CN116655830A - Cyclodextrin derivative and preparation method and application thereof - Google Patents
Cyclodextrin derivative and preparation method and application thereof Download PDFInfo
- Publication number
- CN116655830A CN116655830A CN202310723685.1A CN202310723685A CN116655830A CN 116655830 A CN116655830 A CN 116655830A CN 202310723685 A CN202310723685 A CN 202310723685A CN 116655830 A CN116655830 A CN 116655830A
- Authority
- CN
- China
- Prior art keywords
- cyclodextrin
- antibacterial
- essential oil
- toluenesulfonyl chloride
- inclusion
- 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.)
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- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical class O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 title claims abstract description 107
- 238000002360 preparation method Methods 0.000 title claims abstract description 35
- 229920000858 Cyclodextrin Polymers 0.000 claims abstract description 121
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims abstract description 88
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 88
- 239000000341 volatile oil Substances 0.000 claims abstract description 66
- 235000017858 Laurus nobilis Nutrition 0.000 claims abstract description 59
- 235000005212 Terminalia tomentosa Nutrition 0.000 claims abstract description 59
- 244000125380 Terminalia tomentosa Species 0.000 claims abstract description 59
- -1 p-toluene sulfonated cyclodextrin Chemical class 0.000 claims abstract description 50
- MTCFGRXMJLQNBG-UHFFFAOYSA-M serinate Chemical compound OCC(N)C([O-])=O MTCFGRXMJLQNBG-UHFFFAOYSA-M 0.000 claims abstract description 37
- 239000008367 deionised water Substances 0.000 claims abstract description 35
- 229910021641 deionized water Inorganic materials 0.000 claims abstract description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 35
- 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 abstract description 32
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 21
- GKCXXDSWWDWUHS-BYPYZUCNSA-N ethyl (2s)-2-amino-3-hydroxypropanoate Chemical compound CCOC(=O)[C@@H](N)CO GKCXXDSWWDWUHS-BYPYZUCNSA-N 0.000 claims abstract description 18
- 238000002156 mixing Methods 0.000 claims abstract description 18
- 241000196324 Embryophyta Species 0.000 claims description 11
- 230000000845 anti-microbial effect Effects 0.000 claims description 5
- 239000005018 casein Substances 0.000 claims description 5
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 claims description 5
- 235000021240 caseins Nutrition 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 239000004599 antimicrobial Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000012567 medical material Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract description 68
- 230000007774 longterm Effects 0.000 abstract description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
- 238000003756 stirring Methods 0.000 description 23
- 230000000052 comparative effect Effects 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 14
- 238000001035 drying Methods 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 229960004853 betadex Drugs 0.000 description 12
- 239000001116 FEMA 4028 Substances 0.000 description 11
- 108010013296 Sericins Proteins 0.000 description 11
- 235000011175 beta-cyclodextrine Nutrition 0.000 description 11
- 230000000694 effects Effects 0.000 description 11
- 238000001914 filtration Methods 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 238000009210 therapy by ultrasound Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 230000002209 hydrophobic effect Effects 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000012716 precipitator Substances 0.000 description 4
- 238000000967 suction filtration Methods 0.000 description 4
- AXTGDCSMTYGJND-UHFFFAOYSA-N 1-dodecylazepan-2-one Chemical compound CCCCCCCCCCCCN1CCCCCC1=O AXTGDCSMTYGJND-UHFFFAOYSA-N 0.000 description 3
- 125000004185 ester group Chemical group 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229960003639 laurocapram Drugs 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 description 1
- 229920000856 Amylose Polymers 0.000 description 1
- 241000193830 Bacillus <bacterium> Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical group OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 102000000340 Glucosyltransferases Human genes 0.000 description 1
- 108010055629 Glucosyltransferases Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 108091034117 Oligonucleotide Proteins 0.000 description 1
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 1
- 238000005411 Van der Waals force Methods 0.000 description 1
- JLCPHMBAVCMARE-UHFFFAOYSA-N [3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[3-[[3-[[3-[[3-[[3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-[[5-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(6-aminopurin-9-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl [5-(6-aminopurin-9-yl)-2-(hydroxymethyl)oxolan-3-yl] hydrogen phosphate Polymers Cc1cn(C2CC(OP(O)(=O)OCC3OC(CC3OP(O)(=O)OCC3OC(CC3O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c3nc(N)[nH]c4=O)C(COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3COP(O)(=O)OC3CC(OC3CO)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3ccc(N)nc3=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cc(C)c(=O)[nH]c3=O)n3cc(C)c(=O)[nH]c3=O)n3ccc(N)nc3=O)n3cc(C)c(=O)[nH]c3=O)n3cnc4c3nc(N)[nH]c4=O)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)n3cnc4c(N)ncnc34)O2)c(=O)[nH]c1=O JLCPHMBAVCMARE-UHFFFAOYSA-N 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 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 description 1
