CN115177539A - Preparation method of water-soluble fullerene nano solution - Google Patents
Preparation method of water-soluble fullerene nano solution Download PDFInfo
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- CN115177539A CN115177539A CN202210934926.2A CN202210934926A CN115177539A CN 115177539 A CN115177539 A CN 115177539A CN 202210934926 A CN202210934926 A CN 202210934926A CN 115177539 A CN115177539 A CN 115177539A
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- fullerene
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- soluble
- ball mill
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- XMWRBQBLMFGWIX-UHFFFAOYSA-N C60 fullerene Chemical compound C12=C3C(C4=C56)=C7C8=C5C5=C9C%10=C6C6=C4C1=C1C4=C6C6=C%10C%10=C9C9=C%11C5=C8C5=C8C7=C3C3=C7C2=C1C1=C2C4=C6C4=C%10C6=C9C9=C%11C5=C5C8=C3C3=C7C1=C1C2=C4C6=C2C9=C5C3=C12 XMWRBQBLMFGWIX-UHFFFAOYSA-N 0.000 title claims abstract description 126
- 229910003472 fullerene Inorganic materials 0.000 title claims abstract description 79
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 238000000227 grinding Methods 0.000 claims abstract description 61
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 30
- 239000001116 FEMA 4028 Substances 0.000 claims abstract description 26
- 229960004853 betadex Drugs 0.000 claims abstract description 26
- 239000012528 membrane Substances 0.000 claims abstract description 19
- 238000001914 filtration Methods 0.000 claims abstract description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims abstract description 17
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 claims abstract description 17
- 229920000053 polysorbate 80 Polymers 0.000 claims abstract description 17
- 239000000203 mixture Substances 0.000 claims abstract description 13
- 238000000498 ball milling Methods 0.000 claims abstract description 5
- 238000002156 mixing Methods 0.000 claims abstract description 4
- 239000000463 material Substances 0.000 claims description 22
- 239000004094 surface-active agent Substances 0.000 claims description 16
- 238000005303 weighing Methods 0.000 claims description 16
- 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 description 9
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 claims description 9
- 239000008103 glucose Substances 0.000 claims description 9
- 239000008101 lactose Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 229920001983 poloxamer Polymers 0.000 claims description 7
- RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 claims description 6
- 229960000502 poloxamer Drugs 0.000 claims description 6
- ODLHGICHYURWBS-LKONHMLTSA-N trappsol cyclo Chemical compound CC(O)COC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](COCC(C)O)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)COCC(O)C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1COCC(C)O ODLHGICHYURWBS-LKONHMLTSA-N 0.000 claims description 6
- JLPULHDHAOZNQI-ZTIMHPMXSA-N 1-hexadecanoyl-2-(9Z,12Z-octadecadienoyl)-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCC\C=C/C\C=C/CCCCC JLPULHDHAOZNQI-ZTIMHPMXSA-N 0.000 claims description 5
- 229940083466 soybean lecithin Drugs 0.000 claims description 5
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 claims description 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 2
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 claims description 2
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 claims description 2
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 2
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 2
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 2
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 2
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 claims description 2
- 229940097362 cyclodextrins Drugs 0.000 claims description 2
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 2
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 2
- 235000010445 lecithin Nutrition 0.000 claims description 2
- 239000000787 lecithin Substances 0.000 claims description 2
- 229940067606 lecithin Drugs 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 35
- 239000002245 particle Substances 0.000 description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000012071 phase Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 239000002537 cosmetic Substances 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000003814 drug Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 238000001514 detection method Methods 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000013558 reference substance Substances 0.000 description 4
- 238000005063 solubilization Methods 0.000 description 4
- 230000007928 solubilization Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 3
- 230000032683 aging Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 229910002804 graphite Inorganic materials 0.000 description 2
- 239000010439 graphite Substances 0.000 description 2
- 238000009776 industrial production Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 230000002000 scavenging effect Effects 0.000 description 2
