | 2020-01-10 | 常州大学 | Antibacterial agent FAM-AMP containing gelatinase enzyme digestion sequence for detecting Saureus |
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