CN113019347A - Preparation method and application of polyphenol substance-loaded mesoporous silicon composite material - Google Patents
Preparation method and application of polyphenol substance-loaded mesoporous silicon composite material Download PDFInfo
- Publication number
- CN113019347A CN113019347A CN202110254933.3A CN202110254933A CN113019347A CN 113019347 A CN113019347 A CN 113019347A CN 202110254933 A CN202110254933 A CN 202110254933A CN 113019347 A CN113019347 A CN 113019347A
- Authority
- CN
- China
- Prior art keywords
- mesoporous silicon
- silicon nanoparticles
- polyphenol
- aminated
- mixed solution
- 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
- 235000013824 polyphenols Nutrition 0.000 title claims abstract description 87
- 150000008442 polyphenolic compounds Chemical class 0.000 title claims abstract description 86
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 74
- 239000010703 silicon Substances 0.000 title claims abstract description 74
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 71
- 239000000126 substance Substances 0.000 title claims abstract description 67
- 239000002131 composite material Substances 0.000 title claims abstract description 62
- 238000002360 preparation method Methods 0.000 title claims abstract description 34
- 239000005543 nano-size silicon particle Substances 0.000 claims abstract description 123
- 239000011259 mixed solution Substances 0.000 claims abstract description 77
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 41
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 34
- 238000000034 method Methods 0.000 claims abstract description 26
- 239000011148 porous material Substances 0.000 claims abstract description 22
- 238000002156 mixing Methods 0.000 claims abstract description 16
- 238000006243 chemical reaction Methods 0.000 claims abstract description 14
- 239000004094 surface-active agent Substances 0.000 claims abstract description 14
- 230000002152 alkylating effect Effects 0.000 claims abstract description 13
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 13
- 239000002904 solvent Substances 0.000 claims abstract description 8
- IYRMWMYZSQPJKC-UHFFFAOYSA-N kaempferol Chemical compound C1=CC(O)=CC=C1C1=C(O)C(=O)C2=C(O)C=C(O)C=C2O1 IYRMWMYZSQPJKC-UHFFFAOYSA-N 0.000 claims description 86
- 238000003756 stirring Methods 0.000 claims description 50
- 239000000243 solution Substances 0.000 claims description 45
- UBSCDKPKWHYZNX-UHFFFAOYSA-N Demethoxycapillarisin Natural products C1=CC(O)=CC=C1OC1=CC(=O)C2=C(O)C=C(O)C=C2O1 UBSCDKPKWHYZNX-UHFFFAOYSA-N 0.000 claims description 43
- MWDZOUNAPSSOEL-UHFFFAOYSA-N kaempferol Natural products OC1=C(C(=O)c2cc(O)cc(O)c2O1)c3ccc(O)cc3 MWDZOUNAPSSOEL-UHFFFAOYSA-N 0.000 claims description 43
- 235000008777 kaempferol Nutrition 0.000 claims description 43
- UXOUKMQIEVGVLY-UHFFFAOYSA-N morin Natural products OC1=CC(O)=CC(C2=C(C(=O)C3=C(O)C=C(O)C=C3O2)O)=C1 UXOUKMQIEVGVLY-UHFFFAOYSA-N 0.000 claims description 43
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 32
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 27
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 27
- 239000012153 distilled water Substances 0.000 claims description 23
- 238000010438 heat treatment Methods 0.000 claims description 21
- 239000002244 precipitate Substances 0.000 claims description 18
- 238000010992 reflux Methods 0.000 claims description 18
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 claims description 15
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 claims description 15
- 239000006228 supernatant Substances 0.000 claims description 15
- 238000009833 condensation Methods 0.000 claims description 12
- 230000005494 condensation Effects 0.000 claims description 12
- 239000006185 dispersion Substances 0.000 claims description 12
- 239000012465 retentate Substances 0.000 claims description 12
- ULSUXBXHSYSGDT-UHFFFAOYSA-N tangeretin Chemical compound C1=CC(OC)=CC=C1C1=CC(=O)C2=C(OC)C(OC)=C(OC)C(OC)=C2O1 ULSUXBXHSYSGDT-UHFFFAOYSA-N 0.000 claims description 12
- 238000009210 therapy by ultrasound Methods 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 10
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical group CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 9
- 238000001035 drying Methods 0.000 claims description 9
- 238000005406 washing Methods 0.000 claims description 8
- 238000005303 weighing Methods 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 6
- LZZYPRNAOMGNLH-UHFFFAOYSA-M Cetrimonium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+](C)(C)C LZZYPRNAOMGNLH-UHFFFAOYSA-M 0.000 claims description 6
- 244000282866 Euchlaena mexicana Species 0.000 claims description 6
- 235000011114 ammonium hydroxide Nutrition 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 238000001816 cooling Methods 0.000 claims description 6
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N daidzein Chemical compound C1=CC(O)=CC=C1C1=COC2=CC(O)=CC=C2C1=O ZQSIJRDFPHDXIC-UHFFFAOYSA-N 0.000 claims description 6
- IECRXMSGDFIOEY-UHFFFAOYSA-N Tangeretin Natural products COC=1C(OC)=C(OC)C(OC)=C(C(C=2)=O)C=1OC=2C1=CC=C(O)C=C1 IECRXMSGDFIOEY-UHFFFAOYSA-N 0.000 claims description 5
- 235000013305 food Nutrition 0.000 claims description 5
- 238000004108 freeze drying Methods 0.000 claims description 5
- 238000004140 cleaning Methods 0.000 claims description 3
- 235000007240 daidzein Nutrition 0.000 claims description 3
- 239000012530 fluid Substances 0.000 claims description 3
- 238000001291 vacuum drying Methods 0.000 claims description 3
- 239000002168 alkylating agent Substances 0.000 claims description 2
- 229940100198 alkylating agent Drugs 0.000 claims description 2
- 239000003814 drug Substances 0.000 abstract description 17
- 229940079593 drug Drugs 0.000 abstract description 16
- 238000011068 loading method Methods 0.000 abstract description 12
- 239000002994 raw material Substances 0.000 abstract description 3
- 239000002105 nanoparticle Substances 0.000 description 31
- 210000003743 erythrocyte Anatomy 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 230000005540 biological transmission Effects 0.000 description 6
- 210000004027 cell Anatomy 0.000 description 6
- 238000005538 encapsulation Methods 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000002835 absorbance Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000031700 light absorption Effects 0.000 description 3
- 238000003760 magnetic stirring Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 239000002539 nanocarrier Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 235000016709 nutrition Nutrition 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000013641 positive control Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000002336 sorption--desorption measurement Methods 0.000 description 3
- 230000004083 survival effect Effects 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 229910008051 Si-OH Inorganic materials 0.000 description 2
- 229910006358 Si—OH Inorganic materials 0.000 description 2
- 238000005452 bending Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000012512 characterization method Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000009826 distribution Methods 0.000 description 2
- 238000012377 drug delivery Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 235000012055 fruits and vegetables Nutrition 0.000 description 2
- 125000000524 functional group Chemical group 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- LXEKPEMOWBOYRF-QDBORUFSSA-N AAPH Chemical compound Cl.Cl.NC(=N)C(C)(C)\N=N\C(C)(C)C(N)=N LXEKPEMOWBOYRF-QDBORUFSSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 206010018910 Haemolysis Diseases 0.000 description 1
- 241000395033 Kaempferia Species 0.000 description 1
- 235000013422 Kaempferia rotunda Nutrition 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- 230000001133 acceleration Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 230000010100 anticoagulation Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000036765 blood level Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003833 cell viability Effects 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 210000002919 epithelial cell Anatomy 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- 230000008588 hemolysis Effects 0.000 description 1
- 238000013537 high throughput screening Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 238000012844 infrared spectroscopy analysis Methods 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000002502 liposome Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000013335 mesoporous material Substances 0.000 description 1
- 239000002082 metal nanoparticle Substances 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 210000004877 mucosa Anatomy 0.000 description 1
- QPJSUIGXIBEQAC-UHFFFAOYSA-N n-(2,4-dichloro-5-propan-2-yloxyphenyl)acetamide Chemical compound CC(C)OC1=CC(NC(C)=O)=C(Cl)C=C1Cl QPJSUIGXIBEQAC-UHFFFAOYSA-N 0.000 description 1
- -1 nano valves Substances 0.000 description 1
- 239000002159 nanocrystal Substances 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 238000000696 nitrogen adsorption--desorption isotherm Methods 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035699 permeability Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000002096 quantum dot Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 230000001953 sensory effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- JXOHGGNKMLTUBP-HSUXUTPPSA-N shikimic acid Chemical compound O[C@@H]1CC(C(O)=O)=C[C@@H](O)[C@H]1O JXOHGGNKMLTUBP-HSUXUTPPSA-N 0.000 description 1
