CN106166292B - Preparation method of teicoplanin functional gold nanoparticles and products thereof and application - Google Patents
Preparation method of teicoplanin functional gold nanoparticles and products thereof and application Download PDFInfo
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- CN106166292B CN106166292B CN201610488526.8A CN201610488526A CN106166292B CN 106166292 B CN106166292 B CN 106166292B CN 201610488526 A CN201610488526 A CN 201610488526A CN 106166292 B CN106166292 B CN 106166292B
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- 108010053950 Teicoplanin Proteins 0.000 title claims abstract description 51
- DDTDNCYHLGRFBM-YZEKDTGTSA-N chembl2367892 Chemical compound CC(=O)N[C@H]1[C@@H](O)[C@H](O)[C@H](CO)O[C@H]1O[C@@H]([C@H]1C(N[C@@H](C2=CC(O)=CC(O[C@@H]3[C@H]([C@H](O)[C@H](O)[C@@H](CO)O3)O)=C2C=2C(O)=CC=C(C=2)[C@@H](NC(=O)[C@@H]2NC(=O)[C@@H]3C=4C=C(O)C=C(C=4)OC=4C(O)=CC=C(C=4)[C@@H](N)C(=O)N[C@H](CC=4C=C(Cl)C(O5)=CC=4)C(=O)N3)C(=O)N1)C(O)=O)=O)C(C=C1Cl)=CC=C1OC1=C(O[C@H]3[C@H]([C@@H](O)[C@H](O)[C@H](CO)O3)NC(C)=O)C5=CC2=C1 DDTDNCYHLGRFBM-YZEKDTGTSA-N 0.000 title claims abstract description 51
- 229960001608 teicoplanin Drugs 0.000 title claims abstract description 51
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 title claims abstract description 22
- 239000010931 gold Substances 0.000 title claims abstract description 22
- 229910052737 gold Inorganic materials 0.000 title claims abstract description 22
- 239000002105 nanoparticle Substances 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title claims abstract description 18
- FDWREHZXQUYJFJ-UHFFFAOYSA-M gold monochloride Chemical compound [Cl-].[Au+] FDWREHZXQUYJFJ-UHFFFAOYSA-M 0.000 claims abstract description 12
- 241000894006 Bacteria Species 0.000 claims abstract description 7
- 239000002245 particle Substances 0.000 claims abstract description 7
- 238000000502 dialysis Methods 0.000 claims abstract description 5
- 238000007306 functionalization reaction Methods 0.000 claims abstract description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003513 alkali Substances 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 5
- 239000000872 buffer Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- 239000000835 fiber Substances 0.000 claims description 3
- 229910021642 ultra pure water Inorganic materials 0.000 claims description 3
- 239000012498 ultrapure water Substances 0.000 claims description 3
- BRSVJNYNWNMJKC-UHFFFAOYSA-N [Cl].[Au] Chemical compound [Cl].[Au] BRSVJNYNWNMJKC-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 9
- 238000006243 chemical reaction Methods 0.000 abstract description 4
- 238000000034 method Methods 0.000 abstract description 4
- 239000003638 chemical reducing agent Substances 0.000 abstract description 2
- MPOKJOWFCMDRKP-UHFFFAOYSA-N gold;hydrate Chemical compound O.[Au] MPOKJOWFCMDRKP-UHFFFAOYSA-N 0.000 abstract description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 239000003381 stabilizer Substances 0.000 abstract description 2
- 208000035473 Communicable disease Diseases 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 230000003115 biocidal effect Effects 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 229910004042 HAuCl4 Inorganic materials 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 239000003242 anti bacterial agent Substances 0.000 description 2
- 230000009286 beneficial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000004627 transmission electron microscopy Methods 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 206010059866 Drug resistance Diseases 0.000 description 1
- 206010014889 Enterococcal infections Diseases 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000000635 electron micrograph Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229960003085 meticillin Drugs 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000002715 modification method Methods 0.000 description 1
- 231100000417 nephrotoxicity Toxicity 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 239000003910 polypeptide antibiotic agent Substances 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
- A61K38/14—Peptides containing saccharide radicals; Derivatives thereof, e.g. bleomycin, phleomycin, muramylpeptides or vancomycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K41/00—Medicinal preparations obtained by treating materials with wave energy or particle radiation ; Therapies using these preparations
- A61K41/0052—Thermotherapy; Hyperthermia; Magnetic induction; Induction heating therapy
-
- 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
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- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nanotechnology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Crystallography & Structural Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Epidemiology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Physics & Mathematics (AREA)
- Immunology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Manufacturing & Machinery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Gastroenterology & Hepatology (AREA)
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Abstract
The invention discloses preparation methods of teicoplanin functional gold nanoparticles and products thereof and application, the preparation method includes the following steps: teicoplanin, gold chloride and water being mixed into solution, adjusting solution ph solution between 10~14 with alkali is in brown, 0.5h~for 24 hours is stirred to react under the conditions of 20~25 DEG C to solution in claret, dialysis removes unreacted teicoplanin or gold chloride to get the nanogold particle of teicoplanin functionalization.The present invention is by teicoplanin and gold chloride one kettle way hybrid reaction, and the hydroxyl and amino contained in teicoplanin molecular structure can be directly as the stabilizer and reducing agent of this reaction, and this method very simple is easy；And the antibacterial effect of the anti-gram positive bacteria of teicoplanin functional gold nanoparticles prepared by the present invention is more preferable than teicoplanin, can be applied to biomedicine field.