- 238000012216 screening Methods 0.000 description 2
- 241001556567 Acanthamoeba polyphaga mimivirus Species 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- ATLMFJTZZPOKLC-UHFFFAOYSA-N C70 fullerene Chemical compound C12=C(C3=C4C5=C67)C8=C9C%10=C%11C%12=C%13C(C%14=C%15C%16=%17)=C%18C%19=C%20C%21=C%22C%23=C%24C%21=C%21C(C=%25%26)=C%20C%18=C%12C%26=C%10C8=C4C=%25C%21=C5C%24=C6C(C4=C56)=C%23C5=C5C%22=C%19C%14=C5C=%17C6=C5C6=C4C7=C3C1=C6C1=C5C%16=C3C%15=C%13C%11=C4C9=C2C1=C34 ATLMFJTZZPOKLC-UHFFFAOYSA-N 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 208000018737 Parkinson disease Diseases 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical class N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000002635 aromatic organic solvent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000007760 free radical scavenging Effects 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 229940023490 ophthalmic product Drugs 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005070 sampling Methods 0.000 description 1
- 230000003381 solubilizing effect Effects 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/19—Cosmetics or similar toiletry preparations characterised by the composition containing inorganic ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K33/00—Medicinal preparations containing inorganic active ingredients
- A61K33/44—Elemental carbon, e.g. charcoal, carbon black
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/26—Carbohydrates, e.g. sugar alcohols, amino sugars, nucleic acids, mono-, di- or oligo-saccharides; Derivatives thereof, e.g. polysorbates, sorbitan fatty acid esters or glycyrrhizin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/49—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds
- A61K8/4993—Derivatives containing from 2 to 10 oxyalkylene groups
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/18—Antioxidants, e.g. antiradicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B02—CRUSHING, PULVERISING, OR DISINTEGRATING; PREPARATORY TREATMENT OF GRAIN FOR MILLING
- B02C—CRUSHING, PULVERISING, OR DISINTEGRATING IN GENERAL; MILLING GRAIN
- B02C17/00—Disintegrating by tumbling mills, i.e. mills having a container charged with the material to be disintegrated with or without special disintegrating members such as pebbles or balls
- B02C17/10—Disintegrating by tumbling mills, i.e. mills having a container charged with the material to be disintegrated with or without special disintegrating members such as pebbles or balls with one or a few disintegrating members arranged in the container
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B02—CRUSHING, PULVERISING, OR DISINTEGRATING; PREPARATORY TREATMENT OF GRAIN FOR MILLING
- B02C—CRUSHING, PULVERISING, OR DISINTEGRATING IN GENERAL; MILLING GRAIN
- B02C23/00—Auxiliary methods or auxiliary devices or accessories specially adapted for crushing or disintegrating not provided for in preceding groups or not specially adapted to apparatus covered by a single preceding group
- B02C23/06—Selection or use of additives to aid disintegrating
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y40/00—Manufacture or treatment of nanostructures
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B82—NANOTECHNOLOGY
- B82Y—SPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
- B82Y5/00—Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/41—Particular ingredients further characterized by their size
- A61K2800/413—Nanosized, i.e. having sizes below 100 nm
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/52—Stabilizers
- A61K2800/522—Antioxidants; Radical scavengers
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/80—Process related aspects concerning the preparation of the cosmetic composition or the storage or application thereof
- A61K2800/805—Corresponding aspects not provided for by any of codes A61K2800/81 - A61K2800/95
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nanotechnology (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Molecular Biology (AREA)
- Birds (AREA)
- Food Science & Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
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- Gerontology & Geriatric Medicine (AREA)
- General Engineering & Computer Science (AREA)
- Medical Informatics (AREA)
- Biophysics (AREA)
- Toxicology (AREA)
- Physics & Mathematics (AREA)
- Condensed Matter Physics & Semiconductors (AREA)
- General Physics & Mathematics (AREA)
- Manufacturing & Machinery (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Carbon And Carbon Compounds (AREA)
Abstract
The invention relates to a preparation method of a water-soluble fullerene nano solution, which comprises the following steps: mixing fullerene C60 and sulfobutyl-beta-cyclodextrin, putting the mixture into an agate ball milling tank, adding grinding balls into a planetary ball mill, grinding the mixture, dissolving the mixture by using a Tween 80 solution, and filtering the mixture by using a water-phase filter membrane to obtain a water-soluble fullerene nano solution.
