CN104379175B - 高度支化的α-D-葡聚糖 - Google Patents
高度支化的α-D-葡聚糖 Download PDFInfo
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- CN104379175B CN104379175B CN201380032127.5A CN201380032127A CN104379175B CN 104379175 B CN104379175 B CN 104379175B CN 201380032127 A CN201380032127 A CN 201380032127A CN 104379175 B CN104379175 B CN 104379175B
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Abstract
本文描述了包含高度支化的α‑D‑葡聚糖或其改性形式和溶质化合物的组合物。所述组合物可为所述溶质化合物提供增加的水溶解度和/或增加的溶解速率。所述组合物还可为所述溶质化合物提供增加的稳定性。还描述了制备和使用包含溶质化合物和高度支化的α‑D‑葡聚糖的组合物的方法。
Description
继续申请资料
本申请要求2012年4月19日提交的美国临时专利申请第61/635,453号的权益,所述案件通过援引加入本文。
政府资助
本发明至少部分在美国国家科学基金会的第DMR1006301号拨款下受政府支持而作出。因此,美国政府对本发明具有一定的权利。
发明领域
概括地说,本发明涉及用于增加其中的溶质化合物的溶解度和稳定性的组合物,更具体地涉及包含高度支化的多糖的组合物,所述多糖可用于改善用于食品、营养保健品、个人护理、皮肤护理、化妆品、药品、医疗、油漆和涂料以及农业行业的溶质化合物的溶解度、稳定性和/或生物利用度。
背景技术
在例如食品、饲料、农业、药物、动物药、个人护理、皮肤护理等的行业中,某些成分或提取物的使用是困难的,因为它们的组成材料在水中具有低或差的溶解度,这导致低的稳定性、易接受性(accessibility)、利用度或生物利用度。此类成分、合成化合物或提取物的实例可包括酚类化合物(例如,类黄酮、类姜黄素)、类胡萝卜素和活性药物成分(API,例如药物),以及来自草药、微生物和动物的粗提取物或纯化提取物。
此类成分或提取物的一个具体实例包括酚类化合物,例如槲皮素和姜黄素。槲皮素和姜黄素是强抗氧化剂,并且具有抗炎、抗病毒和抗癌效力。具体地,姜黄素是可在临床上使用的有效抗癌药物。然而,它们的低溶解度妨碍其在食品、营养保健品、化妆品和医药制剂中的使用。为解决这个问题,已经使用各种技术来改善此类低溶解性或不溶性酚类化合物的水溶解度。例如,已经提出使用分散姜黄素并改善其溶解度的特定化合物(例如,胡椒碱)、聚合物纳米粒子囊封或表面活性剂胶束来改善姜黄素的溶解度。然而,这些方法昂贵和/或溶解酚类化合物的能力有限。另外,这些策略中的一些完全无效。
一些活性药物成分(API),例如多种药物的较差水溶解度是药物配制和药物吸收中的主要问题之一。改善这些药物的水溶解度的系统对其生物利用度来说必不可少。例如,紫杉醇在癌症治疗中的应用受限于其低水溶解度,并且目前的溶解紫杉醇的作法通常导致短期物理稳定性与药物分子的快速沉淀。为增强紫杉醇的溶解度和物理稳定性,助水溶物已被用于与药物分子复合。然而,为达到有效,助水溶物的浓度需要非常高,这可能会导致配制和给药困难。
另一个实例是布洛芬。布洛芬是非甾体抗炎药(NSAID),并且是WHO基本药物标准清单中的核心药物。它被广泛地用于缓解关节炎和发热的症状,并且在存在炎性成分和痛经的情况下用作镇痛药。布洛芬属于生物药剂学分类系统(BCS)的第二类,对于此类药物,药物溶解速率或药物溶解度是吸收中的限速步骤。
另一个实例是灰黄霉素。灰黄霉素是在皮肤、头发和指甲的霉菌性疾病的治疗中广泛使用的抗真菌药物。灰黄霉素难溶于水,并且在增加药物的生物利用度的研究中被用作标准物。
类似的问题仍然存在于与来自植物、微生物或动物有机体的药用、营养或功能材料的提取和配制相关的行业中,例如草药提取物、中药和着色剂。在此类行业中,存在许多提取方法,包括:(1)水性提取;(2)基于溶剂的提取;和(3)超临界流体提取。在许多情况下,溶质化合物(或材料)具有低的水溶解度,这使得难以配制为产品。此外,在与饲料、动物药、个人护理、化妆品、油漆、杀虫剂、除草剂或其它食品和非食品领域相关的行业中,产品中某些材料的低溶解度是此类产品的配制、处理和/或功能的许多困难的来源。
发明内容
本文描述了用于增加溶质化合物的溶解度和稳定性的组合物。更具体地,描述了包含高度支化的α-D-葡聚糖的组合物,所述α-D-葡聚糖可用于改善用于食品、营养保健品、个人护理、皮肤护理、化妆品、药品、医疗、油漆和涂料以及农业行业的溶质化合物的溶解度、稳定性和/或生物利用度。
本发明人已经惊奇地发现,高度支化的α-D-葡聚糖,例如植物糖原(及其改性形式),可用于显著增加多种相对水不溶性化合物的溶解度,例如一些酚类化合物(例如,槲皮素和姜黄素),或药物,例如布洛芬、灰黄霉素等。本发明人还发现,由所述高度支化的α-D-葡聚糖和所述溶质化合物形成的组合物与不含高度支化的α-D-葡聚糖的组合物相比在正常储存条件下更稳定。因此,所述高度支化的α-D-葡聚糖的作用是:(1)稳定所述溶质化合物,例如,稳定活性药物成分(API)在固体分散体中的无定形状态,从而在与水接触时,所述溶质可以被释放以形成过饱和溶液(在这种情况下,不一定形成所述溶质化合物和所述高度支化的α-D-葡聚糖在水中的复合物);和(2)形成所述溶质化合物和所述高度支化的α-D-葡聚糖的可溶性复合物,从而所述复合物的溶解度影响药物的总体溶解度。
附图说明
通过参考以下附图可以更容易地理解本发明,其中:
图1是糖原的示意图,其示出了该分子的树枝状结构。
图2是植物糖原纳米粒子的透射电子显微镜(TEM)图像。
图3是示出了在22℃和pH 6.6下植物糖原的浓度对槲皮素的溶解度的影响的图。
图4是示出了在22℃和pH 6.6下植物糖原和植物糖原辛烯基琥珀酸酯(PG-OS)的浓度对姜黄素的溶解度的影响的图。
图5是示出了灰黄霉素在各种系统中的归一化DSC曲线的图。G:灰黄霉素。G-DMSO:溶解于DMSO中随后除去溶剂的灰黄霉素。PG-G、PGS-G和PGSPEG-G:分别为使用DMSO作为溶剂随后除去溶剂与天然PG、PG-琥珀酸(PG-S)和PG-琥珀酸-PEG(PG-S-PEG)复合的灰黄霉素。将这些复合物在22℃下放置37天,然后进行DSC测试。PG-G/PM、PGS-G/PM和PGSPEG-G/PM:分别为使用研钵和研棒与天然PG、PG-S和PG-S-PEG物理混合的灰黄霉素。对于所有的混合物,灰黄霉素/载体比为1/3(w/w)。
图6是示出了PG复合之前和之后布洛芬的组织(结晶)结构的含量的图。A:DSC热流曲线;B:X射线粉末结晶衍射图。样品标记在图A与图B之间共享。PG:天然PG;PG-D:用DMSO处理(溶解,随后除去溶剂)的PG;Ibu:未处理的布洛芬;Ibu-D:用DMSO处理(溶解,随后除去溶剂)的布洛芬;1/3:布洛芬(1份)与PG(3份)的DMSO介导的复合;1/3PM-D:用DMSO处理的布洛芬(1份)与PG(3份)之间的物理混合物;1/3PM:未处理的布洛芬(1份)与PG(3份)之间的物理混合物;1/5:布洛芬(1份)与PG(5份)的DMSO介导的复合;1/5PM:未处理的布洛芬(1份)与PG(3份)之间的物理混合物。
