CN116003368A - Catechin nanosphere reversible self-assembly material, preparation method and biological application thereof - Google Patents
Catechin nanosphere reversible self-assembly material, preparation method and biological application thereof Download PDFInfo
- Publication number
- CN116003368A CN116003368A CN202211646067.3A CN202211646067A CN116003368A CN 116003368 A CN116003368 A CN 116003368A CN 202211646067 A CN202211646067 A CN 202211646067A CN 116003368 A CN116003368 A CN 116003368A
- Authority
- CN
- China
- Prior art keywords
- catechin
- self
- assembled
- nanosphere
- assembly
- 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.)
- Pending
Links
- ADRVNXBAWSRFAJ-UHFFFAOYSA-N catechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3ccc(O)c(O)c3 ADRVNXBAWSRFAJ-UHFFFAOYSA-N 0.000 title claims abstract description 95
- 235000005487 catechin Nutrition 0.000 title claims abstract description 95
- 229950001002 cianidanol Drugs 0.000 title claims abstract description 95
- 239000002077 nanosphere Substances 0.000 title claims abstract description 87
- PFTAWBLQPZVEMU-DZGCQCFKSA-N (+)-catechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-DZGCQCFKSA-N 0.000 title claims abstract description 83
- 238000001338 self-assembly Methods 0.000 title claims abstract description 53
- 230000002441 reversible effect Effects 0.000 title claims abstract description 41
- 239000000463 material Substances 0.000 title claims abstract description 38
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- 239000007864 aqueous solution Substances 0.000 claims abstract description 48
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 239000002086 nanomaterial Substances 0.000 claims abstract description 32
- 229910052751 metal Inorganic materials 0.000 claims abstract description 24
- 239000002184 metal Substances 0.000 claims abstract description 24
- -1 catechin compound Chemical class 0.000 claims abstract description 19
- 150000001765 catechin Chemical class 0.000 claims abstract description 9
- 244000052616 bacterial pathogen Species 0.000 claims abstract description 6
- 230000002147 killing effect Effects 0.000 claims abstract description 6
- 239000003242 anti bacterial agent Substances 0.000 claims abstract description 5
- WMBWREPUVVBILR-WIYYLYMNSA-N (-)-Epigallocatechin-3-o-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=C(O)C=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-WIYYLYMNSA-N 0.000 claims description 103
- WMBWREPUVVBILR-UHFFFAOYSA-N GCG Natural products C=1C(O)=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 WMBWREPUVVBILR-UHFFFAOYSA-N 0.000 claims description 103
- 229940030275 epigallocatechin gallate Drugs 0.000 claims description 103
- 239000000243 solution Substances 0.000 claims description 44
- XMOCLSLCDHWDHP-IUODEOHRSA-N epi-Gallocatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-IUODEOHRSA-N 0.000 claims description 16
- 241000588724 Escherichia coli Species 0.000 claims description 14
- 150000001768 cations Chemical class 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 10
- PFTAWBLQPZVEMU-ZFWWWQNUSA-N (+)-epicatechin Natural products C1([C@@H]2OC3=CC(O)=CC(O)=C3C[C@@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-ZFWWWQNUSA-N 0.000 claims description 8
- PFTAWBLQPZVEMU-UKRRQHHQSA-N (-)-epicatechin Chemical compound C1([C@H]2OC3=CC(O)=CC(O)=C3C[C@H]2O)=CC=C(O)C(O)=C1 PFTAWBLQPZVEMU-UKRRQHHQSA-N 0.000 claims description 8
- LSHVYAFMTMFKBA-TZIWHRDSSA-N (-)-epicatechin-3-O-gallate Chemical compound O([C@@H]1CC2=C(O)C=C(C=C2O[C@@H]1C=1C=C(O)C(O)=CC=1)O)C(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-TZIWHRDSSA-N 0.000 claims description 8
- LSHVYAFMTMFKBA-UHFFFAOYSA-N ECG Natural products C=1C=C(O)C(O)=CC=1C1OC2=CC(O)=CC(O)=C2CC1OC(=O)C1=CC(O)=C(O)C(O)=C1 LSHVYAFMTMFKBA-UHFFFAOYSA-N 0.000 claims description 8
- XMOCLSLCDHWDHP-UHFFFAOYSA-N L-Epigallocatechin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C1=CC(O)=C(O)C(O)=C1 XMOCLSLCDHWDHP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- LPTRNLNOHUVQMS-UHFFFAOYSA-N epicatechin Natural products Cc1cc(O)cc2OC(C(O)Cc12)c1ccc(O)c(O)c1 LPTRNLNOHUVQMS-UHFFFAOYSA-N 0.000 claims description 8
- 235000012734 epicatechin Nutrition 0.000 claims description 8
- DZYNKLUGCOSVKS-UHFFFAOYSA-N epigallocatechin Natural products OC1Cc2cc(O)cc(O)c2OC1c3cc(O)c(O)c(O)c3 DZYNKLUGCOSVKS-UHFFFAOYSA-N 0.000 claims description 8
- 241000191967 Staphylococcus aureus Species 0.000 claims description 5
- 230000001105 regulatory effect Effects 0.000 claims description 4
- 239000003814 drug Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 150000003057 platinum Chemical class 0.000 claims description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002505 iron Chemical class 0.000 claims 1
- 229910052752 metalloid Inorganic materials 0.000 claims 1
- 150000002738 metalloids Chemical class 0.000 claims 1
- 229910021645 metal ion Inorganic materials 0.000 abstract description 8
- 230000002378 acidificating effect Effects 0.000 abstract description 6
- 231100000419 toxicity Toxicity 0.000 abstract description 6
- 230000001988 toxicity Effects 0.000 abstract description 6
- 230000002779 inactivation Effects 0.000 abstract description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 39
- 210000004027 cell Anatomy 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000000862 absorption spectrum Methods 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 238000010521 absorption reaction Methods 0.000 description 10
- 230000004083 survival effect Effects 0.000 description 10
- 239000010931 gold Substances 0.000 description 9
- 235000013824 polyphenols Nutrition 0.000 description 9
- 238000000108 ultra-filtration Methods 0.000 description 9
- 238000000746 purification Methods 0.000 description 7
- 238000002835 absorbance Methods 0.000 description 6
