CN115181195A - 一种含喹啉基团的壳寡糖季铵盐衍生物及制备方法和应用 - Google Patents
一种含喹啉基团的壳寡糖季铵盐衍生物及制备方法和应用 Download PDFInfo
- Publication number
- CN115181195A CN115181195A CN202211106642.0A CN202211106642A CN115181195A CN 115181195 A CN115181195 A CN 115181195A CN 202211106642 A CN202211106642 A CN 202211106642A CN 115181195 A CN115181195 A CN 115181195A
- Authority
- CN
- China
- Prior art keywords
- chitosan oligosaccharide
- quaternary ammonium
- ammonium salt
- quinoline group
- quinoline
- 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.)
- Granted
Links
- -1 Quaternary ammonium salt derivative of chitosan oligosaccharide Chemical class 0.000 title claims abstract description 96
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 title claims abstract description 45
- 238000002360 preparation method Methods 0.000 title abstract description 10
- 229920001661 Chitosan Polymers 0.000 claims abstract description 21
- 230000003078 antioxidant effect Effects 0.000 claims abstract description 15
- 239000003814 drug Substances 0.000 claims abstract description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002537 cosmetic Substances 0.000 claims abstract description 12
- 235000013376 functional food Nutrition 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 72
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 65
- RQFQJYYMBWVMQG-IXDPLRRUSA-N chitotriose Chemical compound O[C@@H]1[C@@H](N)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](N)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O2)N)[C@@H](CO)O1 RQFQJYYMBWVMQG-IXDPLRRUSA-N 0.000 claims description 53
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 48
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims description 48
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 36
- 238000006243 chemical reaction Methods 0.000 claims description 34
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 32
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 30
- 235000019441 ethanol Nutrition 0.000 claims description 23
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 22
- 239000012065 filter cake Substances 0.000 claims description 21
- 238000005406 washing Methods 0.000 claims description 21
- 230000001376 precipitating effect Effects 0.000 claims description 19
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 claims description 16
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 16
- 235000009518 sodium iodide Nutrition 0.000 claims description 16
- 238000004108 freeze drying Methods 0.000 claims description 14
- 238000000967 suction filtration Methods 0.000 claims description 11
- SVNCRRZKBNSMIV-UHFFFAOYSA-N 3-Aminoquinoline Chemical compound C1=CC=CC2=CC(N)=CN=C21 SVNCRRZKBNSMIV-UHFFFAOYSA-N 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 10