图7是示出了姜黄素的溶解度和体外渗透性的改善的图。图A示出了在Na2HPO4-柠檬酸缓冲液(pH 3.0-6.6)中植物糖原(PG)的姜黄素溶解度提高效力。无PG:未使用PG,姜黄素被均质化于缓冲液中;1%PG:具有1.0%PG的PG-姜黄素复合物的分散体;5%PG:具有5.0%PG的PG-姜黄素复合物的分散体。图B示出了PG复合和在顶端隔室(Caco-2细胞单层模型)中加入的酶(α-淀粉酶和淀粉葡糖苷酶)对姜黄素在基底外侧隔室中累积的影响。HBSS-CCM:均质化于汉克斯平衡盐溶液(HBSS)中的姜黄素粉末;HBSS-CCM-Enz:均质化于HBSS中,然后加入酶的姜黄素粉末;PG-CCM:在HBSS中的PG-姜黄素复合物;PG-CCM-Enz:在加入酶的HBSS中的PG-姜黄素复合物。对于所有的试验,姜黄素在顶端隔室中的起始浓度均为60μg/mL。
图8提供的照示出了植物糖原-麝香草酚复合物制剂和单独麝香草酚制剂中的麝香草酚的最小抑制浓度(MIC)的检测。清澈透明的液体表明细菌生长可以忽略。
具体实施方式
如本文所用的,水溶液是其中水为主要溶剂的任何溶液。所述水溶液可包含其它溶剂以及一种或多种另外的溶质,而仍旧是水溶液。水溶液的实例包括缓冲溶液、盐水、饮料例如咖啡、茶、啤酒、葡萄酒和果汁、醋等。水溶液也可以是乳液(例如乳膏、洗剂)、胶体、混悬剂或气溶胶的相。
如本文所用的,溶解度是指溶质化合物溶解在液体溶剂中以形成所述溶质在所述溶剂中的均匀溶液的能力。溶质化合物的溶解度可以取决于许多因素,例如温度、压力和溶液的pH而变化。如本文所用的,增加的溶解度是指在一组给定的条件下增加的量的溶质溶解在给定组成的水溶液中的能力。物质在特定溶剂中的溶解度的程度被测量为动力学上稳定的浓度,其中,加入更多的溶质不会增加溶液的浓度并且过量的溶质开始沉淀。溶解度通常以浓度表示。
本文描述了用于增加溶质化合物的溶解度的组合物。所述组合物包含高度支化的α-D-葡聚糖和溶质化合物。在所述高度支化的α-D-葡聚糖的存在下,所述溶质化合物表现出改善的性质,例如增加的溶解度、增加的溶解速率、增加的稳定性和/或增加的膜渗透性。尽管在一些实施方案中可存在其它成分,例如药物载体,但对增加所述溶质化合物的溶解度来说必不可少的主要化合物是所述高度支化的α-D-葡聚糖(例如,植物糖原)。
高度支化的α-D-葡聚糖
如本文所用的,术语“高度支化的α-D-葡聚糖”是指由α-D-葡萄糖分子形成的高度支化的多糖,例如糖原、植物糖原、支链淀粉或其改性形式。在一些实施方案中,所述多糖通过α-D-1,4-糖苷键和α-D-1,6-糖苷键连接。然而,在其它实施方案中,可使用化学改性(例如,焦糊精化(pyrodextrinization))来提供包含其它类型的键(例如α-D-1,2键和α-D-1,3键)的高度支化的α-D-葡聚糖。高度支化的α-D-葡聚糖可以从植物材料、微生物(例如,细菌)或者人或非人动物获得、衍生或提取,或者由葡萄糖、葡聚糖或其它材料合成。在一个实例中,高度支化的α-D-葡聚糖包括糖原、植物糖原、支链淀粉和/或其改性形式,例如用辛烯基琥珀酸酯(OS)或聚乙二醇(PEG)改性。
如本文所用的,高度支化的多糖是具有至少约4%的支化密度的多糖。在一些实施方案中,高度支化的α-D-葡聚糖的支化密度可为约5%到约30%。在其它实施方案中,支化密度为至少5%、至少6%、至少7%或至少8%。在其它实施方案中,支化密度可为例如约7%到约16%。例如,支链淀粉的支化密度可为约4%-6%,并且糖原和植物糖原的支化密度可为约8%-11%。例如,对于仅含有α-D-1,4-糖苷键和α-D-1,6-糖苷键的糖原,支化密度可以通过如下比较α-D-1,4-糖苷键和α-D-1,6-糖苷键的数量来确定:支化密度百分比=α-D-1,6-糖苷键的数量/(α-D-1,4-糖苷键的数量+α-D-1,6-糖苷键的数量)*100。通常,支化密度是以葡聚糖分子中的所有糖苷键计,分支点的百分比。
在一些实施方案中,高度支化的α-D-葡聚糖具有树枝状结构。在树枝状结构中,多糖链是球状组织,如同从作为结构核心处的基点(primer)的中心位置发出的树枝一样。
支化的α-D-葡聚糖的支化密度可以通过多种方法测定,例如还原性末端分析、NMR和色谱分析。参见Shin等人,Journal of Agricultural and Food Chemistry,56:10879-10886(2008);Yao等人,Plant Physiology,136:3515-3523(2004);以及Yun和Matheson,Carbohydrate Research,243:307-321(1993)。酶处理可以通过产生或裂解α-D-1,4-糖苷键和/或α-D-1,6-糖苷键影响支化密度。这些酶可以是α-淀粉酶、β-淀粉酶、脱支酶(例如,支链淀粉酶和异淀粉酶)、转葡糖苷酶、淀粉葡糖苷酶等。其它方法也可影响α-D-葡聚糖的支化密度,例如酸或碱处理以及氧化。在一个实例中,高度支化的α-D-葡聚糖可以是单一类型的高度支化的α-D-葡聚糖。或者,高度支化的α-D-葡聚糖可以是包含多种不同的高度支化的α-D-葡聚糖的混合物。
在一些实施方案中,α-D-葡聚糖是植物糖原。植物糖原是由植物产生的水溶性的糖原类α-D-葡聚糖。植物糖原的最大来源之一是玉米突变体sugary-1(su1)(甜玉米的主要基因型)的籽粒。su1突变导致SU1不足,SU1是异淀粉酶型淀粉脱支酶(DBE)(James等人,Plant Cell,7:417-429(1995))。在淀粉的生物合成中,淀粉合成酶、淀粉分支酶和DBE协调地工作以产生淀粉颗粒(Yao,“Biosynthesis of starch”,Comprehensive Glycoscience,Hans Kamerling编,Elsevier(2007))。DBE的主要作用是修剪抑制淀粉晶体和颗粒的形成的异常分支。参见Myers等人,Plant Physiology,122;989-997(2000)和Nakarnura,Plantand Cell Physiology,43:718-725(2002)。在不存在DBE时,形成高度支化的植物糖原以代替淀粉颗粒。大多数粒子约40-50nm。
各植物糖原粒子包含数百或数千条葡聚糖链,从而形成高密实结构。植物糖原的高度支化的结构产生其异乎寻常地高的分散分子密度。在水稻中,PG的分散分子密度超过淀粉的10倍(Wong等人,Journal of Cereal Science,37:139-149(2003))。来自玉米的PG的分子密度约为1198g/mol·nm3,相比之下,淀粉的支链淀粉约为62g/mol·nm3(Huang和Yao,Carbohydrate Polymers,83,1665-1671(2011))。高密度呈现PG的结构完整性,并允许密集地接枝官能团。尽管未完全理解,但可能的是植物糖原纳米粒子在表面处通过链的周期性分支和延长从葡聚糖链的非还原性末端生长。
在一些实施方案中,高度支化的α-D-葡聚糖是改性的高度支化的α-D-葡聚糖。改性的高度支化的α-D-葡聚糖是已经通过使用化学方法、酶方法、物理方法、生物方法或上述的组合改性的高度支化的α-D-葡聚糖。可将高度支化的α-D-葡聚糖改性以具有不同的电荷、不同的疏水性、改变的分子量、增加或减小的侧链长度、化学或生物化学官能团、降低或增加的支化密度、改变的粒子大小或它们的组合。