- 229940043377 alpha-cyclodextrin Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001212 derivatisation Methods 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000007306 functionalization reaction Methods 0.000 description 1
- 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 description 1
- 229940080345 gamma-cyclodextrin Drugs 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000006916 nutrient agar Substances 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
- A01N25/10—Macromolecular compounds
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/26—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests in coated particulate form
- A01N25/28—Microcapsules or nanocapsules
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/08—Magnoliopsida [dicotyledons]
- A01N65/24—Lauraceae [Laurel family], e.g. laurel, avocado, sassafras, cinnamon or camphor
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P1/00—Disinfectants; Antimicrobial compounds or mixtures thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P3/00—Fungicides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08B—POLYSACCHARIDES; DERIVATIVES THEREOF
- C08B37/00—Preparation of polysaccharides not provided for in groups C08B1/00 - C08B35/00; Derivatives thereof
- C08B37/0006—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid
- C08B37/0009—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid alpha-D-Glucans, e.g. polydextrose, alternan, glycogen; (alpha-1,4)(alpha-1,6)-D-Glucans; (alpha-1,3)(alpha-1,4)-D-Glucans, e.g. isolichenan or nigeran; (alpha-1,4)-D-Glucans; (alpha-1,3)-D-Glucans, e.g. pseudonigeran; Derivatives thereof
- C08B37/0012—Cyclodextrin [CD], e.g. cycle with 6 units (alpha), with 7 units (beta) and with 8 units (gamma), large-ring cyclodextrin or cycloamylose with 9 units or more; Derivatives thereof
- C08B37/0015—Inclusion compounds, i.e. host-guest compounds, e.g. polyrotaxanes
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Abstract
The invention discloses a cyclodextrin derivative, a preparation method and application thereof, belongs to the technical field of cyclodextrin derivative, and particularly relates to a cyclodextrin derivative, which comprises the following components: beta-CD reacts with p-toluenesulfonyl chloride to generate p-toluene sulfonated cyclodextrin, and the p-toluene sulfonated cyclodextrin reacts with serine ethyl ester to obtain serinate cyclodextrin; mixing beta-CD in deionized water; the p-toluenesulfonyl chloride is used in the form of a solution of p-toluenesulfonyl chloride obtained by dissolving it in acetonitrile, the serine ethyl ester being used in an amount of 6-14% by weight of p-toluene sulphonated cyclodextrin. The antibacterial inclusion compound is prepared from the serinate cyclodextrin and the laurel essential oil, has good inclusion rate, good embedding rate and good placement stability, and has good antibacterial effect after long-term placement.
Description
Technical Field
The invention belongs to the technical field of cyclodextrin derivatization, and particularly relates to a cyclodextrin derivative, and a preparation method and application thereof.
Background
Cyclodextrin is a generic term for a series of cyclic oligosaccharides produced by amylose under the action of a cyclodextrin glucosyltransferase produced by Bacillus, and is usually composed of 6-12D-coresGlucopyranosyl is formed by connecting alpha-1, 4 glycosidic bonds, and is respectively alpha, beta and gamma-cyclodextrin. The cyclodextrin molecule has a slightly conical hollow cylinder three-dimensional ring structure, and the outer upper end (larger opening end) is formed by C 2 And C 3 Is composed of secondary hydroxyl groups, the lower end (smaller open end) of which is C 6 Is hydrophilic and the cavity is shielded by C-H bonds to form a hydrophobic region. The special hydrophobic cavity can be used for identifying various guest molecules such as hydrophobic small molecules, ions, proteins, oligonucleotides and the like by utilizing hydrophobic acting force, oxygen bond, van der Waals force and the like to form inclusion complex, and the reactivity of the guest molecules and the properties of the solution and the like are greatly changed. The special inclusion has the advantages of low cost, easy obtainment and the like, and has wide application in the fields of pharmacy, separation, catalysis, food, textile and the like.
The glucopyranose unit of cyclodextrin has multiple hydroxyl groups, can be used as active sites for further functionalization, and can be modified by chemical or enzymatic reaction to obtain cyclodextrin derivatives of different types for improving the inclusion capacity and other application properties of cyclodextrin. Taking beta-cyclodextrin as an example, beta-cyclodextrin derivatives can be generally classified into three types of hydrophilic, hydrophobic and ionic according to the nature of the modifying group. The present invention aims to provide a novel cyclodextrin derivative and its use.
