CN117431062B - Preparation method and application of green luminous amino acid derivative antibacterial carbon dot - Google Patents
Preparation method and application of green luminous amino acid derivative antibacterial carbon dot Download PDFInfo
- Publication number
- CN117431062B CN117431062B CN202311151142.3A CN202311151142A CN117431062B CN 117431062 B CN117431062 B CN 117431062B CN 202311151142 A CN202311151142 A CN 202311151142A CN 117431062 B CN117431062 B CN 117431062B
- Authority
- CN
- China
- Prior art keywords
- amino acid
- antibacterial
- carbon dot
- aqueous solution
- preparation
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 title claims abstract description 49
- 229910052799 carbon Inorganic materials 0.000 title claims abstract description 49
- 230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 45
- 150000003862 amino acid derivatives Chemical class 0.000 title claims abstract description 19
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims abstract description 25
- 150000001413 amino acids Chemical class 0.000 claims abstract description 22
- 238000010438 heat treatment Methods 0.000 claims abstract description 22
- 239000007864 aqueous solution Substances 0.000 claims abstract description 19
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims abstract description 18
- 239000008103 glucose Substances 0.000 claims abstract description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 17
- 239000008367 deionised water Substances 0.000 claims abstract description 16
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 16
- 238000001816 cooling Methods 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 3
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 239000000243 solution Substances 0.000 claims description 19
- 241000588724 Escherichia coli Species 0.000 claims description 15
- 239000012528 membrane Substances 0.000 claims description 13
- 239000002245 particle Substances 0.000 claims description 13
- 238000001914 filtration Methods 0.000 claims description 11
- 241000894006 Bacteria Species 0.000 claims description 10
- 238000004108 freeze drying Methods 0.000 claims description 10
- 239000002244 precipitate Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 6
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 5
- 239000004472 Lysine Substances 0.000 claims description 5
- 239000004475 Arginine Substances 0.000 claims description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 3
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 3
- 241000192125 Firmicutes Species 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- 241000191967 Staphylococcus aureus Species 0.000 claims description 2
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- 230000001580 bacterial effect Effects 0.000 abstract description 8
- 238000000034 method Methods 0.000 abstract description 5
- 230000000694 effects Effects 0.000 abstract description 3
- 238000001027 hydrothermal synthesis Methods 0.000 abstract description 3
- 230000007246 mechanism Effects 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- 230000002195 synergetic effect Effects 0.000 abstract description 2
- 239000000203 mixture Substances 0.000 abstract 2
- 238000012984 biological imaging Methods 0.000 abstract 1
- 239000002131 composite material Substances 0.000 abstract 1
- 230000005764 inhibitory process Effects 0.000 abstract 1
- 235000001014 amino acid Nutrition 0.000 description 17
- 239000000843 powder Substances 0.000 description 17
- 239000007788 liquid Substances 0.000 description 11
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 230000000845 anti-microbial effect Effects 0.000 description 7
- 238000007605 air drying Methods 0.000 description 6
- 238000005303 weighing Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 229940124350 antibacterial drug Drugs 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000002504 physiological saline solution Substances 0.000 description 4
- 238000007747 plating Methods 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 206010059866 Drug resistance Diseases 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 230000003013 cytotoxicity Effects 0.000 description 3
- 231100000135 cytotoxicity Toxicity 0.000 description 3
- 239000002086 nanomaterial Substances 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 208000035143 Bacterial infection Diseases 0.000 description 2
- 206010034133 Pathogen resistance Diseases 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 230000007812 deficiency Effects 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000003642 reactive oxygen metabolite Substances 0.000 description 2
- 238000004659 sterilization and disinfection Methods 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 108020004414 DNA Proteins 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000032770 biofilm formation Effects 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 210000002421 cell wall Anatomy 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 231100000433 cytotoxic Toxicity 0.000 description 1
- 230000001472 cytotoxic effect Effects 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000007850 fluorescent dye Substances 0.000 description 1
- 238000001215 fluorescent labelling Methods 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 230000002779 inactivation Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 210000004962 mammalian cell Anatomy 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 230000036542 oxidative stress Effects 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- 230000001699 photocatalysis Effects 0.000 description 1