在一些实施方案中,改性的高度支化的α-D-葡聚糖可经改性以包含选自以下的官能团:乙酸酯、磷酸酯、辛烯基琥珀酸酯、琥珀酸酯、羟丙基、羟乙基、阳离子基团例如含有季铵阳离子的那些(例如,使用2,3-环氧丙基三甲基氯化铵(EPTAC)和(3-氯-2-羟基丙基)三甲基氯化铵(CHPTAC)形成)、羧甲基、聚乙二醇(PEG或聚环氧乙烷)、聚丙二醇(或聚环氧丙烷),或上述的组合。
在一些实施方案中,高度支化的α-D-葡聚糖也可以通过漂白、酸水解、氧化、焦糊精化或上述的组合进行改性。
在一些实施方案中,高度支化的α-D-葡聚糖也可以通过剪切力、高压处理、均质化、热液处理、微波、辐射、干燥加热或上述的组合进行处理。
在一些实施方案中,高度支化的α-D-葡聚糖也可以通过与生物活性基团或配体或者官能基团或配体结合进行处理,例如抗体、抗原、适体、蛋白质、肽、氨基酸、环糊精、糖、脂质、核酸和核苷酸、树枝状聚合物、酶、荧光基团或染料、磁性基团、金属离子、金属纳米粒子、量子点、聚合物和嵌段共聚物、放射性基团或上述的组合。
在一些实施方案中,高度支化的α-D-葡聚糖可以用酶进行改性,例如α-淀粉酶、β-淀粉酶、脱支酶(例如,支链淀粉酶和异淀粉酶)、转葡糖苷酶、淀粉葡糖苷酶、蛋白酶等,或上述的组合。
在一些实施方案中,高度支化的α-D-葡聚糖的改性可以通过使用酶方法、物理方法、化学方法、生物方法或上文提到的其它方法的组合来进行。改性的高度支化的α-D-葡聚糖可具有不同的溶解度特性,例如在诸如乙醇的非水性溶剂中增加的溶解度,并且可具有与其环境(例如pH、离子强度、温度、生物环境、磁场或多种类型的辐射的存在,或上述的组合)相关的溶解度、溶解速率和/或其它性质。
溶质化合物
在一个方面中,本文所述的发明提供用于增加溶质化合物的溶解度的组合物。应注意,术语“溶质化合物”在本文中用作方便的标记,但高度支化的α-D-葡聚糖可用于除增加溶解度以外的目的,例如溶质化合物的物理稳定性、化学稳定性或物理化学稳定性。物理稳定性包括溶质化合物在其无定形形式、晶体大小、结晶结构或形式(例如多晶型物)或它们的组合方面的稳定性。化学稳定性包括溶质化合物在其抗氧化、抗还原、抗化学反应、抗结构变化或抗降解或它们的组合方面的稳定性。物理化学稳定性包括物理稳定性、化学稳定性或它们的组合。
可使用各种不同的溶质化合物。尽管不希望受理论限制,但相信高度支化的α-D-葡聚糖(及其改性形式)增加溶质化合物的溶解度,这是由于溶质化合物与α-D-葡聚糖的高度支化的链缔合或嵌入α-D-葡聚糖的高度支化的链中,并且相信这些化合物的溶解度随后显现出更像它们所悬浮于其中的高度支化的α-D-葡聚糖的特性,而不是单独存在的化合物的溶解度。由于具有非常不同的疏水性的溶质化合物可以嵌入高度支化的α-D-葡聚糖的结构内,所以,本发明特别可用于增加疏水性或亲脂性化合物、特别是生物活性疏水性化合物的水溶解度。许多生物活性化合物是高度疏水的,这意味着它们有可能溶于脂质(油)和一些有机溶剂中,而基本上不溶于水溶液中。生物活性化合物在水溶液中溶解度不足是限制它们的治疗应用的重要因素。
在另一个方面中,一些溶质化合物(例如灰黄霉素)具有牢固的结晶结构。热力学稳定的结晶结构驱使化合物的无定形形式向结晶的快速转化,这导致无定形形式的低稳定性。当这些化合物与高度支化的α-D-葡聚糖或其衍生物缔合时,结晶速率可降低。这会有助于溶质化合物的稳定性和溶解度的增加。在其它情况下,一些溶质化合物容易被氧化或降解,例如柠檬油和维生素E。当这些化合物与高度支化的α-D-葡聚糖或其改性形式缔合时,氧化速率可降低。
通常,溶质化合物可包括希望在水溶液(例如水)中具有改善的溶解度或溶解速率的任何一种物质或物质的组合。由于它们在水中的低溶解度或低溶解速率,这些化合物在单独使用时具有有限的易接受性和生物利用度。因此,本发明的组合物可包含至少一种溶质化合物,所述溶质化合物的水溶解度和/或溶解速率大于不存在所述高度支化的α-D-葡聚糖或其改性形式时所述溶质化合物的水溶解度和/或溶解速率。在一些情况下,溶质化合物可以是一种选自以下的化合物或选自以下的化合物的混合物:营养物、维生素、药物、着色剂、农用化学品、杀虫剂、除草剂、抗氧化剂、着色剂、激素、精油、来自植物、中药、动物或微生物有机体的提取物,以及它们的组合。
溶质化合物可以各种不同方式进行分类。在一些情况下,高度支化的α-D-葡聚糖或其改性形式可以与具有约10000道尔顿到约100000道尔顿的大小的相对大的溶质化合物一起使用。在其它实施方案中,溶质化合物的分子量或平均分子量小于约10000道尔顿。在其它实施方案中,溶质化合物的分子量或平均分子量小于约1000道尔顿。在其它实施方案中,溶质化合物是生物活性的疏水性化合物。疏水性化合物的实例包括植物化合物(phytochemicals)、类胡萝卜素、来自植物、动物或微生物的提取物,以及药物。
植物化合物包括酚类化合物,例如儿茶素、姜黄素、槲皮素、芦丁、白藜芦醇、染料木黄酮、黄豆苷元和山奈酚;以及类胡萝卜素,例如番茄红素、β-胡萝卜素和叶黄素。
来自植物、动物或微生物有机体的提取物(例如,膳食补充剂或药物提取物)包括来自以下的提取物:葡萄籽、石榴、橄榄叶、姜黄、绿茶、红茶、可可、昆虫、甲壳动物、酵母、真菌、蘑菇、人参、丁香、马齿苋、刺五加、冬凌草、葛根、灵芝、泽泻、枸杞子、当归、栀子、金银花、槐花、苦参、五味子、决明子、丹参、淫羊藿、甘草、柴胡、白头翁、鱼腥草、黄连、青蒿、黄芩、党参、连翘、喜树和穿心莲。
本发明的溶质化合物可以是在其它方面难以给药的活性药物成分(例如,药物),例如疏水性药物。药物包括抗肿瘤剂,例如紫杉醇、沙戈匹隆(sagopilone)、多西紫杉醇、雷帕霉素、多柔比星、柔红霉素、伊达比星、表柔比星、卡培他滨、丝裂霉素C、安吖啶、白消安、维A酸、依托泊苷、苯丁酸氮芥、氮芥、美法仑和苄基苯基脲化合物;类固醇化合物,例如天然和合成的类固醇,以及类固醇衍生物,例如环杷明(cyclopamine);抗病毒剂,例如阿昔洛韦、茚地那韦、拉米夫定、司他夫定、奈韦拉平、利托那韦、更昔洛韦、沙奎那韦、洛匹那韦和奈非那韦;抗真菌剂,例如伊曲康唑、酮康唑、咪康唑、奥昔康唑、舍他康唑、两性霉素B和灰黄霉素;抗菌剂,例如喹诺酮类,例如环丙沙星、氧氟沙星、莫西沙星、甲氧氟沙星(methoxyfloxacin)、培氟沙星、诺氟沙星、司帕沙星、替马沙星、左氧氟沙星、洛美沙星和西诺沙星;抗菌剂,例如青霉素类,例如氯唑西林、苄基青霉素和苯基甲氧基青霉素;抗菌剂,例如氨基糖苷类,例如,红霉素和其它大环内酯类;抗结核剂,例如利福平和利福喷丁;以及抗炎剂,例如布洛芬、吲哚美辛、酮洛芬、萘普生、奥沙普秦、吡罗昔康和舒林酸。
在一些实施方案中,溶质化合物是具有低或差的水溶解度的活性药物成分,例如对乙酰氨基酚、乙酰唑胺、阿苯达唑、胺碘酮、两性霉素、阿伐他汀、阿奇霉素、硫唑嘌呤、比卡鲁胺、卡马西平、卡维地洛、头孢地尼、头孢丙烯、塞来考昔、氯丙嗪、氯噻嗪、西沙比利、克拉霉素、氯法齐明、氯吡格雷、粘菌素、环孢霉素、环丙孕酮、达那唑、氨苯砜、双氯芬酸、二氟尼柳、二氯尼特、依法韦仑、依泽替米贝、非诺贝特、氟比洛芬、呋塞米、优降糖(glibenclamide)、格列美脲、格列吡嗪、格列本脲(glyburide)、灰黄霉素、氟哌啶醇、氢氯噻嗪、双羟萘酸羟嗪、布洛芬、甲磺酸伊马替尼、厄贝沙坦、异维A酸、茚地那韦、吲哚美辛、伊曲康唑、伊维菌素、酮康唑、酮洛芬、兰索拉唑、拉莫三嗪、利奈唑胺、洛匹那韦、洛伐他汀、氯雷他定、乙酸甲羟孕酮、美洛昔康、美他沙酮、盐酸哌甲酯、莫达非尼、盐酸莫西沙星、霉酚酸酯、甲苯达唑、甲氟喹、萘啶酸、萘普生、新霉素、奈韦拉平、奈非那韦、硝苯地平、氯硝柳胺、制霉菌素、氧氟沙星、奥氮平、奥卡西平、盐酸羟考酮、奥沙普秦、奥利司他、非那吡啶、苯妥英、吡罗昔康、吡喹酮、盐酸吡格列酮、噻嘧啶、喹硫平、雷洛昔芬、视黄醇、利福平、利培酮、利托那韦、罗非考昔、沙奎那韦、辛伐他汀、西罗莫司、螺内酯、磺胺甲噁唑、柳氮磺胺吡啶、他克莫司、他莫昔芬、替米沙坦、他林洛尔、特非那定、甲氧苄啶、伐地考昔、缬沙坦、丙戊酸和华法林。
