CN117481984A - 一种超分子红没药醇低共熔溶剂及其制备方法与应用 - Google Patents
一种超分子红没药醇低共熔溶剂及其制备方法与应用 Download PDFInfo
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- CN117481984A CN117481984A CN202311375431.1A CN202311375431A CN117481984A CN 117481984 A CN117481984 A CN 117481984A CN 202311375431 A CN202311375431 A CN 202311375431A CN 117481984 A CN117481984 A CN 117481984A
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- bisabolol
- eutectic solvent
- supermolecule
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- acid
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Abstract
本发明涉及超分子低共熔溶剂领域,尤其涉及一种超分子红没药醇低共熔溶剂及其制备方法与应用。本发明所述超分子红没药醇低共熔溶剂包括红没药醇和配体;所述配体包括环己醇类化合物、酚类化合物、羧酸类化合物、非环状单元醇、多元醇中的至少一种;所述红没药醇和配体的摩尔比为红没药醇:配体=1:(0.1‑10)。超分子红没药醇低共熔溶剂的可针对性设计,使超分子红没药醇低共熔溶剂微脂囊具有促进溶解性、增强活性物经皮促渗、共递送活性物等优良特点,可以较好应用在化妆品、保健品、食品等领域。
Description
技术领域
本发明涉及超分子低共熔溶剂领域,尤其涉及一种超分子红没药醇低共熔溶剂及其制备方法与应用。
背景技术
红没药醇在洋甘菊精油中其含量可以高达17%,其主要为α-红没药醇,具有抗炎、舒缓、抗阵痛、美白等多种功效作用,具有很大的开发价值及临床应用研究。其本身为粘稠液体,具有轻微气味,易溶于甲醇乙醇等有机溶剂中,但几乎不溶于甘油和水,在化妆品配方中添加量为0.2%以上1.0%以下,过度的添加反而降低红没药醇的功效作用,天然的红没药醇拥有比合成的红没药醇更好的功效作用。
低共熔溶剂是指由两种或两种以上化学物质通过物理相互作用形成室温下为液体状态的稳定混合物。其主要是通过化合物之间官能团的非共价键作用而形成,例如分子间氢键、范德华力等。低共熔溶剂相对于前体来说,自身化学性质没有改变,但一些物理特性发生改变,例如熔点、粘度、状态、蒸气压物质性质等。这种非共价键作用形成的物质一般称之为超分子物质,因此低共熔溶剂也称之为超分子溶剂或超分子低共熔溶剂。超分子低共熔溶剂具有许多优良的性质,在有机合成领域以替代有机溶剂而表现出低潜在毒性、高安全性和价格合适,并对反应具有催化作用、反应条件温和,具有良好的相容性等优点。同时,也具有增强活性物的溶解性、增强活性物的功效等作用,在化妆品、保健品、食品等领域具有较广泛应用。低共熔溶剂因单体的可设计性,通过选择特定功能结构单体以获得最大/最优程度的应用。因此对于低共熔溶剂的前体单体选择至关重要,选择合适的单体可以产生增效作用。
微脂囊包裹技术是目前护肤品渗透工艺中最顶尖科技,这是脂质体、脂肪乳、胶束、囊泡、纳米粒、pickering乳液的统称。它们具有0.05~0.5μm的粒径,能够将活性成分包载其中,并保护活性物稳定性,减小活性物刺激性,增强透皮效果,缓释活性物、靶向运输活性物等的特点,目前已广泛应用于化妆品、保健品、食品中。