Disclosure of Invention
The invention aims to provide a cyclodextrin derivative which can contain antibacterial substances and has good inclusion rate and embedding rate, and a preparation method thereof.
The technical scheme adopted by the invention for achieving the purpose is as follows:
a cyclodextrin derivative comprising: beta-CD reacts with p-toluenesulfonyl chloride to generate p-toluene sulfonated cyclodextrin, and the p-toluene sulfonated cyclodextrin reacts with serine ethyl ester to obtain serinate cyclodextrin; mixing beta-CD in deionized water; the p-toluenesulfonyl chloride is used in the form of a solution of p-toluenesulfonyl chloride obtained by dissolving it in acetonitrile, the serine ethyl ester being used in an amount of 6-14% by weight of p-toluene sulphonated cyclodextrin.
Preferably, the beta-CD is used in an amount of 65-75wt% of deionized water.
Preferably, the p-toluenesulfonyl chloride solution contains 40-60wt% of p-toluenesulfonyl chloride.
Preferably, the p-toluenesulfonyl chloride solution contains 40-60wt% of p-toluenesulfonyl chloride.
More preferably, the serinate-based cyclodextrin is obtained by reacting beta-CD with p-toluenesulfonyl chloride after activation with serine ethyl ester.
More preferably, in the preparation of the serinate-based cyclodextrin, beta-CD is added into deionized water, sodium hydroxide is added under stirring, then p-toluenesulfonyl chloride solution is added, stirring is carried out at the temperature of minus 5 ℃ to 0 ℃ for 2-6 h, after the reaction is finished, a precipitator is added for separating out solid, filtering, drying, extracting and removing the p-toluenesulfonyl chloride by diethyl ether, then drying to obtain p-toluenesulfonated cyclodextrin, the p-toluenesulfonated cyclodextrin solution is prepared, serine ethyl ester is added, stirring and mixing are carried out, stirring is carried out at the temperature of 60-90 ℃ for 1-6 h, after the reaction is finished, most of solvent is removed under reduced pressure, then the solvent is transferred into absolute ethyl alcohol for precipitation, standing is carried out at the temperature of minus 5 ℃ to 0 ℃ for 12-36 h, and suction filtration is carried out, so as to obtain the serinate-based cyclodextrin.
Still more preferably, in the preparation of the serinate-based cyclodextrin, the beta-CD is used in an amount of 65-75wt% of deionized water.
Still more preferably, in the preparation of the serinate-based cyclodextrin, sodium hydroxide is used in an amount of 16-25wt% of deionized water.
Still more preferably, in the preparation of the serinyl cyclodextrin, the p-toluenesulfonyl chloride solution is obtained by dissolving p-toluenesulfonyl chloride in acetonitrile, and the p-toluenesulfonyl chloride solution contains 40-60wt% of p-toluenesulfonyl chloride.
Still more preferably, in the preparation of the serinate-based cyclodextrin, the precipitant is deionized water.
Still more preferably, in the preparation of the serinate-based cyclodextrin, the p-toluene sulfonated cyclodextrin solution is obtained by adding p-toluene sulfonated cyclodextrin into deionized water, and the p-toluene sulfonated cyclodextrin solution contains 10-40wt% of p-toluene sulfonated cyclodextrin.
Still more preferably, serine ethyl ester is used in the preparation of serinate-based cyclodextrin in an amount of 6 to 14wt% of p-toluene sulfonated cyclodextrin.
The invention discloses an antibacterial inclusion compound, which comprises the following components: the cyclodextrin derivative and plant essential oil are obtained. After the beta-CD reacts with the p-toluenesulfonyl chloride, serine ethyl ester is introduced to obtain the serinate-based cyclodextrin, after the serinate-based cyclodextrin is mixed with the plant essential oil, the plant essential oil is captured by the serinate-based cyclodextrin to be included, after the serine ethyl ester is introduced, the inclusion performance of the cyclodextrin is improved, the inclusion and embedding effect of the plant essential oil is greatly improved, and the plant essential oil can be stored for a long time and still has high antibacterial effect after being placed for a long time.
Preferably, the plant essential oil is laurel essential oil.
Preferably, the amount of laurel essential oil is 1-20wt% of the cyclodextrin derivative.
Preferably, the cyclodextrin derivative is replaced with a serinate-based cyclodextrin complex containing casein acid.