Description
Technical Field
The invention belongs to the field of medicines and cosmetics, and particularly relates to a preparation method of a water-soluble fullerene nano solution.
Technical Field
Fullerene (Fullerene) is the third allotrope found in elemental carbon, in addition to diamond and graphite. In 1985, kroto et al, university of Rice, USA, found for the first time in laser vaporization graphite experiments that clusters containing 60 carbon atoms are named C60 and clusters containing 70 carbon atoms are named C70, both C60 and C70 have cage structures and can be regarded as three-dimensional aromatic compounds in physical and chemical properties, and the molecular stereo configuration belongs to point group symmetry of D5 h. For example, 20 regular hexagons and 12 regular pentagons in C60 form a spherical structure with a total of 60 vertices, each occupied by 60 carbon atoms, and they are confirmed to belong to a third allotrope of carbon, named Fullerene (Fullerene). Fullerene C60 has thirty conjugated double bonds, and its unique molecular structure makes it have effects of resisting oxidation, resisting aging, scavenging free radicals, etc., and is an excellent raw material for cosmetics. Research also finds that the fullerene has the effects of resisting tumors, treating Alzheimer's disease, treating Parkinson's disease, reducing blood fat, dissolving vascular plaque and the like, and the fullerene can be developed into a medicament.
The fullerene is used as a cosmetic raw material, and the fullerene can have better effects of resisting oxidation, resisting aging, scavenging free radicals and the like only by being prepared into the water-soluble nano solution. The particular molecular structure of fullerenes is manifested in its unique physicochemical properties, such as solubility: is insoluble in water and most of organic solvents, and only dissolves in part of aromatic organic solvents. Therefore, the preparation of the fullerene into the water-soluble nano solution has certain technical challenges, and the method for preparing the water-soluble nano solution by adding the surfactant for solubilization after the fullerene is subjected to ball milling is not reported in documents.
Disclosure of Invention
The invention aims to provide a preparation method of a water-soluble fullerene nano solution, which has the advantages of simple preparation process, convenient operation and the like and is suitable for industrial production in the future.
The technical route exploration idea of the invention is as follows:
fullerene is an allotrope of carbon, is a simple substance of carbon consisting of more than 60 carbon atoms, is insoluble in water, is insoluble in most organic solvents, is soluble only in partial aromatic hydrocarbon solvents, and has certain technical challenges for the water-soluble nano solution. According to the powder engineering and physical and chemical principles and referring to the preparation methods of some nano-drugs, when fullerene is ground to the particle size of less than 1 μm by a ball mill, the fullerene can be dissolved into a transparent aqueous solution of dozens of nanometers through the solubilization of a surfactant, and the Tyndall effect is weakened. The fullerene nano-particles adsorb a layer of surfactant on the surface of the aqueous solution, so that the stability is improved. The fullerene material is sticky and difficult to grind when being independently ground by the ball mill, grinding auxiliary materials are added according to a certain proportion, so that the grinding is facilitated, the grinding efficiency and the grinding effect are obviously improved, and the method is suitable for industrial production.
The preparation method of the water-soluble fullerene nano solution comprises the following steps:
(1) Mixing fullerene and auxiliary grinding aids, putting the mixture into a ball milling tank, adding grinding balls, and grinding in a planetary ball mill;
(2) Dissolving the ground material with surfactant solution, and filtering with 0.22 μm water phase filter membrane to obtain water soluble fullerene nanometer solution.