- JXOHGGNKMLTUBP-JKUQZMGJSA-N shikimic acid Natural products O[C@@H]1CC(C(O)=O)=C[C@H](O)[C@@H]1O JXOHGGNKMLTUBP-JKUQZMGJSA-N 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006557 surface reaction Methods 0.000 description 1
- 235000008603 tangeritin Nutrition 0.000 description 1
- 238000012876 topography Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229940043263 traditional drug Drugs 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000004627 transmission electron microscopy Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
Images
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28054—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their surface properties or porosity
- B01J20/28078—Pore diameter
- B01J20/28083—Pore diameter being in the range 2-50 nm, i.e. mesopores
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
- A23L33/105—Plant extracts, their artificial duplicates or their derivatives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23P—SHAPING OR WORKING OF FOODSTUFFS, NOT FULLY COVERED BY A SINGLE OTHER SUBCLASS
- A23P10/00—Shaping or working of foodstuffs characterised by the products
- A23P10/40—Shaping or working of foodstuffs characterised by the products free-flowing powder or instant powder, i.e. powder which is reconstituted rapidly when liquid is added
- A23P10/47—Shaping or working of foodstuffs characterised by the products free-flowing powder or instant powder, i.e. powder which is reconstituted rapidly when liquid is added using additives, e.g. emulsifiers, wetting agents or dust-binding agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
- A61K31/352—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom condensed with carbocyclic rings, e.g. methantheline
-
- 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
- A61K47/50—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
- A61K47/69—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit
- A61K47/6949—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 the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the conjugate being characterised by physical or galenical forms, e.g. emulsion, particle, inclusion complex, stent or kit inclusion complexes, e.g. clathrates, cavitates or fullerenes
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28002—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their physical properties
- B01J20/28004—Sorbent size or size distribution, e.g. particle size
- B01J20/28007—Sorbent size or size distribution, e.g. particle size with size in the range 1-100 nanometers, e.g. nanosized particles, nanofibers, nanotubes, nanowires or the like
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/28—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties
- B01J20/28014—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof characterised by their form or physical properties characterised by their form
- B01J20/28016—Particle form
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J20/00—Solid sorbent compositions or filter aid compositions; Sorbents for chromatography; Processes for preparing, regenerating or reactivating thereof
- B01J20/30—Processes for preparing, regenerating, or reactivating
- B01J20/305—Addition of material, later completely removed, e.g. as result of heat treatment, leaching or washing, e.g. for forming pores
- B01J20/3057—Use of a templating or imprinting material ; filling pores of a substrate or matrix followed by the removal of the substrate or matrix
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Analytical Chemistry (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Food Science & Technology (AREA)
- Nanotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Mycology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Materials Engineering (AREA)
- Crystallography & Structural Chemistry (AREA)
- Nutrition Science (AREA)
- Botany (AREA)
- Physics & Mathematics (AREA)
- Thermal Sciences (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Silicates, Zeolites, And Molecular Sieves (AREA)
Abstract
The invention discloses a preparation method and application of a mesoporous silicon composite material loaded with polyphenol substances, wherein the preparation method comprises the following steps: the method comprises the following steps: s1, preparing coarse mesoporous silicon nanoparticles by using a sol-gel and surfactant template method; s2, dispersing the coarse mesoporous silicon nanoparticles obtained in the step S1 in a solvent, and adding an alkylating reagent to obtain surface aminated mesoporous silicon nanoparticles; s3, placing the mesoporous silicon nanoparticles with aminated surfaces obtained in the step S2 in a mixed solution of alcohol/hydrochloric acid, and eluting the template to obtain aminated mesoporous silicon nanoparticles with regular pore channels; and S4, mixing the aminated mesoporous silicon nanoparticles obtained in the step S3 with a polyphenol substance for reaction to obtain the polyphenol substance-loaded mesoporous silicon nanoparticles. The preparation method is simple, the raw materials are low in cost and easy to obtain, and the obtained polyphenol substance-loaded mesoporous silicon composite material is good in dispersibility, large in specific surface area, high in drug loading rate and environment-friendly.
Description
Technical Field
The invention relates to the technical field of biological materials, in particular to a preparation method and application of a mesoporous silicon composite material loaded with polyphenol substances.
Background
The polyphenol is an important secondary metabolite in plants, is synthesized mainly through a shikimic acid and malonic acid way, widely exists in fruits and vegetables, and is a main determinant factor of sensory quality and nutritional quality of fruits and vegetables. With the development of modern separation technology and high-throughput screening means, more and more polyphenol functional components are discovered. Polyphenols have a long history of research and have been shown to possess a variety of biological activities. Although the substances have better biological activity and nutritional value, the substances generally have the characteristics of high melting point, low water solubility, easy crystallization and the like, a plurality of hydroxyl groups exist in the structure, the substances have chemical instability, and the substances are easy to deteriorate by oxygen, heat and light. Therefore, the compound preparation is not easy to store, has low bioavailability, not only greatly limits the application of the compound preparation in various fields of food, medicines, agriculture and the like, but also is difficult to be absorbed by epithelial cells in small intestines after being orally taken in vivo, so that the bioavailability is reduced, and the exertion of the nutritional efficacy is greatly limited. Also, because of the relatively low bioavailability, higher doses are required until the blood levels reach significant levels, but increased doses sometimes result in local toxicity of the orally active substance in the gastrointestinal tract, thereby reducing compliance with human use. Therefore, various technical means are required to improve the bioavailability.
At present, although various preparation technologies, such as synthesis of water-soluble precursors, inclusion compound, nanocrystal, self-emulsification, and the like, exist, respectively, the dissolution rate and bioavailability of the drug are improved by methods of reducing the particle size of the drug, enabling the drug to exist in a molecular state, changing the affinity and permeability of the drug with gastrointestinal mucosa, and the like, the existing methods all have the problem of low embedding or loading rate. Therefore, a drug delivery system with high drug loading and wide application range, which meets the characteristics of polyphenol, is urgently needed to be found.
Compared with traditional drug carriers such as liposome, emulsion and polymer nanoparticles, the inorganic carrier has the advantages of good physical stability, simple control of particle size and form, easy surface functionalization and the like, and has great application prospect in the fields of food and medicine. In recent years, many inorganic materials with different structural characteristics, such as metal nanoparticles, nano valves, quantum dots, MOF systems, have received much attention and interest for drug delivery.
Disclosure of Invention
An object of the present invention is to solve at least the above problems and to provide at least the advantages described later.
The invention also aims to provide a preparation method of the polyphenol substance-loaded mesoporous silicon composite material, which has the advantages of simple preparation method, low raw material cost and easy acquisition, and ensures that the obtained polyphenol substance-loaded mesoporous silicon composite material has good dispersibility, large specific surface area, high drug loading rate and environmental protection.