Preferably, in the preparation of the antibacterial inclusion compound, the silk-urethane-based cyclodextrin is added into deionized water, stirred and mixed for 1-3 hours at the temperature of 40-60 ℃ to obtain silk-urethane-based cyclodextrin solution, then the laurel essential oil solution is added into the silk-urethane-based cyclodextrin solution, stirred for 1-4 hours at the temperature of 50-80 ℃, then the ultrasonic treatment is carried out for 20-60 minutes, finally the cold storage is carried out for 16-48 hours at the temperature of 0-5 ℃, after the cold storage is finished, the filtration is carried out, and the drying is carried out at the temperature of 25-35 ℃ to obtain the laurel essential oil-ester-based cyclodextrin inclusion compound, namely the antibacterial inclusion compound.
More preferably, the antimicrobial clathrate is prepared by a solution of sericin containing 5-20wt% sericin.
More preferably, in the preparation of the antibacterial inclusion compound, the laurel essential oil solution is obtained by adding and mixing laurel essential oil into methanol, wherein the laurel essential oil solution contains 10-25wt% of laurel essential oil.
More preferably, in the preparation of the antibacterial clathrate, the laurel essential oil solution is used in such an amount that the amount of laurel essential oil therein is 1 to 20wt% of the serinate-based cyclodextrin.
Preferably, in the preparation of the silk-urethane-based cyclodextrin complex, silk-urethane-based cyclodextrin and casein acid are added into deionized water, stirred for 1-3 hours at 50-70 ℃, cooled and freeze-dried to obtain the silk-urethane-based cyclodextrin complex. After the butyric acid and the silk amino ester cyclodextrin are mixed, only a small amount of the obtained silk amino ester cyclodextrin compound is needed, when the silk amino ester cyclodextrin compound is used for clathrating plant essential oil, the effect of clathrating rate and embedding rate of the plant essential oil is improved, the antibacterial effect of the antibacterial clathrate compound after long-term storage is improved, and the effect of improving the release of the plant essential oil is achieved under the same conditions possibly due to the use of the butyric acid.
More preferably, in the preparation of the serinate-based cyclodextrin complex, the amount of casein acid used is 0.3 to 1.5wt% of serinate-based cyclodextrin.
More preferably, in the preparation of the sericin-based cyclodextrin complex, sericin-based cyclodextrin is used in an amount of 5 to 15wt% of deionized water.
Preferably, in the preparation of the antibacterial inclusion compound, the silk-urethane-based cyclodextrin compound is added into deionized water, stirred and mixed for 1-3 hours at the temperature of 40-60 ℃ to obtain silk-urethane-based cyclodextrin compound solution, then the laurel essential oil solution is added into the silk-urethane-based cyclodextrin compound solution, stirred for 1-4 hours at the temperature of 50-80 ℃, then the ultrasonic treatment is carried out for 20-60 minutes, finally the cold storage is carried out for 16-48 hours at the temperature of 0-5 ℃, after the cold storage is finished, the filtering is carried out, and the drying is carried out at the temperature of 25-35 ℃ to obtain the laurel essential oil-ester-based cyclodextrin compound inclusion compound, namely the antibacterial inclusion compound.
More preferably, the antimicrobial clathrate is prepared by a solution of silk-urethane-based cyclodextrin complex containing 5-20wt% silk-urethane-based cyclodextrin complex.
More preferably, in the preparation of the antibacterial inclusion compound, the laurel essential oil solution is obtained by adding and mixing laurel essential oil into methanol, wherein the laurel essential oil solution contains 10-25wt% of laurel essential oil.
More preferably, in the preparation of the antibacterial clathrate, the laurel essential oil solution is used in such an amount that the amount of laurel essential oil therein is 1 to 20wt% of the serinate-based cyclodextrin complex.
The invention discloses application of the cyclodextrin derivative in preparing an antibacterial material and/or a medical material.
The invention adopts beta-CD and p-toluenesulfonyl chloride to react to generate p-toluenesulfonyl sulfonated cyclodextrin, and the serinate cyclodextrin obtained by the reaction of the p-toluenesulfonyl sulfonated cyclodextrin and serine ethyl ester is applied to the inclusion of laurel essential oil to obtain the antibacterial inclusion compound, so that the invention has the following beneficial effects: the inclusion rate of the antibacterial inclusion compound is good, and the inclusion rate is 60-70%; the antibacterial inclusion compound has good embedding rate, and the embedding rate is 72-84%; the antibacterial inclusion compound has good placement stability and good antibacterial effect after long-term placement. Therefore, the invention is a cyclodextrin derivative which can contain antibacterial substances and has good inclusion rate and embedding rate, and a preparation method thereof.