红没药醇通常具有抗炎、舒缓、美白功效作用,通过设计另一单体结构,以获得红没药醇类低共熔溶剂,并将其应用于化妆品、保健食品领域,开发红没药醇增效产品将具有重大意义。
发明内容
本发明的目的在于克服现有技术存在的不足之处而提供一种超分子红没药醇低共熔溶剂及其制备方法与应用;将红没药醇与配体结合(特定功能结构单体)得到超分子低共熔溶剂,具有促进溶解性、增强活性物经皮促渗、共递送活性物等优良特点,可以较好应用在化妆品、保健品、食品等领域。
为实现上述目的,本发明采取的技术方案为:
第一方面,本发明提供了一种超分子红没药醇低共熔溶剂,所述超分子红没药醇低共熔溶剂由红没药醇和配体组成;所述配体包括环己醇类化合物、酚类化合物、羧酸类化合物、非环状单元醇、多元醇中的至少一种;所述红没药醇和配体的摩尔比为红没药醇:配体=1:(0.1-10)。
本发明通过将红没药醇与环己醇类化合物、酚类化合物、羧酸类化合物、非环状单元醇、多元醇等配体混合,通过化合物之间官能团的非共价键作用例如分子间氢键、范德华力等而形成低共熔溶剂。选择本发明特定的配体与红没药醇相互作用,两者的配比在本发明范围内可产生增效作用。
优选地,所述环己醇类化合物包括4-叔丁基环己醇、薄荷醇、冰片、薄荷醇乳酸酯、薄荷酮甘油缩酮、薄荷氧基丙二醇中的至少一种;所述酚类化合物包括丹皮酚、4-正丁基间苯二酚、茶多酚、丁香酚、厚朴酚、麝香草酚、桃柁酚中的至少一种;所述羧酸类化合物包括辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、油酸、亚油酸、10-羟基癸酸、硫辛酸、二十二碳六烯酸、二十碳五烯酸中的至少一种;所述非环状单元醇包括癸醇、香叶醇、叶绿醇、辛基十二醇中的至少一种;所述多元醇包括丁二醇、丙二醇、1,2-己二醇、1,2-戊二醇、双丙甘醇、甘油中的至少一种。
超分子红没药醇低共熔溶剂可以选择不同的配体而具有可设计性,这也使得超分子红没药醇低共熔溶剂微脂囊具有设计性。
第二方面,本发明提供了上述超分子红没药醇低共熔溶剂的制备方法,包括如下步骤:在空气或氮气的保护下,将红没药醇和配体混合,搅拌、加热,充分溶解,冷却得到所述超分子红没药醇低共熔溶剂。
优选地,所述充分溶解的方法为:加入水或醇溶解,待冷却后,再去除水或醇。
优选地,可以采用超声、研磨、均质剪切、高压处理等手段帮助溶质充分溶解。
将红没药醇与配体混合后,在含有或不含水或醇,以及空气或氮气保护的条件下混合,施加一定的物理作用,最后除去溶液,形成室温条件下为均一稳定液体。对于熔点低的配体物质,不需要加溶液进行分散;对于熔点高的配体物质,若配体为水溶性的固体、粘稠液体或油溶性物质,则需要加入水或醇进行分散、溶解。
优选地,所述醇为甲醇、乙醇、丙二醇、丁二醇中的至少一种。
优选地,采用冷冻干燥、真空干燥、旋蒸干燥、直接干燥等方式去除水或醇。
第三方面,本发明提供了一种超分子红没药醇低共熔溶剂微脂囊,所述超分子红没药醇低共熔溶剂微脂囊包括上述的超分子红没药醇低共熔溶剂、乳化剂和溶液;所述溶液为水、多元醇中的至少一种;所述多元醇包括丙二醇、丁二醇、1,2-戊二醇、1,2-己二醇、双丙甘醇、甘油中的至少一种。
红没药醇通过超分子低共熔溶剂改性,以获得红没药醇类低共熔溶剂,并使用微脂囊包裹技术和超分子低共熔溶剂技术递送活性物,改善活性物自身稳定性、刺激性、促进透皮吸收效果、缓释和靶向效果。
优选地,所述乳化剂包括PEG改性油酯类化合物、山梨醇聚醚类化合物、鲸蜡硬脂醇聚醚-25、烷基糖苷、硬脂酰基谷氨酸钠、椰油酰基谷氨酸钠、聚甘油-10硬脂酸酯、聚甘油-10肉豆蔻酸酯、聚甘油-10月桂酸酯、肉豆蔻酰基谷氨酸钠、月桂酰基谷氨酸钠、硬脂酰基甘氨酸钠、油酰基甘氨酸钠、棕榈酰基甘氨酸钠、肉豆蔻酰基甘氨酸钠、月桂酰基甘氨酸钠、硬脂酸钠、油酸、棕榈酸钠、肉豆蔻酸钠、月桂酸及其钠/钾盐、卵磷脂、大豆磷脂、氢化卵磷脂中的至少一种。