To achieve these objects and other advantages in accordance with the present invention, there is provided a method for preparing a polyphenol substance-loaded mesoporous silicon composite material, comprising the steps of:
s1, preparing coarse mesoporous silicon nanoparticles by using a sol-gel and surfactant template method;
s2, dispersing the coarse mesoporous silicon nanoparticles obtained in the step S1 in a solvent, and adding an alkylating reagent to obtain surface aminated mesoporous silicon nanoparticles;
s3, placing the mesoporous silicon nanoparticles with aminated surfaces obtained in the step S2 in a mixed solution of alcohol/hydrochloric acid, and eluting the template to obtain aminated mesoporous silicon nanoparticles with regular pore channels;
and S4, mixing the aminated mesoporous silicon nanoparticles obtained in the step S3 with a polyphenol substance for reaction to obtain the polyphenol substance-loaded mesoporous silicon nanoparticles.
Preferably, in the preparation method of the polyphenol substance-loaded mesoporous silicon composite material, in S1, the preparation of the coarse mesoporous silicon nanoparticles by using the sol-gel and surfactant template method specifically includes:
s1-1, mixing a surfactant and triethylamine TEA according to a mass-to-volume ratio of 1-3 g: uniformly dispersing 50 ul of the mixture in a flask filled with 20 mL of distilled water, stirring and heating to 80-100 ℃, and performing reflux condensation to obtain a mixed solution I;
s1-2, heating the mixed solution I to 80-100 ℃, standing at a constant temperature for 5-10 min, dropwise adding 0.5-2 ml of tetraethyl orthosilicate TEOS into the mixed solution I under the stirring condition, continuously stirring for reaction for 1-2 h, and performing reflux condensation to obtain a mixed solution II;
s1-3, heating the mixed solution II to 80-100 ℃, dropwise adding 0.5-2 ml of TEOS and 0.5-2 ml of 2-bis [3- (triethoxysilyl) propyl ] tetrasulfide BTESPT into the mixed solution II, continuously stirring for reacting for 4-6 h, and performing reflux condensation to obtain a mixed solution III;
s1-4, cooling the mixed solution III to room temperature, centrifuging at 3000 rpm for 10-30 min, collecting the precipitate, washing the precipitate with distilled water, and vacuum drying at-90 to-70 ℃ to obtain the coarse mesoporous silicon nanoparticles.
Preferably, in the preparation method of the mesoporous silicon composite material loaded with the polyphenol substances, the surface catalyst is one of cetyltrimethyl ammonium bromide (CTAB) and cetyltrimethyl ammonium chloride (CTAC).
Preferably, in the preparation method of the polyphenol substance-loaded mesoporous silicon composite material, in S2, the step of dispersing the coarse mesoporous silicon nanoparticles in a solvent, and adding an alkylating reagent to obtain surface aminated mesoporous silicon nanoparticles specifically includes:
dispersing the coarse mesoporous silicon nanoparticles into methanol according to the mass-volume ratio of 0.5-1.5 g: 75 mL, adding an alkylating reagent, stirring at room temperature for 20-30 h, centrifuging at 3000 rpm for 10-30 min, and collecting to obtain the surface aminated mesoporous silicon nanoparticles.
Preferably, in the preparation method of the mesoporous silicon composite material loaded with the polyphenol substances, the alkylating reagent is 3-Aminopropyltriethoxysilane (APTES).
Preferably, in the preparation method of the polyphenol substance-loaded mesoporous silicon composite material, in S3, the step of placing the mesoporous silicon nanoparticles with aminated surfaces in a mixed solution of alcohol and hydrochloric acid, and eluting the template to obtain aminated mesoporous silicon nanoparticles with regular pore channels specifically includes:
s3-1, weighing 1 g of the mesoporous silicon nanoparticles with aminated surfaces, and placing the mesoporous silicon nanoparticles with aminated surfaces in a volume ratio of 80-100 mL: carrying out ultrasonic treatment on 10 mL of alcohol/hydrochloric acid mixed solution for 5-15 min to obtain a dispersion solution;
s3-2, placing the dispersion solution in a water bath kettle at the temperature of 75-85 ℃ to be continuously stirred for 20-30 h, and centrifuging to remove supernatant fluid to obtain a retentate;
s3-3, adding 2-4 ml of ammonia water into the retentate overnight, centrifuging at the rotating speed of 3000 rpm for 10-30 min, adding 100 ml of distilled water, and stirring at the constant temperature of 75-85 ℃ for 4-8 h to obtain a stirring solution;
s3-4, centrifuging the stirred solution at the rotating speed of 3000 rpm for 10-30 min, and drying the collected precipitate in vacuum at the temperature of-90 to-70 ℃ to obtain the aminated mesoporous silicon nano-particles.
Preferably, in the preparation method of the mesoporous silicon composite material loaded with polyphenol substances, the alcohol in the alcohol/hydrochloric acid mixed solution is one of methanol and ethanol.
Preferably, in the preparation method of the polyphenol substance-loaded mesoporous silicon composite material, in S4, the mixing and reacting of the aminated mesoporous silicon nanoparticles and the polyphenol substance to obtain the polyphenol substance-loaded mesoporous silicon nanoparticles specifically includes:
s4-1, mixing the aminated mesoporous silicon nanoparticles according to the mass-volume ratio of 450-550 mg: uniformly dispersing 100 mL of the mixture in ethanol, and performing ultrasonic treatment for 5-15 min to obtain an ultrasonic solution;
s4-2, adding 550 mg of 450-550 mg of polyphenol material into the ultrasonic solution, and stirring for 20-30 h at room temperature in a dark place to obtain a polyphenol mixed solution;
s4-3, centrifuging the polyphenol mixed solution at the rotating speed of 3000 rpm for 10-30 min, removing supernatant, adding 100 ml of distilled water into residues, cleaning, and freeze-drying in a freeze vacuum dryer to obtain the mesoporous silicon nanoparticles loaded with the polyphenol substances.
Preferably, in the preparation method of the mesoporous silicon composite material loaded with polyphenol substances, the polyphenol substances are any one of kaempferol, tangeretin and daidzein.
Application of polyphenol substance-loaded mesoporous silicon nanoparticles obtained by applying a preparation method of polyphenol substance-loaded mesoporous silicon composite material in food and biomedicine.
The invention at least comprises the following beneficial effects:
in the preparation method of the polyphenol substance-loaded mesoporous silicon composite material, coarse mesoporous silicon nanoparticles are prepared by utilizing a sol-gel and surfactant template method; then dispersing the coarse mesoporous silicon nanoparticles into a solvent, and adding an alkylating reagent to obtain surface aminated mesoporous silicon nanoparticles; then putting the mesoporous silicon nano-particles with aminated surfaces into a mixed solution of alcohol/hydrochloric acid, and eluting the template to obtain aminated mesoporous silicon nano-particles with regular pore channels; finally, the aminated mesoporous silicon nanoparticles are mixed with polyphenol substances for reaction, so that the mesoporous silicon nanoparticles loaded with the polyphenol substances can be obtained, the operation steps are simple, special and complex equipment is not needed, the raw material obtaining mode is simple and convenient, the cost is low, the method is generally applicable, the yield is high, and the method is suitable for large-scale popularization and application.
The surface of the mesoporous silicon composite material prepared by the preparation method of the polyphenol substance-loaded mesoporous silicon composite material has rich silicon hydroxyl groups, and on one hand, the mesoporous silicon composite material can interact with certain polyphenol molecules, so that the polyphenol molecules are uniformly loaded into a pore channel; on the other hand, the mesoporous silicon composite material can react with an alkylating reagent to carry out functional group modification on the surface so as to load more polyphenol, and meanwhile, the mesoporous silicon composite material has higher chemical and thermodynamic stability, so that the polyphenol is not easy to leak and degrade in the storage process.