- 238000007146 photocatalysis Methods 0.000 description 1
- 239000003504 photosensitizing agent Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 230000011506 response to oxidative stress Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000035882 stress Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/08—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials
- C09K11/65—Luminescent, e.g. electroluminescent, chemiluminescent materials containing inorganic luminescent materials containing carbon
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
-
- 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
- A61K41/0057—Photodynamic therapy with a photosensitizer, i.e. agent able to produce reactive oxygen species upon exposure to light or radiation, e.g. UV or visible light; photocleavage of nucleic acids with an agent
-
- 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
- A61L2/00—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor
- A61L2/02—Methods or apparatus for disinfecting or sterilising materials or objects other than foodstuffs or contact lenses; Accessories therefor using physical phenomena
- A61L2/08—Radiation
- A61L2/088—Radiation using a photocatalyst or photosensitiser
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C01—INORGANIC CHEMISTRY
- C01B—NON-METALLIC ELEMENTS; COMPOUNDS THEREOF; METALLOIDS OR COMPOUNDS THEREOF NOT COVERED BY SUBCLASS C01C
- C01B32/00—Carbon; Compounds thereof
- C01B32/15—Nano-sized carbon materials
-
- 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
- A61L2101/00—Chemical composition of materials used in disinfecting, sterilising or deodorising
- A61L2101/02—Inorganic materials
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Zoology (AREA)
- Medicinal Chemistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Materials Engineering (AREA)
- Nanotechnology (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Luminescent Compositions (AREA)
Abstract
The invention discloses a preparation method and application of an antibacterial carbon dot derived from green luminescent amino acid, comprising the steps of mixing glucose and positively charged amino acid, dissolving the mixture in deionized water, and uniformly stirring the mixture by ultrasonic waves to prepare a uniformly mixed aqueous solution; heating the uniformly mixed aqueous solution, and cooling to obtain a heat-treated aqueous solution; the method can synthesize the amino acid derivative carbon dots with a multi-effect synergistic antibacterial mechanism by a one-step hydrothermal method to realize the inhibition effect on bacterial growth, and has the advantages of simple preparation process, environment friendliness, high product purity, good fluorescence performance and wide application prospect in the aspects of antibacterial materials, biological imaging, fluorescent composite materials and the like.
Description
Technical Field
The invention belongs to the field of nano materials, and particularly relates to a preparation method and application of an antibacterial carbon dot derived from green luminescent amino acid.
Background
Bacterial infection has been a threat to human life health. It is well known that many bacteria attach to living or non-living solid surfaces to form structured communities, known as "biofilms". Biofilm formation generally allows the aggregation of bacterial colonies, and thus, abuse of antibiotics results in the production of drug resistant bacteria, and overcoming bacterial resistance is one of the more effective antimicrobial strategies. Among them, the antibacterial mechanism for widely researching drug resistance mainly includes electrostatic acting force and oxidation stress reaction, the electrostatic acting force damages cell walls/membranes through electrostatic adsorption, thereby realizing a certain sterilizing effect.
Oxidative stress, also known as photodynamic antibacterial therapy (aPDT), is a promising new therapy for the treatment of bacterial infections, which uses light sources of specific wavelengths to stimulate photosensitizer molecules to generate highly cytotoxic Reactive Oxygen Species (ROS), oxidizing and destroying biological macromolecules such as phospholipids, enzymes, proteins and DNA, leading to the effective inactivation of pathogenic microorganisms, thereby achieving an antibacterial effect.
For any antibacterial material, a major problem in biomedical applications is its cytotoxicity, balancing antibacterial drug activity with biosafety is a major challenge, and thus, there is a need to solve the bacterial resistance and cytotoxicity problems, and recent advances in carbon-based nanomaterials bring new promise for combating infections. Unlike commonly used metal and metal oxide nanoparticles, carbon-based nanomaterials have relatively low side effects on mammalian cells and tissues. The zero-dimensional Carbon Quantum Dots (CQDs) in recent years have the advantages of excellent fluorescence performance, extremely small size, energy conservation, environmental protection, low cytotoxicity, good light stability, excellent biocompatibility and the like. These advantages make CQDs of great potential use in a variety of fields including biosensing, photocatalysis, food detection, bioimaging, fluorescent labeling, and the like.