- XMIAFAKRAAMSGX-UHFFFAOYSA-N quinolin-5-amine Chemical compound C1=CC=C2C(N)=CC=CC2=N1 XMIAFAKRAAMSGX-UHFFFAOYSA-N 0.000 claims description 10
- RJSRSRITMWVIQT-UHFFFAOYSA-N quinolin-6-amine Chemical compound N1=CC=CC2=CC(N)=CC=C21 RJSRSRITMWVIQT-UHFFFAOYSA-N 0.000 claims description 10
- WREVVZMUNPAPOV-UHFFFAOYSA-N 8-aminoquinoline Chemical compound C1=CN=C2C(N)=CC=CC2=C1 WREVVZMUNPAPOV-UHFFFAOYSA-N 0.000 claims description 9
- 239000003963 antioxidant agent Substances 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- 238000001556 precipitation Methods 0.000 claims description 8
- 230000008961 swelling Effects 0.000 claims description 8
- 238000009777 vacuum freeze-drying Methods 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- 150000003248 quinolines Chemical class 0.000 claims description 4
- 239000003899 bactericide agent Substances 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 230000004071 biological effect Effects 0.000 abstract description 4
- 238000011160 research Methods 0.000 abstract description 4
- 229920001542 oligosaccharide Polymers 0.000 abstract description 3
- 150000002482 oligosaccharides Chemical class 0.000 abstract description 3
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 239000000463 material Substances 0.000 abstract description 2
- 238000007086 side reaction Methods 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 239000000243 solution Substances 0.000 description 18
- 238000010521 absorption reaction Methods 0.000 description 13
- 239000000523 sample Substances 0.000 description 12
- 238000002835 absorbance Methods 0.000 description 8
- 238000002329 infrared spectrum Methods 0.000 description 7
- 230000003385 bacteriostatic effect Effects 0.000 description 6
- 230000002000 scavenging effect Effects 0.000 description 6
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- 239000008367 deionised water Substances 0.000 description 4
- 229910021641 deionized water Inorganic materials 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000012488 sample solution Substances 0.000 description 4
- 229920002101 Chitin Polymers 0.000 description 3
- 239000003242 anti bacterial agent Substances 0.000 description 3
- 230000003064 anti-oxidating effect Effects 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 238000012258 culturing Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- 230000002292 Radical scavenging effect Effects 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000007853 buffer solution Substances 0.000 description 2
- 238000007385 chemical modification Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000010413 mother solution Substances 0.000 description 2
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 2