Wherein, the fullerene in the step (1) is C60 or C70, and a mixture of C60 and C70.
Wherein, the weight ratio of the fullerene to the grinding aid auxiliary material in the step (1) is 1; preferably 1:5.
wherein the grinding aid auxiliary materials in the step (1) are alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin, water-soluble derivatives of the cyclodextrins, and water-soluble auxiliary materials such as glucose, lactose, maltose and the like. Preferably, the grinding aid auxiliary material is sulfobutyl-beta-cyclodextrin.
Wherein, the surfactant in the step (2) is Tween 80, poloxamer, lecithin and the like. Preferably, the surfactant is tween 80.
Most preferably, the preparation method of the water-soluble fullerene nano solution comprises the following steps:
weighing 1.00g of fullerene C60 and 5g of sulfobutyl-beta-cyclodextrin, putting the fullerene C60 and 5g of sulfobutyl-beta-cyclodextrin into an agate ball mill, adding grinding balls, grinding for 3 hours in a planetary ball mill, dissolving the fullerene C60 and the sulfobutyl-beta-cyclodextrin by using 250ml of 0.2% Tween 80, filtering by using a 0.22 mu m water-phase filter membrane to obtain a water-soluble fullerene nano solution, and detecting that the content of the fullerene C60 is 3.92mg/ml and the average particle size is 42nm.
In order to detect the fullerene content and the particle size in the water-soluble nano solution, the invention provides a detection method, which comprises the following detection processes:
1. required instruments and equipment
Shimadzu liquid chromatograph, model: LC-2030C 3D; a mettler-tollido XP205DR type electronic balance; malvern laser particle sizer Mastersizer 3000; an Aikepu AML-0502-M type pure water preparation machine; KQ-250DB type ultrasonic degasser.
2. Required reagent
Fullerene C60 reference substance (the content is more than or equal to 99.9 percent, purchased from Sigma, batch number is 210316); fullerene C70 reference substance (content is more than or equal to 99.9%, purchased from Sigma, lot number 210428); toluene (chromatographically pure, batch No. 210902, denko chemical reagents, inc., tianjin); acetonitrile (chromatographically pure, batch No. 210907, mimi European Chemicals Co., tianjin, ltd.); the water is ultrapure water, and is self-made.
3. Preparation of test article
Preparation of a reference substance: accurately weighing C60 and C70 reference substances respectively, and dissolving toluene to obtain a solution with a concentration of 0.2mg/ml;
sample preparation: precisely sucking 0.5ml of water-soluble fullerene nano solution, precisely adding 2.5ml of saturated ammonium sulfate solution, uniformly mixing, and adding 3ml of toluene for extraction.
4. Detection of
A chromatographic column: a Saimei flying ODS-C18 chromatographic column; 4.6mm 250mm;5 mu m;
mobile phase: toluene: acetonitrile = 7;
detection wavelength: 325nm;
column temperature: at 30 ℃.
Compared with the existing preparation method, the invention has the following beneficial effects:
(1) The prepared water-soluble fullerene nano solution has small particle size below 100 nm, can completely pass through a 0.22-micron filter membrane, can be used as a cosmetic raw material, and can also be developed as a pharmaceutical preparation, such as fullerene nano oral liquid, fullerene nano injection and the like.
(2) The grinding aid auxiliary materials and the surfactant are in pharmaceutical grade and cosmetic grade, and the safety is fully ensured.
(3) The prepared water-soluble fullerene nano solution has the advantages of high fullerene solubility, small particle size, uniform particle size distribution, good stability and the like.
(4) The water-soluble fullerene nano solution has small particle size, is developed as a pharmaceutical preparation, is easy to be absorbed by a human body and has high bioavailability; the product can be used as cosmetic raw material, and has strong antioxidant, antiaging, and free radical scavenging effects.
Detailed Description
The present invention is further illustrated by the following specific examples, which are not intended to be limiting of the invention.