在一些实施方案中,溶质化合物是细胞培养物组分,包括但不限于以下化合物中的一种或多种:6,7-ADTN HBr、R(-)-N-烯丙基降阿朴吗啡HBr、对氨基可乐定HCl、(±)-对氨基格鲁米特、R(+)-阿替洛尔、S(-)-阿替洛尔、布他拉莫、氯霉素、4’-氯地西泮、氯噻酮、CNQX、硫酸可待因、CV-1808、8-环戊基-1,3-对磺苯基黄嘌呤、地塞米松、地西泮、地高辛、7,9-二甲基尿酸、7,9-二甲基黄嘌呤、3,5-二硝基儿茶酚、1,3-二丙基-8-对磺苯基黄嘌呤、DNQX、(S)-ENBA、雌二醇、FG-7142、呋塞米、L-谷氨酸HCl、L-谷氨酸二乙酯HCl、格鲁米特、氟哌啶醇、六氢硅杂地芬尼多HCl(Hexahydro-sila-difenidol HCl)、六氢硅杂地芬尼多HCl的对氟类似物、氢化可的松、6-羟基多巴胺HBr、3-羟甲基-6-咔啉、吲哚美辛、碘杀结核菌素、异丁基甲基黄嘌呤、(-)-MDO-NPA HCl、甲氨蝶呤、2-甲硫基ATP、纳曲吲哚HCl、哇巴因、罂粟碱HCl、2-苯基氨基腺苷、R(-)-PIA、S(+)-PIA、匹仑哌隆、丙氯拉嗪、孕酮、DL(±)-普萘洛尔、(-)-使君子氨酸、雷尼替丁HCl、Ro 15-4513、Ro 20-1724、PDE抑制剂、Ro 41-0960、COMT抑制剂、兰尼碱、SKF-83566HCl、螺哌隆HCl、舒必利、睾酮、四氢大麻酚、藜芦定、维生素A、维生素D。
在一些实施方案中,溶质化合物是酚类化合物。酚类化合物是具有一个或多个芳环并且在环上带有一个或多个羟基取代基的物质,包括官能衍生物,例如酯、甲基醚、糖苷和对本领域技术人员显而易见的其它衍生物。在酚类化合物的定义中包括具有复杂的取代模式的多酚化合物、具有稠环的化合物和含有一个或多个胺基团和/或羧酸基团的酚类化合物。天然存在的酚类化合物的实例包括但不限于:佛手酚、咖啡酸、辣椒素、香豆素、黄豆苷元、2,5-二羟基苯甲酸、阿魏酸、类黄酮、黄豆黄素(异黄酮)、4-羟基肉桂酸、4-羟基香豆素、异虎耳草素、白藜芦醇、芥子酸、香草酸和香草醛。
合成和天然存在的酚类化合物是许多药物的一部分,其中一些酚类化合物可以含有胺基团、羧酸基团或氨基酸。这些药用酚类化合物的实例包括醋硝香豆素、乙酰胂胺、阿克汀喹、肾上腺酮、阿利苯多、氨基水杨酸、阿莫地喹、茴香脑、巴柳氮、巴美生、苄丝肼、苯替酪胺、苯扎隆、苯喹胺、贝凡洛尔、戊双氟酚、丁氯柳胺、丁苯碘胺、氯新生霉素、氯烯雌醚、氯二甲酚、西阿尼醇、桂哌齐特、西尼必利、桂哌齐特、桂美辛、氯波必利、氯马斯汀、氯碘羟喹、香豆霉素A1、环香草酮、西那林、地诺帕明、右旋甲状腺素、双醋瑞因、双氯酚、己二烯雌酚、己烯雌酚、二氟尼柳、双碘喹啉、地拉卓、地来洛尔、甲己烯雌酚、地莫昔林、地奥司明、地蒽酚、多巴酚丁胺、多奈哌齐、多巴胺、多培沙明、多沙唑嗪、恩他卡朋、依泮洛尔、表美雌醇、肾上腺素、戊酸雌二醇、雌三醇、琥珀酸雌三醇、雌酮、香草二乙胺、酚磺乙胺、依沙维林、依索唑胺、双香豆乙酯、依替福林、依塞罗酯、依沙酰胺、依昔苯酮、芬度柳、甲磺酸非诺多泮、非诺特罗、非诺地尔、芬替克洛、夫洛丙酮、夫洛地尔、荧光素、七叶吗啉、福莫特罗、戈洛帕米、龙胆酸、格拉齐文、优降糖、葡美辛、愈创木酚、哈喹诺、六氯酚、己烷雌酚、海索苯定、海索那林、己雷琐辛、水杨酸羟乙酯、羟乙磺酸羟芪巴脒、羟甲香豆素、艾芬地尔、吲哚美辛、依普黄酮、异他林、异丙肾上腺素、异克舒林、盐酸伊托必利、凯托米酮、凯林、拉贝洛尔、乳酰对乙氧苯胺、左旋多巴、左美丙嗪、左啡诺、左旋甲状腺素、美贝维林、甲氧拉敏、美非沙胺、米帕林、美沙拉嗪、美雌醇、间羟胺、美索巴莫、甲氧明、甲氧沙林、甲基多巴、米多君、米托蒽醌、吗氯酮、萘丁美酮、萘普生、硝羟喹啉、去甲苯福林、喹啉甲双酚、新生霉素、奥克巴胺、奥美拉唑、奥西那林、奥洛福林、羟色氨酸、奥昔非君、奥昔哌汀、羟布宗、双醋酚丁、羟喹啉、罂粟碱、醋氨酚、对乙氧卡因、非那卡因、非那西丁、非那佐辛、酚酞、苯丙香豆素、酚妥拉明、phloedrine、吡考他胺、匹莫苯、普瑞特罗、伯氨喹、普罗加胺、丙泮尼地、普罗托醇、丙美卡因、盐酸雷洛昔芬、瑞格列奈、瑞普特罗、利米特罗、利托君、醋水杨胺、柳氮磺胺吡啶、沙丁胺醇、水杨酰胺、水杨酸、沙美特罗、双水杨酯、西地那非、水飞蓟宾、三甲硫吗啉、坦洛新、特拉唑嗪、特布他林、四氧普林、茶碱那林、噻氯香豆素、噻克索酮、α-生育酚(维生素E)、托非索泮、托卡朋、托特罗定、曲尼司特、曲托喹酚、三氯生、曲马唑嗪、曲美他嗪、曲美苄胺、甲氧苄啶、曲美托嗪、葡糖醛酸三甲曲沙、曲昔派特、维拉帕米、维司力农、维曲布汀、维洛沙秦、华法林、扎莫特罗。
在其它实施方案中,溶质化合物可以是作为植物的粗提取物或纯化提取物的精油,单独的化合物或它们的混合物,和/或它们相应的合成物质。例如,麝香草酚是百里香油的组分。精油可以是沉香油(agar oil)、香旱芹籽油(ajwain oil)、当归根油、茴香油、阿魏油、香胶油(balsam oil)、罗勒油、香叶油、香柠檬油、黑胡椒精油、香桦油、樟脑油、大麻花精油、藏茴香油、豆蔻籽油、胡萝卜籽油、雪松木油(cedarwood oil)、春黄菊油、菖蒲根油、肉桂油、岩蔷薇属油、香茅油、洋苏叶油(clary sage)、丁香叶油、咖啡油、芫荽子油、艾菊油、木香根油、蔓越莓籽油、荜澄茄油、枯茗油/黑种草籽油、柏油、香附子油、咖喱叶油、印蒿油、莳萝油、土木香油、桉树油、小茴香籽油、胡芦巴油、冷杉叶油、乳香油、高良姜油、白松香油、天竺葵油、姜油、黄花油、葡萄柚油、指甲花油、蜡菊油、山核桃油、辣根油、牛膝草油、爱达荷州艾菊油、茉莉油、刺柏油、月桂油、薰衣草油、杜香油、柠檬油、香茅草油、白柠檬油、山苍子油、橘皮油、马郁兰油、白千层茶树油、蜂花油(香蜂叶)、薄荷油、野鼠尾草油、艾草油、芥子油、没药油、桃金娘油、印度楝树油、橙花油、肉豆蔻油、橙油、牛至油、鸢尾草油、圣木油(palo santo)、欧芹油、广藿香油、紫苏精油、辣薄荷油、橙叶油、松油、罗文莎叶油、血柏木油、罗马甘菊油、玫瑰油、玫瑰果油、迷迭香油、蔷薇木油、鼠尾草油、檀香木油、黄樟油、欧洲薄荷油、五味子油、留兰香油、甘松油、云杉油、八角茴香油、红橘油、龙蒿油、茶树油、百里香油、铁杉油、姜黄油、缬草油、香根草油、西方红雪松油、冬青油、蓍草油、衣兰油、蓬莪术油。
在优选的实施方案中,溶质化合物是选自以下中的一种或多种的生物活性疏水性化合物:类胡萝卜素、类姜黄素、类黄酮、甾醇、植物甾醇、皂苷、苷元或皂苷的苷元(即皂苷元)。在另一个实施方案中,溶质化合物可以选自姜黄素、槲皮素、白藜芦醇、麝香草酚、紫杉醇、布洛芬和灰黄霉素。
在一些实施方案中,溶质化合物是疏水性维生素,例如维生素A、维生素E、维生素D和维生素K。
在一些实施方案中,溶质化合物是疏水性着色剂,例如类胡萝卜素、叶黄素、卡红、姜黄、可可、胭脂树红(红木素)、辣椒红、苏木素、花青素、紫胶染料、叶绿酸、胭脂虫红、番茄红素。