The mesoporous silicon composite material prepared by the preparation method of the polyphenol substance-loaded mesoporous silicon composite material can be subjected to functional modification or composite with other polyphenols to obtain a multifunctional nano material, so that multiple functions which cannot be realized by a single material are realized.
The mesoporous silicon composite material prepared by the preparation method of the polyphenol substance-loaded mesoporous silicon composite material has the advantages of large specific surface area, large pore volume, highly ordered pore channel structure, uniform and adjustable pore size distribution, capability of effectively loading polyphenol, improvement of polyphenol utilization rate, small toxic and side effects, good biocompatibility and huge development potential.
Additional advantages, objects, and features of the invention will be set forth in part in the description which follows and in part will become apparent to those having ordinary skill in the art upon examination of the following or may be learned from practice of the invention.
Drawings
FIG. 1 is a scanning electron microscope topography of the mesoporous silicon nanoparticles loaded with polyphenol substances according to the present invention;
FIG. 2 is a transmission electron microscope image of the mesoporous silicon nanoparticles loaded with polyphenol substances according to the present invention;
FIG. 3 is an infrared spectrum of mesoporous silicon nanoparticles loaded with polyphenolic substances according to the present invention;
FIG. 4 is a nitrogen adsorption desorption isotherm graph of the mesoporous silicon nanoparticles loaded with polyphenol substances according to the present invention;
FIG. 5 is a standard curve of kaempferol concentration versus absorbance;
FIG. 6 is a comparison graph of hemolysis of red blood cells by the mesoporous silicon nanoparticles loaded with polyphenol substances according to the present invention;
fig. 7 is a relationship diagram of the influence of the mesoporous silicon nanoparticles loaded with polyphenol substances on cell viability according to the present invention.
Detailed Description
The present invention is further described in detail below with reference to the attached drawings so that those skilled in the art can implement the invention by referring to the description text.
It will be understood that terms such as "having," "including," and "comprising," as used herein, do not preclude the presence or addition of one or more other elements or groups thereof.
The invention provides a preparation method of a mesoporous silicon composite material loaded with polyphenol substances, which comprises the following steps:
s1, preparing coarse mesoporous silicon nanoparticles by using a sol-gel and surfactant template method;
s2, dispersing the coarse mesoporous silicon nanoparticles obtained in the step S1 in a solvent, and adding an alkylating reagent to obtain surface aminated mesoporous silicon nanoparticles;
s3, placing the mesoporous silicon nanoparticles with aminated surfaces obtained in the step S2 in a mixed solution of alcohol/hydrochloric acid, and eluting the template to obtain aminated mesoporous silicon nanoparticles with regular pore channels;
and S4, mixing the aminated mesoporous silicon nanoparticles obtained in the step S3 with a polyphenol substance for reaction to obtain the polyphenol substance-loaded mesoporous silicon nanoparticles.
In a preferred embodiment, in S1, the preparing of the coarse mesoporous silica nanoparticles by using the sol-gel and surfactant template method specifically includes:
s1-1, mixing a surfactant and triethylamine TEA according to a mass-to-volume ratio of 1-3 g: uniformly dispersing 50 ul of the mixture in a flask filled with 20 mL of distilled water, stirring and heating to 80-100 ℃, and performing reflux condensation to obtain a mixed solution I;
s1-2, heating the mixed solution I to 80-100 ℃, standing at a constant temperature for 5-10 min, dropwise adding 0.5-2 ml of tetraethyl orthosilicate TEOS into the mixed solution I under the stirring condition, continuously stirring for reaction for 1-2 h, and performing reflux condensation to obtain a mixed solution II;
s1-3, heating the mixed solution II to 80-100 ℃, dropwise adding 0.5-2 ml of TEOS and 0.5-2 ml of 2-bis [3- (triethoxysilyl) propyl ] tetrasulfide BTESPT into the mixed solution II, continuously stirring for reacting for 4-6 h, and performing reflux condensation to obtain a mixed solution III;
s1-4, cooling the mixed solution III to room temperature, centrifuging at 3000 rpm for 10-30 min, collecting the precipitate, washing the precipitate with distilled water, and vacuum drying at-90 to-70 ℃ to obtain the coarse mesoporous silicon nanoparticles.
In a preferred embodiment, the surface catalyst is one of cetyltrimethylammonium bromide CTAB and cetyltrimethylammonium chloride CTAC.
In a preferred embodiment, in S2, dispersing the coarse mesoporous silicon nanoparticles in a solvent, and adding an alkylating reagent to obtain surface-aminated mesoporous silicon nanoparticles specifically includes:
dispersing the coarse mesoporous silicon nanoparticles into methanol according to the mass-volume ratio of 0.5-1.5 g: 75 mL, adding an alkylating reagent, stirring at room temperature for 20-30 h, centrifuging at 3000 rpm for 10-30 min, and collecting to obtain the surface aminated mesoporous silicon nanoparticles.
In a preferred embodiment, the alkylating agent is 3-Aminopropyltriethoxysilane (APTES).
In a preferred embodiment, in S3, the step of placing the mesoporous silicon nanoparticles with aminated surface in a mixed solution of alcohol/hydrochloric acid, and eluting the template to obtain aminated mesoporous silicon nanoparticles with regular pore channels specifically includes:
s3-1, weighing 1 g of the mesoporous silicon nanoparticles with aminated surfaces, and placing the mesoporous silicon nanoparticles with aminated surfaces in a volume ratio of 80-100 mL: carrying out ultrasonic treatment on 10 mL of alcohol/hydrochloric acid mixed solution for 5-15 min to obtain a dispersion solution;
s3-2, placing the dispersion solution in a water bath kettle at the temperature of 75-85 ℃ to be continuously stirred for 20-30 h, and centrifuging to remove supernatant fluid to obtain a retentate;
s3-3, adding 2-4 ml of ammonia water into the retentate overnight, centrifuging at the rotating speed of 3000 rpm for 10-30 min, adding 100 ml of distilled water, and stirring at the constant temperature of 75-85 ℃ for 4-8 h to obtain a stirring solution;
s3-4, centrifuging the stirred solution at the rotating speed of 3000 rpm for 10-30 min, and drying the collected precipitate in vacuum at the temperature of-90 to-70 ℃ to obtain the aminated mesoporous silicon nano-particles.
In a preferred embodiment, the alcohol in the alcohol/hydrochloric acid mixed solution is one of methanol and ethanol.
In a preferred embodiment, in S4, the mixing and reacting of the aminated mesoporous silicon nanoparticles with the polyphenol substance to obtain the polyphenol substance-loaded mesoporous silicon nanoparticles specifically includes:
s4-1, mixing the aminated mesoporous silicon nanoparticles according to the mass-volume ratio of 450-550 mg: uniformly dispersing 100 mL of the mixture in ethanol, and performing ultrasonic treatment for 5-15 min to obtain an ultrasonic solution;
s4-2, adding 550 mg of 450-550 mg of polyphenol material into the ultrasonic solution, and stirring for 20-30 h at room temperature in a dark place to obtain a polyphenol mixed solution;
s4-3, centrifuging the polyphenol mixed solution at the rotating speed of 3000 rpm for 10-30 min, removing supernatant, adding 100 ml of distilled water into residues, cleaning, and freeze-drying in a freeze vacuum dryer to obtain the mesoporous silicon nanoparticles loaded with the polyphenol substances.
In a preferred embodiment, the polyphenol substance is any one of kaempferol, tangeretin and daidzein.
Application of polyphenol substance-loaded mesoporous silicon nanoparticles obtained by applying a preparation method of polyphenol substance-loaded mesoporous silicon composite material in food and biomedicine.