- 230000004071 biological effect Effects 0.000 description 6
- 230000008859 change Effects 0.000 description 6
- 229910052709 silver Inorganic materials 0.000 description 6
- 239000004332 silver Substances 0.000 description 6
- 241001122767 Theaceae Species 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 206010058467 Lung neoplasm malignant Diseases 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229910052737 gold Inorganic materials 0.000 description 4
- 230000003993 interaction Effects 0.000 description 4
- 201000005202 lung cancer Diseases 0.000 description 4
- 208000020816 lung neoplasm Diseases 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229910021642 ultra pure water Inorganic materials 0.000 description 4
- 239000012498 ultrapure water Substances 0.000 description 4
- 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 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 238000002189 fluorescence spectrum Methods 0.000 description 3
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 3
- 239000002082 metal nanoparticle Substances 0.000 description 3
- 229960003085 meticillin Drugs 0.000 description 3
- 231100000956 nontoxicity Toxicity 0.000 description 3
- 150000008442 polyphenolic compounds Chemical class 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000035899 viability Effects 0.000 description 3
- 101710134784 Agnoprotein Proteins 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000000026 X-ray photoelectron spectrum Methods 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- 230000003385 bacteriostatic effect Effects 0.000 description 2
- 229910002091 carbon monoxide Inorganic materials 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000000338 in vitro Methods 0.000 description 2
- 238000001095 inductively coupled plasma mass spectrometry Methods 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 239000007769 metal material Substances 0.000 description 2
- 238000001000 micrograph Methods 0.000 description 2
- 239000002105 nanoparticle Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000012679 serum free medium Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000012224 working solution Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- IPMYMEWFZKHGAX-UHFFFAOYSA-N Isotheaflavin Natural products OC1CC2=C(O)C=C(O)C=C2OC1C(C1=C2)=CC(O)=C(O)C1=C(O)C(=O)C=C2C1C(O)CC2=C(O)C=C(O)C=C2O1 IPMYMEWFZKHGAX-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- UXRMWRBWCAGDQB-UHFFFAOYSA-N Theaflavin Natural products C1=CC(C2C(CC3=C(O)C=C(O)C=C3O2)O)=C(O)C(=O)C2=C1C(C1OC3=CC(O)=CC(O)=C3CC1O)=CC(O)=C2O UXRMWRBWCAGDQB-UHFFFAOYSA-N 0.000 description 1
- 238000004833 X-ray photoelectron spectroscopy Methods 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 229940098773 bovine serum albumin Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004403 catechin group Chemical group 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 210000002308 embryonic cell Anatomy 0.000 description 1
- 210000002889 endothelial cell Anatomy 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000002272 high-resolution X-ray photoelectron spectroscopy Methods 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 230000000670 limiting effect Effects 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000014620 theaflavin Nutrition 0.000 description 1
- IPMYMEWFZKHGAX-ZKSIBHASSA-N theaflavin Chemical compound C1=C2C([C@H]3OC4=CC(O)=CC(O)=C4C[C@H]3O)=CC(O)=C(O)C2=C(O)C(=O)C=C1[C@@H]1[C@H](O)CC2=C(O)C=C(O)C=C2O1 IPMYMEWFZKHGAX-ZKSIBHASSA-N 0.000 description 1
- 229940026509 theaflavin Drugs 0.000 description 1
- 235000008118 thearubigins Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- 210000003606 umbilical vein Anatomy 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- 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
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention provides a catechin nanosphere reversible self-assembly material, a preparation method and biological application thereof: adding alkaline aqueous solution into aqueous solution of catechin compound, adjusting pH to 8-9, and performing self-assembly reaction to obtain the catechin nanosphere reversible self-assembly material. And provides catechin self-assembled metal nano-materials constructed based on catechin nano-spheres reversible self-assembled materials and application thereof in preparing antibacterial agents for killing pathogenic bacteria. The invention develops the reversible self-assembly material of the catechin nanospheres for the first time, and the material has steady state property under alkaline condition, can be stored for a long time without inactivation, can be disassembled under acidic condition, and releases catechin compounds. Catechin self-assembled metal nano material reduces the toxicity of metal ions and can have high-efficiency killing power on pathogenic bacteria under the condition of safe dosage.
Description
Technical Field
The invention relates to a catechin nanosphere reversible self-assembly material, a preparation method and biological application thereof.
Background
The natural catechin monomers in tea mainly comprise epigallocatechin gallate (EGCG), epigallocatechin (EGC), epicatechin (EC), epicatechin gallate (ECG) and other components, and have good physiological activities of resisting tumor, resisting bacteria, resisting inflammation, preventing diabetes and cardiovascular diseases. However, the compound has a plurality of phenolic hydroxyl structures, is easily influenced by oxygen, pH and other environments in vitro to cause structural change, and is easily subjected to complex reaction with protein, metal ions and the like in vivo to cause activity change, so that the compound has low bioavailability in organisms and greatly limits the biological application.
Disclosure of Invention
In order to solve the technical problems, the invention develops a reversible self-assembly material of catechin nanospheres, catechin monomers are self-assembled to form stable nanospheres under alkaline conditions, and are disassembled and assembled under acidic conditions, so that the nanospheres have good biological safety and stability, and the catechin monomers are disassembled and assembled to become catechin monomers under weak acidic conditions, so that the biological activity is recovered, the bioavailability of catechin can be improved, and the biological application field of catechin is greatly expanded.
The technical scheme adopted by the invention is as follows:
a reversible self-assembly material of catechin nanospheres is prepared by adjusting the pH of aqueous solution of catechin compounds to 8-9 and performing self-assembly reaction.
The invention also provides a preparation method of the catechin nanosphere reversible self-assembly material, which comprises the following steps: adding alkaline aqueous solution into aqueous solution of catechin compound, adjusting pH to 8-9, and performing self-assembly reaction to obtain the catechin nanosphere reversible self-assembly material.
The catechin compound is one or more of epigallocatechin gallate (EGCG), epigallocatechin (EGC), epicatechin (EC) and epicatechin gallate (ECG), preferably EGCG.
In the aqueous solution of the catechin compound, the concentration of the catechin compound is preferably 0.1-1000 mmol/L, preferably 0.1-10 mmol/L; more preferably 1 to 5mmol/L.
The alkaline aqueous solution is typically an aqueous solution of NaOH, KOH, etc. that ionizes OH.
The concentration of the aqueous alkaline solution is generally 0.1 to 5M.
In the preparation method, after the pH of the aqueous solution of the catechin compound is regulated to 8-9, self-assembly reaction is carried out, the solution changes color, and the catechin nanosphere reversible self-assembly material is prepared from colorless to colored.
The color of the solution is changed from colorless to colored and is generally changed into pale yellow to yellowish-brown, the color is influenced by the pH value, the higher the pH value is, the darker the color is, the pale yellow is formed when the pH value is 7-8, the yellowish-brown is formed when the pH value is 8-9, and the reddish brown is formed when the pH value is more than 10. In addition, the concentration of the catechin compound increases, and the color of the solution also increases. However, the change of color from colorless to colored was very remarkable, and the occurrence of the change of color indicates the progress of the self-assembly reaction.
The principle of the self-assembly reaction is as follows: under alkaline condition, catechin compounds form supermolecule nanospheres through hydrogen bond, pi-pi interaction and the like between benzene ring structures and phenolic hydroxyl groups.
The self-assembly reaction is preferably carried out with stirring.
The catechin nanospheres reversible self-assembly material is a colored uniform solution, self-assembled nanoparticles are dispersed in a solvent, can be stably stored for more than half a year, cannot undergo solid-liquid separation, and have no obvious change in physical and chemical properties and biological activity.
Or freeze-drying the solution of the reversible self-assembly material of the catechin nanospheres to prepare solid dry powder.
The invention also provides application of the catechin nanosphere reversible self-assembly material in disassembly and assembly reaction, and the application method comprises the following steps: the pH value of the catechin nanosphere reversible self-assembly material is regulated to be less than 7.0, and the catechin nanosphere reversible self-assembly material undergoes a disassembly assembly reaction and is changed into a colorless aqueous solution of catechin compounds.
In the disassembly reaction, the color of the solution is changed from colored to colorless.
In the disassembly reaction, the pH is generally adjusted to less than 7.0 by the addition of acid.
The acid used is generally 0.1 to 5M hydrochloric acid, sulfuric acid, etc.
The invention also provides application of the catechin nanosphere reversible self-assembly material in steady state preservation under alkaline condition and release of catechin compounds by assembly reaction under acidic environment.
Furthermore, the invention also provides a catechin self-assembled metal-like nanomaterial constructed based on the catechin nanosphere reversible self-assembled material, wherein the catechin self-assembled metal-like nanomaterial is prepared by the following steps:
adding alkaline aqueous solution into aqueous solution of catechin compound, adjusting pH to 8-9, performing self-assembly reaction, changing the color of the solution from colorless to colored to obtain catechin nanosphere reversible self-assembly material, adding metal cation aqueous solution, and deepening the color of the reaction solution to obtain catechin self-assembly metal nanomaterial.
The metal cation aqueous solution is an aqueous solution of water-soluble silver salt, water-soluble ferric salt, water-soluble magnesium salt, water-soluble platinum salt or chloroauric acid. Preferably an aqueous solution of silver nitrate, chloroauric acid or ferric nitrate.
The ratio of the catechin compound to the metal cation in the metal cation aqueous solution is 1:0.5-2.
The reaction system is preferably stirred at room temperature, typically at a stirring rate of 500-1000rpm/min.
The catechin self-assembled metal-like nano material can be prepared within a few seconds after the metal cation aqueous solution is added. The color of the reaction liquid is deepened, and the catechin self-assembled metal-like nano material is prepared.
In the invention, catechin compounds self-assemble to form catechin nanospheres under alkaline conditions, after metal cations are added, strong polyphenol-metal interaction occurs, and phenolic hydroxyl groups reduce metal ions to form metal nano particles under alkaline conditions, so that catechin self-assembled metal nano materials are obtained.
The catechin self-assembled metal-like nanomaterial is further purified to obtain a purified catechin self-assembled metal-like nanomaterial, and the purification method comprises the following steps: firstly, performing centrifugal ultrafiltration by using an ultrafiltration tube (Millipore) with the molecular weight cutoff of 50KD, repeating for 2-3 times, removing nano metals with larger particles, and collecting outer tube liquid; and then, performing centrifugal ultrafiltration by using an ultrafiltration tube with a molecular retention of 10KD, repeating for 2-3 times, removing unreacted catechin compounds and metal cations, and finally collecting inner tube liquid to obtain the purified catechin self-assembled metal nano material.
The purified catechin self-assembled metal-like nano material is a uniform solution, the color is darker when the concentration is high, and the color of the solution becomes lighter after the concentration is diluted, so that the catechin self-assembled metal-like nano material is a uniform transparent solution. The metal nano particles are dispersed in water, can be stably stored for more than half a year, can not generate solid-liquid separation, and has no obvious change in physical and chemical properties and biological activity.
Or freeze drying the solution containing catechin self-assembled nanometer metal material to obtain solid dry powder.
And (3) carrying out ultraviolet absorption detection on the outer tube supernatant in the subsequent centrifugal ultrafiltration until no ultraviolet absorption peak exists, which represents complete purification.
The invention also provides application of the catechin self-assembled metal nano material in preparing an antibacterial agent for killing pathogenic bacteria, and further can be used for preparing an antibacterial agent for killing drug-resistant staphylococcus aureus or escherichia coli.
The invention has the technical effects that:
1. the invention provides a reversible self-assembly material of catechin nanospheres, which has steady state property under alkaline condition, can be stored for a long time without inactivation, and can be disassembled under acidic condition to release catechin compounds.
2. The catechin nanosphere reversible self-assembly material can be synthesized with metal ions to obtain the catechin self-assembly metal-like nanomaterial, so that the toxicity of the metal ions is reduced, the catechin nanosphere reversible self-assembly material has good biological safety, and can be used for killing pathogenic bacteria with high efficiency under a safe dosage. The catechin self-assembled metal-like nano material can release metal ions under the weak acid microenvironment of an infection part, and can be used for sterilizing cooperatively with catechin.
3. The catechin self-assembly metal-like nano material is constructed based on the reversible self-assembly property of catechin, and has simple synthesis and mild condition. The synthesis is carried out in one step in a few seconds in the aqueous solution at normal temperature and normal pressure, is environment-friendly, does not generate toxic and harmful waste gas and waste liquid, and can be produced in large scale.
4. Catechin structural instability has been a technical barrier and scientific challenge limiting its application in the life-health field. The reversible self-assembly strategy of catechin designed by the invention creatively solves the problem of instability of catechin in vitro, and can be assembled to release catechin under specific environment, and the reversible self-assembly and disassembly reaction is the first development of the invention, provides a basis for development and application of catechin functional products, and provides a new direction for utilization of 4700 mu (data cut-off 2020) tea resources in China.
Drawings
FIG. 1 is a photograph of a reaction solution for reversible self-assembly of EGCG to produce nanospheres and unassembled nanospheres.
FIG. 2 is a graph showing the ultraviolet absorption spectrum of EGCG, EGCG nanospheres (pH 8) and EGCG solution after nanospheres are assembled (pH 6.5).
FIG. 3 is a graph showing fluorescence spectra of EGCG, EGCG nanospheres (pH 8) and EGCG solutions after nanospheres are assembled (pH 6.5).
Fig. 4 is a high resolution mass spectrum of EGCG, EGCG nanospheres and nanospheres after assembly.
Fig. 5 is a graph of EGCG self-assembled nanosphere biological transmission electron microscopy.
Fig. 6 is a bar graph of bacterial viability of aqueous EGCG, EGCG nanospheres and nanosphere disassembled solutions treated with methicillin-resistant staphylococcus aureus MRSA at a concentration of 10 μm, respectively.
FIG. 7 is a bar graph of survival of human lung cancer A549 cells treated with aqueous EGCG solutions of different concentrations, EGCG nanospheres and solutions after nanosphere reassembly.
Fig. 8 is a schematic diagram of the reaction principle of catechin self-assembled metal nanomaterial.
Fig. 9 is a transmission electron microscope image of EGCG self-assembled nanosilver.
Fig. 10 is an ultraviolet absorption spectrum of EGCG and EGCG nanosilver.
FIG. 11 is a high resolution XPS spectrum of Ag in EGCG self-assembled nanosilver.
Fig. 12 is a graph of MRSA and e.coli growth after treatment with EGCG self-assembled nanosilver at different concentrations.
Fig. 13 is a photograph of the turbidity appearance of MRSA and e.coli after 8h treatment with EGCG self-assembled nanosilver at different concentrations.
Fig. 14 is a safety evaluation chart of EGCG self-assembled nano silver, and fig. 14, a graph a is a histogram of survival rate of HUVEC cells from EGCG self-assembled nano silver at different concentrations; panel B is a histogram of survival rates of self-assembled nano silver at different concentrations for NIH-3T3 cells; panel C is a bar graph of viability of different concentrations of silver ions versus HUVEC cells.
FIG. 15 is a photograph and ultraviolet absorption spectrum of ECG-Au, ECG-Ag, EC-Au, EC-Ag, EGC-Au and EGC-Ag self-assembled nanomaterial, wherein graph A is a photograph of appearance of ECG-Au, ECG-Ag, EC-Au, EC-Ag, EGC-Au and EGC-Ag self-assembled nanomaterial, and graphs B-D are corresponding ultraviolet absorption spectrum.
Detailed Description
The invention is further described in connection with the following specific embodiments, in which numerous specific details are set forth in order to provide a thorough understanding of the invention, but the scope of the invention is not limited to the specific embodiments disclosed below.
EXAMPLE 1 reversible self-Assembly Properties of catechin nanospheres
2mL of 2mM EGCG aqueous solution is added with a stirrer to be stirred at normal temperature (rotating speed: 1000 rpm), then 10 mu L of 0.5M NaOH aqueous solution is dripped, the pH value is regulated to 8, and the solution immediately turns into pale yellow, thus obtaining the EGCG self-assembled nanospheres.
As shown in fig. 1, the EGCG aqueous solution (1) before the reaction is colorless and transparent, and when an alkaline solution is added, ph=8 (i.e., pH > 7), it becomes a pale yellow homogeneous solution, as shown in solution (2) in fig. 1, to obtain the EGCG self-assembled nanospheres.
And (3) dropwise adding a hydrochloric acid solution with the concentration of 0.5M into the 2mLEGCG self-assembled nanospheres, adjusting the pH value to be 6.5, and changing the EGCG nanospheres into a colorless EGCG aqueous solution after assembly, as shown in a solution (3) in fig. 1.
The colorless aqueous catechin monomer solution (1) changes color under alkaline conditions, the pH8 becomes a pale yellow uniform solution (2), the conventional idea is that the pale yellow solution may be oxidized into theaflavin or thearubigin, and the process is irreversible, but the applicant finds that the pale yellow solution becomes colorless transparent solution (3) after adding the acidic solution for the first time.
The ultraviolet absorption spectrum of the EGCG aqueous solution, the EGCG nanospheres (pH 8) and the nanospheres after assembly (pH 6.5) become the EGCG solution, and the result is shown as a figure 2, and shows that the EGCG aqueous solution has characteristic absorption peaks at 275nm, and new absorption peaks after the EGCG self-assembled nanospheres appear at 288 and 325 nm. When the nanospheres are assembled, the absorption peak position is changed back to 275nm, namely the EGCG absorption peak position.
The fluorescence spectrum chart of the EGCG aqueous solution, the EGCG nanospheres (pH 8) and the EGCG solution changed into the EGCG solution after the nanospheres are disassembled (pH 6.5) is shown as figure 3, and figure 3 shows that the EGCG nanospheres have blue fluorescence characteristic, the emission wavelength is 402nm, and no obvious fluorescence peak exists after the EGCG and the nanospheres are disassembled. Secondly, the high-resolution mass spectrum also proves that the mass spectrum peak after the assembly of the nanospheres is consistent with the mass spectrum peak of the EGCG, namely, the self-assembly of the EGCG is changed into the EGCG after the assembly (figure 4).
Therefore, various characterization data of ultraviolet absorption spectrum, fluorescence spectrum and high-resolution mass spectrum prove that the solution (3) is the EGCG aqueous solution which is changed after EGCG nanosphere assembly.
The EGCG self-assembled nanosphere biological transmission electron microscope image is shown in figure 5, which proves that the solution (2) is nanospheres with the size of 50-80nm and good steady state property.
At present, experiments record that the longest storage time is half a year of refrigeration (4 ℃), and the physicochemical properties and the biological activities of the EGCG self-assembled nanospheres are not obviously changed within half a year.
The above results demonstrate that EGCG has the property of reversible self-assembly into nanospheres.
Incubating EGCG aqueous solution, EGCG self-assembled nanospheres solution with methicillin-resistant staphylococcus aureus (MRSA) in 96-well plates with final concentration of 10 μm, wherein C represents blank control group, and incubating for about 8h to OD of blank control group 600 After reaching around 1, incubation was stopped and absorbance (OD) of the bacterial suspension at 600nm was measured with a microplate reader 600 ) And evaluating the bacteriostatic activity of different materials on MRSA according to the absorbance.
The bar graph of bacterial survival rate of EGCG aqueous solution with concentration of 10 mu M, EGCG nanospheres and solution after nanosphere disassembly on MRSA is shown in figure 6, the survival rate of MRSA is only 52.1% after the EGCG aqueous solution with concentration of 10 mu M is incubated with MRSA for 8 hours, the EGCG nanospheres with concentration have no toxicity on MRSA, and the survival rate of MRSA is only 55.7% after nanosphere disassembly under weak acid condition.
It can be seen that EGCG nanospheres with a concentration of 10. Mu.M have no biological activity, and that EGCG aqueous solution and nanosphere assembly can resist MRSA growth after EGCG is changed into EGCG.
Human lung cancer A549 cells were inoculated into 96-well plates and cultured in 1640 medium (Hyclone) containing 10% bovine serum albumin for 24h at 37℃at 5% CO 2 . Then the culture medium is removed, and EGCG aqueous solution with the final concentration of 10, 50 and 100 mu M, EGCG nanospheres and solution after nanosphere disassembly are respectively added for 24 hours of culture. After 24 hours, the cells were washed three times with serum-free medium, then added with CCK-8 working solution, cultured in a cell incubator for 20 minutes, and absorbance at 450nm was measured using a microplate reader. The survival rate of the control group without any material was defined as 100%.
As shown in FIG. 7, the survival rate bar graph of human lung cancer A549 cells treated by the EGCG aqueous solution with different concentrations, EGCG nanospheres and the solution after the nanospheres are disassembled is shown, the toxicity to human lung cancer A549 cells is larger and larger along with the increase of the EGCG concentration (10-100 mu M), but the EGCG nanospheres have no toxicity, and the anti-tumor activity is recovered after the assembly is changed into EGCG under the weak acidic condition. The above results all prove that the EGCG self-assembled nanospheres have good biological safety, and the biological activity is recovered after the EGCG self-assembled nanospheres are disassembled under the weak acid condition.
Example 2 rapid preparation, purification and characterization of catechin self-assembled nanosilver
The reaction principle of the catechin self-assembled metal nano material is shown in figure 8, and the catechin forms supermolecule nanospheres through hydrogen bond and pi-pi interaction between benzene ring structures and phenolic hydroxyl groups under alkaline conditions. Then adding metal ions to generate strong polyphenol-metal interaction, and reducing the metal ions by phenolic hydroxyl groups under alkaline conditions to form metal nano particles, thus obtaining the catechin self-assembled metal-like nano material.
Preparing 2mL of 2mM EGCG aqueous solution, adding a stirrer into a reaction vial, stirring at normal temperature (rotating speed: 1000 rpm), then dripping 24 mu L of 1M NaOH aqueous solution, immediately turning the solution into light yellow to obtain EGCG self-assembled nanospheres, and then dripping 100 mu L of 25mM AgNO 3 The aqueous solution is continuously stirred, the reaction solution is immediately blackened, and the EGCG self-assembled nano silver is obtained, and the whole reaction process only takes a few seconds. Purifying EGCG nano silver obtained by the reaction, firstly purifying by an ultrafiltration tube with a molecular weight cutoff of 50KD, centrifuging at 8000rpm for 10min, adding ultrapure water into an inner tube, continuously centrifuging for 3 times, removing nano silver with larger particles, and collecting outer tube liquid; and secondly, placing the outer tube liquid into an ultrafiltration tube with the molecular weight cut-off of 10KD for continuous purification, centrifuging at 8000rpm for 10min, adding ultrapure water for continuous purification during the period, removing unreacted EGCG and silver ions, and finally collecting the inner tube liquid to obtain purified EGCG self-assembled nano silver which can be stably stored for a long time at 4 ℃. The silver element concentration was measured by inductively coupled plasma mass spectrometry (ICP-MS) and the yield was calculated to be 80.64%.
As shown in a transmission electron microscope graph 9 of the EGCG self-assembled nano silver, the EGCG self-assembled nano silver is uniformly distributed on an ultrathin carbon film, has good dispersity and has a particle size of about 3.5 nm.
The ultraviolet absorption spectrum of EGCG and EGCG nano silver is shown in figure 10, and compared with the absorption peak (275 nm) of EGCG, the EGCG self-assembled nano silver has obvious absorption peak at 406 nm.
The high-resolution XPS spectrum of Ag in EGCG self-assembled nano silver is shown in figure 11. The generation of Ag-O chemical bonds can be observed from high-resolution X-ray photoelectron spectroscopy (XPS), and the effect of phenolic hydroxyl groups on EGCG and Ag is proved to form nano particles.
Example 3 antibacterial Effect of EGCG self-assembled nanosilver on methicillin-resistant Staphylococcus aureus (MRSA) and Escherichia coli (E.coli)
EGCG self-assembled nano silver (0, 10,20,30 and 40 mu M, diluted and prepared by LB culture medium) with different concentrations is respectively incubated with MRSA and E.coli in a 96-well plate, then absorbance of the MRSA and the E.coli at 600nm is monitored by an enzyme-labeled instrument, and bacteriostatic activity of the EGCG nano silver on the MRSA and the E.coli is evaluated according to the absorbance.
The graph of MRSA and E.coli growth after treatment with self-assembled nano silver at different concentrations of EGCG is shown in FIG. 12, and it can be seen that EGCG nano silver can significantly inhibit MRSA and E.coli growth and has obvious concentration dependence.
The apparent photographs of the turbidity of MRSA and E.coli after 8h treatment with EGCG self-assembled nano silver with different concentrations are shown in FIG. 13, and the turbidity of MRSA and E.coli is also reduced along with the increase of EGCG nano silver concentration, which indicates that the toxicity is bigger and bigger.
Example 4 safety evaluation of EGCG self-assembled nanosilver
To evaluate the biosafety of EGCG nanosilver against human normal cells, mouse embryonic cells (NIH-3T 3) and Human Umbilical Vein Endothelial Cells (HUVEC) were selected as subjects and cell viability was determined using the cell counting kit (CCK-8). First 2X 10 4 The NIH-3T3 and HUVEC cells were seeded into 96-well plates at 37℃and 5% CO, respectively 2 Culturing for 24h under the condition, and then adding EGCG self-assembled nano silver with different concentrations0,10,20,30, 40 μm) for 24h, 6 replicates per group. After 24 hours, the cells were washed three times with serum-free medium, then added with CCK-8 working solution, cultured in a cell incubator for 20 minutes, and absorbance at 450nm was measured using a microplate reader.
The safety evaluation chart of the EGCG self-assembled nano silver is shown in fig. 14, and the A chart is a histogram of survival rate of the EGCG self-assembled nano silver with different concentrations to HUVEC cells; panel B is a histogram of survival rates of self-assembled nano silver at different concentrations for NIH-3T3 cells; panel C is a bar graph of viability of different concentrations of silver ions versus HUVEC cells.
It can be seen that EGCG self-assembled nano silver has no toxicity to NIH-3T3 and HUVEC cells even under the condition of high concentration (40 mu M), and MRSA and E.coli bacteria are all dead under the condition of the concentration, which proves that EGCG nano silver has good biological safety and can kill pathogenic bacteria with high efficiency under the safety dosage. In addition, 20 μm of silver ions had generated significant toxicity to HUVEC cells (shown in panel C of fig. 14), further demonstrating that EGCG reduced ag+ toxicity after self-assembly of nano silver, improving biosafety.
EXAMPLE 5 Synthesis of other catechin reversible self-assembled Metal nanomaterials
Preparing 2mL of catechin (ECG, EC, EGC) aqueous solution with concentration of 2mM in a reaction vial, adding a stirrer, stirring at normal temperature (rotating speed: 1000 rpm), then dropwise adding 24 mu L of 1M NaOH aqueous solution, immediately turning the solution into light yellow to obtain different self-assembled tea polyphenol nanospheres, and then dropwise adding 160 mu L of HAuCl with concentration of 25mM 4 Or AgNO 3 The aqueous solution is continuously stirred, and the reaction solution is immediately blackened, namely the ECG-Au, ECG-Ag, EC-Au, EC-Ag, EGC-Au and EGC-Ag self-assembled nano metal materials are respectively obtained (as shown in figure 15A), and the whole synthesis process only needs a few seconds. Purifying the tea polyphenol nano silver or gold obtained by the reaction, firstly purifying by an ultrafiltration tube with the molecular weight cut-off of 50KD, centrifuging at 8000rpm for 10min, adding ultrapure water into an inner tube, continuously centrifuging, repeating for 3 times, removing nano silver or gold particles with larger particle size, and collecting outer tube liquid; secondly, adding the outer tube liquid into an ultrafiltration tube with the molecular weight cut-off of 10KD for continuous purification, and centrifuging at 8000rpm for 10minAdding ultrapure water for continuous purification for several times, removing unreacted EGCG and silver ions or gold ions, and finally collecting inner tube liquid to obtain the purified tea polyphenol self-assembled nano silver or gold. The photographs and ultraviolet absorption spectra of ECG-Au, ECG-Ag, EC-Au, EC-Ag, EGC-Au, and EGC-Ag self-assembled nanomaterial are shown in FIG. 15, wherein the A-plot is a photograph of the appearance of the ECG-Au, ECG-Ag, EC-Au, EC-Ag, EGC-Au, and EGC-Ag self-assembled nanomaterial, the B-plot is a ultraviolet absorption spectrum of ECG-Au, ECG-Ag, and ECG, the C-plot is a ultraviolet absorption spectrum of EC-Au, EC-Ag, and EC, and the D-plot is a ultraviolet absorption spectrum of EGC-Au, EGC-Ag, and EGC.
The ultraviolet absorption spectrum also demonstrates that the corresponding nanosilver and nanogold materials have specific absorption peaks compared to the catechin absorption peaks such as ECG, EC, EGC (see FIGS. 15B-D).
Claims (10)
1. A preparation method of a catechin nanosphere reversible self-assembly material is characterized by comprising the following steps: adding alkaline aqueous solution into aqueous solution of catechin compound, adjusting pH to 8-9, and performing self-assembly reaction to obtain the catechin nanosphere reversible self-assembly material.
2. The method for preparing the catechin nanosphere reversible self-assembly material as claimed in claim 1, wherein the catechin compound is one or more of epigallocatechin gallate, epigallocatechin, epicatechin and epicatechin gallate.
3. The method for preparing the catechin nanosphere reversible self-assembly material according to claim 1, wherein in the method, after the pH of an aqueous solution of catechin compounds is adjusted to 8-9, self-assembly reaction occurs, the solution changes color from colorless to colored, and the catechin nanosphere reversible self-assembly material is prepared.
4. The catechin nanospheres prepared by the method of claims 1-3 are reversible self-assembled materials.
5. The application of the reversible self-assembly material of catechin nanospheres for carrying out disassembly reaction as claimed in claim 4, wherein the application method is as follows: the pH value of the catechin nanosphere reversible self-assembly material is regulated to be less than 7.0, and the catechin nanosphere reversible self-assembly material undergoes a disassembly assembly reaction and is changed into a colorless aqueous solution of catechin compounds.
6. A catechin self-assembled metal-like nanomaterial constructed based on the catechin nanosphere reversible self-assembled material as claimed in claim 4, wherein the catechin self-assembled metal-like nanomaterial is prepared by the following method:
adding alkaline aqueous solution into aqueous solution of catechin compound, adjusting pH to 8-9, performing self-assembly reaction, changing the color of the solution from colorless to colored to obtain catechin nanosphere reversible self-assembly material, adding metal cation aqueous solution, and deepening the color of the reaction solution to obtain catechin self-assembly metal nanomaterial.
7. The catechin self-assembled metal-like nanomaterial of claim 6, wherein the aqueous metal cation solution is an aqueous solution of a water-soluble silver salt, a water-soluble iron salt, a water-soluble magnesium salt, a water-soluble platinum salt, or chloroauric acid.
8. The catechin self-assembled metal-like nanomaterial of claim 6, wherein the ratio of the amounts of the catechin compound to the metal cation in the metal cation aqueous solution is 1:0.5-2.
9. Use of a catechin self-assembled metalloid nanomaterial according to any one of claims 6 to 8 in the preparation of an antibacterial agent for killing pathogenic bacteria.
10. The use according to claim 9, characterized in that said catechin self-assembled metal-like nanomaterial is used for the preparation of an antibacterial agent against drug-resistant staphylococcus aureus or escherichia coli.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211646067.3A CN116003368A (en) | 2022-12-21 | 2022-12-21 | Catechin nanosphere reversible self-assembly material, preparation method and biological application thereof |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211646067.3A CN116003368A (en) | 2022-12-21 | 2022-12-21 | Catechin nanosphere reversible self-assembly material, preparation method and biological application thereof |
Publications (1)
Publication Number | Publication Date |
---|---|
CN116003368A true CN116003368A (en) | 2023-04-25 |
Family
ID=86029071
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202211646067.3A Pending CN116003368A (en) | 2022-12-21 | 2022-12-21 | Catechin nanosphere reversible self-assembly material, preparation method and biological application thereof |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN116003368A (en) |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100021989A1 (en) * | 2008-07-28 | 2010-01-28 | Steve Baugh | Compositions and methods of controlling and administering redox specific forms of drugs, foods and dietary supplements |
US20130190515A1 (en) * | 2012-01-20 | 2013-07-25 | Gold Nano Tech Inc. | Physical Nano-complexes for Preventing and Treating Cancer and Method for Manufacturing the Same |
CN103820492A (en) * | 2013-10-29 | 2014-05-28 | 王深明 | Functional nano catechin gene-introduction material and preparation method thereof |
CN113577101A (en) * | 2020-04-30 | 2021-11-02 | 四川大学 | Tea polyphenol-metal nanoparticles, drug-loaded nanoparticles, preparation method and application thereof |
CN116173006A (en) * | 2021-11-29 | 2023-05-30 | 中南大学 | Polyphenol self-polymerization nano-particle and preparation method and application thereof |
-
2022
- 2022-12-21 CN CN202211646067.3A patent/CN116003368A/en active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20100021989A1 (en) * | 2008-07-28 | 2010-01-28 | Steve Baugh | Compositions and methods of controlling and administering redox specific forms of drugs, foods and dietary supplements |
US20130190515A1 (en) * | 2012-01-20 | 2013-07-25 | Gold Nano Tech Inc. | Physical Nano-complexes for Preventing and Treating Cancer and Method for Manufacturing the Same |
CN103820492A (en) * | 2013-10-29 | 2014-05-28 | 王深明 | Functional nano catechin gene-introduction material and preparation method thereof |
CN113577101A (en) * | 2020-04-30 | 2021-11-02 | 四川大学 | Tea polyphenol-metal nanoparticles, drug-loaded nanoparticles, preparation method and application thereof |
CN116173006A (en) * | 2021-11-29 | 2023-05-30 | 中南大学 | Polyphenol self-polymerization nano-particle and preparation method and application thereof |
Non-Patent Citations (3)
Title |
---|
XIAOYAN SUN等: "A phenolic based tumor-permeated nanoframework for immunogenic cell death induction combined with PD-L1 immune checkpoint blockade", BIOMATER. SCI., no. 10, 31 October 2022 (2022-10-31), pages 3808 * |
俞蓉欣等: "儿茶素生物医用纳米材料研究进展", 茶叶科学, vol. 42, no. 4, 31 August 2022 (2022-08-31), pages 447 - 462 * |
邢雅艳: "植物儿茶素复合纳米材料的制备及应用研究", 东北林业大学硕士学位论文, 31 December 2021 (2021-12-31) * |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Wang et al. | Insights into rapid photodynamic inactivation mechanism of Staphylococcus aureus via rational design of multifunctional nitrogen-rich carbon-coated bismuth/cobalt nanoparticles | |
Zhang et al. | Synthesis of lanthanum doped carbon dots for detection of mercury ion, multi-color imaging of cells and tissue, and bacteriostasis | |
Basavegowda et al. | Phyto-synthesis of gold nanoparticles using fruit extract of Hovenia dulcis and their biological activities | |
de Faria et al. | Eco-friendly decoration of graphene oxide with biogenic silver nanoparticles: antibacterial and antibiofilm activity | |
Yang et al. | Carbon‐Dot‐Decorated TiO2 Nanotubes toward Photodynamic Therapy Based on Water‐Splitting Mechanism | |
Mosaiab et al. | Recyclable and stable silver deposited magnetic nanoparticles with poly (vinyl pyrrolidone)-catechol coated iron oxide for antimicrobial activity | |
CN110787186B (en) | Ga3+PDA (personal digital Assistant) targeted synergistic antibacterial nano material as well as preparation and application thereof | |
CN107926979A (en) | The application of a kind of preparation method and the carbon dots of argentiferous carbon dots on antiseptic is prepared | |
Zhang et al. | Superior antibacterial activity of Fe 3 O 4@ copper (ii) metal–organic framework core–shell magnetic microspheres | |
Meng et al. | pH-responsive curcumin-based nanoscale ZIF-8 combining chemophotodynamic therapy for excellent antibacterial activity | |
Vandhana et al. | Biogenic synthesis of Mn-Ag co-doped FeO (Fe1-2xMnxAgx) nanoparticles: As an effective disinfectant and anticancer agent | |
Durán et al. | Biotechnological routes to metallic nanoparticles production: mechanistic aspects, antimicrobial activity, toxicity and industrial applications | |
Li et al. | Cytocompatible amphipathic carbon quantum dots as potent membrane-active antibacterial agents with low drug resistance and effective inhibition of biofilm formation | |
Kuang et al. | Biomimetic FeCo@ PDA nanozyme platform with Fenton catalytic activity as efficient antibacterial agent | |
Nikmah et al. | Excellent antimicrobial activity of Fe3O4/SiO2/Ag nanocomposites | |
Wang et al. | Bacteria-triggered radical anions amplifier of pillar [5] arene/perylene diimide nanosheets with highly selective antibacterial activity | |
Sathiyaseelan et al. | Biosynthesis of gallic acid fabricated tellurium nanoparticles (GA-Te NPs) for enhanced antibacterial, antioxidant, and cytotoxicity applications | |
Yu et al. | Preparation of Ag nanoparticle dispersed silk fibroin compact | |
CN113305299A (en) | Method for green preparation of silver nanoparticles by cooperation of hesperidin and pectin and application of silver nanoparticles | |
CN116003368A (en) | Catechin nanosphere reversible self-assembly material, preparation method and biological application thereof | |
CN111134133B (en) | Bio-based antibacterial and antiviral nano material and preparation method and application thereof | |
Long et al. | Preparation and Antimicrobial Activity of Antibacterial Silver-Loaded Polyphosphazene Microspheres | |
CN113384606A (en) | Preparation method and application of melanin-nano silver | |
Liu et al. | Synthesis, antibacterial activity and action mechanism of silver-based nanomaterials with thermosensitive polymer-decorated graphene oxide as a stable support | |
Sindhu et al. | Gold nanoparticles as antimicrobial agents: A mini-review |
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 |