Description
Technical field
The invention belongs to antibacterials synthesize field, and in particular to the preparation method of teicoplanin functional gold nanoparticles and its
Product and application.
Background technique
The outburst of food safety caused by pathogen and infectious diseases is social people's livelihood hot issue in recent years.Bacterium
Effective treatment of caused infectious diseases relies primarily on antibiotic, due to the abuse of various antibiotic, especially third generation head
The application of spore bacterium is so that many bacterial strains produce drug resistance.
Teicoplanin (Teicoplanin) is a kind of glycopeptide antibiotics, has stronger antibacterial to gram-positive bacteria
Activity.Teicoplanin can be easier to penetrate into tissue and cell since it shows strong lipophilicity with unique aliphatic chain, with
After bacterial action, by the normal synthesis of block cell wall and cell membrane, and lead to bacterial death.Clinically it is mainly used at present
Treat severe staphylococcus and enterococcal infection or multi-drug resistant bacteria infection, especially methicillin-resistant staphylococcus aureus
(MRSA) infectious diseases caused by.In addition, the toxic side effect of teicoplanin is small, there is lower renal toxicity, have good
Tolerance.
Nanogold (AuNPs) is gold particle of the diameter in 1-100nm, it mainly has, and synthesis step is simple, stability is good,
Toxicity is relatively small, good biocompatibility, easily in conjunction with biomolecule and special optical absorption, scattering, photo-thermal effect, therefore
It is widely used in biology and medicine etc..
Antibiotic molecule and gold nanoparticle are compounded to form new nano antibacterial agent, felt caused by pathogenic bacteria for improving
Infectious diseases curative effect reduces antibiotic usage amount, increases its tolerance and be of great significance.Currently, antibiotic-Jenner's grain of rice is multiple
The preparation of object is closed mainly by complicated, time-consuming multi step modification method.Therefore, a kind of new antibiotic-Jenner's grain of rice is constructed
Compound antibacterial agent, simplified preparation method has its necessity simultaneously.
Summary of the invention
In view of this, the purpose of the present invention is to provide preparation methods of teicoplanin functional gold nanoparticles and products thereof.
Teicoplanin functional gold nanoparticles disclosed by the invention have antibacterial activity more better than teicoplanin.
In order to achieve the above objectives, the present invention provides the following technical solutions:
1, the preparation method of teicoplanin functional gold nanoparticles includes the following steps: to mix in teicoplanin, gold chloride and water
Synthetic solvent adjusts solution ph to 10~14 with alkali, and solution is in brown, and 0.5h~for 24 hours is stirred to react under the conditions of 20~25 DEG C
It is in claret to solution, dialysis removes unreacted teicoplanin or gold chloride to get the nanogold of teicoplanin functionalization
Grain.
Preferably, with sodium hydrate regulator solution pH value to 12, solution is in brown, is stirred to react under the conditions of 20~25 DEG C
0.5h is to solution in claret.
Preferably, the dialysis uses film for the bag filter of regenerated fiber film, and buffer is ultrapure water.
Preferably, the size of the nanogold particle of the teicoplanin functionalization with gold chloride and teicoplanin molar ratio
Increase and increases.