Currently, CQDs having bactericidal activity are also reported gradually, but their antibacterial effect is poor.
Disclosure of Invention
This section is intended to outline some aspects of embodiments of the application and to briefly introduce some preferred embodiments. Some simplifications or omissions may be made in this section as well as in the description of the application and in the title of the application, which may not be used to limit the scope of the application.
The present invention has been made in view of the above and/or problems occurring in the prior art.
Therefore, the invention aims to overcome the defects in the prior art and provide a preparation method of green luminescent amino acid derivative antibacterial carbon dots.
In order to solve the technical problems, the invention provides the following technical scheme: a preparation method of green luminescent amino acid derivative antibacterial carbon dots, which comprises the following steps,
Mixing glucose and positively charged amino acid, dissolving in deionized water, and stirring uniformly by ultrasonic to obtain a uniformly mixed aqueous solution;
heating the uniformly mixed aqueous solution, and cooling to obtain a heat-treated aqueous solution;
and removing insoluble precipitate and large-particle-size aggregates from the heat-treated aqueous solution through a filtering membrane to obtain a clear carbon dot solution, and freeze-drying to obtain the green luminescent amino acid derivative antibacterial carbon dot.
As a preferred embodiment of the preparation process according to the invention, there is provided: the positively charged amino acids include arginine, lysine, and histidine.
As a preferred embodiment of the preparation process according to the invention, there is provided: the mass ratio of the glucose to the positively charged amino acid is 1g: 1.83-3.88 g.
As a preferred embodiment of the preparation process according to the invention, there is provided: the mass volume ratio of the glucose to the deionized water is 1g: 30-40 mL.
As a preferred embodiment of the preparation process according to the invention, there is provided: the heating treatment, wherein the reaction temperature is 100-220 ℃ and the reaction time is 1-6 h.
As a preferred embodiment of the preparation process according to the invention, there is provided: the cooling includes cooling to room temperature.
As a preferred embodiment of the preparation process according to the invention, there is provided: the specification of the filtering membrane is 0.22um.
It is still another object of the present invention to overcome the deficiencies of the prior art and to provide a product made by a method for preparing green luminescent amino acid derived antimicrobial carbon dots having a particle size of 100 to 300nm.
Another object of the present invention is to overcome the deficiencies of the prior art and to provide an application of an antimicrobial carbon dot in inhibiting gram-positive bacteria, which are staphylococcus aureus, and gram-negative bacteria, which are escherichia coli.
The invention has the beneficial effects that:
(1) According to the invention, glucose and positively charged amino acid are specifically selected as carbon sources to prepare the carbon dots by heating, and the green luminescent amino acid derivative antibacterial carbon dots which can realize the synergistic effect of various antibacterial mechanisms such as electrostatic acting force and oxidative stress reaction can be synthesized by a one-step simple hydrothermal method.
(2) The amino acid derivative has the advantages of good water solubility, stable photochemical performance, antibacterial drug resistance, biosafety and the like, and has wide application prospect in the antibacterial field.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings that are needed in the description of the embodiments will be briefly described below, it being obvious that the drawings in the following description are only some embodiments of the present invention, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art. Wherein:
FIG. 1 is a diagram of green luminescent amino acid derivative antibacterial carbon dots obtained by the invention in green light emission under 365nm ultraviolet light;
FIG. 2 is a graph of the ultraviolet-visible absorption spectrum of the green luminescent amino acid-derived antibacterial carbon dots obtained by the invention;
FIG. 3 is a graph showing the antibacterial effect of the green luminescent amino acid derived antibacterial carbon dots of the invention on S.aureus and E.coli;
FIG. 4 is a MIC plot of the green luminescent amino acid derived antimicrobial carbon dot versus S.aureus and E.coli obtained in accordance with the present invention;
FIG. 5 is a MBC plot of the green luminescent amino acid derived antimicrobial carbon dot versus S.aureus and E.coli obtained in accordance with the present invention.
FIG. 6 is a graph showing the particle size of the antibacterial carbon dots derived from the green luminescent amino acid prepared in example 1 of the present invention.