Drawings
FIG. 1 is an infrared spectrum of a serinate-based cyclodextrin;
FIG. 2 is a graph of inclusion rate of an antimicrobial clathrate;
FIG. 3 is a graph of the entrapment rate of antimicrobial inclusion compounds;
fig. 4 is a graph showing the antibacterial rate of the antibacterial clathrate after long-term storage.
Detailed Description
The technical scheme of the invention is further described in detail below with reference to the specific embodiments and the attached drawings:
example 1:
a method for preparing serinate cyclodextrin,
preparation of serinate-based cyclodextrin: adding beta-CD into deionized water, adding sodium hydroxide under stirring, adding a p-toluenesulfonyl chloride solution, stirring at a temperature of 0 ℃ for reaction for 4h, adding a precipitator to separate out solid after the reaction is completed, filtering, drying, extracting with diethyl ether to remove p-toluenesulfonyl chloride, then drying to obtain p-toluenesulfonated cyclodextrin, preparing a p-toluenesulfonated cyclodextrin solution, adding serine ethyl ester, stirring and mixing, stirring at a temperature of 90 ℃ for reaction for 4h, distilling under reduced pressure to remove most of the solvent after the reaction is completed, transferring to absolute ethyl alcohol, separating out precipitate, standing at a temperature of 0 ℃ for 24h, and performing suction filtration to obtain the serinate-based cyclodextrin. The beta-CD is 70wt% of deionized water, the sodium hydroxide is 21wt% of deionized water, the p-toluenesulfonyl chloride solution is obtained by dissolving p-toluenesulfonyl chloride in acetonitrile, the p-toluenesulfonyl chloride solution contains 50wt% of p-toluenesulfonyl chloride, the precipitant is deionized water, the p-toluenesulfonyl cyclodextrin solution is obtained by adding p-toluenesulfonyl cyclodextrin into deionized water, the p-toluenesulfonyl cyclodextrin solution contains 30wt% of p-toluenesulfonyl cyclodextrin, and the serine ethyl ester is 11wt% of p-toluenesulfonyl cyclodextrin.
Example 2:
a preparation method of an antibacterial inclusion compound,
preparation of serinate-based cyclodextrin: adding beta-CD into deionized water, adding sodium hydroxide under stirring, adding a p-toluenesulfonyl chloride solution, stirring at a temperature of 0 ℃ for reaction for 4h, adding a precipitator to separate out solid after the reaction is completed, filtering, drying, extracting with diethyl ether to remove p-toluenesulfonyl chloride, then drying to obtain p-toluenesulfonated cyclodextrin, preparing a p-toluenesulfonated cyclodextrin solution, adding serine ethyl ester, stirring and mixing, stirring at a temperature of 90 ℃ for reaction for 4h, distilling under reduced pressure to remove most of the solvent after the reaction is completed, transferring to absolute ethyl alcohol, separating out precipitate, standing at a temperature of 0 ℃ for 24h, and performing suction filtration to obtain the serinate-based cyclodextrin. The beta-CD is 70wt% of deionized water, the sodium hydroxide is 21wt% of deionized water, the p-toluenesulfonyl chloride solution is obtained by dissolving p-toluenesulfonyl chloride in acetonitrile, the p-toluenesulfonyl chloride solution contains 50wt% of p-toluenesulfonyl chloride, the precipitant is deionized water, the p-toluenesulfonyl cyclodextrin solution is obtained by adding p-toluenesulfonyl cyclodextrin into deionized water, the p-toluenesulfonyl cyclodextrin solution contains 30wt% of p-toluenesulfonyl cyclodextrin, and the serine ethyl ester is 11wt% of p-toluenesulfonyl cyclodextrin.
Preparation of antibacterial inclusion compound: adding silk amino ester cyclodextrin into deionized water, stirring and mixing for 2 hours at 50 ℃ to obtain silk amino ester cyclodextrin solution, adding the laurel essential oil solution into the silk amino ester cyclodextrin solution, stirring for 2 hours at 60 ℃, performing ultrasonic treatment for 40 minutes, refrigerating for 24 hours at 0 ℃, filtering after the refrigerating is finished, and drying at 30 ℃ to obtain the laurel essential oil-ester cyclodextrin inclusion compound, namely the antibacterial inclusion compound. The silk ammonia ester group cyclodextrin solution contains 10wt% of silk ammonia ester group cyclodextrin, the laurel essential oil solution is obtained by adding laurel essential oil into methanol and mixing, the laurel essential oil solution contains 15wt% of laurel essential oil, and the use amount of the laurel essential oil solution is such that the amount of the laurel essential oil is 10wt% of the silk ammonia ester group cyclodextrin.
Example 3:
a preparation method of an antibacterial inclusion compound,
preparation of serinate-based cyclodextrin: adding beta-CD into deionized water, adding sodium hydroxide under stirring, adding a p-toluenesulfonyl chloride solution, stirring at a temperature of 0 ℃ for reaction for 4h, adding a precipitator to separate out solid after the reaction is completed, filtering, drying, extracting with diethyl ether to remove p-toluenesulfonyl chloride, then drying to obtain p-toluenesulfonated cyclodextrin, preparing a p-toluenesulfonated cyclodextrin solution, adding serine ethyl ester, stirring and mixing, stirring at a temperature of 90 ℃ for reaction for 4h, distilling under reduced pressure to remove most of the solvent after the reaction is completed, transferring to absolute ethyl alcohol, separating out precipitate, standing at a temperature of 0 ℃ for 24h, and performing suction filtration to obtain the serinate-based cyclodextrin. The beta-CD is 70wt% of deionized water, the sodium hydroxide is 21wt% of deionized water, the p-toluenesulfonyl chloride solution is obtained by dissolving p-toluenesulfonyl chloride in acetonitrile, the p-toluenesulfonyl chloride solution contains 50wt% of p-toluenesulfonyl chloride, the precipitant is deionized water, the p-toluenesulfonyl cyclodextrin solution is obtained by adding p-toluenesulfonyl cyclodextrin into deionized water, the p-toluenesulfonyl cyclodextrin solution contains 30wt% of p-toluenesulfonyl cyclodextrin, and the serine ethyl ester is 11wt% of p-toluenesulfonyl cyclodextrin.
Preparation of serinate-based cyclodextrin complexes: adding the silk amino ester cyclodextrin and the butyric acid into deionized water, stirring for 1-3 hours at 50-70 ℃, cooling and freeze-drying to obtain the silk amino ester cyclodextrin compound. The amount of butyric acid is 0.7wt% of silk-urethane-based cyclodextrin, and the amount of silk-urethane-based cyclodextrin is 5-15wt% of deionized water.
Preparation of antibacterial inclusion compound: adding the silk-urethane-based cyclodextrin compound into deionized water, stirring and mixing for 2 hours at 50 ℃ to obtain a silk-urethane-based cyclodextrin compound solution, adding the laurel essential oil solution into the silk-urethane-based cyclodextrin compound solution, stirring for 2 hours at 60 ℃, performing ultrasonic treatment for 40 minutes, refrigerating for 24 hours at 0 ℃, filtering after the refrigerating is finished, and drying at 30 ℃ to obtain the laurel essential oil-ester-based cyclodextrin compound inclusion compound, namely the antibacterial inclusion compound. The silk ammonia ester group cyclodextrin compound solution contains 10wt% of silk ammonia ester group cyclodextrin compound, the laurel essential oil solution is obtained by adding laurel essential oil into methanol and mixing, the laurel essential oil solution contains 15wt% of laurel essential oil, and the use amount of the laurel essential oil solution is such that the amount of the laurel essential oil is 10wt% of the silk ammonia ester group cyclodextrin compound.
Example 4:
a preparation method of an antibacterial inclusion compound,
this example differs from example 3 only in that in the preparation of the sericin-based cyclodextrin complex, casein is used in an amount of 1.2wt% of sericin-based cyclodextrin.
Comparative example 1:
a preparation method of an antibacterial inclusion compound,
preparation of antibacterial inclusion compound: adding beta-cyclodextrin into deionized water, stirring and mixing for 2 hours at 50 ℃ to obtain beta-cyclodextrin solution, adding the laurel essential oil solution into the beta-cyclodextrin solution, stirring for 2 hours at 60 ℃, performing ultrasonic treatment for 40 minutes, refrigerating for 24 hours at 0 ℃, filtering after the refrigerating is finished, and drying at 30 ℃ to obtain the laurel essential oil-cyclodextrin inclusion compound, namely the antibacterial inclusion compound. The beta-cyclodextrin solution contains 10wt% of beta-cyclodextrin, the laurel essential oil solution is obtained by adding laurel essential oil into methanol and mixing, the laurel essential oil solution contains 15wt% of laurel essential oil, and the use amount of the laurel essential oil solution is such that the amount of the laurel essential oil is 10wt% of the beta-cyclodextrin.
Test example:
1. infrared sign
The serinate-based cyclodextrin prepared in example 7 was tabletted with potassium bromide and detected by infrared.