Preferably, the molar ratio 4:1 of gold chloride and teicoplanin, prepared teicoplanin-nanogold is having a size of 11.5
±2.7nm。
2, the teicoplanin functional gold nanoparticles prepared according to the preparation method.
3, application of the teicoplanin functional gold nanoparticles in anti-gram positive bacteria.
The beneficial effects of the present invention are:
1, the present invention is by teicoplanin and gold chloride one kettle way hybrid reaction, the hydroxyl contained in teicoplanin molecular structure
Can be directly as the stabilizer and reducing agent of this reaction with amino, this method very simple is easy；
2, teicoplanin functional gold nanoparticles antibacterial effect prepared by the present invention is more preferable than teicoplanin, can be applied to biology
Field of medicaments.
Detailed description of the invention
In order to keep the purpose of the present invention, technical scheme and beneficial effects clearer, the present invention provides following attached drawing:
Fig. 1 shows the ultra-violet absorption spectrums of teicoplanin-nanogold (Tecoplanin-AuNPs) prepared by embodiment 1；
Fig. 2 indicates teicoplanin-nanogold particle pictorial diagram；
Fig. 3 indicates the infrared absorption spectrum of teicoplanin-nanogold (Tecoplanin-AuNPs) prepared by embodiment 1
Figure；
Fig. 4 indicates teicoplanin-nanogold (Tecoplanin-AuNPs) transmission electron microscopy figure prepared by embodiment 1
(A) and size distribution plot (B)；
Fig. 5 indicates the X-ray electron spectrum of teicoplanin-nanogold (Tecoplanin-AuNPs) prepared by embodiment 1；
Fig. 6 indicates the antibacterial of teicoplanin-nanogold (Tecoplanin-AuNPs) and other drugs prepared by embodiment 1
Active comparison diagram.
Specific embodiment
A preferred embodiment of the present invention will be described in detail below.The experiment side of actual conditions is not specified in embodiment
Method, usually according to conventional conditions or according to the manufacturer's recommendations.
The preparation of 1 teicoplanin functional gold nanoparticles of embodiment
Taking mass concentration is 1% gold chloride (HAuCl4) be added in round-bottomed flask, adding mass concentration is 1%
Teicoplanin, wherein HAuCl4Molar ratio with teicoplanin is 4:1, adds a certain amount of water, stirs under the conditions of 20~25 DEG C
Mix 15min, then solution adjusts pH value of solution to 12 with NaOH, solution is in brown, continues to stir under the conditions of 20~25 DEG C in faint yellow
30min is mixed, solution is in claret, uses film for the bag filter of regenerated fiber film, and buffer is that ultrapure water dialyses to solution
Purifying is to get teicoplanin-nanogold (Teicoplanin-AuNPs).
The teicoplanin prepared to embodiment 1-nanogold carries out ultra-violet absorption spectrum detection, obtains light as shown in Figure 1
Spectrogram, teicoplanin-nanogold maximum absorption wavelength indicate teicoplanin-nanogold particle reality in 520nm or so, Fig. 2
Object figure is in claret.
The teicoplanin prepared to embodiment 1-nanogold carries out infrared absorption spectrum detection, obtains light as shown in Figure 3
Spectrogram, teicoplanin-nanogold is in 3500cm-1、1650cm-1、1550cm-1、1450cm-1There is absorption peak in left and right.
The teicoplanin prepared to embodiment 1-nanogold carries out transmission electron microscopy detection, obtains as shown in Figure 4 saturating
Penetrate electron micrograph (A) and size distribution plot (B)；Can obtain prepared teicoplanin-nanogold size be about 11.5 ±
2.7nm。
The teicoplanin prepared to embodiment 1-nanogold carries out the detection of X-ray electron spectrum, obtains X as shown in Figure 5
Ray electronic energy spectrum contains O1s (531.38eV), N1s (399.88eV), C1s in teicoplanin-nanogold
The peak XPS of the elements such as (284.78eV), Cl2p (198.67eV), Au4f (83.41eV).
The verifying of 2 teicoplanins of embodiment-nanogold antibacterial activity
By 103CFU/mL staphylococcus aureus respectively with phosphate buffer (PBS, 0.01M, pH7.4), impersonate drawing
Rather-nanogold (0.2mg/mL), trisodium citrate modification nanogold (citrate-AuNPs) solution (0.2mg/mL),
The mixing of Teicoplanin (0.2mg/mL) solution, is then incubated for 2h under the conditions of 37 DEG C of temperature, 100 μ L is respectively taken to be coated on agar
On plate, 37 DEG C of constant temperature incubations for 24 hours, observe the quantity of bacterium colony on plate.Obtain antibacterial activity comparison diagram as shown in FIG. 6.By
Fig. 6 can be seen that its bactericidal effect of teicoplanin-nanogold is best.