Detailed Description
In order that the above-recited objects, features and advantages of the present invention will become more apparent, a more particular description of the invention will be rendered by reference to specific embodiments thereof which are illustrated in the appended drawings.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present invention, but the present invention may be practiced in other ways other than those described herein, and persons skilled in the art will readily appreciate that the present invention is not limited to the specific embodiments disclosed below.
Further, reference herein to "one embodiment" or "an embodiment" means that a particular feature, structure, or characteristic can be included in at least one implementation of the invention. The appearances of the phrase "in one embodiment" in various places in the specification are not necessarily all referring to the same embodiment, nor are separate or alternative embodiments mutually exclusive of other embodiments.
Example 1
The preparation method of the green luminescent amino acid derivative antibacterial carbon dot comprises the following steps:
(1) Weighing 1g of glucose and 2.17g of arginine, dissolving in 30ml of deionized water, stirring by ultrasonic waves, pouring the uniformly mixed aqueous solution into a reaction kettle, placing the reaction kettle in a forced air drying oven, heating for 180min, reacting at 160 ℃, stopping heating after full reaction, and naturally cooling to room temperature.
(2) Removing insoluble precipitate and large-particle aggregate from the above liquid by filtering membrane, placing the clear carbon dot solution in a freeze dryer, lyophilizing (freeze drying parameter: temperature-30deg.C, pressure: 8 Pa) to obtain carbon dot powder, and collecting carbon dot powder in refrigerator.
The Arg-CDs prepared as described above had an average particle diameter of 190nm (see FIG. 6), and were green-emitting under irradiation of 365nm ultraviolet lamp, and had a strong ultraviolet absorption peak at 327 nm.
Example 2
The preparation method of the green luminescent amino acid derivative antibacterial carbon dot comprises the following steps:
(1) Weighing 1g of glucose and 1.83g of lysine, dissolving in 30ml of deionized water, stirring by ultrasonic, pouring the uniformly mixed aqueous solution into a reaction kettle, placing the reaction kettle in a forced air drying oven, heating for 180min, reacting at 160 ℃, stopping heating after full reaction, and naturally cooling to room temperature.
(2) Removing insoluble precipitate and large-particle aggregate from the above liquid by filtering membrane, placing the clear carbon dot solution in a freeze dryer, lyophilizing (freeze drying parameter: temperature-30deg.C, pressure: 8 Pa) to obtain carbon dot powder, and collecting carbon dot powder in refrigerator.
The average particle size of the prepared Lys-CDs is 295nm, green light is emitted under the irradiation of a 365nm ultraviolet lamp, and a strong ultraviolet absorption peak exists at 322 nm.
Example 3
The preparation method of the green luminescent amino acid derivative antibacterial carbon dot comprises the following steps:
(1) 1g of glucose and 3.88g of histidine are weighed, dissolved in 30ml of deionized water, stirred by ultrasonic, the evenly mixed aqueous solution is poured into a reaction kettle, and the reaction kettle is placed in a blast drying box for heating for 180min, the reaction temperature is 160 ℃, and after the reaction is fully carried out, the heating is stopped, and the reaction kettle is naturally cooled to room temperature.
(2) Removing insoluble precipitate and large-particle aggregate from the above liquid by filtering membrane, placing the clear carbon dot solution in a freeze dryer, lyophilizing (freeze drying parameter: temperature-30deg.C, pressure: 8 Pa) to obtain carbon dot powder, and collecting carbon dot powder in refrigerator.
The average grain diameter of the His-CDs prepared is 396nm, green light is emitted under 365nm ultraviolet lamp irradiation, and a strong ultraviolet absorption peak exists at 331 nm.
Application example 1
The application example explores the differences of antibacterial activity and antibacterial drug resistance of carbon dots prepared by respectively reacting glucose with different positively charged amino acids, as shown in figures 3 and 4.
Three amino acid derived carbon dots were prepared by the procedure described in examples 1-3.
The specific operation of the antibacterial experiment is as follows:
firstly, weighing 20mg of amino acid derivative carbon dot powder on a balance, adding 20mL of deionized water for dissolution, preparing an amino acid derivative carbon dot solution with the concentration of 1mg/mL, equally dividing into 10 centrifuge tubes, adding deionized water with different volumes according to the set concentration gradient for dilution, setting a blank control tube as deionized water, and shaking for later use.