The serinate-based cyclodextrin prepared by the invention is shown in figure 1, wherein 3418cm -1 The infrared absorption peak of hydroxyl is wider, 2941cm -1 The position is methyl infrared absorption peak, 2862cm -1 Is provided with methylene infrared absorption peak (1682 cm) -1 The position is carbonyl infrared absorption peak, 1603cm -1 The infrared absorption peak of nitrogen and hydrogen is shown to obtain the serinate cyclodextrin.
2. Inclusion rate test of antibacterial inclusion compound
Test sample: antibacterial inclusion compounds prepared in examples 2 to 4 and comparative example 1.
The raw materials and test samples before inclusion were weighed separately.
The inclusion rate was calculated as follows:
inclusion ratio = weight of test sample/total weight of raw material x 100%.
In example 2, the starting material was laurocapram, a pre-inclusion serinate cyclodextrin.
In examples 3-4, the starting material was laurocapram, a pre-inclusion serinate cyclodextrin complex.
In comparative example 1, the raw materials were laurocapram essential oil, β -cyclodextrin before inclusion.
The inclusion rate test result of the antibacterial inclusion compound prepared by the method is shown in fig. 2, wherein A is example 2, B is example 3, C is example 4, D is comparative example 1, the inclusion rate of the antibacterial inclusion compound prepared in example 2 is 61.71%, the inclusion rate of the antibacterial inclusion compound prepared in comparative example 1 is 61.71%, and compared with comparative example 1, example 2 shows that the silk-urethane-based cyclodextrin prepared by the method has better inclusion effect on the laurel essential oil, the inclusion effect of the silk-urethane-based cyclodextrin on the laurel essential oil is superior to that of beta-cyclodextrin, and compared with comparative example 1, the inclusion rate of the antibacterial inclusion compound prepared in example 2 is improved by 15.04%; the inclusion ratio of the antibacterial inclusion compound prepared in example 3 was 66.09%, the inclusion ratio of the antibacterial inclusion compound prepared in example 4 was 68.12%, and examples 3 to 4 compared with example 1 showed that the antibacterial inclusion compound prepared by mixing sericin with butyric acid showed excellent inclusion effect when the sericin cyclodextrin compound was used to include laurel essential oil, compared with example 2, the inclusion ratio of the antibacterial inclusion compound of example 3 was improved by 7.10%, and the inclusion ratio of the antibacterial inclusion compound of example 4 was improved by 10.39%.
The inclusion rate of the antibacterial inclusion compound prepared by the invention is 60-70%.
3. Antibacterial inclusion compound embedding rate test
Test sample: antibacterial inclusion compounds prepared in examples 2 to 4 and comparative example 1.
Adding the test sample into absolute ethyl alcohol, carrying out ultrasonic treatment at 40 ℃ to enable the test sample to be fully dispersed, fully releasing the laurel essential oil included in the test sample, and detecting the concentration of the laurel essential oil in the inclusion compound by adopting HPLC (high performance liquid chromatography) for filtering the filtrate through a filter membrane of 0.22 mu m to ensure that the release is fully achieved for 5 hours.
The embedding rate of the laurel essential oil is calculated according to the following formula:
embedding rate = concentration of laurel essential oil in inclusion compound/concentration of laurel essential oil in initial inclusion x 100%.
The embedding rate test result of the antibacterial inclusion compound prepared by the method is shown in fig. 3, wherein A is example 2, B is example 3, C is example 4, D is comparative example 1, the embedding rate of the antibacterial inclusion compound prepared in example 2 is 74.53%, the embedding rate of the antibacterial inclusion compound prepared in comparative example 1 is 79.48%, and compared with comparative example 1, example 2 shows that the silk-urethane-based cyclodextrin prepared by the method has better embedding effect on the laurel essential oil, the embedding effect of the silk-urethane-based cyclodextrin on the laurel essential oil is better than that of beta-cyclodextrin, and compared with comparative example 1, the embedding rate of the antibacterial inclusion compound prepared in example 2 is improved by 27.14%; the inclusion rate of the antibacterial inclusion compound prepared in example 3 was 79.48%, the inclusion rate of the antibacterial inclusion compound prepared in example 4 was 81.27%, and examples 3 to 4 compared with example 1 showed that the antibacterial inclusion compound prepared by mixing sericin with butyric acid, and the use of sericin cyclodextrin compound to form a sericin complex, when used to include laurel essential oil, had excellent inclusion effect, improved the inclusion rate of the antibacterial inclusion compound in example 3 by 6.64% and the inclusion rate of the antibacterial inclusion compound in example 4 by 9.04%, compared with example 2.
The embedding rate of the antibacterial inclusion compound prepared by the invention is 72-84%.
4. Antibacterial effect test after long-term placement
Test sample: antibacterial inclusion compounds prepared in examples 2 to 4 and comparative example 1.