优选地,所述超分子红没药醇低共熔溶剂、乳化剂和溶液的重量份比为超分子红没药醇低共熔溶剂:乳化剂:溶液=(0.5-20):(0.5-20):(44-99)。
在本发明特定范围内,制备得到的超分子红没药醇低共熔溶剂微脂囊具有促进溶解性、增强活性物经皮促渗、缓释和靶向等优良特点。
第四方面,本发明提供了上述超分子红没药醇低共熔溶剂微脂囊的制备方法,包括如下步骤:
(1)将超分子红没药醇低共熔溶剂、乳化剂和溶液混合后,均质剪切得到初乳液;
(2)将步骤(1)所得初乳液进行高压均质剪切得到所述超分子红没药醇低共熔溶剂微脂囊。
在高压均质作用下,超分子红没药醇低共熔溶剂、乳化剂、溶液形成均一稳定的超分子红没药醇低共熔溶剂微脂囊。
优选地,所述步骤(2)中,高压均质剪切的条件为温度20-100℃,压力0-2000bar。(或同等换算下的psi值)。
优选地,所述高压均质所用的设备为高压均质机、高压微射流、高压微流控等。
第五方面,本发明提供了上述的超分子红没药醇低共熔溶剂微脂囊在制备化妆品、保健品、食品中的应用。
本发明的超分子红没药醇低共熔溶剂微脂囊可应用于植物萃取、协同促渗、搭载递送等技术开发应用上。通过特定设计的超分子红没药醇低共熔溶剂微脂囊具有提高活性物溶解性、增强活性物经皮促渗、共递送活性物等优良特点。
本发明的有益效果为:
(1)通过本发明制备方法得到的超分子红没药醇低共熔溶剂微脂囊,其通过单体的可设计性而可以得到不同功能的超分子红没药醇低共熔溶剂,从而可以设计出不同功能的超分子红没药醇低共熔溶剂微脂囊。
(2)本发明的超分子红没药醇低共熔溶剂微脂囊,在对难溶性物质的溶解中表现出优异的促溶效率。
(3)本发明的超分子红没药醇低共熔溶剂微脂囊,表现出与活性物协同递送,活性物增效促渗吸收的作用。
红没药醇通过超分子低共熔溶剂改性,以获得红没药醇类低共熔溶剂并搭载活性物,并使用微脂囊包裹技术递送超分子红没药醇低共熔溶剂和活性物,改善活性物自身稳定性、刺激性、透皮吸收效果、共递送效果具有积极意义。同时也是为化妆品、食品、保健品的品类开发和科技研发重要影响。
附图说明
图1为本发明的超分子红没药醇低共熔溶剂的外观图;从左到右分别为实施例1、26、22、15、17。
图2为本发明的超分子红没药醇低共熔溶剂微脂囊的外观图;从左到右分别为实施例1、26、22、15、17。
图3为本发明测试例2的超分子红没药醇低共熔溶剂微脂囊的粒径结果。
图4为本发明的测试例2中的组2制备的超分子红没药醇低共熔溶剂微脂囊的粒径图。
图5为本发明的测试例2中的组2制备的超分子红没药醇低共熔溶剂微脂囊的透射电镜图。
图6为本发明的测试例2中的组2制备的超分子红没药醇低共熔溶剂微脂囊的透皮促渗效果。
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1-13:
本发明所述超分子红没药醇低共熔溶剂微脂囊的实施例;所述超分子红没药醇低共熔溶剂微脂囊包括超分子红没药醇低共熔溶剂、乳化剂和溶液。
所述乳化剂为PEG-400氢化蓖麻油。
所述溶液为多元醇和水;所述多元醇为丁二醇。
所述超分子红没药醇低共熔溶剂微脂囊中,超分子红没药醇低共熔溶剂、乳化剂、多元醇、水的重量份比为超分子红没药醇低共熔溶剂:乳化剂:多元醇:水=5:5:15:75。
所述超分子红没药醇低共熔溶剂由红没药醇和配体组成;所述配体为酚类化合物;所述酚类化合物的种类、红没药醇和配体的摩尔比如表1所示。
表1红没药醇与酚类化合物的配比