Example 1
Weighing 1.00g of fullerene C60 and 5g of sulfobutyl-beta-cyclodextrin, putting the fullerene C60 and 5g of sulfobutyl-beta-cyclodextrin into an agate ball mill, adding grinding balls, grinding for 3 hours in a planetary ball mill, dissolving the fullerene C60 and the sulfobutyl-beta-cyclodextrin by using 250ml of 0.2% Tween 80, filtering by using a 0.22 mu m water-phase filter membrane to obtain a water-soluble fullerene nano solution, and detecting that the content of the fullerene C60 is 3.92mg/ml and the average particle size is 42nm.
Example 2
Weighing 1.00g of fullerene C60 and 5g of hydroxypropyl-beta-cyclodextrin, putting the fullerene C60 and 5g of hydroxypropyl-beta-cyclodextrin into an agate ball mill, adding grinding balls, grinding for 3 hours in a planetary ball mill, dissolving the mixture by 250ml of poloxamer with the concentration of 0.2 percent, filtering by a 0.22 mu m water-phase filter membrane to obtain a water-soluble fullerene nano solution, and detecting that the content of the fullerene C60 is 3.58mg/ml and the average particle size is 51nm.
Example 3
Weighing 1.00g of fullerene C60 and 5g of lactose, putting the fullerene C60 and the lactose into an agate ball mill, adding grinding balls, grinding for 3 hours in a planetary ball mill, dissolving the fullerene C60 and the lactose by using 250ml of soybean lecithin with the concentration of 0.2 percent, filtering by using a 0.22 mu m water-phase filter membrane to obtain a water-soluble fullerene nano solution, and detecting that the content of the fullerene C60 is 3.62mg/ml and the average particle size is 48nm.
Example 4
Weighing 1.00g of fullerene C60 and 5g of glucose, putting the fullerene C60 and the glucose into an agate ball mill, adding agate balls for milling, grinding for 3 hours in a planet ball mill, dissolving the fullerene C60 and the glucose with 250ml of Tween 80 with the concentration of 0.2 percent, filtering with a 0.22 mu m water-phase filter membrane to obtain a water-soluble fullerene nano solution, and detecting that the content of the fullerene C60 is 3.54mg/ml and the average particle size is 53nm.
Experimental example 1 screening
(1) Selecting auxiliary grinding aids: firstly, the medical or cosmetic grade auxiliary material with good grinding aid effect is selected, secondly, the auxiliary material with small hygroscopicity is selected according to the physicochemical property of the auxiliary material, so that the grinding operation is easier, and thirdly, the auxiliary material with good water solubility is selected. Therefore, a comparative experiment is carried out on the sulfobutyl-beta-cyclodextrin, the hydroxypropyl-beta-cyclodextrin, the lactose and the glucose, and the experimental method comprises the following steps: weighing 1.00g of fullerene C60 and 5g of the auxiliary grinding aids, respectively putting the fullerene C60 and the auxiliary grinding aids into an agate ball milling tank, grinding for 3 hours by using a planetary ball mill, dissolving the fullerene C60 in 250ml of Tween 80 with the concentration of 0.2 percent, filtering by using a 0.22 mu m aqueous phase filter membrane to obtain a water-soluble fullerene nano solution, and detecting the content and the average particle size of the fullerene C60, wherein the results are as follows:
| auxiliary grinding aid | Content (mg/ml) | Average particle diameter (nm) |
| Hydroxypropyl-beta-cyclodextrin | 3.56 | 52 |
| Lactose | 3.61 | 48 |
| Glucose | 3.54 | 53 |
| Sulfobutyl-beta-cyclodextrin | 3.92 | 42 |
The experimental results show that the water-soluble fullerene nano solution obtained by taking the sulfobutyl-beta-cyclodextrin as the grinding aid auxiliary material has the highest fullerene C60 content and the smallest particle size, so that the water-soluble fullerene nano solution is the optimal grinding aid auxiliary material. The sulfobutyl-beta-cyclodextrin is a high-water-solubility pharmaceutic adjuvant, has small hygroscopicity, is used for injections, oral medicines, nasal medicines and ophthalmic medicines, is an excellent pharmaceutic adjuvant, and is an optimal candidate grinding aid adjuvant for water-soluble fullerene nano solutions.