Secondly, 66 centrifuge tubes are taken, 11 centrifuge tubes are taken as a group, 3 groups are S.aureus experiments, and 3 groups are E.coli experiments.
3200Ul of 0.9% sodium chloride physiological saline was added to the 6 groups of centrifuge tubes, and the centrifuge tubes were covered with a centrifuge cover and placed in an ultra clean bench.
After ultraviolet sterilization is carried out on an ultra-clean bench for 30min, respectively taking two bacterial solutions of original S.aureus and E.coli after being subjected to constant-temperature shake culture for 24 hours at 35 ℃ to dilute to 10 6 cfu/mL, and then sucking 400ul of the two bacterial solutions into a centrifuge tube filled with 0.9% sodium chloride physiological saline, wherein 3 groups of S.aureus and E.coli are respectively arranged.
Finally, adding 400ul of amino acid derivative carbon dot solution with different concentrations into 9 centrifuge tubes of each group respectively, enabling carbon dots contained in each tube to be in a series of decreasing concentrations of 100 ug/mL-0 ug/mL, shaking each tube uniformly, and culturing in a constant temperature shaking machine at 35 ℃ for 24-48 hours.
The turbidity of each test tube was observed with naked eyes, and the lowest concentration capable of inhibiting bacterial growth was recorded as MIC.
Further coating and counting the culture solution with the concentration of the carbon dots before and after the non-growing test tube, observing the growth condition of bacteria on a nutrient agar culture medium, if bacteria grow again, the concentration has only antibacterial effect, if the bacteria grow again, the concentration is considered to have antibacterial effect, and the concentration is recorded as MBC.
The antibacterial activity and antibacterial resistance of the amino acid derivative antibacterial carbon point to S.aureus and E.coli are shown in figures 3 and 4, MIC is used for measuring the antibacterial activity of the antibacterial drug, MBC is used for measuring the resistance of microorganisms to the tested drug, and obviously, the green luminescent amino acid derivative antibacterial carbon point synthesized by the one-step hydrothermal method has good antibacterial activity and antibacterial resistance, and Lys-CDs > His-CDs > Arg-CDs.
Application example 2
The application example explores the antibacterial effect of preparing carbon dots by respectively reacting glucose with different positively charged amino acids. Three amino acid derived carbon dots were prepared by the procedure described in examples 1-3.
The specific operation of the antibacterial experiment is as follows:
first, 4 centrifuge tubes were used as a group, 1 as s.aureus, and 1 as e.coli antimicrobial. 3600ul of 0.9% sodium chloride physiological saline is added into the 2 groups of centrifuge tubes, and then the centrifuge tubes are covered with a centrifuge cover and placed in an ultra clean bench for standby.
Secondly, after ultraviolet sterilization is carried out on an ultra-clean bench and a centrifuge tube filled with 0.9% sodium chloride physiological saline for 30min, 400ul of the original S.aureus and E.coli bacterial liquid which are cultured for 24 hours by a constant temperature shaking machine at 35 ℃ are respectively added into the separated S.aureus and E.coli groups.
Then 0.02g of amino acid derived carbon dots are added so that the concentration of the carbon dots in each tube is the same, each group has a blank control tube without carbon dots, after shaking evenly, the tubes are placed in a constant temperature shaking machine at 35 ℃ for culturing for 18-24 hours. Meanwhile, respectively sucking the original bacterial liquid, carrying out gradient dilution plating at 103-106 cfu/mL, plating the plates in parallel for 2 times, and culturing in a 35 ℃ incubator for 18-24 hours.
The next day, the colony growth conditions are observed to determine that the proper dilution factors are 10 4 cfu/mL, the S.aureus and E.coli groups are subjected to gradient dilution to 10 4 cfu/mL, 40ul of bacteria liquid is respectively taken for plating, the plating is carried out for 2 times in parallel, and the bacterial growth conditions are observed after the bacteria are cultured for 18-24 hours at the constant temperature of 35 ℃.
The antimicrobial effect of the amino acid derived carbon dots prepared by the procedure described in examples 1-3 on S.aureus and E.coli was 80/79, 96/95, 88/90, respectively, according to GB/T21510-2008 test standard.