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- OARRHUQTFTUEOS-UHFFFAOYSA-N safranin Chemical compound [Cl-].C=12C=C(N)C(C)=CC2=NC2=CC(C)=C(N)C=C2[N+]=1C1=CC=CC=C1 OARRHUQTFTUEOS-UHFFFAOYSA-N 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 230000002194 synthesizing effect Effects 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 235000015655 Crocus sativus Nutrition 0.000 description 1
- 244000124209 Crocus sativus Species 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000005010 aminoquinolines Chemical class 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000003430 antimalarial agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 238000002144 chemical decomposition reaction Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000006196 deacetylation Effects 0.000 description 1
- 238000003381 deacetylation reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
Images
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
- C08B37/0024—Homoglycans, i.e. polysaccharides having a main chain consisting of one single sugar, e.g. colominic acid beta-D-Glucans; (beta-1,3)-D-Glucans, e.g. paramylon, coriolan, sclerotan, pachyman, callose, scleroglucan, schizophyllan, laminaran, lentinan or curdlan; (beta-1,6)-D-Glucans, e.g. pustulan; (beta-1,4)-D-Glucans; (beta-1,3)(beta-1,4)-D-Glucans, e.g. lichenan; Derivatives thereof
- C08B37/0027—2-Acetamido-2-deoxy-beta-glucans; Derivatives thereof
- C08B37/003—Chitin, i.e. 2-acetamido-2-deoxy-(beta-1,4)-D-glucan or N-acetyl-beta-1,4-D-glucosamine; Chitosan, i.e. deacetylated product of chitin or (beta-1,4)-D-glucosamine; 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
-
- 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
- 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
- A23L33/125—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives containing carbohydrate syrups; containing sugars; containing sugar alcohols; containing starch hydrolysates
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/715—Polysaccharides, i.e. having more than five saccharide radicals attached to each other by glycosidic linkages; Derivatives thereof, e.g. ethers, esters
- A61K31/716—Glucans
- A61K31/722—Chitin, chitosan
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/736—Chitin; Chitosan; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
- A61P39/06—Free radical scavengers or antioxidants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/005—Antimicrobial preparations
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
- A61Q19/08—Anti-ageing preparations
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Molecular Biology (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Plant Pathology (AREA)
- Epidemiology (AREA)