(2) Selection of surfactant: mainly selects a medical or cosmetic grade surfactant with good solubilization effect. For this reason, comparative experiments were carried out on tween 80, poloxamer and soybean lecithin, and the experimental method was: weighing 1.00g of fullerene C60 and 5g of sulfobutyl-beta-cyclodextrin, putting the fullerene C60 and 5g of sulfobutyl-beta-cyclodextrin into an agate ball mill, grinding the mixture for 3 hours by using a planetary ball mill, respectively dissolving the fullerene C60 and 5g of sulfobutyl-beta-cyclodextrin by using 250ml of Tween 80 with the concentration of 0.2%, poloxamer and soybean lecithin, filtering the solution by using a 0.22 mu m water-phase filter membrane to obtain a water-soluble fullerene nano solution, and detecting the content and the average particle size of the fullerene C60, wherein the results are as follows:
| surface active agent | Content (mg/ml) | Average particle diameter (nm) |
| Poloxamers | 3.51 | 53 |
| Soybean lecithin | 3.60 | 46 |
| Tween 80 | 3.92 | 42 |
The experimental results show that the water-soluble fullerene nano solution prepared by solubilizing the Tween 80 serving as the surfactant has the highest fullerene C60 content and the smallest particle size, so that the water-soluble fullerene nano solution is the surfactant for optimal solubilization.
(3) Examination of grinding time:
weighing 1.00g of fullerene C60 and 5g of sulfobutyl-beta-cyclodextrin, putting the fullerene C60 and 5g of sulfobutyl-beta-cyclodextrin into an agate ball mill, adding grinding balls, grinding in a planetary ball mill, sampling 0.3g of the fullerene C at different time points, dissolving the fullerene C in 12.5ml of 0.2 percent Tween 80, filtering the fullerene C with a 0.22 mu m aqueous phase filter membrane to obtain a water-soluble fullerene nano solution, and measuring the content and the particle size of the fullerene.
| Grinding time (h) | Content (mg/ml) | Average particle diameter (nm) |
| 0.5 | 0.82 | 154 |
| 1.0 | 1.48 | 104 |
| 1.5 | 2.46 | 86 |
| 2.0 | 3.27 | 59 |
| 2.5 | 3.91 | 42 |
| 3.0 | 3.92 | 42 |
| 3.5 | 3.86 | 47 |
The experimental result shows that the fullerene content is highest and the particle size is smallest after 3 hours of grinding, and the optimal grinding time is determined to be 3 hours.
(4) Screening the weight ratio of fullerene to grinding-aid auxiliary materials:
respectively weighing 1.00g of fullerene C60 and sulfobutyl-beta-cyclodextrin with different weights, filling the fullerene C60 and the sulfobutyl-beta-cyclodextrin into an agate ball mill, adding grinding balls, grinding the mixture for 3 hours in a planetary ball mill, respectively dissolving the mixture by 250ml of Tween 80 with the concentration of 0.2 percent, filtering the mixture by using a 0.22 mu m water-phase filter membrane to obtain a water-soluble fullerene nano solution, and detecting the content and the average particle size of the fullerene C60.
Experimental results show that when the weight ratio of the fullerene to the sulfobutyl-beta-cyclodextrin is 1.
Experimental example 2, control experiment
(1) Grinding is directly carried out without adding grinding auxiliary materials: weighing 1.00g of pure fullerene, putting the pure fullerene into an agate ball mill tank, adding grinding balls, grinding the pure fullerene in a planetary ball mill for 3 hours, wherein the fullerene is seriously agglomerated and cannot be normally ground, taking out the pure fullerene, dissolving the pure fullerene by using 250ml of Tween 80 with the concentration of 0.2 percent, and filtering the pure fullerene by using a 0.22 mu m water-phase filter membrane, wherein the solution is turbid and cannot be dissolved, and the pure fullerene is colorless and is completely intercepted.