在空气或氮气的保护下,将红没药醇和配体按照表1的摩尔比混合,在存在或不存在溶剂(水或醇)的条件下搅拌溶解,升温至60℃,待两者混合为一相后,降温冷却,旋转蒸发除去溶剂,即得到超分子红没药醇低共熔溶剂。
本发明所述超分子红没药醇低共熔溶剂微脂囊的制备方法包括如下步骤:
(1)将超分子红没药醇低共熔溶剂、乳化剂和溶液混合后,均质剪切得到初乳液;
(2)将步骤(1)所得初乳液在温度为60℃,压力600bar下,高压均质4次得到所述超分子红没药醇低共熔溶剂微脂囊。
实施例14-20:
本发明所述超分子红没药醇低共熔溶剂微脂囊的实施例;所述超分子红没药醇低共熔溶剂微脂囊包括超分子红没药醇低共熔溶剂、乳化剂和溶液。
所述乳化剂为鲸蜡硬脂醇聚醚-25。
所述溶液为多元醇:水;所述多元醇为丁二醇。
所述超分子红没药醇低共熔溶剂微脂囊中,超分子红没药醇低共熔溶剂、乳化剂、多元醇、水的重量份比为超分子红没药醇低共熔溶剂:乳化剂:多元醇:水=5:5:15:75。
所述超分子红没药醇低共熔溶剂由红没药醇和配体组成;所述配体为环己醇类化合物;所述环己醇类化合物的种类、红没药醇和配体的摩尔比如表2所示。
表2红没药醇与环己醇类化合物的配比
在空气或氮气的保护下,将红没药醇和配体按照表2的摩尔比混合,在存在或不存在溶剂(水或醇)的条件下搅拌溶解,升温至30-80℃,待两者混合为一相后,降温冷却,旋转蒸发除去溶剂,即得到超分子红没药醇低共熔溶剂。
本发明所述超分子红没药醇低共熔溶剂微脂囊的制备方法包括如下步骤:
(1)将超分子红没药醇低共熔溶剂、乳化剂和溶液混合后,均质剪切得到初乳液;
(2)将步骤(1)所得初乳液在温度为40℃,压力500bar下,高压均质4次得到所述超分子红没药醇低共熔溶剂微脂囊。
实施例21-32:
本发明所述超分子红没药醇低共熔溶剂微脂囊的实施例;所述超分子红没药醇低共熔溶剂微脂囊包括超分子红没药醇低共熔溶剂、乳化剂和溶液。
所述超分子红没药醇低共熔溶剂由红没药醇和配体组成;所述配体为羧酸类化合物;所述乳化剂为聚甘油-10硬脂酸酯。
所述超分子红没药醇低共熔溶剂微脂囊中,超分子红没药醇低共熔溶剂、乳化剂的重量份比为超分子红没药醇低共熔溶剂:乳化剂=5:5。
本发明所述超分子红没药醇低共熔溶剂微脂囊的制备方法包括如下步骤:
(1)将超分子红没药醇低共熔溶剂、乳化剂和溶液混合后均质剪切得到初乳液;
(2)将步骤(1)所得初乳液在温度为60℃,压力600bar下,高压均质4次得到所述超分子红没药醇低共熔溶剂微脂囊。
所述超分子红没药醇低共熔溶剂配体的羧酸类化合物种类、红没药醇和配体的摩尔比、溶液中多元醇的种类、多元醇与水的配比如表3所示。
在空气或氮气的保护下,将红没药醇和配体按照表3的摩尔比混合,在存在或不存在溶剂(水或醇)的条件下搅拌升温至70-80℃,待两者混合为一相后,降温冷却,旋转蒸发除去溶剂,即得到超分子红没药醇低共熔溶剂。
表3红没药醇低共熔溶剂组成及其制备过程中的溶液种类
摩尔比例 | 溶液 | |
实施例21 | 红没药醇:辛酸=1:1 | 丙二醇:水=15:75 |
实施例22 | 红没药醇:癸酸=1:1 | PEG-400:水=15:75 |
实施例23 | 红没药醇:月桂酸=1:1 | 丁二醇:水=15:75 |
实施例24 | 红没药醇:10-羟基癸酸=3:1 | 1,2-戊二醇:水=15:75 |
实施例25 | 红没药醇:10-羟基癸酸=2:1 | 1,2-己二醇:水=15:75 |
实施例26 | 红没药醇:α-硫辛酸=1:1 | PEG-400:水=15:75 |
实施例27 | 红没药醇:二十碳五烯酸=2:1 | 双丙二醇:水=15:75 |
实施例28 | 红没药醇:二十二碳六烯酸=2:1 | 甘油:水=15:75 |