Referring to the method of GB/T21510-2008, a test sample is placed in a room with the temperature of 25 ℃ and the humidity of 30%, placed for 30d, then placed in deionized solution, the solid content reaches 2%, fixed on a shaking table of a shaking incubator with the temperature of 25 ℃, and shaking for 30min at the speed of 20r/min, 1.0mL of shaking solution is respectively sucked and inoculated into a sterilization plate, 50 ℃ dissolved nutrient agar culture medium is added, the plate is turned over after solidification, and placed in a constant temperature incubator with the temperature of 37 ℃ to count the colony number of each plate. And determining the antibacterial property of the inclusion compound according to the antibacterial rate. And setting a blank group, wherein the blank group is to replace the oscillating liquid with deionized water.
The calculation formula of the bacteriostasis rate is as follows:
antibacterial ratio= (number of colonies in blank group-number of colonies in test group)/number of colonies in blank group×100%.
The antibacterial rate test result of the antibacterial inclusion compound prepared by the method is shown in fig. 4, wherein A is example 2, B is example 3, C is example 4, D is comparative example 1, the antibacterial rate of the antibacterial inclusion compound prepared in example 2 is 84.8%, the antibacterial rate of the antibacterial inclusion compound prepared in comparative example 1 is 63.3%, and compared with comparative example 1, the antibacterial inclusion compound prepared by the method of example 2 has longer preservation property, good antibacterial effect after long-term storage is still achieved, the long-term storage effect of the serine amino cyclodextrin on the laurel essential oil is better than that of beta-cyclodextrin, and compared with comparative example 1, the antibacterial rate of the antibacterial inclusion compound prepared in example 2 is improved by 33.97%; the antibacterial inclusion compound prepared in example 3 has a antibacterial rate of 92.3%, and the antibacterial inclusion compound prepared in example 4 has a antibacterial rate of 98.6%, and examples 3 to 4 compared with example 1 show that after the silk-urethane-based cyclodextrin compound is prepared by mixing silk-urethane-based cyclodextrin with butyric acid, the antibacterial inclusion compound has an excellent long-term storage effect and a good antibacterial effect after long-term storage when the silk-urethane-based cyclodextrin compound is used for inclusion of laurel essential oil, and compared with example 2, the antibacterial rate of the antibacterial inclusion compound of example 3 is improved by 8.84%, and the inclusion rate of the antibacterial inclusion compound of example 4 is improved by 16.27%.
The antibacterial inclusion compound prepared by the invention has good antibacterial effect after being placed for 30 d.
The above embodiments are merely for illustrating the present invention and not for limiting the same, and various changes and modifications may be made by one of ordinary skill in the art without departing from the spirit and scope of the invention. Therefore, all equivalent technical solutions are also within the scope of the present invention, which is defined by the claims.
Claims (9)
1. A cyclodextrin derivative comprising: beta-CD reacts with p-toluenesulfonyl chloride to generate p-toluene sulfonated cyclodextrin, and the p-toluene sulfonated cyclodextrin reacts with serine ethyl ester to obtain serinate cyclodextrin; the beta-CD is mixed in deionized water; the p-toluenesulfonyl chloride is used in the form of a solution of p-toluenesulfonyl chloride obtained by dissolving in acetonitrile, and the serine ethyl ester is used in an amount of 6-14wt% of p-toluene sulfonated cyclodextrin.
2. A cyclodextrin derivative according to claim 1, characterized in that: the beta-CD is used in an amount of 65-75wt% of deionized water.
3. A cyclodextrin derivative according to claim 1, characterized in that: the p-toluenesulfonyl chloride solution contains 40-60wt% of p-toluenesulfonyl chloride.
4. A cyclodextrin derivative according to claim 1, characterized in that: the p-toluenesulfonyl chloride solution contains 40-60wt% of p-toluenesulfonyl chloride.
5. An antimicrobial clathrate comprising: the cyclodextrin derivative according to any one of claims 1 to 4, which is obtained by mixing a plant essential oil with the cyclodextrin derivative.
6. An antibacterial clathrate according to claim 5, characterized in that: the plant essential oil is laurel essential oil.
7. An antibacterial clathrate according to claim 5, characterized in that: the amount of the laurel essential oil is 1-20wt% of the cyclodextrin derivative.
8. An antibacterial clathrate according to claim 5, characterized in that: the cyclodextrin derivative is replaced by a serinate-based cyclodextrin complex, and the serinate-based cyclodextrin complex contains casein acid.
9. Use of a cyclodextrin derivative according to claim 1 for the preparation of an antibacterial material and/or a medical material.
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