在一些实施方案中,本发明的组合物在水中表现出增加的溶解度,并且允许制备各种浓度的水溶液。由于浓溶液可以任何比例在宽范围的pH条件下用水性介质稀释而不会造成疏水性化合物的分离或沉淀,因此,化合物的溶解度在生理条件下,例如在口服或肠胃外给药所述组合物后得以保持。这通常实现溶质化合物的改善的生物利用度。
本发明的可溶性组合物可以容易地掺入药物、营养保健品、药品或化妆品制剂中,溶质化合物在其中表现出改善的生物利用度。此类制剂还可以含有其它活性成分和/或药学上或美容上可接受的添加剂或媒介物,包括溶剂、表面活性剂、辅剂、质构剂(textureagents)、填充剂、赋形剂、甜味剂、填料、着色剂、调味剂、润滑剂、结合剂、保湿剂、防腐剂以及它们的混合物。总的来说,这些其它制剂材料可被称为药学上可接受的载体。如本文所用的,“药学上可接受的”是指载体适合给药到用于本文所述方法的个体,而没有过度有害的副作用。所述制剂可以采取适合局部(例如,乳膏、洗剂、凝胶剂、软膏、皮肤粘合贴片)、口服(例如,胶囊、片剂、囊片、颗粒、粉末、液体)或胃肠外(例如,栓剂、无菌溶液)给药的形式。可用于通过注射给药的可接受的媒介物和溶剂包括水、轻度酸化水、林格氏溶液和等渗氯化钠溶液。
在其它实施方案中,包含溶质化合物和高度支化的α-D-葡聚糖的可溶性组合物可以掺入其它类型的制剂中。这些其它制剂的实例包括食品和饮料、食品补充剂、细胞培养物、农用化学品例如肥料和杀虫剂、油漆和涂料等。此类营养、农业或化学制剂的配制对于本领域技术人员来说是已知的。
本发明的包含生物活性疏水性化合物的组合物可以给药到需要预防或治疗的温血动物,特别是人。用于治疗疾病或病症的生物活性疏水性化合物的剂量及其与高度支化的α-D-葡聚糖(或其改性形式)一起的可溶性组合物的相应剂量会根据给药方式、个体的年龄、性别、体重,以及所治疗的病况而变化,并且最终由主治医生或兽医决定。此类由主治医生或兽医确定的呈水溶性组合物形式的生物活性化合物的量在本文中称为“治疗有效量”。
溶质化合物与高度支化的α-D-葡聚糖的质量比可以为约100:1到约1:1000。溶质化合物与高度支化的α-D-葡聚糖的比可以根据所提供的组合物的类型而变化。例如,在意欲稳定呈干燥形式的溶质化合物的组合物中,可使用约100:1到约1:50的溶质化合物与高度支化的α-D-葡聚糖的质量比,其中优选约2:1到约1:20的质量比。或者,在用于增加溶质化合物的溶解度的组合物中,可使用较低的溶质化合物与高度支化的α-D-葡聚糖的比。例如,对于可溶性组合物,可使用约1:1到约1:1000的溶质化合物与α-D-葡聚糖的质量比,其中优选约1:5到约1:50的质量比。质量比的下限并不重要,并且可以任意过量使用高度支化的α-D-葡聚糖。然而,这在一些应用中是不希望的,因为增加高度支化的α-D-葡聚糖的量会降低活性成分在组合物和其水溶液中的浓度。
使用高度支化的α-D-葡聚糖增加溶解度、溶解速率和/或稳定性
高度支化的α-D-葡聚糖或其改性形式与溶质化合物的组合提供多种益处。在一些实施方案中,本发明提供通过将溶质化合物与有效量的高度支化的α-D-葡聚糖混合来增加溶质化合物的溶解度、溶解速率和/或稳定性的方法。
本发明提供增加溶质化合物的溶解度和/或溶解速率的方法。所述方法包括以下步骤:将有效量的至少一种高度支化的α-D-葡聚糖或其改性形式与溶剂混合,将溶质化合物与第二溶剂混合,并将两者加在一起。在一些实施方案中,首先将溶质化合物和高度支化的α-D-葡聚糖混合,然后将其加入溶剂中。然而,所述方法不必遵循描述这些步骤的顺序。换句话说,在一些实施方案中,可能优选的是,将溶质化合物加入溶剂中,然后加入高度支化的α-D-葡聚糖。一旦在涉及使用溶剂或不使用溶剂的过程中将溶质化合物与高度支化的α-D-葡聚糖放置在一起,即表现出增加的溶解度。所述溶剂可以是相对极性的溶剂,并且在一些实施方案中是水性溶剂(例如,水),并且在一些实施方案中是水性溶剂和非水性溶剂的混合物。如本文所述,向溶质化合物中加入高度支化的α-D-葡聚糖导致溶质化合物与α-D-葡聚糖的分支缔合或陷入α-D-葡聚糖的分支中,致使溶质化合物随高度支化的α-D-葡聚糖一起溶解。
在一些实施方案中,为实现溶质化合物的提高的溶解度和/或溶解速率,将溶质化合物与高度支化的α-D-葡聚糖或其改性形式混合并不需要溶剂,因为该高度支化的α-D-葡聚糖或其改性形式可以在不使用溶剂的情况下与溶质化合物相互作用、溶解溶质化合物或吸附溶质化合物。用于此类无溶剂混合的处理可通过以下方式加以协助:挤出、压制、均质化、研磨、辊压(rolling)、捏合、超声处理或上述的组合。
使用高度支化的α-D-葡聚糖(例如植物糖原)或其改性形式增加溶质化合物的溶解度可以将溶质化合物的溶解度增加到不同程度,这取决于溶质化合物、高度支化的α-D-葡聚糖或其改性形式以及溶质化合物所处的溶液的详情。例如,在一些实施方案中,所述方法将溶质化合物的溶解度增加到不存在高度支化的α-D-葡聚糖时溶质化合物的溶解度的至少约两倍。换句话说,在一些情况下,溶质化合物的溶解度可以是不存在高度支化的α-D-葡聚糖时溶质化合物的溶解度的至少两倍。在其它情况下,溶质化合物的溶解度可以是不存在高度支化的α-D-葡聚糖时溶质化合物的溶解度的至少五倍。在其它情况下,溶质化合物的水溶解度可以是不存在高度支化的α-D-葡聚糖时溶质化合物的溶解度的至少十倍,并且在又一些其它实施方案中,当与高度支化的α-D-葡聚糖组合时,溶质化合物的溶解度高是至少一百倍高。
酚类化合物是溶解度可以被高度支化的α-D-葡聚糖或其改性形式显著提高的一类溶质化合物。本发明能够将一些酚类化合物的溶解度增加到不存在高度支化的α-D-葡聚糖时它们的溶解度的至少10倍。例如,使用植物糖原可以将姜黄素在水溶液中的溶解度增加到至少100倍,并且可以使槲皮素在水溶液中的溶解度增加到至少10倍。
在其它实施方案中,提供增加溶质化合物的稳定性的方法。所述方法包括以下步骤:将有效量的至少一种高度支化的α-D-葡聚糖或其改性形式加入溶质化合物中,并将所述溶质化合物与溶剂混合。与用于增加溶解度的方法一样,该方法的步骤可以任何顺序进行。与不存在高度支化的α-D-葡聚糖时的溶质化合物相比,与高度支化的α-D-葡聚糖或其改性形式复合的溶质化合物更抗结晶、氧化、还原、结构变化、变质和降解、酶反应、化学反应或其组合。另外,由于结晶降低溶质化合物的溶解度和/或溶解速率,所以,非结晶形式的溶质化合物的稳定化提高溶解度和/或溶解速率。包含溶质化合物和高度支化的α-D-葡聚糖的组合物在长时间内,在一个实施方案中在室温下在一个月内,在另一个实施方案中在一年内,显示优异的稳定性。
在一些实施方案中,为增强溶质化合物的稳定性,将溶质化合物与高度支化的α-D-葡聚糖或其改性形式混合可不需要溶剂,因为该高度支化的α-D-葡聚糖或其改性形式可以在不使用溶剂的情况下与溶质化合物相互作用、溶解溶质化合物或吸附溶质化合物。用于此类无溶剂混合的处理可以是挤出、压制、均质化、研磨、辊压、捏合、超声处理或上述的组合。
图5示出了植物糖原的改性形式可以稳定灰黄霉素的无定形(或接近无定形)形式以阻止其转化成结晶结构。该图中溶质化合物(灰黄霉素)与植物糖原的改性形式的比为1/3(w/w)。当放置得与水性体系接触时(例如,在胃肠道中),无定形药物会形成过饱和溶液并在吸收的时标中实现更高的渗透。
包含溶质化合物和高度支化的α-D-葡聚糖或其改性形式的组合物的制备