实施例29 | 红没药醇:肉豆蔻酸=1:1 | 丁二醇:水=25:65 |
实施例30 | 红没药醇:棕榈酸=1:1 | 丁二醇:水=45:45 |
实施例31 | 红没药醇:油酸=1:1 | 丁二醇:水=65:25 |
实施例32 | 红没药醇:亚油酸=1:1 | 丁二醇:水=75:15 |
实施例33-43:
本发明所述超分子红没药醇低共熔溶剂微脂囊的实施例;所述超分子红没药醇低共熔溶剂微脂囊包括超分子红没药醇低共熔溶剂、乳化剂和溶液。
所述乳化剂为鲸蜡硬脂醇聚醚-25。
所述溶液为多元醇和水;所述多元醇为丁二醇。
所述超分子红没药醇低共熔溶剂微脂囊中,超分子红没药醇低共熔溶剂、乳化剂、多元醇、水的重量份比为超分子红没药醇低共熔溶剂:乳化剂:多元醇:水=5:5:15:75。
所述超分子红没药醇低共熔溶剂由红没药醇和配体组成;所述配体的种类、红没药醇和配体的摩尔比如表4所示。
表4红没药醇低共熔溶剂的组成及配比
实施例33 | 红没药醇:癸醇=1:1 |
实施例34 | 红没药醇:香叶醇=1:1 |
实施例35 | 红没药醇:叶绿醇=1:1 |
实施例36 | 红没药醇:辛基十二醇=1:1 |
实施例37 | 红没药醇:丁二醇=2:1 |
实施例38 | 红没药醇:双丙甘醇1:1 |
实施例39 | 红没药醇:1,2-己二醇=1:1 |
实施例40 | 红没药醇:甘油=1:1 |
实施例41 | 红没药醇:丙二醇=1:1 |
实施例42 | 红没药醇:1,2-戊二醇=1:1 |
实施例43 | 红没药醇:泛醇=1:1,溶剂水 |
在空气或氮气的保护下,将红没药醇和配体按照表2的摩尔比混合,在存在或不存在溶剂(水或醇)的条件下搅拌溶解,升温至30-80℃,待两者混合为一相后,降温冷却,旋转蒸发除去溶剂,即得到超分子红没药醇低共熔溶剂。
本发明所述超分子红没药醇低共熔溶剂微脂囊的制备方法包括如下步骤:
(1)将超分子红没药醇低共熔溶剂、乳化剂和溶液混合后均质剪切得到初乳液;
(2)将步骤(1)所得初乳液在温度为60℃,压力600bar下,高压均质4次得到所述超分子红没药醇低共熔溶剂微脂囊。
实施例44-64:
本发明所述超分子红没药醇低共熔溶剂微脂囊的实施例;所述超分子红没药醇低共熔溶剂微脂囊包括超分子红没药醇低共熔溶剂、乳化剂和溶液。
所述溶液为多元醇和水;所述多元醇为丁二醇。
所述多元醇和水的重量份比为多元醇:水=15:75。
所述超分子红没药醇低共熔溶剂由红没药醇和配体组成;所述配体为酚类化合物;所述酚类化合物为丹皮酚;所述红没药醇和配体的摩尔比为1:1。所述乳化剂的种类、超分子红没药醇低共熔溶剂与乳化剂的重量配比如表5所示。
表5超分子红没药醇低共熔溶剂微脂囊组分组成
在空气或氮气的保护下,将红没药醇和配体按照表2的摩尔比混合,在存在或不存在溶剂(水或醇)的条件下搅拌溶解,升温至60℃,待两者混合为一相后,降温冷却,旋转蒸发除去溶剂,即得到超分子红没药醇低共熔溶剂。
本发明所述超分子红没药醇低共熔溶剂微脂囊的制备方法包括如下步骤:
(1)将超分子红没药醇低共熔溶剂、乳化剂和溶液混合后均质剪切得到初乳液;
(2)将步骤(1)所得初乳液进行高压均质4次得到所述超分子红没药醇低共熔溶剂微脂囊。
对比例1-8:
本发明所述超分子红没药醇低共熔溶剂微脂囊的对比例;本对比例为红没药醇微脂囊;所述红没药醇微脂囊组成和质量份与本发明对应部分实施例相同,其对应关系与如表6所示。
表6红没药醇微脂囊的组分组成
本对比例所述红没药醇微脂囊的制备方法包括如下步骤:
(1)将红没药醇、配体、乳化剂按比例混合得到油相;将溶液混合后得到水相;将所得油相加入到水相混合后均质剪切得到初乳液;
(2)将步骤(1)所得初乳液在温度为60℃,压力600bar下,高压均质4次得到所述红没药醇微脂囊。