Example 1
The preparation method of the kaempferol/mesoporous silicon composite nano-particles comprises the following steps:
s1, synthesizing coarse mesoporous silicon nanoparticles by using a surfactant, namely cetyl trimethyl ammonium chloride CTAC, a silicon source TEOS, BTESPT and a catalyst TEA, and specifically comprising the following steps:
CTAC and TEA were mixed in a mass to volume ratio of 2 g: uniformly dispersing 50 ul of TEOS in a flask filled with 20 mL of distilled water, adding a rotor for magnetic stirring, stirring vigorously, heating to 95 ℃, refluxing and condensing to obtain a mixed solution I, heating the mixed solution I to 95 ℃, standing for 5 min, dropwise adding 1 mL of TEOS into the mixed solution I under the stirring condition, continuously stirring for reaction for 1 h, and refluxing and condensing to obtain a mixed solution II; heating the mixed solution II to 95 ℃, then dropwise adding 1 ml of TEOS and 1 ml of BTESPT into the mixed solution II and 1 ml of the mixed solution II, continuously stirring for reaction for 4 hours, and performing reflux condensation to obtain a mixed solution III; and finally stopping heating, cooling the mixed solution III to room temperature, centrifuging for 15 min at the rotating speed of 3000 rpm by using a high-speed centrifuge, collecting yellow precipitate, washing the precipitate for multiple times by using distilled water, and drying in vacuum at the temperature of minus 80 ℃ to obtain the coarse mesoporous silicon nanoparticles.
S2, dispersing the coarse mesoporous silicon nanoparticles into methanol according to the mass-volume ratio of 1 g: 75 mL, adding APTES, stirring at room temperature for 24 h, centrifuging at 3000 rpm for 15 min, and collecting the mesoporous silicon nanoparticles with aminated surfaces.
S3, weighing 1 g of the mesoporous silicon nanoparticles with aminated surfaces, placing the mesoporous silicon nanoparticles with aminated surfaces in a volume ratio of 90 mL: carrying out ultrasonic treatment on 10 mL of ethanol/hydrochloric acid mixed solution for 10 min to obtain a dispersion solution, then placing the dispersion solution in a water bath kettle at 80 ℃ for continuously stirring for 24 h, centrifuging to remove supernatant to obtain a retentate, then adding 3 mL of ammonia water into the retentate overnight, centrifuging for 15 min at the rotating speed of 3000 rpm, then adding 100 mL of distilled water, and stirring for 4 h at the constant temperature of 80 ℃ to obtain a stirring solution; and finally, centrifuging the stirred solution at the rotating speed of 3000 rpm for 15 min, and drying the collected precipitate at the temperature of minus 80 ℃ in vacuum to obtain the aminated mesoporous silicon nano-particles.
S4, mixing the aminated mesoporous silicon nanoparticles according to the mass-volume ratio of 500 mg: uniformly dispersing 100 mL of the mixture in ethanol, and performing ultrasonic treatment for 10 min to obtain an ultrasonic solution; and then adding 500 mg of kaempferol powder into the ultrasonic solution, stirring for 24 hours in a dark place at room temperature to obtain a polyphenol mixed solution, finally centrifuging the polyphenol mixed solution at the rotating speed of 3000 rpm for 15 minutes, removing supernatant, adding 100 ml of distilled water into residues, washing for 3 times to remove free polyphenol substances, and freeze-drying in a freeze vacuum dryer to obtain the kaempferol/mesoporous silicon composite nano-particles.
Example 2
The preparation method of the tangeritin/mesoporous silicon composite nanoparticles comprises the following steps:
s1, synthesizing coarse mesoporous silicon nanoparticles by using a surfactant, namely cetyl trimethyl ammonium chloride CTAC, a silicon source TEOS, BTESPT and a catalyst TEA, and specifically comprising the following steps:
CTAC and TEA were mixed in a mass to volume ratio of 2 g: uniformly dispersing 50 ul of TEOS in a flask filled with 20 mL of distilled water, adding a rotor for magnetic stirring, stirring vigorously, heating to 95 ℃, refluxing and condensing to obtain a mixed solution I, heating the mixed solution I to 95 ℃, standing for 5 min, dropwise adding 1 mL of TEOS into the mixed solution I under the stirring condition, continuously stirring for reaction for 1 h, and refluxing and condensing to obtain a mixed solution II; heating the mixed solution II to 95 ℃, then dropwise adding 1 ml of TEOS and 1 ml of BTESPT into the mixed solution II and 1 ml of the mixed solution II, continuously stirring for reaction for 4 hours, and performing reflux condensation to obtain a mixed solution III; and finally stopping heating, cooling the mixed solution III to room temperature, centrifuging for 15 min at the rotating speed of 3000 rpm by using a high-speed centrifuge, collecting yellow precipitate, washing the precipitate for multiple times by using distilled water, and drying in vacuum at the temperature of minus 80 ℃ to obtain the coarse mesoporous silicon nanoparticles.
S2, dispersing the coarse mesoporous silicon nanoparticles into methanol according to the mass-volume ratio of 1 g: 75 mL, adding APTES, stirring for 24 hours at room temperature, centrifuging for 15 min at the rotating speed of 3000 rpm, and collecting the mesoporous silicon nanoparticles with aminated surfaces.
S3, weighing 1 g of the mesoporous silicon nanoparticles with aminated surfaces, placing the mesoporous silicon nanoparticles with aminated surfaces in a volume ratio of 90 mL: carrying out ultrasonic treatment on 10 mL of ethanol/hydrochloric acid mixed solution for 10 min to obtain a dispersion solution, then placing the dispersion solution in a water bath kettle at 80 ℃ for continuously stirring for 24 h, centrifuging to remove supernatant to obtain a retentate, then adding 3 mL of ammonia water into the retentate overnight, centrifuging for 15 min at the rotating speed of 3000 rpm, then adding 100 mL of distilled water, and stirring for 4 h at the constant temperature of 80 ℃ to obtain a stirring solution; and finally, centrifuging the stirred solution at the rotating speed of 3000 rpm for 15 min, and drying the collected precipitate at the temperature of minus 80 ℃ in vacuum to obtain the aminated mesoporous silicon nano-particles.
S4, mixing the aminated mesoporous silicon nanoparticles according to the mass-volume ratio of 500 mg: uniformly dispersing 100 mL of the mixture in ethanol, and performing ultrasonic treatment for 10 min to obtain an ultrasonic solution; and then adding 500 mg of tangeretin powder into the ultrasonic solution, stirring for 24 h in a dark place at room temperature to obtain a polyphenol mixed solution, finally centrifuging the polyphenol mixed solution at the rotating speed of 3000 rpm for 15 min, removing supernatant, adding 100 ml of distilled water into residues, washing for 3 times to remove free polyphenol substances, and freeze-drying in a freeze vacuum dryer to obtain the tangeretin/mesoporous silicon composite nanoparticles.
Comparative example 1
The preparation of the mesoporous silicon composite nano-particles comprises the following steps:
s1, synthesizing coarse mesoporous silicon nanoparticles by using a surfactant, namely cetyl trimethyl ammonium chloride CTAC, a silicon source TEOS, BTESPT and a catalyst TEA, and specifically comprising the following steps:
CTAC and TEA were mixed in a mass to volume ratio of 2 g: uniformly dispersing 50 ul of TEOS in a flask filled with 20 mL of distilled water, adding a rotor for magnetic stirring, stirring vigorously, heating to 95 ℃, refluxing and condensing to obtain a mixed solution I, heating the mixed solution I to 95 ℃, standing for 5 min, dropwise adding 1 mL of TEOS into the mixed solution I under the stirring condition, continuously stirring for reaction for 1 h, and refluxing and condensing to obtain a mixed solution II; heating the mixed solution II to 95 ℃, then dropwise adding 1 ml of TEOS and 1 ml of BTESPT into the mixed solution II and 1 ml of the mixed solution II, continuously stirring for reaction for 4 hours, and performing reflux condensation to obtain a mixed solution III; and finally stopping heating, cooling the mixed solution III to room temperature, centrifuging for 15 min at the rotating speed of 3000 rpm by using a high-speed centrifuge, collecting yellow precipitate, washing the precipitate for multiple times by using distilled water, and drying in vacuum at the temperature of minus 80 ℃ to obtain the coarse mesoporous silicon nanoparticles.
S2, dispersing the coarse mesoporous silicon nanoparticles into methanol according to the mass-volume ratio of 1 g: 75 mL, adding APTES, stirring for 24 hours at room temperature, centrifuging for 15 min at the rotating speed of 3000 rpm, and collecting the mesoporous silicon nanoparticles with aminated surfaces.
S3, weighing 1 g of the mesoporous silicon nanoparticles with aminated surfaces, placing the mesoporous silicon nanoparticles with aminated surfaces in a volume ratio of 90 mL: carrying out ultrasonic treatment on 10 mL of ethanol/hydrochloric acid mixed solution for 10 min to obtain a dispersion solution, then placing the dispersion solution in a water bath kettle at 80 ℃ for continuously stirring for 24 h, centrifuging to remove supernatant to obtain a retentate, then adding 3 mL of ammonia water into the retentate overnight, centrifuging for 15 min at the rotating speed of 3000 rpm, then adding 100 mL of distilled water, and stirring for 4 h at the constant temperature of 80 ℃ to obtain a stirring solution; and finally, centrifuging the stirred solution at the rotating speed of 3000 rpm for 15 min, and drying the collected precipitate at the temperature of minus 80 ℃ in vacuum to obtain the aminated mesoporous silicon nano-particles.
Characterization differences of the aminated mesoporous silicon nanoparticles and the kaempferol/mesoporous silicon composite nanoparticles were investigated by example 1 and comparative example 1.
1. Analysis by scanning Electron microscope and Transmission Electron microscope
Scanning electron microscope analysis: determining the appearance characteristics of the aminated mesoporous silicon nanoparticles and the kaempferol/mesoporous silicon composite nanoparticles by adopting a scanning electron microscope, wherein the vacuum degree is more than 1.33 multiplied by 10-9kPa, acceleration voltage 10.0, 20.0 kV.
Transmission electron microscopy analysis: respectively analyzing the characteristics of the inner pore channels of the aminated mesoporous silicon nanoparticles and the kaempferol/mesoporous silicon composite nanoparticles by a transmission electron microscope, and specifically operating as follows: weighing a proper amount of aminated mesoporous silicon nanoparticles and kaempferol/mesoporous silicon composite nanoparticle freeze-dried powder respectively, preparing a nanoparticle suspension solution by using deionized water, sucking a proper amount of uniformly mixed suspension solution by using a liquid transfer gun, dripping the suspension solution on a 400-mesh transmission electron microscope carbon film copper net, naturally airing, and placing a sample in a transmission electron microscope to observe the shape and size of nanoparticles.
The characterization results of the scanning electron microscope and the transmission electron microscope are shown in fig. 1 and fig. 2. As can be seen from FIGS. 1 and 2, the prepared aminated mesoporous silicon nanoparticles are nearly circular, uniform in size, and have certain dispersibility and particle size of 80-150 nm. In addition, the narrow and long channels, hexagonal honeycomb mesoporous structure and highly ordered arrangement of mesoporous silicon can be obviously seen. The kaempferol/mesoporous silicon composite nano-particles are in a needle-punched round shape, and the pore channels become small, which indicates that kaempferol is combined on the surface of the mesoporous silicon and in the pore channels.
2. Infrared spectroscopic analysis for determining structure and functional group characteristics of nanoparticles
About 1mg of each of the samples prepared in example 1 and comparative example 1 was taken, and the KBr pellet was used in a wave number range of 400-4000 cm-1Resolution of 4 cm-1And the number of scanning times is 32.
The results are shown in FIG. 3, 793, 460 cm-1The absorption peak of the stretching vibration and the bending vibration of Si-O-Si is positioned; 3460 cm-1The point is the bending vibration peak of silicon hydroxyl Si-OH; 954 cm-1The position is a silicon hydroxyl Si-OH symmetrical telescopic vibration absorption peak; 2950 cm-1The vibration absorption peak is consistent with the C-H stretching vibration absorption peak of the aminated mesoporous silicon nano-particles. Kaempferia galangaPhenol content at 3446 cm-1The characteristic absorption peak at (A) belongs to the phenolic hydroxyl group. The kaempferol/mesoporous silicon composite nano-particles have characteristic peaks of kaempferol and mesoporous silicon at the same time, and the successful synthesis of the kaempferol/mesoporous silicon composite nano-particles is proved.
3. Nitrogen adsorption/desorption analysis
And analyzing the specific surface and pore size distribution of the kaempferol/mesoporous silicon composite nano particles and the aminated mesoporous silicon nano particles by adopting a nitrogen adsorption-desorption method. The samples of example 1 and comparative example 1 were vacuum degassed at 250 ℃ for 2 hours, respectively, were pretreated, and then nitrogen adsorption-desorption experiments were performed under conditions in which the experiment pressure and the initial pressure ratio (PIPS) were 0.01 to 0.99. According to BET and BJH formulas, the specific surface areas and the pore volumes of the kaempferol/mesoporous silicon composite nano-particles and the aminated mesoporous silicon nano-particles are respectively calculated.
As shown in fig. 4, both samples show a distinct type IV isotherm and a distinct hysteresis loop, which belongs to a characteristic curve of a typical mesoporous material, and it can be determined that both samples have good mesoporous properties. As can be seen from Table 1 below, the kaempferol/mesoporous silicon composite nanoparticles have smaller pore size (average pore size is reduced from 3.808 nm to 2.447 nm) and larger specific surface area (from 14.151 cm)-2The/g is increased to 38.092 cm-2In terms of/g). These changes indicate that kaempferol can enter the pore channels of the mesoporous silicon and adhere to the surface of the mesoporous silicon.
TABLE 1 Kaempferol/mesoporous silicon composite nanoparticles specific surface area and pore diameter
| Sample name | Specific surface area (cm)-2/g) | Pore size (nm) |
| Mesoporous silicon | 14.151 | 3.808 |
| Kaempferol/mesoporous silicon | 38.092 | 2.447 |
4. Drug loading and encapsulation efficiency
7 kaempferol solution samples with different concentrations of 0.1, 0.075, 0.05, 0.025, 0.01, 0.0075 and 0.005 mg/ml were prepared. The absorbance value (y) of the sample is measured by an ultraviolet spectrophotometer by taking an ethanol solution as a blank control, the measurement wavelength of the kaempferol is 314 nm, and each sample is tested repeatedly for three times. Plotting different kaempferol concentration values corresponding to the light absorption values, performing linear equation fitting, and determining a standard curve of the concentration and the light absorption values, as shown in FIG. 5.
The drug loading and encapsulation efficiency of kaempferol are measured by spectrophotometry. Weighing freeze-dried kaempferol// mesoporous silicon composite nanoparticles with the mass of about 2.5 mg, adding the freeze-dried kaempferol// mesoporous silicon composite nanoparticles into 10 ml of hydrofluoric acid (HF) solution, shaking and uniformly mixing the mixture, and standing overnight. Placing in a centrifuge tube, and centrifuging at high speed (12000 r/min, 15 min). And taking out the supernatant of the sample, adding the supernatant into a quartz dish, and measuring the light absorption value of the sample by using an ultraviolet spectrophotometer, wherein the measuring wavelength of the kaempferol is 490 nm. And substituting the supernatant absorbance value (y) of each sample into a previously determined kaempferol concentration standard curve, and calculating the kaempferol concentration in each sample and the kaempferol mass in each sample. The drug loading and encapsulation efficiency of each sample were calculated by substituting the following calculation formula for drug loading and encapsulation efficiency, and the experiment was repeated three times.
Drug loading (%) = kaempferol mass in nano carrier x 100/nano carrier mass
Encapsulation efficiency (%) = kaempferol mass in nanocarrier × 100/total mass of kaempferol put
The kaempferol/mesoporous silicon composite nano-particles have the drug loading rate of 40.60 +/-0.15 percent and the encapsulation rate of 81.21 +/-0.31 percent by calculation, and the drug loading rate of 20 percent is greatly improved compared with the traditional mesoporous silicon.
5. Biocompatibility analysis
The method comprises the following steps: preparation of a 2% erythrocyte suspension: 2 ml of whole mouse blood was collected and placed in an anticoagulation tube, centrifuged at 1500 rpm for 5 min, and the upper plasma was discarded. 5 ml of 0.9% NaCl solution was added to the tube and gently and repeatedly purged with a capillary. Centrifuging at 1500 rpm for 5 min, discarding the supernatant, and repeating the above steps for 3-4 times. The resulting red blood cells were made into a 2% suspension of red blood cells using a 0.9% NaCl solution. The nanoparticles were added to the prepared 2% erythrocyte suspension to give kaempferol/mesoporous silica composite nanoparticles with final concentrations of 5, 10, 20, 40 and 80 mg/ml, using deionized water as a positive control, 0.9% NaCl solution as a negative control, and 2,2' -azobisisobutylamidine dihydrochloride (AAPH) as a positive control. All samples were incubated at 37 ℃ for 24 h and photographed for observation.
After 24 h, as shown in FIG. 6, in the positive control, the entire tube appeared red, indicating that the red blood cells were destroyed and the membrane ruptured. And (3) carrying out interference pretreatment on the negative control group and amination mesoporous silicon nanoparticles and kaempferol/mesoporous silicon composite nanoparticles with various concentrations, wherein the red blood cells sink to the bottom, and the upper layer is clear and transparent. The kaempferol/mesoporous silicon composite nano-particles are high in biocompatibility.
The method 2 comprises the following steps: caco-2 cells were seeded at 5000 cells/well in 96-well plates and cultured in an incubator for 24 h. Adding culture media containing kaempferol/mesoporous silicon composite nanoparticles with different concentrations, aminated mesoporous silicon nanoparticles and kaempferol to replace the original culture media, setting 5 parallel groups for each concentration, and culturing for 48 h. After the incubation was completed, the drug-containing medium was discarded, and 100. mu.L of MTT solution (0.500 mg/mL) was added to each well and incubated for 4 h. The MTT solution was then discarded, 100. mu.L of DMSO was added to each well, and the absorbance of each well at 570 nm was measured using a microplate reader. Relative viability of cells (%) = (OD)Experimental group/ODBlank group) X 100. The non-dosed group served as blank control.
The results are shown in FIG. 7, the survival rate of Caco-2 cells is kept above 80% in the concentration range of 0-25 mg/ml, which indicates that the prepared material has better biocompatibility. However, when the concentration of the aminated mesoporous silicon nanoparticles is 125 mg/ml, the cell survival rate is reduced to about 50%, and under the same concentration, the cell survival rate of the kaempferol/mesoporous silicon composite nanoparticle dried group is still maintained to about 80%. The toxicity of the kaempferol/mesoporous silicon composite nano-particles is lower than that of the aminated mesoporous silicon nano-particles.
While embodiments of the invention have been described above, it is not limited to the applications set forth in the description and the embodiments, which are fully applicable in various fields of endeavor to which the invention pertains, and further modifications may readily be made by those skilled in the art, it being understood that the invention is not limited to the details shown and described herein without departing from the general concept defined by the appended claims and their equivalents.
Claims (10)
1. A preparation method of a mesoporous silicon composite material loaded with polyphenol substances is characterized by comprising the following steps:
s1, preparing coarse mesoporous silicon nanoparticles by using a sol-gel and surfactant template method;
s2, dispersing the coarse mesoporous silicon nanoparticles obtained in the step S1 in a solvent, and adding an alkylating reagent to obtain surface aminated mesoporous silicon nanoparticles;
s3, placing the mesoporous silicon nanoparticles with aminated surfaces obtained in the step S2 in a mixed solution of alcohol/hydrochloric acid, and eluting the template to obtain aminated mesoporous silicon nanoparticles with regular pore channels;
and S4, mixing the aminated mesoporous silicon nanoparticles obtained in the step S3 with a polyphenol substance for reaction to obtain the polyphenol substance-loaded mesoporous silicon nanoparticles.
2. The method for preparing the polyphenol substance-loaded mesoporous silicon composite material according to claim 1, wherein in S1, the preparation of the coarse mesoporous silicon nanoparticles by using a sol-gel and surfactant template method specifically comprises:
s1-1, mixing a surfactant and triethylamine TEA according to a mass-to-volume ratio of 1-3 g: uniformly dispersing 50 ul of the mixture in a flask filled with 20 mL of distilled water, stirring and heating to 80-100 ℃, and performing reflux condensation to obtain a mixed solution I;
s1-2, heating the mixed solution I to 80-100 ℃, standing at a constant temperature for 5-10 min, dropwise adding 0.5-2 ml of tetraethyl orthosilicate TEOS into the mixed solution I under the stirring condition, continuously stirring for reaction for 1-2 h, and performing reflux condensation to obtain a mixed solution II;
s1-3, heating the mixed solution II to 80-100 ℃, dropwise adding 0.5-2 ml of TEOS and 0.5-2 ml of 2-bis [3- (triethoxysilyl) propyl ] tetrasulfide BTESPT into the mixed solution II, continuously stirring for reacting for 4-6 h, and performing reflux condensation to obtain a mixed solution III;
s1-4, cooling the mixed solution III to room temperature, centrifuging at 3000 rpm for 10-30 min, collecting the precipitate, washing the precipitate with distilled water, and vacuum drying at-90 to-70 ℃ to obtain the coarse mesoporous silicon nanoparticles.
3. The method for preparing the mesoporous silicon composite material with supported polyphenol substances as claimed in claim 2, wherein the surface catalyst is one of cetyltrimethyl ammonium bromide CTAB and cetyltrimethyl ammonium chloride CTAC.
4. The method of claim 1, wherein in step S2, the step of dispersing the coarse mesoporous silicon nanoparticles in a solvent and adding an alkylating agent to obtain the mesoporous silicon nanoparticles with aminated surface comprises:
dispersing the coarse mesoporous silicon nanoparticles into methanol according to the mass-volume ratio of 0.5-1.5 g: 75 mL, adding an alkylating reagent, stirring at room temperature for 20-30 h, centrifuging at 3000 rpm for 10-30 min, and collecting to obtain the surface aminated mesoporous silicon nanoparticles.
5. The method for preparing the mesoporous silicon composite material with the polyphenol substances as claimed in claim 4, wherein the alkylating reagent is 3-Aminopropyltriethoxysilane (APTES).