本发明的另一个方面涉及用于制备可溶性组合物的方法。在一个实施方案中,所述方法包括将溶质化合物溶解在溶剂中以形成溶液;将所述溶液与高度支化的α-D-葡聚糖或其改性形式混合;并除去溶剂以获得所述可溶性组合物。在一些实施方案中,所述溶剂是非水性溶剂和水性溶剂的混合物。
在另一个实施方案中,所述用于制备可溶性组合物的方法包括以下步骤:将至少一种溶质化合物溶解或分散于第一溶剂中以形成第一溶液或分散液;将至少一种高度支化的α-D-葡聚糖或其改性形式溶解或分散于第二溶剂中以形成第二溶液或分散液;将所述第一溶液或分散液和所述第二溶液或分散液混合在一起以形成混合物;以及从所述混合物除去溶剂以获得组合物;其中所述组合物中的所述溶质化合物的水溶解度大于不存在所述至少一种高度支化的α-D-葡聚糖或其改性形式时所述溶质化合物的水溶解度。在一些实施方案中,第一溶剂可以是水性溶剂;在一些实施方案中,第一溶剂可以是非水性溶剂;在一些实施方案中,第一溶剂可包含非水性溶剂和水性溶剂的混合物。在其它实施方案中,第二溶剂可以是水性溶剂;在一些实施方案中,第二溶剂可以是非水性溶剂;在一些实施方案中,第二溶剂可包含非水性溶剂和水性溶剂的混合物。
在其它实施方案中,用于制备溶质组合物的方法包括将至少一种溶质化合物与至少一种高度支化的α-D-葡聚糖或其改性形式混合的步骤。该混合可以在溶剂中,或者在没有任何溶剂的情况下进行。
在一些实施方案中,溶剂是非水性溶剂。非水性溶剂的实例可以选自戊烷、环戊烷、己烷、环己烷;苯;甲苯;1,4-二噁烷、氯仿、乙醚、二氯甲烷、四氢呋喃、乙酸乙酯、丙酮、二甲基甲酰胺、乙腈、二甲亚砜、甲酸、正丁醇、异丙醇、正丙醇、乙醇、甲醇、乙酸和它们的组合。在一些实施方案中,溶剂可以是非水性溶剂。在一些实施方案中,溶剂可包含非水性溶剂和水性溶剂的混合物。
在一些实施方案中,包含溶质化合物和高度支化的α-D-葡聚糖或其改性形式的可溶性组合物可用额外的处理步骤来制备。例如,在一些实施方案中,高度支化的α-D-葡聚糖是衍生自或提取自植物来源、动物来源或微生物来源,或是合成的,或它们的组合。在另外的实施方案中,可溶性组合物的制备还包括通过以下方式处理混合物的步骤:捏合、挤出、均质化、超声处理、高压处理、高速处理、微波处理、辐射处理、热处理或它们的组合。在又一些其它实施方案中,所述方法包括通过以下方式从混合物除去溶剂:喷雾干燥、真空干燥、冷冻干燥、滚筒干燥、加热干燥、挤出、超临界提取或它们的组合。
当将溶质化合物与高度支化的α-D-葡聚糖混合时,找到其中可溶解载体和溶质化合物二者的单一溶剂有时具有挑战性。在这方面,DMSO是特别有效的溶剂,但在复合后除去DMSO较为困难。在这些情况下,优选制备可溶于乙醇、丙酮或这种类型的低极性或非极性溶剂中的高度支化的α-D-葡聚糖的改性形式。例如,植物糖原已被改性成植物糖原辛烯基琥珀酸酯(PG-OS),其可以溶解在非极性或低极性溶剂中。为了进一步改善α-D-葡聚糖的溶解性,可在PG-OS上添加聚乙二醇(PEG)链,由此产生PG-OS-PEG。这种新材料的溶解度与PG-OS相比大大增强。
在一些实施方案中,将溶质化合物与高度支化的α-D-葡聚糖或其改性形式混合不需要溶剂,因为该高度支化的α-D-葡聚糖或其改性形式可以在不使用溶剂的情况下与溶质化合物相互作用、溶解溶质化合物或吸附溶质化合物。用于此类无溶剂混合的处理可通过以下方式加以协助:掺合、挤出、压制、压片、均质化、研磨、辊压、捏合、超声处理或上述的组合。
通过以下实施例对本发明进行说明。应理解,特定的实施例、材料、量和步骤应根据如本文所述的本发明的范围和精神宽泛地解释。
实施例
实施例1:使用植物糖原和PG-OS增加槲皮素和姜黄素的溶解度
使用含su1的甜玉米的成熟籽粒提取植物糖原。槲皮素和姜黄素购自Sigma-Aldrich(St.Louis,MO),并且未经进一步纯化即使用。槲皮素(7mg/mL)和姜黄素(4.25mg/mL)的原液在乙醇中制备,并且在4℃下在黑暗中储存在琥珀色瓶中。所使用的其它化学品均为分析试剂级。自始至终使用去离子水。
植物糖原的提取
将甜玉米籽粒磨成粗粉,然后与4-6倍重量的去离子水混合。将悬浮液使用高速搅拌器(Waring Laboratory,Torrington,CT)均质化,然后在8000×g下离心20分钟。收集上清液,而将固体使用去离子水再提取两次。此后,将各批次的上清液合并,并通过270目筛。然后,将液体加入乙醇中以沉淀多糖。离心和倾析上清液后,将沉淀用乙醇再分散并离心。将最后一次加入乙醇后的悬浮液过滤以除去过量的液体。将固体置于通风橱中以除去残余的乙醇。所收集的粉末含有植物糖原。
植物糖原辛烯基琥珀酸酯(PG-OS)的制备
向植物糖原的悬浮液中加入1-辛烯基琥珀酸酐。使用NaOH将pH保持在8.5-9.0。在24小时后通过使用HCl将pH降低到6.5终止反应。为收集取代的葡聚糖,向反应混合物中加入3倍体积的乙醇。收集沉淀,并使用3个乙醇悬浮-离心循环进一步脱水。将过滤后收集的固体置于通风橱中以除去残余的乙醇。
将槲皮素或姜黄素与植物糖原混合
在Na2HPO4-柠檬酸缓冲液(pH 6.6)中制备0.1%、0.5%、1.0%和5.0%的10ml植物糖原水分散液,并填充在螺旋盖试管中。将槲皮素或姜黄素原液的0.1mL等分部分加入植物糖原分散液中,随后在22℃下搅拌2小时。此后,通过离心除去不溶性槲皮素或姜黄素。
通过毛细管电泳(CE)定量槲皮素
使用CE测定槲皮素在水性体系中的浓度。用装备有分光光度检测器的Beckman仪器MDQ P/ACE(Palo Alto,CA,USA)进行CE实验。用从Polymicro Technologies(Phoenix,AZ,USA)获得的未涂覆的熔融二氧化硅毛细管(47.0cm×50μm ID×375μm OD)进行分离。毛细管的温度保持在25℃。在254nm下进行UV检测。使用0.05M硼酸盐(pH 9.0)的运行缓冲液。所施加的电压为20kV的正极性电压。包括标准溶液在内的所有样品均通过0.45μm注射器式过滤器进行过滤。迁移率测量重复进行三次。使用Beckman 32karat软件(版本7.0)进行峰面积的定量。
姜黄素的分光光度测定
将姜黄素-植物糖原混合物加入乙醇中,以沉淀多糖并提取姜黄素。离心后,用UV-Vis分光光度计(Varian Instruments,Walnut Creek,CA)测定上清液。在425nm下对照试剂空白测定溶液的吸光度,所制备的所述试剂空白具有相同的试剂浓度,但不含姜黄素。使用姜黄素在80%乙醇中的1.0-8.0μg/ml溶液制备标准曲线。
使用植物糖原增加槲皮素的溶解度
图3示出了槲皮素在各种浓度的植物糖原分散液中的溶解度。已发现,随着植物糖原的浓度增加,槲皮素的溶解度显著增加。与单独的槲皮素(0.0%植物糖原)相比,使用1.0%和5.0%植物糖原分别使槲皮素的溶解度增加到约5.0倍和97.4倍。
使用植物糖原和PG-OS增加姜黄素的溶解度
图4示出了在各种浓度的植物糖原下姜黄素的溶解度。据报道,姜黄素的估计水溶解度为11.0ng/mL(Kaminaga等人,Letters,555,311-316(2003))。在我们的测试中,姜黄素的溶解度低于检测限(0.30μg/mL)。已发现,姜黄素的溶解度随植物糖原或PG-OS的浓度增加而显著增加。例如,对于5.0%的植物糖原和PG-OS分散液,姜黄素的溶解度分别为29.1μg/mL和31.8μg/mL,其是单独的姜黄素的报道值的接近3,000倍高。
实施例2:植物糖原辛烯基琥珀酸酯(PG-OS)和聚乙二醇化的植物糖原辛烯基琥珀
酸酯(PG-OS-PEG)的制备