- Polymers & Plastics (AREA)
- Environmental Sciences (AREA)
- Zoology (AREA)
- Biochemistry (AREA)
- Dermatology (AREA)
- Wood Science & Technology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Gerontology & Geriatric Medicine (AREA)
- Toxicology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Agronomy & Crop Science (AREA)
- Mycology (AREA)
- Nutrition Science (AREA)
- Food Science & Technology (AREA)
- Birds (AREA)
- Materials Engineering (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Cosmetics (AREA)
Abstract
Description
技术领域
本发明涉及海洋化工工程技术领域,具体涉及一种含喹啉基团的壳寡糖季铵盐衍生物及其制备方法和医药、功能食品保健、化妆品等领域中的应用。
背景技术
壳聚糖(CTS)是甲壳素脱乙酰度达到50%以上的天然高分子化合物, 不但保持了甲壳素的生物相容性, 而且应用性能比甲壳素明显改善。壳寡糖(COS)是由壳聚糖经过酶催化降解或化学降解得到的线性低分子量寡糖,具有一定的生物活性。此外,壳寡糖中的氨基(-NH2)和羟基(-OH)基团为通过化学修饰引入各种外部官能团提供了有效的反应位点,极大地改善了功能性能,进一步拓宽了应用领域。
喹啉是一种含氮杂环化合物,在医学等领域发挥着重要作用,并广泛应用于药物的设计与合成。据报道,喹啉及其衍生物具有抗氧化、抗菌、抗癌、抗疟及抗炎等多种生物活性。
根据活性叠加原理,具有相同或相近生物活性的壳聚糖季铵盐与喹啉及氨基喹啉通过化学方法接枝合成得到的目标衍生物,具有更高的生物活性。
抗氧化是抗氧化自由基的简称。科学研究表明,癌症、衰老或其它疾病大都与过量自由基的产生有关联。研究抗氧化可有效克服其所带来的危害,抗氧化为保健品、化妆品领域主要的研发方向之一,也是最重要的功能性诉求之一。
现有的抗菌剂尽管在某些情况下有效,但通常存在副作用和生物相容性问题,迫切需要开发新的抗菌剂。壳寡糖具有一定的抑菌活性和优良的生物相容性,其在抗菌剂研发领域扮演着重要角色。
发明内容
本发明的目的是提供一种含喹啉基团的壳寡糖季铵盐衍生物及其制备方法和医药、功能食品保健、化妆品等领域中的应用。
为实现上述目的,本发明采用的具体技术方案如下:
一种含喹啉基团的壳寡糖季铵盐衍生物,含喹啉基团的壳寡糖季铵盐衍生物的结构如式一所示:
式一
含喹啉基团的壳寡糖季铵盐衍生物的制备方法:首先将壳寡糖分散于N-甲基吡咯烷酮(NMP)中溶胀,溶胀后依次加入无水碘化钠、氢氧化钠溶液和碘甲烷,回流反应2-4小时,然后醇沉得壳寡糖季铵盐;随后将壳寡糖季铵盐溶于N,N-二甲基甲酰胺(DMF)中,加入氯乙酰氯,30-40℃反应12-18小时,然后用丙酮沉淀,得到氯乙酰化壳寡糖季铵盐;最后将氯乙酰化壳寡糖季铵盐溶于N,N-二甲基甲酰胺中,加入经氨基取代或未取代的喹啉,60-70℃反应24-30小时,然后用丙酮沉淀,得到最终产物。
所述将壳寡糖分散于NMP中,室温下溶胀反应0.5-1小时,依次加入无水碘化钠、氢氧化钠溶液、碘甲烷,于60-70℃条件下回流反应2-4小时;然后经无水乙醇沉淀,并用乙醇洗涤抽滤得到滤饼,真空冷冻干燥至恒重,即得到壳寡糖季铵盐;将所得壳寡糖季铵盐溶于DMF中,室温下滴加氯乙酰氯,随后30-40℃反应12-18小时,反应完成后用丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,得到氯乙酰化壳寡糖季铵盐。
所述每1-2g壳寡糖,使用N-甲基吡咯烷酮20-40mL、无水碘化钠2.5-5g、氢氧化钠1.5-3g、碘甲烷10-20mL、氯乙酰氯0.75-1.5mL,N,N-二甲基甲酰胺20-40mL。
所述将所得氯乙酰化壳寡糖季铵盐溶于DMF中,室温下加入经氨基取代或未取代的喹啉,随后60-70℃反应24-30小时,反应完成后用丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,即得到式一所示含喹啉基团的壳寡糖季铵盐。
所述经氨基取代或未取代的喹啉分别为喹啉、3-氨基喹啉、5-氨基喹啉、6-氨基喹啉或8-氨基喹啉。
所述每1-2g的氯乙酰化壳寡糖季铵盐,使用经氨基取代或未取代的喹啉0.95-3g,N,N-二甲基甲酰胺20-40mL。
含喹啉基团的壳寡糖季铵盐衍生物的应用,所述的含喹啉基团的壳寡糖季铵盐可应用于医药、功能食品保健、化妆品领域中。
所述的含喹啉基团的壳寡糖季铵盐在医药、功能食品保健、化妆品领域中作为抗氧化剂的应用。
所述的含喹啉基团的壳寡糖季铵盐在医药、功能食品保健、化妆品领域中作为杀菌剂的应用。
与现有技术相比,本发明的有益技术效果如下:
(1)本发明所得衍生物具有很好的抗氧化活性,研究表明含喹啉基团的壳寡糖季铵盐衍生物的抗氧化活性明显高于壳寡糖和氯乙酰化壳寡糖季铵盐;同时所得衍生物还具有良好的抑菌活性,研究表明含喹啉基团的壳寡糖季铵盐衍生物的抑菌活性高于壳寡糖和氯乙酰化壳寡糖季铵盐;
(2)本发明所得衍生物水溶性良好,并且具有很好的抗氧化活性和抑菌活性,进而可应用在医药、功能食品保健中,特别是化妆品行业,都有广大应用价值;
(3)本发明所述衍生物制备过程简单,副反应少,所用材料成本低。且抗氧化活性和抑菌活性好,具备大规模制备的技术与经济可行性。
附图说明
图1为壳寡糖的红外光谱图;
图2为本发明实施例1提供氯乙酰化壳寡糖季铵盐的红外光谱图;
图3为本发明实施例1提供含喹啉的壳寡糖季铵盐的红外光谱图;
图4为本发明实施例2提供含3-氨基喹啉的壳寡糖季铵盐的红外光谱图;
图5为本发明实施例3提供含5-氨基喹啉的壳寡糖季铵盐的红外光谱图;
图6为本发明实施例4提供含6-氨基喹啉的壳寡糖季铵盐的红外光谱图;
图7为本发明实施例5提供含8-氨基喹啉的壳寡糖季铵盐的红外光谱图。
具体实施方式
以下结合实例对本发明的具体实施方式做进一步说明,应当指出的是,此处所描述的具体实施方式只是为了说明和解释本发明,并不局限于本发明。