Comparative example 1
(1) Weighing 1g of glucose and 1g of lysine, dissolving in 30ml of deionized water, stirring by ultrasonic, pouring the uniformly mixed aqueous solution into a reaction kettle, heating in a forced air drying oven for 180min at the reaction temperature of 160 ℃, stopping heating after full reaction, and naturally cooling to room temperature.
(2) Removing insoluble precipitate and large-particle aggregate from the above liquid by filtering membrane, placing the clear carbon dot solution in a freeze dryer, lyophilizing (freeze drying parameter: temperature-30deg.C, pressure: 8 Pa) to obtain carbon dot powder, and collecting carbon dot powder in refrigerator.
Comparative example 2
(1) Weighing 1g of glucose and 2.2g of lysine, dissolving in 30ml of deionized water, stirring by ultrasonic, pouring the uniformly mixed aqueous solution into a reaction kettle, placing the reaction kettle in a forced air drying oven, heating for 180min, reacting at 160 ℃, stopping heating after full reaction, and naturally cooling to room temperature.
(2) Removing insoluble precipitate and large-particle aggregate from the above liquid by filtering membrane, placing the clear carbon dot solution in a freeze dryer, lyophilizing (freeze drying parameter: temperature-30deg.C, pressure: 8 Pa) to obtain carbon dot powder, and collecting carbon dot powder in refrigerator.
Comparative example 3
(1) 1G of glucose and 1.83g of tryptophan are weighed, dissolved in 30ml of deionized water, stirred by ultrasonic, the evenly mixed aqueous solution is poured into a reaction kettle, and the reaction kettle is placed in a forced air drying oven for heating for 180min, the reaction temperature is 160 ℃, and after the reaction is fully carried out, the heating is stopped, and the reaction kettle is naturally cooled to room temperature.
(2) Removing insoluble precipitate and large-particle aggregate from the above liquid by filtering membrane, placing the clear carbon dot solution in a freeze dryer, lyophilizing (freeze drying parameter: temperature-30deg.C, pressure: 8 Pa) to obtain carbon dot powder, and collecting carbon dot powder in refrigerator.
Comparative example 4
(1) 1G of glucose and 1.83g of glutamic acid are weighed, dissolved in 30ml of deionized water, stirred by ultrasonic, the evenly mixed aqueous solution is poured into a reaction kettle, and the reaction kettle is placed in a blast drying box for heating for 180min, the reaction temperature is 160 ℃, and after the reaction is fully carried out, the heating is stopped, and the reaction kettle is naturally cooled to room temperature.
(2) Removing insoluble precipitate and large-particle aggregate from the above liquid by filtering membrane, placing the clear carbon dot solution in a freeze dryer, lyophilizing (freeze drying parameter: temperature-30deg.C, pressure: 8 Pa) to obtain carbon dot powder, and collecting carbon dot powder in refrigerator.
Comparative example 5
(1) Weighing 1g of glucose and 1.83g of cysteine, dissolving in 30ml of deionized water, stirring by ultrasonic, pouring the uniformly mixed aqueous solution into a reaction kettle, placing the reaction kettle in a forced air drying oven, heating for 180min, reacting at 160 ℃, stopping heating after full reaction, and naturally cooling to room temperature.
(2) Removing insoluble precipitate and large-particle aggregate from the above liquid by filtering membrane, placing the clear carbon dot solution in a freeze dryer, lyophilizing (freeze drying parameter: temperature-30deg.C, pressure: 8 Pa) to obtain carbon dot powder, and collecting carbon dot powder in refrigerator.
Antibacterial effects on s.aureus and e.coli, see table 1.
TABLE 1
It should be noted that the above embodiments are only for illustrating the technical solution of the present invention and not for limiting the same, and although the present invention has been described in detail with reference to the preferred embodiments, it should be understood by those skilled in the art that the technical solution of the present invention may be modified or substituted without departing from the spirit and scope of the technical solution of the present invention, and it should be covered in the scope of the present invention.