Finally, it is stated that preferred embodiment above is only used to illustrate the technical scheme of the present invention and not to limit it, although logical
It crosses above preferred embodiment the present invention is described in detail, however, those skilled in the art should understand that, can be
Various changes are made to it in form and in details, without departing from claims of the present invention limited range.
Claims (7)
1. the preparation method of teicoplanin functional gold nanoparticles, which comprises the steps of: by teicoplanin, chlorine gold
Acid is mixed into solution with water, adjusts solution ph to 10 ~ 14 with alkali, solution is in brown, is stirred to react 0.5h under the conditions of 20 ~ 25 DEG C
~ it is in for 24 hours claret to solution, dialysis removes unreacted teicoplanin or gold chloride to get the nanometer of teicoplanin functionalization
Gold particle.
2. the preparation method of teicoplanin functional gold nanoparticles according to claim 1, which is characterized in that with sodium hydroxide tune
Solution ph is saved to 12, solution is in brown, and 0.5h is stirred to react under the conditions of 20 ~ 25 DEG C to solution in claret.
3. the preparation method of teicoplanin functional gold nanoparticles according to claim 1, which is characterized in that the dialysis uses
Film is the bag filter of regenerated fiber film, and buffer is ultrapure water.
4. the preparation method of teicoplanin functional gold nanoparticles according to claim 1, which is characterized in that the teicoplanin
The size of the nanogold particle of functionalization increases with the molar ratio of gold chloride and teicoplanin and is increased.
5. the preparation method of teicoplanin functional gold nanoparticles according to claim 1, which is characterized in that gold chloride with impersonate
Peaceful molar ratio 4:1 is drawn, prepared teicoplanin-nanogold is having a size of 11.5 ± 2.7nm.
6. the teicoplanin functional gold nanoparticles of any one preparation method preparation according to claim 1 ~ 5.
7. teicoplanin functional gold nanoparticles described in claim 6 are preparing the application in anti-gram positive bacteria drug.
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|---|---|---|---|
| CN201610488526.8A CN106166292B (en) | 2016-06-28 | 2016-06-28 | Preparation method of teicoplanin functional gold nanoparticles and products thereof and application |
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| CN201610488526.8A CN106166292B (en) | 2016-06-28 | 2016-06-28 | Preparation method of teicoplanin functional gold nanoparticles and products thereof and application |
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| CN106166292A CN106166292A (en) | 2016-11-30 |
| CN106166292B true CN106166292B (en) | 2019-08-06 |
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| CN115178748B (en) * | 2022-09-13 | 2022-12-20 | 中国科学院烟台海岸带研究所 | Method for improving stability of monodisperse gold nanoparticles |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103976958A (en) * | 2014-05-28 | 2014-08-13 | 国家纳米科学中心 | Application of gold nanoparticles in preparing anticoagulants or antiplatelet drugs |
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2016
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103976958A (en) * | 2014-05-28 | 2014-08-13 | 国家纳米科学中心 | Application of gold nanoparticles in preparing anticoagulants or antiplatelet drugs |
Non-Patent Citations (4)
| Title |
|---|
| Antibiotic mediated synthesis of gold nanoparticles with potent antimicrobial;Akhilesh Rai等;《Journal of Materials Chemistry》;20100705;第20卷;第6789–6798页 |
| Dual Recognition Strategy for Specific and Sensitive Detection of Bacteria Using Aptamer-Coated Magnetic Beads and Antibiotic-Capped Gold Nanoclusters;Dan Cheng等;《Analytical Chemistry》;20151207;第88卷(第1期);第820-825页 |
| In Vitro Structural and Functional Evaluation of Gold Nanoparticles Conjugated Antibiotics;Biswarup Saha等;《Nanoscale Research Letters》;20071107;第2卷;第614–622页 |
| Presenting Vancomycin on Nanoparticles to Enhance Antimicrobial Activities;Hongwei Gu等;《Nano Letters》;20030930;第3卷(第9期);第1261-1263页 |
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