下述各实施例中采用的壳寡糖分子量为5000-10000。
实施例1
式(1)
含喹啉的壳寡糖季铵盐的结构式如式(1),其中n的平均取值范围是30-60。
壳寡糖季铵盐的制备:以壳寡糖、无水碘化钠、碘甲烷、氢氧化钠、N-甲基吡咯烷酮(NMP)、氯乙酰氯、N,N-二甲基甲酰胺为原料;称取1.61g的壳寡糖分散于30mL NMP中,室温下溶胀反应0.5-1小时,依次加入4.5g无水碘化钠、15mL15%的氢氧化钠溶液、15mL碘甲烷,于60-70℃条件下回流反应2-4小时;然后加入适量无水乙醇沉淀,并用乙醇洗涤抽滤得到滤饼,真空冷冻干燥至恒重,即得到壳寡糖季铵盐。取壳寡糖季铵盐1g溶于20mL DMF中,加入0.75mL氯乙酰氯,30-40℃反应12-18小时,反应完成后用适量丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,得到氯乙酰化壳寡糖季铵盐。
上述氯乙酰化壳寡糖季铵盐1g溶于20mL DMF中,加入0.95g喹啉,60-70℃反应24-30小时,反应完成后用适量丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,即得到式(1)所示含喹啉的壳寡糖季铵盐。
从图2可知,与壳寡糖原料(参见图1)相比,氯乙酰化壳寡糖季铵盐在1473cm-1处出现了季铵盐的振动吸收峰,1752cm-1处出现了酯基的振动吸收峰,788cm-1出现了碳-氯键的吸收振动峰,以上分析数据,证明氯乙酰化壳寡糖季铵盐合成成功。
并进一步从图3可知,1473cm-1与1750cm-1处的振动吸收峰依然还在,且在779cm-1处、1376cm-1、1645cm-1以及1648cm-1出现喹啉环的振动吸收峰,由此证明含喹啉壳寡糖季铵盐衍生物合成成功。
实施例2
式(2)
含3-氨基喹啉的壳寡糖季铵盐的结构式如式(2),其中n的平均取值范围是30-60。
与实施例1不同之处在于:
以壳寡糖、无水碘化钠、碘甲烷、氢氧化钠、N-甲基吡咯烷酮(NMP)、氯乙酰氯、N,N-二甲基甲酰胺为原料,称取1g的壳寡糖分散于20mL NMP中,室温下溶胀反应0.5-1小时,依次加入2.5g无水碘化钠、10mL15%的氢氧化钠溶液、10mL碘甲烷,于60-70℃条件下回流反应2-4小时;然后加入适量无水乙醇沉淀,并用乙醇洗涤抽滤得到滤饼,真空冷冻干燥至恒重,即得到壳寡糖季铵盐。取获得的壳寡糖季铵盐1.5g溶于20mL DMF中,加入1.2mL氯乙酰氯,30-40℃反应12-18小时,反应完成后用适量丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,得到氯乙酰化壳寡糖季铵盐。
上述氯乙酰化壳寡糖季铵盐1g溶于20mL DMF中,加入1.06g 3-氨基喹啉,60-70℃反应24-30小时,反应完成后用适量丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,即得到式(2)所示含3-氨基喹啉的壳寡糖季铵盐。
从图4可知,1472cm-1与1750cm-1处的振动吸收峰依然还在,且在773cm-1处、1377cm-1、1531cm-1以及1635cm-1出现喹啉环的振动吸收峰,由此证明含3-氨基喹啉壳寡糖季铵盐衍生物合成成功。
实施例3
式(3)
含5-氨基喹啉的壳寡糖季铵盐的结构式如式(3),其中n的平均取值范围是30-60。
与实施例1不同之处在于:
以壳寡糖、无水碘化钠、碘甲烷、氢氧化钠、N-甲基吡咯烷酮(NMP)、氯乙酰氯、N,N-二甲基甲酰胺为原料,称取1.5g的壳寡糖分散于25mL NMP中,室温下溶胀反应0.5-1小时,依次加入4.2g无水碘化钠、14mL15%的氢氧化钠溶液、14mL碘甲烷,于60-70℃条件下回流反应2-4小时;然后加入适量无水乙醇沉淀,并用乙醇洗涤抽滤得到滤饼,真空冷冻干燥至恒重,即得到壳寡糖季铵盐。取壳寡糖季铵盐1.6g溶于20mL DMF中,加入1.3mL氯乙酰氯,30-40℃反应12-18小时,反应完成后用适量丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,得到氯乙酰化壳寡糖季铵盐。
上述氯乙酰化壳寡糖季铵盐1g溶于20mL DMF中,加入1.06g 5-氨基喹啉,60-70℃反应24-30小时,反应完成后用适量丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,即得到式(3)所示含5-氨基喹啉的壳寡糖季铵盐。
从图5可知,1473cm-1与1748cm-1处的振动吸收峰依然还在,且在786cm-1处、1375cm-1以及1633cm-1出现喹啉环的振动吸收峰,由此可证明含5-氨基喹啉壳寡糖季铵盐衍生物合成成功。
实施例4
式(4)
含6-氨基喹啉的壳寡糖季铵盐的结构式如式(4),其中n的平均取值范围是30-60。
与实施例1不同之处在于:
以壳寡糖、无水碘化钠、碘甲烷、氢氧化钠、N-甲基吡咯烷酮(NMP)、氯乙酰氯、N,N-二甲基甲酰胺为原料,称取1.7g的壳寡糖分散于30mL NMP中,室温下溶胀反应0.5-1小时,依次加入4.8g无水碘化钠、16mL15%的氢氧化钠溶液、16mL碘甲烷,于60-70℃条件下回流反应2-4小时;然后加入适量无水乙醇沉淀,并用乙醇洗涤抽滤得到滤饼,真空冷冻干燥至恒重,即得到壳寡糖季铵盐。取壳寡糖季铵盐1.7g溶于25mL DMF中,加入1.4mL氯乙酰氯,30-40℃反应12-18小时,反应完成后用适量丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,得到氯乙酰化壳寡糖季铵盐。
上述氯乙酰化壳寡糖季铵盐1g溶于20mL DMF中,加入1.06g 6-氨基喹啉,60-70℃反应24-30小时,反应完成后用适量丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,即得到式(4)所示含6-氨基喹啉的壳寡糖季铵盐。
从图6可知,1471cm-1与1749cm-1处的振动吸收峰依然还在,且在1379cm-1、1542cm-1以及1627cm-1出现喹啉环的振动吸收峰,由此证明含6-氨基喹啉壳寡糖季铵盐衍生物合成成功。
实施例5
式(5)
含8-氨基喹啉的壳寡糖季铵盐的结构式如式(5),其中n的平均取值范围是30-60。