对比例9:
本发明所述超分子红没药醇低共熔溶剂微脂囊的对比例;本对比例与实施例1的区别为红没药醇:丹皮酚的摩尔比=30:0.5,其余与实施例1相同。
本对比例的超分子红没药醇低共熔溶剂微脂囊的制备方法同实施例1。
对比例10:
本发明所述超分子红没药醇低共熔溶剂微脂囊的对比例;本对比例与实施例1的区别为制备过程中不进行步骤(2)中的高压均质处理,其余与实施例1相同。
对比例11:
本发明所述超分子红没药醇低共熔溶剂微脂囊的对比例;本对比例与实施例1的区别为:不含红没药醇的配体,其余与实施例1相同。
本对比例的超分子红没药醇低共熔溶剂微脂囊的制备方法同实施例1。
测试例1:外观观察
将实施例1、15、17、22、26制备的超分子红没药醇低共熔溶剂和超分子红没药醇低共熔溶剂微脂囊进行外观观察,结果如图1、2所示。
制备得到的超分子红没药醇低共熔溶剂均为透明溶液,实施例1、15、17、呈无色透明状,实施例26(α-硫辛酸)呈黄色透明状。
制备得到的超分子红没药醇低共熔溶剂微脂囊均为乳液,实施例1、15、17、呈乳白色,实施例26(α-硫辛酸)呈浅黄色。
测试例2:活性物增溶测试
设置实验组和对照组,控制活性组分,红没药醇低共熔溶剂10.00g、PEG-400氢化蓖麻油5.00g、丁二醇10g,剩余组分为水(按百分质量为100%计),所有实验组和对照组组分质量百分含量相同。
实验组:将活性组分加入红没药醇低共熔溶剂中作为油相,加热到70~80℃,其余组分作为混合均匀水相。将油相加入水相中剪切乳化后得到超分子红没药醇低共熔溶剂微脂囊初乳液;再通过70~80℃、600bar高压均质4次得到超分子红没药醇低共熔溶剂微脂囊。
对照组:将活性组分、红没药醇、配体简单混合作为油相,加热到70~80℃,其余组分混合均匀作为水相;将油相加入水相中剪切乳化后得到红没药醇初乳液,再通过70~80℃、600bar高压均质4次得到红没药醇微脂囊。
将制备的超分子红没药醇低共熔溶剂微脂囊和红没药醇微脂囊,通过高速离心后,底部固体物用水洗涤并离心3次,最后干燥底部固体物,通过称重方式测定活性成分包封率,以此判断超分子红没药醇低共熔溶剂微脂囊的对活性物增溶效果。
包封率的计算公式如式(1)所示,结果如表7所示。
表7超分子红没药醇低共熔溶剂微脂囊对活性组分的增溶效果
从组1-组8可以看出,超分子红没药醇低共熔溶剂微脂囊和红没药醇微脂囊两者在对活性物的溶解(包裹)上表现出一致性,也即超分子红没药醇低共熔溶剂微脂囊对活性物的包裹显著高于红没药醇微脂囊。
从原理上解释,说明将红没药醇与配体形成低共熔溶剂,以此制备成的超分子红没药醇低共熔溶剂微脂囊增强了活性物在油相中的溶解度,进而增强了超分子红没药醇低共熔溶剂微脂囊对活性物的包载效率。
测试例3透皮促渗效果测试
设置实验组和对照组,控制活性组分、红没药醇低共熔溶剂10.00g、PEG-400氢化蓖麻油5.00g、丁二醇10g、剩余组分为水,所有实验组和对照组组分质量百分含量相同。
实验组:将活性组分加入红没药醇低共熔溶剂中作为油相,加热到70~80℃,其余部分作为水相。将油相加入水相中剪切乳化后得到超分子红没药醇低共熔溶剂微脂囊初乳液,70~80℃、600bar高压均质4次,剪切得到超分子红没药醇低共熔溶剂微脂囊。
对照组1:将活性组分加入红没药醇低共熔溶剂中作为油相,加热到70~80℃,其余部分作为水相。将油相加入水相中剪切乳化后得到超分子红没药醇低共熔溶剂微脂囊初乳液。
对照组2:将活性组分、红没药醇以及另一配体简单混合作为油相,加热到70~80℃,其余部分作为水相。将油相加入水相中剪切乳化后得到红没药醇初乳液,70~80℃、600bar高压均质4次剪切得到红没药醇微脂囊。
按照表8的透皮促渗试验设计进行实验。