将3g植物糖原和5.85g辛烯基琥珀酸酐(OSA)混合在15.0mL二甲亚砜(DMSO)中,然后转移到50mL试管中。将试管在沸水浴中放置3小时以进行反应。此后,将反应物分成两部分。一半用于制备PG-OS-PEG,并且另一半用于分离PG-OS。为分离PG-OS,通过加入20倍的去离子水停止反应,并使用NaOH溶液将液体中和到pH 6.5。然后,对液体进行超滤处理。
为制备PG-OS-PEG,向另一半PG-OS反应物中加入30.6g(聚乙二醇)甲基醚(平均Mn550,mPEG-OH)。将混合物在110℃和真空下保持15小时,每15分钟搅拌一次。此后,将反应物用20倍的去离子水稀释,并使用NaOH溶液将液体中和到pH 6.5。然后,对液体进行超滤处理。
对于稀释并中和的PG-OS和PG-OS-PEG反应物,使用MinimateTM切向流过滤系统(Pall Life Sciences)进行超滤。超滤进行4个循环,并且对于每个循环,将保留物的体积减少到原来的1/20,然后用去离子水加回原来的体积。对最终的保留物进行冷冻干燥,以收集固体PG-OS和PG-OS-PEG。
实施例3:使PG-OS和PG-OS-PEG与姜黄素复合以提高姜黄素的溶解度
在14mL试管中,将30mg PG-OS、PG-OS-PEG、β-环糊精(βCD)和羟丙基β-环糊精(HPβCD)分别与2.97mL乙酸钠(NaAC)缓冲液(10mM,pH 6.5)混合。向各混合物中加入过量的姜黄素粉末,并将混合物使用高速均质化器(T25-DS1Ultra-IKA)在22000rpm下处理7分钟。此后,从各混合物抽取1.0mL分液并进行离心。将上清液加入乙醇中以提取姜黄素。离心除去沉淀后,将上清液进一步稀释在80%乙醇中,并使用UV-Vis分光光度计(VarianInstruments)在425nm下对照标准曲线测定姜黄素的含量。表1示出了当与10mg/mL载体复合时姜黄素的溶解度。显然,PG-OS和PG-OS-PEG比βCD和HPβCD具有更高的提高姜黄素的水溶解度的能力。
表1:受载体影响的姜黄素在pH 6.510mM NaAc缓冲液中的溶解度
载体,10mg/mL | 姜黄素的溶解度,μg/mL | 载体/姜黄素的比,w/w |
PG-OS | 303 | 33.0/1 |
PG-OS-PEG | 367 | 27.5/1 |
βCD* | 45.1 | 222/1 |
HPβCD** | 110 | 91/1 |
*βCD:β-环糊精
**HPβCD:羟丙基β-环糊精
实施例4:植物糖原琥珀酸酯(PG-S)和聚乙二醇化的植物糖原琥珀酸酯(PG-S-
PEG)的制备
为制备PG-S,将3g植物糖原和3.7g琥珀酸酐(SA)混合在15.0mL二甲亚砜(DMSO)中,然后转移到50mL试管中。将试管在沸水浴中放置3小时以进行反应。为分离PG-S,通过加入20倍的去离子水停止反应,并使用NaOH溶液将液体中和到pH 6.5。然后,对液体进行超滤处理。
为制备PG-S-PEG,将3g植物糖原和3.7g琥珀酸酐(SA)混合在15.0mL二甲亚砜(DMSO)中,然后转移到50mL试管中。将试管在沸水浴中放置3小时以进行反应。向PG-S反应物中加入30.6g聚(乙二醇)甲基醚(平均Mn550,mPEG-OH)。将混合物在110℃和真空下保持7小时,每15分钟搅拌一次。此后,将反应物用20倍的去离子水稀释,并使用NaOH溶液将液体中和到pH 6.5。然后,对液体进行超滤处理。
对于稀释并中和的PG-S和PG-S-PEG反应物,使用MinimateTM切向流过滤系统(PallLife Sciences)进行超滤。超滤进行4个循环,并且对于每个循环,将保留物的体积减少到原来的1/20,然后用去离子水加回原来的体积。对最终的保留物进行冷冻干燥,以收集固体PG-S和PG-S-PEG。
实施例5:使PG-S和PG-S-PEG与灰黄霉素复合
使用研钵和研棒,将0.55g灰黄霉素(Sigma-Aldrich)、1.65g PG-S或PG-S-PEG以及6.05g DMSO混合。将混合物转移到玻璃小瓶中,并真空干燥,以完全除去DMSO。作为对照,将灰黄霉素以与复合相同的比率溶解在DMSO中,并进行真空干燥以收集灰黄霉素固体。此外,以1/3的比率制备灰黄霉素和PG-S或PG-S-PEG的物理混合物以作为对照。
在22℃下37天后,对与PG-S和PG-S-PEG复合的灰黄霉素样品以及若干对照进行差示扫描量热(DSC)分析。对于DSC分析,称取材料(3-7mg)并密封在PerkinElmer铝密封盘中。使用DSC Q2000(TA Instruments)以20℃/分钟的扫描速率在20-250℃范围内进行DSC测试。根据各样品的灰黄霉素的含量归一化各样品的热流(W/g)。结果示于图5中。显然,灰黄霉素与PG-S或PG-S-PEG的复合使得在储存37天后产生可忽略不计的结晶,从而表明灰黄霉素的无定形形式的高稳定性。
实施例6:通过与植物糖原复合减少布洛芬结晶
为制备植物糖原-布洛芬复合物,将布洛芬、植物糖原和DMSO以按重量计1:3:6和1:5:10的比率混合。将所得的糊状物置于真空中以除去DMSO,并将所收集的固体磨成粉末。同时,使用DMSO以类似的方式处理布洛芬(溶解在DMSO中,随后除去溶剂),并且所收集的固体用于制备若干个对照样品。制备植物糖原和原始或DMSO处理的布洛芬的干混物。这些材料被用于DSC和X射线粉末衍射分析。
对于DSC分析,称取各固体并密封到PerkinElmer铝密封盘中,并以20℃/分钟的扫描速率在0-250℃范围内进行DSC Q2000(TA Instruments)。使用布洛芬的重量归一化各DSC曲线。对于X射线粉末衍射分析,称取固体粉末,并使用装备有Bragg-Brentano光学装置的Shimadzu XRD-6000X射线粉末衍射仪进行分析。以0.08°的步长从5°-40°2θ扫描样品。DSC和X射线衍射分析的结果示于图6中。显然,植物糖原与布洛芬的复合使得含布洛芬的固体中晶体的量显著降低或可以忽略不计。
实施例7:通过植物糖原复合增加姜黄素的溶解度和Caco-2细胞单层渗透性
通过将10mg姜黄素混合于1.0mL乙醇中,涡旋并离心以收集上清液来制备姜黄素在乙醇中的原液。同时,将2g植物糖原分散在40mLNa2HPO4-柠檬酸缓冲液(pH 3.0-6.6)中。将0.4mL姜黄素原液加入植物糖原分散液中;将混合物离心以除去不溶性的姜黄素。收集上清液并冷冻干燥,以制备植物糖原-姜黄素复合固体。
将植物糖原-姜黄素复合固体分散于缓冲液中,以形成1%和5%(w/v)分散液。离心后,将上清液加入4倍体积的乙醇中,以沉淀多糖并提取姜黄素。离心后,用UV-Vis分光光度计测定上清液。在425nm下测定溶液的吸光度。使用姜黄素在80%乙醇中的标准曲线来测定姜黄素的量。结果示于图7-A中。显然,植物糖原-姜黄素复合显著增加姜黄素在缓冲液中的溶解度。
为进行Caco-2细胞单层渗透测试,将最初从ATCC获得的Caco-2BBe细胞在37℃下在5%CO2和95%空气的气氛下保持在达尔伯克改良型伊格尔培养基(DMEM)中,所述培养基含有FBS(10%)、丙酮酸钠和青霉素/链霉素。将细胞接种在Transwell板的顶侧上,并使其达到100%汇合,并在接种之后分化21天。使用跨上皮电阻(TEER)值来测定各细胞单层的完整性。将Transwell板上的完全分化的Caco-2BBe细胞用汉克斯平衡盐溶液(HBSS)洗涤。为估计从顶端隔室到基底外侧隔室的渗透,向顶侧中加入0.5ml含有姜黄素制剂的HBSS,并向基底外侧中加入1.5ml HBSS。将细胞在37℃下孵育,并且每30分钟,从基底外侧隔室抽出750μl HBSS,并用等体积的新鲜HBSS补充以保持体积。使用LC-MS定量来自基底外侧隔室的HBSS分液中姜黄素的量,以评价单层渗透。
使用过滤器(Waters)对来自基底外侧隔室的含姜黄素的缓冲液进行固相萃取。使用乙腈(ACN)洗脱吸附的姜黄素并真空干燥。然后,将固体用50μL ACN溶解,并转移到注射小瓶中,然后进行LC-MS分析。结果示于图7-B中。显然,姜黄素的溶解度增加使得其Caco-2细胞单层渗透性增加。重要的是,在顶端隔室中使用淀粉酶改善了姜黄素渗透,这表明消化酶对植物糖原降解和姜黄素释放的影响。
实施例8:植物糖原增溶麝香草酚以抑制病原体鼠伤寒沙门氏菌
将3g植物糖原和3g麝香草酚(Sigma-Aldrich)分散在乙酸钠缓冲液(50mM,pH5.5)中,以使两者均为10%(w/v)。对混合物进行高速均质化。均质化后,将分散液离心以收集水性液体。经测定,该植物糖原-麝香草酚液体原液中麝香草酚的浓度约为400μg/mL。通过在乙酸钠缓冲液(50mM,pH5.5)中加入麝香草酚并涡旋制备400μg/mL的在缓冲液中的单独麝香草酚原液作为参考。
将植物糖原-麝香草酚原液和单独麝香草酚原液加入脑心浸液(BHI)肉汤中,以使麝香草酚的浓度为12.5、25、50、80、100和125μg/mL。将鼠伤寒沙门氏菌培养物(约109CFU/mL)以1.0%(v/v)水平接种到含有这些肉汤液体的玻璃试管中,并将所有液体在37℃下孵育24小时。此后,对试管进行拍照,以比较混浊度。混浊的外观表明细菌的生长。
如图8中所示,对于加入植物糖原-麝香草酚复合制剂的BHI肉汤液体,麝香草酚的最小抑制浓度(MIC)为80μg/mL(即,在该麝香草酚浓度下和高于该麝香草酚浓度下,液体澄清,表明细菌的生长可以忽略)。对于加入单独麝香草酚制剂的BHI肉汤,甚至在高达125μg/mL的麝香草酚浓度下也不能检测到MIC。这表明,植物糖原-麝香草酚复合改善麝香草酚的溶解性和对沙门氏菌的利用度。
本文中引用的所有专利、专利申请和出版物以及可电子地获得的材料的全部公开内容通过援引加入本文。上述详细描述和实施例仅为了清楚理解而给出。不应据其理解出不必要的限制。本发明不限于所示出和描述的确切细节,因为对本领域技术人员显而易见的变化将包括在由权利要求所限定的本发明的范围内。
Claims (27)
1.用于增加溶质化合物的水溶解度的组合物,其包含:高度支化的α-D-葡聚糖或其改性形式,其中所述高度支化的α-D-葡聚糖或其改性形式是糖原、植物糖原或其改性形式,并且其中所述改性是含有选自以下的官能团:乙酸酯、磷酸酯、羟丙基、阳离子基团、羧甲基、聚乙二醇、聚丙二醇或其组合;和溶质化合物,所述溶质化合物的水溶解度大于不存在所述高度支化的α-D-葡聚糖时所述溶质化合物的水溶解度。
2.权利要求1所述的组合物,其中所述高度支化的α-D-葡聚糖具有大于约7%的支化密度百分比。
3.权利要求1所述的组合物,其中所述高度支化的α-D-葡聚糖具有树枝状结构。
4.权利要求1所述的组合物,其中所述溶质化合物在水性溶剂中的溶解速率大于不存在所述高度支化的α-D-葡聚糖时所述溶质化合物的溶解速率。
5.权利要求1所述的组合物,其中所述溶解度增加到不存在所述高度支化的α-D-葡聚糖时所述溶质化合物的溶解度的至少约两倍。
6.权利要求1所述的组合物,其中所述高度支化的α-D-葡聚糖是糖原的改性形式或植物糖原的改性形式。
7.权利要求6所述的组合物,其中所述改性的高度支化的α-D-葡聚糖含有至少一个选自以下的基团:抗体、抗原、适体、蛋白质、肽、氨基酸、环糊精、糖、脂质、核酸和核苷酸、酶、荧光基团或染料、磁性基团、金属离子、金属纳米粒子、量子点、聚合物、放射性基团或其组合。
8.权利要求6所述的组合物,其中所述改性的高度支化的α-D-葡聚糖含有至少一个选自以下的基团:树枝状聚合物和嵌段共聚物。
9.权利要求6所述的组合物,其中所述改性的高度支化的α-D-葡聚糖通过至少一种选自以下的处理来制备:酸水解、氧化、焦糊精化、使用α-淀粉酶、β-淀粉酶、脱支酶、转葡糖苷酶、淀粉葡糖苷酶和/或蛋白酶的酶处理、漂白、剪切力处理、挤出、捏合、均质化、热液处理、干燥加热、微波处理、辐射或其组合。
10.权利要求1所述的组合物,其中所述溶质化合物是疏水性化合物。
11.权利要求1所述的组合物,其中所述溶质化合物是酚类化合物。
12.权利要求1所述的组合物,其中所述溶质化合物选自类胡萝卜素、类姜黄素、类黄酮、甾醇、皂苷和皂苷元。
13.权利要求1所述的组合物,其中所述溶质化合物选自植物甾醇。
14.权利要求1所述的组合物,其中所述溶质化合物选自药物、杀虫剂、除草剂、抗氧化剂、着色剂、精油或其组合。
15.权利要求1所述的组合物,其中所述溶质化合物选自草药提取物、激素或其组合。
16.权利要求1所述的组合物,其中所述溶质化合物选自维生素和中药。
17.权利要求1所述的组合物,其中所述溶质化合物选自姜黄素、槲皮素、叶黄素、白藜芦醇、卵磷脂、麝香草酚、紫杉醇、布洛芬和灰黄霉素。
18.权利要求1所述的组合物,其中所述组合物使用包括以下步骤的方法制备:
将至少一种溶质化合物溶解或分散于第一溶剂中以形成第一溶液或分散液;
将至少一种高度支化的α-D-葡聚糖或其改性形式溶解或分散于第二溶剂中以形成第二溶液或分散液;
将所述第一溶液或分散液和所述第二溶液或分散液混合在一起以形成混合物;以及从所述混合物除去溶剂以获得组合物;
其中所述组合物中的所述溶质化合物的水溶解度大于不存在所述至少一种高度支化的α-D-葡聚糖时所述溶质化合物的水溶解度。
19.权利要求18所述的组合物,其中所述方法增加所述溶质化合物的溶解速率和/或稳定性。
20.权利要求18所述的组合物,其还包括通过以下方式处理所述混合物的步骤:捏合、挤出、均质化、超声处理、高压处理、高速处理、微波处理、辐射处理、热处理或其组合。
21.权利要求18所述的组合物,其中通过以下方式从所述混合物除去溶剂:喷雾干燥、真空干燥、冷冻干燥、滚筒干燥、挤出、超临界提取或其组合。
22.权利要求1所述的组合物,其中所述组合物还包含其它成分,包括但不限于药学上可接受的载体。
23.权利要求1所述的组合物,其中所述溶质化合物和所述高度支化的α-D-葡聚糖以约100:1到约1:1000的溶质化合物与高度支化的α-D-葡聚糖的质量比提供。
24.增加溶质化合物的水溶解度、溶解速率和/或稳定性的方法,其包括将至少一种高度支化的α-D-葡聚糖或其改性形式与所述溶质化合物混合的步骤,其中所述高度支化的α-D-葡聚糖或其改性形式是糖原、植物糖原或其改性形式,并且其中所述改性是含有选自以下的官能团:乙酸酯、磷酸酯、羟丙基、阳离子基团、羧甲基、聚乙二醇、聚丙二醇或其组合。
25.权利要求24所述的方法,其中所述混合是在至少一种溶剂存在下进行。
26.权利要求24所述的方法,其还包括通过以下方式处理所述混合物的步骤:捏合、挤出、均质化、超声处理、高压处理、高速处理、微波处理、辐射处理、热处理或其组合。
27.权利要求25所述的方法,其中通过以下方式从所述混合物除去所述溶剂:喷雾干燥、真空干燥、冷冻干燥、滚筒干燥、加热干燥、挤出、超临界提取或其组合。
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