与实施例1不同之处在于:
以壳寡糖、无水碘化钠、碘甲烷、氢氧化钠、N-甲基吡咯烷酮(NMP)、氯乙酰氯、N,N-二甲基甲酰胺为原料,称取2g的壳寡糖分散于40mL NMP中,室温下溶胀反应0.5-1小时,依次加入5g无水碘化钠、20mL15%的氢氧化钠溶液、20mL碘甲烷,于60-70℃条件下回流反应2-4小时;然后加入适量无水乙醇沉淀,并用乙醇洗涤抽滤得到滤饼,真空冷冻干燥至恒重,即得到壳寡糖季铵盐。取壳寡糖季铵盐2g溶于40mL DMF中,加入1.5mL氯乙酰氯,30-40℃反应12-18小时,反应完成后用适量丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,得到氯乙酰化壳寡糖季铵盐。
上述氯乙酰化壳寡糖季铵盐2g溶于40mL DMF中,加入3g 8-氨基喹啉,60-70℃反应24-30小时,反应完成后用适量丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,即得到式(5)所示含8-氨基喹啉的壳寡糖季铵盐。
从图7可知,1482cm-1与1751cm-1处的振动吸收峰依然还在,且在793cm-1处、1380cm-1、1522cm-1以及1644cm-1出现喹啉环的振动吸收峰,由此证明含8-氨基喹啉壳寡糖季铵盐衍生物合成成功。
应用例1
抗氧化活性测定
(1)清除超氧阴离子抗氧化能力的测定:分别测定壳寡糖、氯乙酰化壳寡糖季铵盐、含喹啉壳寡糖季铵盐、含3-氨基喹啉壳寡糖季铵盐、含5-氨基喹啉壳寡糖季铵盐、含6-氨基喹啉壳寡糖季铵盐以及含8-氨基喹啉壳寡糖季铵盐的清除超氧阴离子能力:
具体为:将实施例中实验用壳寡糖、氯乙酰化壳寡糖季铵盐、含喹啉的壳寡糖季铵盐、含3-氨基喹啉壳寡糖季铵盐、含5-氨基喹啉壳寡糖季铵盐、含6-氨基喹啉壳寡糖季铵盐以及含8-氨基喹啉壳寡糖季铵盐真空冷冻干燥至恒重后作为待测样品,将各待测样品分别用Tris-HCl 缓冲溶液(1.9382 g Tris+0.8 mL浓HCl,加水定容至1000 mL) 配制浓度为0.2、0.4、0.8、1.6、3.2 mg/mL的溶液。取1.5 mL不同浓度的样品溶液,加入0.5 ml NADH(468μM),然后在反应液中加入0.5 mL NBT(144μM)、0.5 mL PMS(60μM),在试管中混匀后,样品的最终浓度为0.1、0.2、0.4、0.8、1.6 mg/mL,室温下静置5 min,在560 nm处测定吸光度。对照组为1.5mL不同浓度的样品溶液、0.5 mL Tris-HCl 缓冲溶液、0.5mL NBT、0.5mLPMS。空白组为1.5mL去离子水、0.5mL NADH、0.5mL NBT、0.5mL PMS ( 注:被测样品均测三次,取平均值)。
清除超氧阴离子能力(%)=[1-(A样品-A对照)/A空白]×100
其中,A样品:样本组吸光度,A对照:对照组吸光度,A空白:空白组吸光度。
清除超氧阴离子抗氧化能力的测定结果如表1所示:
表1 壳寡糖、氯乙酰化壳寡糖季铵盐、含喹啉基团的壳寡糖季铵盐衍生物的清除超氧阴离子能力(%)
(2)清除羟基自由基抗氧化能力的测定:将壳寡糖以及各实施例制备获得壳寡糖衍生物冻干至恒重后,各准确称量60 mg,分别加入6 mL水溶解,配制成浓度为10 mg/mL 的样品母液。羟自由基清除实验:分别量取45、90、180、360、720 μL 的样品母液于试管中,加水至 1 mL。然后依次加入 0.5 mL EDTA-Fe 溶液、1mL 磷酸缓冲液、1mL 番红花红 T 溶液以及 1 mL 3%过氧化氢溶液。样品溶液的终浓度分别为0.1mg/mL、0.2 mg/mL、0.4 mg/mL、0.8 mg/mL、1.6 mg/mL。空白组为1 mL去离子水、0.5 mL EDTA-Fe 溶液、1mL 磷酸缓冲液、1mL 番红花红T 溶液以及1 mL 3%过氧化氢溶液。对照组为1 mL不同浓度样品溶液、0.5 mLEDTA-Fe 溶液、2 mL 磷酸缓冲液、1 mL 番红花红T 溶液。反应体系加塞摇晃均匀后,于37°C 水浴中反应 30 min。反应结束后,放入冰水中淬灭反应,在520 nm波长处测试记录4.5mL 反应液的吸光度。样品的羟自由基清除能力计算式如下:
清除率 (%) = (A样品-A空白) / (A对照-A空白)×100
其中 A空白:空白组吸光度,A样品:样本组吸光度,A对照:对照组吸光度。
清除羟基自由基抗氧化能力的测定结果如表2所示:
表2 壳寡糖、氯乙酰化壳寡糖季铵盐、含喹啉基团的壳寡糖季铵盐的清除羟基自由基能力(%)
应用例2
抑菌活性测定
采用稀释法分别测定壳寡糖、氯乙酰化壳寡糖季铵盐、含喹啉壳寡糖季铵盐、含3-氨基喹啉壳寡糖季铵盐、含5-氨基喹啉壳寡糖季铵盐、含6-氨基喹啉壳寡糖季铵盐以及含8-氨基喹啉壳寡糖季铵盐的抑菌(大肠杆菌和金黄色葡萄球菌)活性:
具体为:将壳寡糖以及实施例制备获得壳寡糖衍生物冻干至恒重后,各准确称取64mg,分别后加入4mL去离子水溶解,配制成16mg/mL的各样品母液。将待测样品母液在96孔板中用去离子水进行倍比稀释,后将100μL不同细菌菌液(过夜培养)分别接种到上述处理好的96孔板中,随后在(35±2)℃的空气环境中培养8h,观察菌落生长状况,得到样品的最低抑菌浓度,后继续培养16h,观察菌落生长状况,得到样品的最低杀菌浓度。
大肠杆菌和金黄色葡萄球菌的菌液为将各菌按照常规方式过夜培养后得到的菌液。
抑细菌能力的测定结果如表3所示:
表3 壳寡糖、氯乙酰化壳寡糖季铵盐、含喹啉基团的壳寡糖季铵盐衍生物的抑菌活性
本发明通过化学修饰,将喹啉基团引入到壳寡糖季铵盐中,得到抗氧化能力和抑菌活性较强的含喹啉基团的壳聚糖季铵盐衍生物,实验结果表明,含喹啉壳寡糖季铵盐、含3-氨基喹啉壳寡糖季铵盐、含5-氨基喹啉壳寡糖季铵盐、含6-氨基喹啉壳寡糖季铵盐以及含8-氨基喹啉壳寡糖季铵盐的清除自由基抗氧化活性与抑细菌活性较壳寡糖有明显增强,且衍生物水溶性良好,在医药、功能食品保健,特别是化妆品行业都有广大应用价值。
Claims (10)
2.如权利要求1所述的含喹啉基团的壳寡糖季铵盐衍生物的制备方法,其特征在于:首先将壳寡糖分散于N-甲基吡咯烷酮中溶胀,溶胀后依次加入无水碘化钠、氢氧化钠溶液和碘甲烷,回流反应2-4小时,然后醇沉得壳寡糖季铵盐;随后将壳寡糖季铵盐溶于N,N-二甲基甲酰胺中,加入氯乙酰氯,30-40℃反应12-18小时,然后用丙酮沉淀,得到氯乙酰化壳寡糖季铵盐;最后将氯乙酰化壳寡糖季铵盐溶于N,N-二甲基甲酰胺中,加入经氨基取代或未取代的喹啉,60-70℃反应24-30小时,然后用丙酮沉淀,得到最终产物。
3.如权利要求2所述的含喹啉基团的壳寡糖季铵盐衍生物的制备方法,其特征在于:将壳寡糖分散于N-甲基吡咯烷酮中,室温下溶胀反应0.5-1小时,依次加入无水碘化钠、氢氧化钠溶液、碘甲烷,于60-70℃条件下回流反应2-4小时;然后经无水乙醇沉淀,并用乙醇洗涤抽滤得到滤饼,真空冷冻干燥至恒重,即得到壳寡糖季铵盐;将所得壳寡糖季铵盐溶于N,N-二甲基甲酰胺中,室温下滴加氯乙酰氯,随后30-40℃反应12-18小时,反应完成后用丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,得到氯乙酰化壳寡糖季铵盐。
4.如权利要求3所述的含喹啉基团的壳寡糖季铵盐衍生物的制备方法,其特征在于:每1-2g壳寡糖,使用N-甲基吡咯烷酮20-40mL、无水碘化钠2.5-5g、氢氧化钠1.5-3g、碘甲烷10-20mL、氯乙酰氯0.75-1.5mL,N,N-二甲基甲酰胺20-40mL。
5.如权利要求2所述的含喹啉基团的壳寡糖季铵盐衍生物的制备方法,其特征在于:将所得氯乙酰化壳寡糖季铵盐溶于N,N-二甲基甲酰胺中,室温下加入经氨基取代或未取代的喹啉,随后60-70℃反应24-30小时,反应完成后用丙酮沉淀,并用乙醇洗涤抽滤得到滤饼,冷冻干燥至恒重,即得到式一所示含喹啉基团的壳寡糖季铵盐。
6.如权利要求3或5所述的含喹啉基团的壳寡糖季铵盐的制备方法,其特征在于:所述经氨基取代或未取代的喹啉分别为喹啉、3-氨基喹啉、5-氨基喹啉、6-氨基喹啉或8-氨基喹啉。
7.如权利要求3或5所述的含喹啉基团的壳寡糖季铵盐的制备方法,其特征在于:每1-2g的氯乙酰化壳寡糖季铵盐,使用经氨基取代或未取代的喹啉0.95-3g,N,N-二甲基甲酰胺20-40mL。
8.如权利要求1所述的含喹啉基团的壳寡糖季铵盐衍生物的应用,其特征在于:所述的含喹啉基团的壳寡糖季铵盐可应用于医药、功能食品保健、化妆品领域中。
9.如权利要求8所述的含喹啉基团的壳寡糖季铵盐衍生物的应用,其特征在于:所述的含喹啉基团的壳寡糖季铵盐在医药、功能食品保健、化妆品领域中作为抗氧化剂的应用。
10.如权利要求8所述的含喹啉基团的壳寡糖季铵盐衍生物的应用,其特征在于:所述的含喹啉基团的壳寡糖季铵盐在医药、功能食品保健、化妆品领域中作为杀菌剂的应用。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211106642.0A CN115181195B (zh) | 2022-09-13 | 2022-09-13 | 一种含喹啉基团的壳寡糖季铵盐衍生物及制备方法和应用 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN202211106642.0A CN115181195B (zh) | 2022-09-13 | 2022-09-13 | 一种含喹啉基团的壳寡糖季铵盐衍生物及制备方法和应用 |
Publications (2)
Publication Number | Publication Date |
---|---|
CN115181195A true CN115181195A (zh) | 2022-10-14 |
CN115181195B CN115181195B (zh) | 2022-11-22 |
Family
ID=83524423
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202211106642.0A Active CN115181195B (zh) | 2022-09-13 | 2022-09-13 | 一种含喹啉基团的壳寡糖季铵盐衍生物及制备方法和应用 |
Country Status (1)
Country | Link |
---|---|
CN (1) | CN115181195B (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116396412A (zh) * | 2022-12-15 | 2023-07-07 | 河南驼人康君抗菌科技有限公司 | 一种新型喹啉/异喹啉季铵盐改性壳聚糖及制备方法与应用 |
CN117903520A (zh) * | 2024-03-15 | 2024-04-19 | 汕头市汇诚包装材料实业有限公司 | 一种抗菌改性聚乙烯薄膜及其制备方法和应用 |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107216411A (zh) * | 2017-07-18 | 2017-09-29 | 中国科学院烟台海岸带研究所 | 一种含脲类乙酰化壳聚糖季铵盐及其制备方法和应用 |
CN107880153A (zh) * | 2017-11-23 | 2018-04-06 | 中国科学院海洋研究所 | 6‑羧基壳聚糖芳香族季铵盐衍生物及其制备和应用 |
CN108752501A (zh) * | 2018-06-01 | 2018-11-06 | 中国科学院烟台海岸带研究所 | 一种含有机酸盐的壳聚糖季铵盐及其制备方法和应用 |
CN110256605A (zh) * | 2019-08-13 | 2019-09-20 | 中国科学院烟台海岸带研究所 | 一种高抗氧化的酚基壳聚糖希夫碱及其制备方法和应用 |
CN110693850A (zh) * | 2019-09-19 | 2020-01-17 | 湖北科益药业股份有限公司 | 一种咪喹莫特壳聚糖纳米粒子制备方法 |
-
2022
- 2022-09-13 CN CN202211106642.0A patent/CN115181195B/zh active Active
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN107216411A (zh) * | 2017-07-18 | 2017-09-29 | 中国科学院烟台海岸带研究所 | 一种含脲类乙酰化壳聚糖季铵盐及其制备方法和应用 |
CN107880153A (zh) * | 2017-11-23 | 2018-04-06 | 中国科学院海洋研究所 | 6‑羧基壳聚糖芳香族季铵盐衍生物及其制备和应用 |
CN108752501A (zh) * | 2018-06-01 | 2018-11-06 | 中国科学院烟台海岸带研究所 | 一种含有机酸盐的壳聚糖季铵盐及其制备方法和应用 |
CN110256605A (zh) * | 2019-08-13 | 2019-09-20 | 中国科学院烟台海岸带研究所 | 一种高抗氧化的酚基壳聚糖希夫碱及其制备方法和应用 |
CN110693850A (zh) * | 2019-09-19 | 2020-01-17 | 湖北科益药业股份有限公司 | 一种咪喹莫特壳聚糖纳米粒子制备方法 |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN116396412A (zh) * | 2022-12-15 | 2023-07-07 | 河南驼人康君抗菌科技有限公司 | 一种新型喹啉/异喹啉季铵盐改性壳聚糖及制备方法与应用 |
CN116396412B (zh) * | 2022-12-15 | 2024-02-27 | 河南驼人康君抗菌科技有限公司 | 一种新型喹啉/异喹啉季铵盐改性壳聚糖及制备方法与应用 |
CN117903520A (zh) * | 2024-03-15 | 2024-04-19 | 汕头市汇诚包装材料实业有限公司 | 一种抗菌改性聚乙烯薄膜及其制备方法和应用 |
CN117903520B (zh) * | 2024-03-15 | 2024-05-24 | 汕头市汇诚包装材料实业有限公司 | 一种抗菌改性聚乙烯薄膜及其制备方法和应用 |
Also Published As
Publication number | Publication date |
---|---|
CN115181195B (zh) | 2022-11-22 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CN115181195B (zh) | 一种含喹啉基团的壳寡糖季铵盐衍生物及制备方法和应用 | |
US20200181292A1 (en) | Novel water-soluble natural polysaccharide antibacterial material and preparation method thereof | |
EP0020183B1 (en) | Poly-ion complex, process for its preparation and shaped articles prepared therefrom | |
CN108752501B (zh) | 一种含有机酸盐的壳聚糖季铵盐及其制备方法和应用 | |
Kamala et al. | Extraction and characterization of water soluble chitosan from parapeneopsis stylifera shrimp shell waste and its antibacterial activity | |
WO2022165940A1 (zh) | 一种壳聚糖衍生物及其制备方法和应用 | |
RU2278669C1 (ru) | Средство, обладающее антимикробной активностью | |
CN113248632A (zh) | 一种多功能中药有机酸接枝壳聚糖季铵盐广谱抗菌剂及其制备方法 | |
CN110003359A (zh) | 一种亲水性高取代度改性壳聚糖制备方法及其应用 | |
Hafsa et al. | SYNTHESIS, CHARACTERIZATION, ANTIOXIDANT AND ANTIBACTERIAL PROPRIETIES OF CHITOSAN ASCORBATE. | |
CN114853922A (zh) | 一种硫辛酰基壳聚糖季铵盐及其制备方法和应用 | |
Huang et al. | Preparation, characterization, and antibacterial activity of oleic acid-grafted chitosan oligosaccharide nanoparticles | |
CN108864324B (zh) | 一种三氮唑基壳聚糖双季铵盐及其制备方法和应用 | |
CN107441494B (zh) | 一种抗菌膜活性的壳寡糖与抗生素及其应用 | |
WO2023131355A1 (zh) | 一种水溶性氯己定类抗菌剂及其制备方法和应用 | |
CN114014955B (zh) | 一种含噻唑盐的n,o-羧甲基壳聚糖及其制备和应用 | |
CN102382206B (zh) | 壳寡糖季铵盐及其制备方法 | |
JPS6256163B2 (zh) | ||
Zhang et al. | Evaluation of sulfonated oxidized chitosan antifungal activity against Fusarium graminearum | |
CN101875704A (zh) | 水溶性壳聚糖西弗碱衍生物及其制备和应用 | |
Ibram | Studies on chitosan, chitin and chitooligosaccharides and their biomedical properties | |
RU2627540C1 (ru) | Способ получения нанокристаллитов низкомолекулярного хитозана | |
Hamdan et al. | Extraction, characterization and bioactivity of chitosan from farms shrimps of Basra province by chemical method | |
CN112442142B (zh) | 一种含卤代苯的羧甲基壳聚糖及其制备方法和应用 | |
WO2020114351A1 (zh) | 水溶性天然多糖抗菌衍生物及其制备方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
GR01 | Patent grant | ||
GR01 | Patent grant |