表8超分子红没药醇低共熔溶剂微脂囊对活性组分的透皮促渗试验设计
1)粒径测试、透射电镜观察
取超分子红没药醇低共熔溶剂微脂囊和红没药醇微脂囊稀释1000倍后,使用粒径电位测量仪进行测量,同时,进行透射电镜观察。本发明的测试例2超分子红没药醇低共熔溶剂微脂囊的粒径结果如图3所示;测试例2中的组2制备的超分子红没药醇低共熔溶剂微脂囊的粒径图如图4所示,透射电镜图如图5所示。
2)渗透测试
将制备的实验组、对照组,使用Franz扩散池,按照猪皮渗透模型,对猪皮进行1h、2h、4h、8h透皮递送实验。
a)通过高效液相色谱检测活性成分皮内滞留量,以表征活性物的透皮效率。
b)对于雨生红球藻提取物,透皮过程及萃取过程中进行充氮保护。
以下是不同活性物在不同条件下的透皮皮内滞留量情况,计算公式如式(2),皮内滞留量结果如表9所示。本发明的测试例2中的组2超分子红没药醇低共熔溶剂微脂囊的透皮促渗效果如图6所示。
表9超分子红没药醇低共熔溶剂微脂囊对活性组分的皮内滞留量结果
可以看出,超分子红没药醇低共熔溶剂微脂囊通过高压均质后粒径会处于亚微米级,而未经过高压均质处理的,则处于微米级。通过渗透原理可以得知,物质粒径在一定程度上越小,其渗透性会增加。
从渗透试验可以看出,超分子红没药醇低共熔溶剂微脂囊在不同时间点(1h、2h、4h、4h)的皮内滞留量都高于超分子红没药醇低共熔溶剂微脂囊初乳液、红没药醇微脂囊。实验组对比对照组-1说明高压均质降低了微粒粒径,进而赋予微粒更好的渗透作用。实验组对比对照组-2说明,低共熔溶剂的存在也会增强活性物的渗透性能,使活性成分透皮吸收更多。
因此,超分子红没药醇低共熔溶剂微脂囊结合超分子低共熔溶剂和高压均质技术,可以赋予活性物更加优秀的渗透吸收作用。
测试例4超分子红没药醇低共熔溶剂微脂囊的细胞功效测试
根据测试例3中“实验组”和“对照组”进行细胞功效实验。按照表10进行功效实验。
表10超分子红没药醇低共熔溶剂微脂囊对细胞功效方向实验设计
具体过程为:
抗皱细胞实验:将人皮肤成纤维细胞悬浮液接种至24孔板,置于培养箱中培养。设置空白对照组、阴性对照组、阳性对照组、样品组。选择UVA(4.8J/cm2)作为刺激条件,使用ELISA试剂检测人皮肤成纤维细胞中MMP-1含量。
抗氧化细胞实验:将人皮肤成纤维细胞悬浮液接种至24孔板,置于培养箱中培养。设置空白对照组、阴性对照组、阳性对照组、样品组。选择UVA(4.8J/cm2)作为刺激条件,使用ELISA试剂检测人皮肤成纤维细胞中ROS含量。
细胞酪氨酸酶实验:将B16小鼠黑色素瘤细胞悬浮液接种至96孔板,置于培养箱中培养。设置空白对照组、阴性对照组、阳性对照组、样品组。选择α-MSH作为刺激条件,检测各孔在490nm处吸光值,以确定酪氨酸酶的抑制结果。
抗炎细胞实验:将人角质细胞悬浮液接种至24孔板,置于培养箱中培养。设置造模组、阴性对照、阳性对照、样品组。选择LPS作为刺激条件,使用ELISA试剂检测角质细胞中IL-6含量。
测试结果如表11所示。
表11超分子红没药醇低共熔溶剂微脂囊细胞功效结果
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可以看出,超分子红没药醇低共熔溶剂微脂囊在各种功效上的相对含量都显著低于超分子红没药醇低共熔溶剂微脂囊初乳液、红没药醇微脂囊微乳液。说明在各个功效上,超分子红没药醇低共熔溶剂微脂囊对活性物功效都具有协同增效的作用。
1)通过本发明制备方法制备的超分子红没药醇低共熔溶剂微脂囊,其通过单体的可设计性而可以得到不同功能的超分子红没药醇低共熔溶剂,从而可以设计出不同功能的超分子红没药醇低共熔溶剂微脂囊。
2)本发明的超分子红没药醇低共熔溶剂微脂囊,在对活性成分促溶解中表现出优异的促溶效率。