Claims (8)
1. A preparation method of a green luminescent amino acid derivative antibacterial carbon dot is characterized by comprising the following steps of: comprising the steps of (a) a step of,
Mixing glucose and positively charged amino acid, dissolving in deionized water, and stirring uniformly by ultrasonic to obtain a uniformly mixed aqueous solution;
heating the uniformly mixed aqueous solution, and cooling to obtain a heat-treated aqueous solution;
Removing insoluble precipitate and large-particle-size aggregates from the heat-treated aqueous solution through a filter membrane to obtain a clear carbon dot solution, and freeze-drying to obtain the green luminescent amino acid derivative antibacterial carbon dot;
Wherein the positively charged amino acid is any one of arginine, lysine and histidine.
2. The method of manufacturing according to claim 1, wherein: the mass ratio of the glucose to the positively charged amino acid is 1g: 1.83-3.88 g.
3. The method of manufacturing as claimed in claim 2, wherein: the mass volume ratio of the glucose to the deionized water is 1g: 30-40 mL.
4. The method of manufacturing according to claim 1, wherein: the heating treatment is carried out, wherein the reaction temperature is 100-220 ℃, and the reaction time is 1-6 h.
5. The method of manufacturing according to claim 1, wherein: the cooling includes cooling to room temperature.
6. The method of manufacturing according to claim 1, wherein: the specification of the filtering membrane is 0.22um.
7. An antibacterial carbon dot prepared by the preparation method according to any one of claims 1 to 6, characterized in that: the particle size of the antibacterial carbon dots is 100-300 nm.
8. Use of the antibacterial carbon dot according to claim 7 for the preparation of an antibacterial agent against gram-positive and gram-negative bacteria, characterized in that: the gram-positive bacteria are staphylococcus aureus, and the gram-negative bacteria are escherichia coli.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311151142.3A CN117431062B (en) | 2023-09-07 | 2023-09-07 | Preparation method and application of green luminous amino acid derivative antibacterial carbon dot |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311151142.3A CN117431062B (en) | 2023-09-07 | 2023-09-07 | Preparation method and application of green luminous amino acid derivative antibacterial carbon dot |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN117431062A CN117431062A (en) | 2024-01-23 |
| CN117431062B true CN117431062B (en) | 2024-05-10 |
Family
ID=89546981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311151142.3A Active CN117431062B (en) | 2023-09-07 | 2023-09-07 | Preparation method and application of green luminous amino acid derivative antibacterial carbon dot |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117431062B (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103342347A (en) * | 2013-05-09 | 2013-10-09 | 江苏大学 | Preparation method of carbon quantum dots with high fluorescence property |
| CN103693633A (en) * | 2013-12-04 | 2014-04-02 | 上海交通大学 | Method for green synthesis of fluorescent chiral carbon dots |
| CN104987863A (en) * | 2015-06-25 | 2015-10-21 | 西安交通大学 | Nitrogen, phosphorus and sulphur doping or co-doping carbon dot and batch controllable preparing method and application thereof |
| CN112494517A (en) * | 2020-12-15 | 2021-03-16 | 中南民族大学 | Fluorescent antibacterial carbon dot, and preparation method and application thereof |
| CN115477299A (en) * | 2022-10-20 | 2022-12-16 | 中南民族大学 | Chiral antibacterial carbon dot, and preparation method and application thereof |
| CN115849347A (en) * | 2023-01-19 | 2023-03-28 | 四川大学 | Preparation method and application of arginine antibacterial carbon dots |
-
2023
- 2023-09-07 CN CN202311151142.3A patent/CN117431062B/en active Active
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103342347A (en) * | 2013-05-09 | 2013-10-09 | 江苏大学 | Preparation method of carbon quantum dots with high fluorescence property |
| CN103693633A (en) * | 2013-12-04 | 2014-04-02 | 上海交通大学 | Method for green synthesis of fluorescent chiral carbon dots |
| CN104987863A (en) * | 2015-06-25 | 2015-10-21 | 西安交通大学 | Nitrogen, phosphorus and sulphur doping or co-doping carbon dot and batch controllable preparing method and application thereof |
| CN112494517A (en) * | 2020-12-15 | 2021-03-16 | 中南民族大学 | Fluorescent antibacterial carbon dot, and preparation method and application thereof |