6. The method of claim 4, wherein in S3, the step of placing the mesoporous silicon nanoparticles with aminated surface into a mixture of alcohol and hydrochloric acid, and eluting the template to obtain aminated mesoporous silicon nanoparticles with regular pores specifically comprises:
s3-1, weighing 1 g of the mesoporous silicon nanoparticles with aminated surfaces, and placing the mesoporous silicon nanoparticles with aminated surfaces in a volume ratio of 80-100 mL: carrying out ultrasonic treatment on 10 mL of alcohol/hydrochloric acid mixed solution for 5-15 min to obtain a dispersion solution;
s3-2, placing the dispersion solution in a water bath kettle at the temperature of 75-85 ℃ to be continuously stirred for 20-30 h, and centrifuging to remove supernatant fluid to obtain a retentate;
s3-3, adding 2-4 ml of ammonia water into the retentate overnight, centrifuging at the rotating speed of 3000 rpm for 10-30 min, adding 100 ml of distilled water, and stirring at the constant temperature of 75-85 ℃ for 4-8 h to obtain a stirring solution;
s3-4, centrifuging the stirred solution at the rotating speed of 3000 rpm for 10-30 min, and drying the collected precipitate in vacuum at the temperature of-90 to-70 ℃ to obtain the aminated mesoporous silicon nano-particles.
7. The method for preparing the mesoporous silicon composite material with the polyphenol substances as claimed in claim 6, wherein the alcohol in the alcohol/hydrochloric acid mixed solution is one of methanol and ethanol.
8. The method of claim 1, wherein in step S4, the mixing and reacting of the aminated mesoporous silicon nanoparticles with the polyphenol material to obtain the polyphenol material-loaded mesoporous silicon nanoparticles specifically comprises:
s4-1, mixing the aminated mesoporous silicon nanoparticles according to the mass-volume ratio of 450-550 mg: uniformly dispersing 100 mL of the mixture in ethanol, and performing ultrasonic treatment for 5-15 min to obtain an ultrasonic solution;
s4-2, adding 550 mg of 450-550 mg of polyphenol material into the ultrasonic solution, and stirring for 20-30 h at room temperature in a dark place to obtain a polyphenol mixed solution;
s4-3, centrifuging the polyphenol mixed solution at the rotating speed of 3000 rpm for 10-30 min, removing supernatant, adding 100 ml of distilled water into residues, cleaning, and freeze-drying in a freeze vacuum dryer to obtain the mesoporous silicon nanoparticles loaded with the polyphenol substances.
9. The method for preparing the mesoporous silicon composite material loaded with polyphenol substances as claimed in claim 8, wherein the polyphenol substances are any one of kaempferol, tangeretin and daidzein.
10. The application of the polyphenol substance-loaded mesoporous silicon nanoparticles prepared by the preparation method of the polyphenol substance-loaded mesoporous silicon composite material disclosed by claim 1 in the aspects of food and biomedicine.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110254933.3A CN113019347A (en) | 2021-03-09 | 2021-03-09 | Preparation method and application of polyphenol substance-loaded mesoporous silicon composite material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110254933.3A CN113019347A (en) | 2021-03-09 | 2021-03-09 | Preparation method and application of polyphenol substance-loaded mesoporous silicon composite material |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN113019347A true CN113019347A (en) | 2021-06-25 |
Family
ID=76467246
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110254933.3A Pending CN113019347A (en) | 2021-03-09 | 2021-03-09 | Preparation method and application of polyphenol substance-loaded mesoporous silicon composite material |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN113019347A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113457633A (en) * | 2021-07-06 | 2021-10-01 | 福州大学 | Polyphenol-modified gamma-alumina-based porous carbon composite material, and preparation method and application thereof |
| CN114948910A (en) * | 2022-06-21 | 2022-08-30 | 武汉工程大学 | Chinese chestnut shell polyphenol sustained-release material with small intestine targeted release, and preparation and application thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105343895A (en) * | 2015-12-04 | 2016-02-24 | 福州大学 | Dual-targeting ursolic acid (UA)/siRNA loaded fluorescent mesoporous silica dioxide-hyaluronic acid and application |
-
2021
- 2021-03-09 CN CN202110254933.3A patent/CN113019347A/en active Pending
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105343895A (en) * | 2015-12-04 | 2016-02-24 | 福州大学 | Dual-targeting ursolic acid (UA)/siRNA loaded fluorescent mesoporous silica dioxide-hyaluronic acid and application |
Non-Patent Citations (2)
| Title |
|---|
| SHUAI JIANG等: "Versatile Preparation of Silica Nanocapsules for Biomedical Applications", 《PART. PART. SYST. CHARACT.》 * |
| ZANIB CHAUDHARY等: "Encapsulation and Controlled Release of Resveratrol Within Functionalized Mesoporous Silica Nanoparticles for Prostate Cancer Therapy", 《FRONTIERS IN BIOENGINEERING AND BIOTECHNOLOGY》 * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113457633A (en) * | 2021-07-06 | 2021-10-01 | 福州大学 | Polyphenol-modified gamma-alumina-based porous carbon composite material, and preparation method and application thereof |
| CN114948910A (en) * | 2022-06-21 | 2022-08-30 | 武汉工程大学 | Chinese chestnut shell polyphenol sustained-release material with small intestine targeted release, and preparation and application thereof |
| CN114948910B (en) * | 2022-06-21 | 2024-04-09 | 武汉工程大学 | Chestnut shell polyphenol slow-release material for targeted release of small intestine and preparation and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN113019347A (en) | Preparation method and application of polyphenol substance-loaded mesoporous silicon composite material | |
| AU2020101112A4 (en) | Carborane-modified mesoporous silica nanosphere (msn) and preparation method thereof | |
| CN109589418A (en) | A kind of mesoporous silicon oxide medicine-carried nano particles and its preparation method and application of the schiff bases copolymer cladding with pH responsiveness | |
| Gai et al. | Uniform and size-tunable mesoporous silica with fibrous morphology for drug delivery | |
| CN107299417B (en) | A kind of WO3/ZnWO4The preparation method and products thereof of composite micro-nano rice fiber | |
| CN107556472B (en) | The covalent organic porous polymer material of hollow/solid controllable spherical of one kind, Preparation method and use | |
| CN106644640B (en) | Load the preparation method of pesticide pyraclostrobin sample, purposes and its in reed stem wilt opportunistic pathogen fluorescent tracing application | |
| CN101948139A (en) | Method for preparing novel mesoporous silica nano balls | |
| CN107474160B (en) | A kind of Phosphorylcholine base polyethylene glycol-chitosan and preparation method thereof | |
| CN113523297B (en) | Method for preparing nano-silver by using peony extract | |
| CN111494337A (en) | ZIF-8 nano particle wrapping anti-aging drug and application thereof | |
| CN114246870B (en) | MIL-101 (Fe) -T705 and preparation method and application thereof | |
| CN115155306A (en) | Efficient remover for indoor formaldehyde and organic volatile matters, and preparation method and application thereof | |
| CN108743960A (en) | A kind of mesoporous carbon nanoparticle and its application | |
| CN109827814A (en) | A kind of sampling film preparation of novel air particulate matter agar and exempt from solvent extraction cell process for exposing | |
| CN103305497A (en) | Immobilized enzyme microcapsule for repairing organic contamination soil and preparation method thereof | |
| Hongtao et al. | Preparation and application of methimazole molecularly imprinted polymer based on silver-loaded dendritic fiber-type silica | |
| KR100992875B1 (en) | Antioxidant loaded sustained release porous silica matrix and preparing method thereof | |
| CN103169667B (en) | Preparation method of multifunctional meso-porous silicon nano preparation carrying gossypol derivative | |
| CN113860380B (en) | Method for preparing hematite nano-particles by using fungus extracellular polymer | |
| CN107149683B (en) | Preparation method and application of mesoporous silica nanoparticles with bell structure | |
| CN115919805A (en) | Sea urchin-shaped mesoporous silica-loaded curcumin nanoparticles and preparation method thereof | |
| CN111515384B (en) | Nano-silver material mediated and synthesized by moringa seed extract | |
| CN111387215B (en) | Application of nano-silver material mediated and synthesized by moringa seed extract in antibiosis and antioxidation | |
| CN100528755C (en) | Plum-blossom-like multicrystal-state nano zinc-oxide purticles and its preparing method |
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 | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20210625 |