(2) Purified water alone without surfactant dissolution: weighing 1.00g of fullerene C60 and 5g of sulfobutyl-beta-cyclodextrin, putting the fullerene C60 and 5g of sulfobutyl-beta-cyclodextrin into an agate ball mill tank, adding grinding balls, grinding for 3 hours in a planetary ball mill, dissolving with 250ml of purified water, filtering with a 0.22 mu m water-phase filter membrane, wherein the solution is turbid and cannot be dissolved, and the filtrate is colorless and is completely intercepted.
Claims (10)
1. A preparation method of a water-soluble fullerene nano solution is characterized by comprising the following steps:
(1) Mixing fullerene and auxiliary grinding aids, putting the mixture into a ball milling tank, adding grinding balls, and grinding in a planetary ball mill;
(2) And dissolving the ground material by using a surfactant solution, and filtering by using a 0.22-micron filter membrane to obtain a water-soluble fullerene nano solution.
2. The method according to claim 1, wherein the fullerene of step (1) is C60 or C70, or a mixture of C60 and C70.
3. The preparation method according to claim 1, wherein the weight ratio of the fullerene to the grinding aid auxiliary material in the step (1) is 1.
4. The preparation method according to claim 1, wherein the weight ratio of the fullerene to the grinding aid auxiliary material in the step (1) is 1.
5. The preparation method of claim 1, wherein the grinding aid auxiliary material in step (1) is alpha-cyclodextrin, beta-cyclodextrin, gamma-cyclodextrin and water-soluble derivatives of these cyclodextrins, and further includes water-soluble auxiliary materials such as glucose, lactose, maltose and the like without being limited to these auxiliary materials.
6. The method according to claim 1, wherein the surfactant in step (2) is Tween 80, poloxamer, lecithin, etc., and is not limited to these surfactants.
7. The method of claim 1, comprising the steps of:
weighing 1.00g of fullerene C60 and 5g of sulfobutyl-beta-cyclodextrin, putting the fullerene C60 and the sulfobutyl-beta-cyclodextrin into an agate ball mill, adding grinding balls, grinding for 3 hours in a planetary ball mill, dissolving the fullerene C in 250ml of 0.2 percent Tween 80, and filtering through a 0.22 mu m water-phase filter membrane to obtain a water-soluble fullerene nano solution.
8. The method of claim 1, comprising the steps of:
weighing 1.00g of fullerene C60 and 5g of hydroxypropyl-beta-cyclodextrin, putting the fullerene C60 and the hydroxypropyl-beta-cyclodextrin into an agate ball mill, adding a grinding ball, grinding for 3 hours in a planet ball mill, dissolving the fullerene C with 250ml of poloxamer with the concentration of 0.2 percent, and filtering through a 0.22 mu m water-phase filter membrane to obtain a water-soluble fullerene nano solution.
9. The method of claim 1, comprising the steps of:
weighing 1.00g of fullerene C60 and 5g of lactose, putting the fullerene C60 and the lactose into an agate ball mill, adding grinding balls, grinding for 3 hours in a planetary ball mill, dissolving the fullerene C with 250ml of soybean lecithin with the concentration of 0.2 percent, and filtering with a 0.22 mu m water-phase filter membrane to obtain a water-soluble fullerene nano solution.
10. The method of claim 1, comprising the steps of:
weighing 1.00g of fullerene C60 and 5g of glucose, putting the fullerene C60 and the glucose into an agate ball mill, adding grinding balls, grinding for 3 hours in a planetary ball mill, dissolving the fullerene C with 250ml of 0.2 percent Tween 80, and filtering with a 0.22 mu m water-phase filter membrane to obtain a water-soluble fullerene nano solution.
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