| CN115477299A (en) * | 2022-10-20 | 2022-12-16 | 中南民族大学 | Chiral antibacterial carbon dot, and preparation method and application thereof |
| CN115849347A (en) * | 2023-01-19 | 2023-03-28 | 四川大学 | Preparation method and application of arginine antibacterial carbon dots |
Non-Patent Citations (2)
| Title |
|---|
| Carbon quantum dots derived from lysine and arginine simultaneously scavenge bacteria and promote tissue repair;Peili Li，et al.;《Applied Materials Today》;20200210;第19卷;100601 * |
| Multimechanism Collaborative Superior Antioxidant CDzymes To Alleviate Salt Stress-Induced Oxidative Damage in Plant Growth;Jiawen Gong，et al.;《ACS Sustainable Chem. Eng.》;20230227;第11卷;4237-4247 * |
Also Published As
| Publication number | Publication date |
|---|---|
| CN117431062A (en) | 2024-01-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Ding et al. | Visible light responsive CuS/protonated g-C3N4 heterostructure for rapid sterilization | |
| Wang et al. | Antibacterial fluorescent nano-sized lanthanum-doped carbon quantum dot embedded polyvinyl alcohol for accelerated wound healing | |
| CN105819433B (en) | Chiral graphene quantum dot, preparation method and application | |
| CN114392388A (en) | Hydrogel composition and application thereof | |
| CN106377433B (en) | A kind of antibiotic property tooth root canal filling material and preparation method thereof | |
| Abalaka et al. | The antibacterial efficacy of gold nanoparticles derived from Gomphrena celosioides and Prunus amygdalus (Almond) leaves on selected bacterial pathogens | |
| CN113025318B (en) | Carbon quantum dot using pepper as carbon source and preparation method and application thereof | |
| WO2022183811A1 (en) | Photocatalytic nano-enzyme with catalase-like activity, and preparation method therefor and use thereof | |
| CN117431062B (en) | Preparation method and application of green luminous amino acid derivative antibacterial carbon dot | |
| CN115849347A (en) | Preparation method and application of arginine antibacterial carbon dots | |
| CN115735912A (en) | Morphology-controllable preparation method of rhamnolipid/fullerene composite material and antibacterial application thereof | |
| CN111514308B (en) | PH-induced charge-inversion antibacterial gold nanorod and preparation method and application thereof | |
| RU2474471C2 (en) | Colloidal solution of silver nanoparticles, metal-polymer nanocomposite film material, methods for production thereof, bactericidal composition based on colloidal solution and bactericidal film made from metal-polymer material | |
| CN111875669B (en) | Theanine polypeptide copper cluster, preparation method thereof and application of theanine polypeptide copper cluster as antibacterial agent | |
| CN114891346B (en) | Polylysine compound based on molybdenum polyacid and application thereof in antibacterial field | |
| Wang et al. | Antibacterial properties of the flower shaped nano-CuFe2O4@ MoS2 composites | |
| CN115744878B (en) | Fluorescent coffee grounds carbon quantum dot and preparation method and application thereof | |
| LU504864B1 (en) | Water-soluble curcumin compound with antibacterial ability, and preparation method and application thereof | |
| Liu et al. | Photothermal-triggered release of alkyl radicals hydrogel via versatile carbon dots chelating Ag+ and its synergistic anti-bacterial and biofilm activities | |
| Zhang et al. | Constructing a highly efficient multifunctional carbon quantum dot platform for the treatment of infectious wounds | |
| Hussein et al. | Biosynthesis of Zinc Oxide nanoparticles by Lantana camara flowers extract characterization and their antibacterial potential against pathogenic bacteria isolated from wounds infections | |
| CN118206706B (en) | Antibacterial material for realizing sterilization by utilizing and improving infection microenvironment and preparation method and application thereof | |
| Zhu et al. | Silent Raman imaging of highly effective anti-bacterial activity synchronous with biofilm breakage using poly (4-cyanostyrene)@ silver@ polylysine nanocomposites | |
| CN113577274B (en) | Antibacterial material based on nano-silver and photodynamic therapy and preparation method and application thereof | |
| CN114949207B (en) | Low-toxicity zinc-doped carbon dot and application thereof |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant |