CN106491386B - 一种环糊精燕麦酰基邻氨基苯甲酸包合物水溶液及其制备方法与应用 - Google Patents
一种环糊精燕麦酰基邻氨基苯甲酸包合物水溶液及其制备方法与应用 Download PDFInfo
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- CN106491386B CN106491386B CN201610944374.8A CN201610944374A CN106491386B CN 106491386 B CN106491386 B CN 106491386B CN 201610944374 A CN201610944374 A CN 201610944374A CN 106491386 B CN106491386 B CN 106491386B
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- aminobenzoic acid
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- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 title claims abstract description 196
- 229920000858 Cyclodextrin Polymers 0.000 title claims abstract description 160
- 125000002252 acyl group Chemical group 0.000 title claims abstract description 109
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound 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 109
- 239000007864 aqueous solution Substances 0.000 title claims abstract description 62
- 150000001875 compounds Chemical class 0.000 title claims abstract description 43
- 238000002360 preparation method Methods 0.000 title claims abstract description 34
- 239000000243 solution Substances 0.000 claims abstract description 18
- 230000001476 alcoholic effect Effects 0.000 claims abstract description 12
- 238000000034 method Methods 0.000 claims abstract description 9
- 239000001116 FEMA 4028 Substances 0.000 claims description 34
- 229960004853 betadex Drugs 0.000 claims description 34
- 229920001450 Alpha-Cyclodextrin Polymers 0.000 claims description 15
- 229940043377 alpha-cyclodextrin Drugs 0.000 claims description 15
- 229940080345 gamma-cyclodextrin Drugs 0.000 claims description 10
- 239000000126 substance Substances 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 235000011175 beta-cyclodextrine Nutrition 0.000 claims description 8
- -1 allyl cyclodextrin Chemical compound 0.000 claims description 6
- WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims description 6
- HFHDHCJBZVLPGP-RWMJIURBSA-N alpha-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO HFHDHCJBZVLPGP-RWMJIURBSA-N 0.000 claims description 5
- GDSRMADSINPKSL-HSEONFRVSA-N gamma-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO GDSRMADSINPKSL-HSEONFRVSA-N 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
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- CUJVBAPGYBSBHJ-YWBSARSQSA-N 2-[[(1R,3R,5R,6S,8R,10R,11S,13R,15R,16S,18R,20R,21R,23R,25R,26R,28R,30R,31R,33R,35R,36R,37R,38R,39R,40R,41R,42R,43R,44R,45R,46R,47R,48R,49R)-36,38,40,42-tetrakis(carboxymethoxy)-10,15-bis(carboxymethoxymethyl)-37,39,41,43,44,45,46,47,48,49-decahydroxy-20,25,30,35-tetrakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.23,6.28,11.213,16.218,21.223,26.228,31]nonatetracontan-5-yl]methoxy]acetic acid Chemical compound OC[C@H]1O[C@@H]2O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCC(O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCC(O)=O)O[C@H]3[C@H](O)[C@@H](O)[C@H](O[C@@H]3COCC(O)=O)O[C@@H]3[C@@H](CO)O[C@H](O[C@@H]4[C@@H](CO)O[C@H](O[C@@H]5[C@@H](CO)O[C@H](O[C@H]1[C@H](OCC(O)=O)[C@H]2O)[C@H](O)[C@H]5OCC(O)=O)[C@H](O)[C@H]4OCC(O)=O)[C@H](O)[C@H]3OCC(O)=O CUJVBAPGYBSBHJ-YWBSARSQSA-N 0.000 claims description 2
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 claims description 2
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
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- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/40—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
- A61K8/44—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof
- A61K8/445—Aminocarboxylic acids or derivatives thereof, e.g. aminocarboxylic acids containing sulfur; Salts; Esters or N-acylated derivatives thereof aromatic, i.e. the carboxylic acid directly linked to the aromatic ring
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- 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
- A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
- A61K31/19—Carboxylic acids, e.g. valproic acid
- A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
- A61K31/196—Carboxylic acids, e.g. valproic acid having an amino group the amino group being directly attached to a ring, e.g. anthranilic acid, mefenamic acid, diclofenac, chlorambucil
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/73—Polysaccharides
- A61K8/738—Cyclodextrins
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/08—Solutions
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- 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
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Medicinal Preparation (AREA)
- Cosmetics (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
本发明公开了一种环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的制备方法,所述方法为:将环糊精水溶液与燕麦酰基邻氨基苯甲酸醇溶液混合,在30~50℃下静置至少1小时,得到环糊精包裹燕麦酰基邻氨基苯甲酸后的水溶液,即环糊精燕麦酰基邻氨基苯甲酸包合物水溶液。所述制备方法原料来源容易、制备方法简单,包合率高;制备得到的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液不仅水溶解度高,而且不易挥发、不易氧化、热稳定性好,大大扩大了燕麦酰基邻氨基苯甲酸的应用范围。
Description
技术领域
本发明涉及一种环糊精包合物及其制备方法与应用,尤其是一种环糊精燕麦酰基邻氨基苯甲酸包合物水溶液及其制备方法与应用。
背景技术
环糊精是环糊精转葡萄糖基酶(CGTase)作用于淀粉的产物,是由六个以上葡萄糖以α—1,4—糖苷键连结的环状寡聚糖,其中最常见、研究最多的是α-环糊精(α-cyclodextrin)、β-环糊精(β-cyclodextrin)、γ-环糊精(γ-cyclodextrin),分别由六个、七个和八个葡萄糖分子构成,是相对大和相对柔性的分子。经X射线衍射和核磁共振研究,证明环糊精分子成锥柱状或圆锥状花环,有许多可旋转的键和羟基,内有一个空腔,表观外型类似于接导管的橡胶塞。空腔内部排列着配糖氧桥原子,氧原子的非键电子对指向中心,使空腔内部具有很高的电子密度,表现出部分路易斯碱的性质。分子构型为葡萄糖的C-1椅式构型,在它的圆筒内部有-CH-葡萄糖苷结合的O原子,故呈疏水性。葡萄糖的2位和3位的-OH基在圆筒的一端开口处,6位的-OH基在圆筒的另一端开口处,所以圆筒的二端开口处都呈亲水性,这样,环糊精的筒形体的内部上层、中层、下层由不同的基团组成。环糊精内腔可以包结物质形成包合物,环糊精作为主体,被包合物作为客体,被包合物能全部或部分进入环糊精空穴内部,形成环糊精包合物,可以改善被包合物的性能。
燕麦酰基邻氨基苯甲酸是燕麦中的主要活性成分,能够抑制P物质诱导肥大细胞释放组胺,有效缓解皮肤瘙痒和发红。同时能够有效抑制组胺血管扩张和增强通透性的作用,还防止皮肤瘙痒引起的二次炎症反应;另一方面,抑制细胞内由NF-κB调控表达的炎症介质,如TNF-α、IL-1β、趋化因子、粘附分子、集落刺激因子等。燕麦酰基邻氨基苯甲酸还能够抑制UV辐射诱导皮肤成纤维细胞分泌基质金属蛋白酶(MMP-1,MMP-3),进一步防止组织间质胶原蛋白的流失。但是燕麦酰基邻氨基苯甲酸水溶性差,不稳定,使其应用范围受到了限制,因为提高其水溶性和稳定性是拓宽其应用范围的关键。
发明内容
基于此,本发明的目的在于克服上述现有技术的不足之处而提供一种水溶性好、热稳定性高的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液及其制备方法与应用。
为实现这一目的,本发明所采取的技术方案为:一种环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的制备方法,所述方法为:
将环糊精水溶液与燕麦酰基邻氨基苯甲酸醇溶液混合,在30~50℃下静置至少1小时,得到环糊精包裹燕麦酰基邻氨基苯甲酸后的水溶液,即环糊精燕麦酰基邻氨基苯甲酸包合物水溶液;
其中,所述燕麦酰基邻氨基苯甲酸化学通式如下:
其中,n为0、1或2,R1为-H或-OH,R2为-H、-OCH3或-OH,R3为-H或-OCH3。
优选地,所述环糊精与燕麦酰基邻氨基苯甲酸的摩尔比为0.3:1~3:1。
更优选地,所述环糊精与燕麦酰基邻氨基苯甲酸的摩尔比为2:1。
本申请发明人经过大量尝试,发现上述摩尔比的环糊精与燕麦酰基邻氨基苯甲酸,包合率高,且包合后,稳定性较好。
优选地,所述环糊精水溶液中环糊精的质量百分比为5~15%,所述燕麦酰基邻氨基苯甲酸醇溶液中燕麦酰基邻氨基苯甲酸的质量百分比为10~30%。
更优选地,所述环糊精水溶液中环糊精的质量百分比为10%,所述燕麦酰基邻氨基苯甲酸醇溶液中燕麦酰基邻氨基苯甲酸的质量百分比为20%。
本申请发明人发现,上述质量百分比的环糊精水溶液和燕麦酰基邻氨基苯甲酸醇溶液,溶剂对环糊精和燕麦酰基邻氨基苯甲酸的溶解度较高,环糊精和燕麦酰基邻氨基苯甲酸的界面接触效率更高,包合速度和包合率也就更高,且包合后,水溶性好,稳定性较高。
优选地,所述环糊精为α-环糊精、β-环糊精、γ-环糊精及它们的衍生物中的至少一种;
所述环糊精的衍生物为羟丙基-α-环糊精、甲基-β-环糊精、羟丙基-β-环糊精、磺丁基-β-环糊精、羧甲基-β-环糊精、羟丁基-β-环糊精、低聚乳酸基-β-环糊精、6-氨基葡萄糖基-6-去氧-β-环糊精、乙二胺基-β-环糊精、多烯多胺-β-环糊精、对甲苯磺酰-β-环糊精、叠氮-β-环糊精、环氧氯丙烷交联-β-环糊精、羟丙基-γ-环糊精、聚合环糊精、碘代-α-环糊精、碘代-β-环糊精、烯丙基环糊精、氨基-α-环糊精、氨基-β-环糊精、氨基-γ-环糊精、单巯基-β-环糊精、全巯基-β-环糊精、全巯基-α-环糊精、巯基-γ-环糊精、磷酸基-α-环糊精、磷酸基-β-环糊精、磷酸基-γ-环糊精中的至少一种。
优选地,所述燕麦酰基邻氨基苯甲酸为
中的至少一种。
更优选地,所述燕麦酰基邻氨基苯甲酸为二氢燕麦酰基邻氨基苯甲酸,化学式如下:
优选地,所述制备方法中,静置时间为1~5小时。
本发明还提供一种由上述方法制备得到的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液。所述水溶液不仅水溶解度高,而且不易挥发、不易氧化,热稳定性好。
同时,本发明还提供了上述环糊精燕麦酰基邻氨基苯甲酸包合物水溶液在化妆品、护理品或药物中的应用。由于燕麦酰基邻氨基苯甲酸在抗组胺、缓解皮肤瘙痒和发红、抗炎、止痒方面的功效,且溶解度越高,抗组胺效果越好,经环糊精包合之后的燕麦酰基邻氨基苯甲酸水溶解度高、热稳定性好,可将其用于抗炎、止痒方面的化妆品、护理品或药物,扩大其应用范围。
相对于现有技术,本发明的有益效果为:
本发明所述制备方法原料来源容易、制备方法简单,包合率高;由于环糊精及其衍生物可以增溶,不易挥发、不易氧化、热稳定性好,因此,制备得到的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液不仅水溶解度高,而且不易挥发、不易氧化,热稳定性好,大大扩大了燕麦酰基邻氨基苯甲酸的应用范围,将会有广阔的应用前景。
附图说明
图1为不同浓度的二氢燕麦酰基邻氨基苯甲酸对P物质诱导小鼠腹腔肥大细胞释放组胺的抑制率。
具体实施方式
为更好的说明本发明的目的、技术方案和优点,下面将结合具体实施例对本发明作进一步说明。
实施例1
本发明所述环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的制备方法的一种实施例,本实施例所述制备方法为:
将环糊精的质量百分比为10%的环糊精水溶液与燕麦酰基邻氨基苯甲酸的质量百分比为20%的燕麦酰基邻氨基苯甲酸醇溶液混合,且环糊精与燕麦酰基邻氨基苯甲酸的摩尔比为0.3:1,在30℃下静置1小时,得到环糊精包裹燕麦酰基邻氨基苯甲酸后的水溶液,即环糊精燕麦酰基邻氨基苯甲酸包合物水溶液,其中环糊精为α-环糊精,燕麦酰基邻氨基苯甲酸为二氢燕麦酰基邻氨基苯甲酸,化学式如下:
一种由本实施例所述制备方法制备得到的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液。
实施例2
本发明所述环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的制备方法的一种实施例,本实施例所述制备方法为:
将环糊精的质量百分比为5%的环糊精水溶液与燕麦酰基邻氨基苯甲酸的质量百分比为10%的燕麦酰基邻氨基苯甲酸醇溶液混合,且环糊精与燕麦酰基邻氨基苯甲酸的摩尔比为3:1,在50℃下静置2小时,得到环糊精包裹燕麦酰基邻氨基苯甲酸后的水溶液,即环糊精燕麦酰基邻氨基苯甲酸包合物水溶液,其中环糊精为β-环糊精,燕麦酰基邻氨基苯甲酸的化学式如下:
一种由本实施例所述制备方法制备得到的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液。
实施例3
本发明所述环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的制备方法的一种实施例,本实施例所述制备方法为:
将环糊精的质量百分比为15%的环糊精水溶液与燕麦酰基邻氨基苯甲酸的质量百分比为30%的燕麦酰基邻氨基苯甲酸醇溶液混合,且环糊精与燕麦酰基邻氨基苯甲酸的摩尔比为1:1,在35℃下静置3小时,得到环糊精包裹燕麦酰基邻氨基苯甲酸后的水溶液,即环糊精燕麦酰基邻氨基苯甲酸包合物水溶液,其中环糊精为γ-环糊精,燕麦酰基邻氨基苯甲酸的化学式如下:
一种由本实施例所述制备方法制备得到的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液。
实施例4
本发明所述环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的制备方法的一种实施例,本实施例所述制备方法为:
将环糊精的质量百分比为10%的环糊精水溶液与燕麦酰基邻氨基苯甲酸的质量百分比为15%的燕麦酰基邻氨基苯甲酸醇溶液混合,且环糊精与燕麦酰基邻氨基苯甲酸的摩尔比为2:1,在40℃下静置4小时,得到环糊精包裹燕麦酰基邻氨基苯甲酸后的水溶液,即环糊精燕麦酰基邻氨基苯甲酸包合物水溶液,其中,环糊精为碘代-α-环糊精,燕麦酰基邻氨基苯甲酸的化学式如下:
一种由本实施例所述制备方法制备得到的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液。
实施例5
本发明所述环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的制备方法的一种实施例,本实施例所述制备方法为:
将环糊精的质量百分比为8%的环糊精水溶液与燕麦酰基邻氨基苯甲酸的质量百分比为25%的燕麦酰基邻氨基苯甲酸醇溶液混合,且环糊精与燕麦酰基邻氨基苯甲酸的摩尔比为1.5:1,在45℃下静置5小时,得到环糊精包裹燕麦酰基邻氨基苯甲酸后的水溶液,即环糊精燕麦酰基邻氨基苯甲酸包合物水溶液,其中,环糊精为羟丁基-β-环糊精,燕麦酰基邻氨基苯甲酸的化学式如下:
一种由本实施例所述制备方法制备得到的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液。
实施例6
本发明所述环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的制备方法的一种实施例,本实施例所述制备方法为:
将环糊精的质量百分比为12%的环糊精水溶液与燕麦酰基邻氨基苯甲酸的质量百分比为18%的燕麦酰基邻氨基苯甲酸醇溶液混合,且环糊精与燕麦酰基邻氨基苯甲酸的摩尔比为2.5:1,在38℃下静置6小时,得到环糊精包裹燕麦酰基邻氨基苯甲酸后的水溶液,即环糊精燕麦酰基邻氨基苯甲酸包合物水溶液,其中,环糊精为氨基-γ-环糊精,燕麦酰基邻氨基苯甲酸的化学式如下:
一种由本实施例所述制备方法制备得到的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液。
实施例7
本实施例以实施例1中用到的二氢燕麦酰基邻氨基苯甲酸为例,对不同浓度的燕麦酰基邻氨基苯甲酸的抗组胺效果进行研究分析,研究方法为:
1.培养小鼠腹膜肥大细胞
2.添加不同浓度的测试物(0.5ppm,5ppm,50ppm,500ppm)和对照物
3.P物质刺激释放组胺
4.离心法收集上清液
5.测组胺含量
不同浓度的二氢燕麦酰基邻氨基苯甲酸对P物质诱导小鼠腹腔肥大细胞释放组胺的抑制率如图1所示:
组胺(histamine)是过敏和干燥皮肤中的致痒介质,由肥大细胞释放;二氢燕麦酰基邻氨基苯甲酸具有抗组胺、抗炎、止痒的功效,能够抑制P物质诱导肥大细胞释放组胺,有效的缓解皮肤瘙痒和发红。因此,二氢燕麦酰基邻氨基苯甲酸(欣敏婷)适用于头屑瘙痒和季节变化引起的干燥性皮肤瘙痒。从图1可以明显的看出,浓度越高,二氢燕麦酰基邻氨基苯甲酸的抗组胺效果越好。
实施例8
本实施例对实施例1~6所制备得到的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的水溶性、热稳定性及抗氧化性进行研究分析,以未经环糊精包合的燕麦酰基邻氨基苯甲酸水溶液作为相应的对照组,其中,每个项目的测试方法为:稳定性:将待测物在50℃加热,测量半个月后待测物氧化成其他产物的质量百分比;测试结果如表1所示:
表1环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的水溶性、热稳定性研究结果
从表1中的数据可以很明显的看出,被环糊精包合之后的燕麦酰基邻氨基苯甲酸在50℃加热,半个月后,仅有1%左右被氧化成其他产物,而未被包合的燕麦酰基邻氨基苯甲酸在50℃加热,半个月后,约有50%左右被氧化成其他产物,相比之下,被环糊精包合之后的燕麦酰基邻氨基苯甲酸热稳定性和抗氧化性得到大大提高;且被环糊精包合之前,燕麦酰基邻氨基苯甲酸水溶性不到万分之一,包合之后,水和燕麦酰基邻氨基苯甲酸可以以任何比例完全水溶。
最后所应当说明的是,以上实施例仅用以说明本发明的技术方案而非对本发明保护范围的限制,尽管参照较佳实施例对本发明作了详细说明,本领域的普通技术人员应当理解,可以对本发明的技术方案进行修改或者等同替换,而不脱离本发明技术方案的实质和范围。
Claims (6)
1.一种环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的制备方法,其特征在于,所述方法为:
将环糊精水溶液与燕麦酰基邻氨基苯甲酸醇溶液混合,在30~50℃下静置1~5小时,得到环糊精包裹燕麦酰基邻氨基苯甲酸后的水溶液,即环糊精燕麦酰基邻氨基苯甲酸包合物水溶液;
其中,所述燕麦酰基邻氨基苯甲酸化学通式如式(1):
其中,n为1,R1为-H或-OH,R2为-H、-OCH3或-OH,R3为-H或-OCH3;
或式(2):
所述环糊精与燕麦酰基邻氨基苯甲酸的摩尔比为0.3:1~3:1;所述环糊精水溶液中环糊精的质量百分比为5~15%,所述燕麦酰基邻氨基苯甲酸醇溶液中燕麦酰基邻氨基苯甲酸的质量百分比为10~30%。
2.如权利要求1所述环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的制备方法,其特征在于,所述环糊精与燕麦酰基邻氨基苯甲酸的摩尔比为2:1。
3.如权利要求1所述环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的制备方法,其特征在于,所述环糊精水溶液中环糊精的质量百分比为10%,所述燕麦酰基邻氨基苯甲酸醇溶液中燕麦酰基邻氨基苯甲酸的质量百分比为20%。
4.如权利要求1所述环糊精燕麦酰基邻氨基苯甲酸包合物水溶液的制备方法,其特征在于,所述环糊精为α-环糊精、β-环糊精、γ-环糊精及环糊精的衍生物中的至少一种;
所述环糊精的衍生物为羟丙基-α-环糊精、甲基-β-环糊精、羟丙基-β-环糊精、磺丁基-β-环糊精、羧甲基-β-环糊精、羟丁基-β-环糊精、低聚乳酸基-β-环糊精、6-氨基葡萄糖基-6-去氧-β-环糊精、乙二胺基-β-环糊精、多烯多胺-β-环糊精、对甲苯磺酰-β-环糊精、叠氮-β-环糊精、环氧氯丙烷交联-β-环糊精、羟丙基-γ-环糊精、聚合环糊精、碘代-α-环糊精、碘代-β-环糊精、烯丙基环糊精、氨基-α-环糊精、氨基-β-环糊精、氨基-γ-环糊精、单巯基-β-环糊精、全巯基-β-环糊精、全巯基-α-环糊精、巯基-γ-环糊精、磷酸基-α-环糊精、磷酸基-β-环糊精、磷酸基-γ-环糊精中的至少一种。
5.一种由权利要求1~4任一所述方法制备得到的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液。
6.如权利要求5所述的环糊精燕麦酰基邻氨基苯甲酸包合物水溶液在制备化妆品或药物中的应用。
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