3)本发明的超分子红没药醇低共熔溶剂微脂囊,表现出和活性物协同递送,活性物增效促渗吸收作用。
本发明的超分子红没药醇低共熔溶剂微脂囊其可应用于植物萃取、协同促渗、搭载递送等技术开发应用上。通过特定设计的超分子红没药醇低共熔溶剂微脂囊具有提高溶解性、增强活性物经皮促渗、共递送活性物等优良特点。
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 (10)
1.一种超分子红没药醇低共熔溶剂,其特征在于,所述超分子红没药醇低共熔溶剂包括红没药醇和配体;所述配体包括环己醇类化合物、酚类化合物、羧酸类化合物、非环状单元醇、多元醇中的至少一种;所述红没药醇和配体的摩尔比为红没药醇:配体=1:(0.1-10)。
2.如权利要求1所述的超分子红没药醇低共熔溶剂,其特征在于,所述环己醇类化合物包括4-叔丁基环己醇、薄荷醇、冰片、薄荷醇乳酸酯、薄荷酮甘油缩酮、薄荷氧基丙二醇中的至少一种;所述酚类化合物包括丹皮酚、4-正丁基间苯二酚、茶多酚、丁香酚、厚朴酚、麝香草酚、桃柁酚中的至少一种;所述羧酸类化合物包括辛酸、癸酸、月桂酸、肉豆蔻酸、棕榈酸、油酸、亚油酸、10-羟基癸酸、硫辛酸、二十二碳六烯酸、二十碳五烯酸中的至少一种;所述非环状单元醇包括癸醇、香叶醇、叶绿醇、辛基十二醇中的至少一种;所述多元醇包括丁二醇、丙二醇、1,2-己二醇、1,2-戊二醇、双丙甘醇、甘油中的至少一种。
3.一种如权利要求1或2所述的超分子红没药醇低共熔溶剂的制备方法,其特征在于,包括如下步骤:在空气或氮气的保护下,将红没药醇和配体混合,搅拌、加热,充分溶解,冷却得到所述超分子红没药醇低共熔溶剂。
4.如权利要求3所述的超分子红没药醇低共熔溶剂的制备方法,其特征在于,所述充分溶解的方法为:加入水或醇溶解,待冷却后再去除水或醇。
5.一种超分子红没药醇低共熔溶剂微脂囊,其特征在于,所述超分子红没药醇低共熔溶剂微脂囊包括权利要求1-2任一项所述的超分子红没药醇低共熔溶剂、乳化剂和溶液;所述溶液为水、多元醇中的至少一种;所述多元醇包括丙二醇、丁二醇、1,2-戊二醇、1,2-己二醇、双丙甘醇、甘油中的至少一种。
6.如权利要求5所述的超分子红没药醇低共熔溶剂微脂囊,其特征在于,所述乳化剂包括PEG改性油酯类化合物、山梨醇聚醚类化合物、鲸蜡硬脂醇聚醚-25、烷基糖苷、硬脂酰基谷氨酸钠、椰油酰基谷氨酸钠、聚甘油-10硬脂酸酯、聚甘油-10肉豆蔻酸酯、聚甘油-10月桂酸酯、肉豆蔻酰基谷氨酸钠、月桂酰基谷氨酸钠、硬脂酰基甘氨酸钠、油酰基甘氨酸钠、棕榈酰基甘氨酸钠、肉豆蔻酰基甘氨酸钠、月桂酰基甘氨酸钠、硬脂酸钠、油酸、棕榈酸钠、肉豆蔻酸钠、月桂酸及其钠/钾盐、卵磷脂、大豆磷脂、氢化卵磷脂中的至少一种。
7.如权利要求5所述的超分子红没药醇低共熔溶剂微脂囊,其特征在于,所述超分子红没药醇低共熔溶剂、乳化剂和溶液的重量份比为超分子红没药醇低共熔溶剂:乳化剂:溶液=(0.5-20):(0.5-20):(44-99)。
8.一种如权利要求5-7任一项所述超分子红没药醇低共熔溶剂微脂囊的制备方法,其特征在于,包括如下步骤:
(1)将超分子红没药醇低共熔溶剂、乳化剂和溶液混合后,均质剪切得到初乳液;
(2)将步骤(1)所得初乳液进行高压均质剪切得到所述超分子红没药醇低共熔溶剂微脂囊。
9.如权利要求8所述的超分子红没药醇低共熔溶剂微脂囊的制备方法,其特征在于,所述步骤(2)中,高压均质剪切的条件为温度20-100℃,压力0-2000bar。
10.如权利要求5-7任一项所述的超分子红没药醇低共熔溶剂微脂囊在制备化妆品、保健品、食品中的应用。
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