CN101557720B - 具有无定形金属盐作为载体的活性成分递送系统 - Google Patents
具有无定形金属盐作为载体的活性成分递送系统 Download PDFInfo
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- CN101557720B CN101557720B CN2007800458499A CN200780045849A CN101557720B CN 101557720 B CN101557720 B CN 101557720B CN 2007800458499 A CN2007800458499 A CN 2007800458499A CN 200780045849 A CN200780045849 A CN 200780045849A CN 101557720 B CN101557720 B CN 101557720B
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- A—HUMAN NECESSITIES
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Abstract
本发明涉及具有无定形金属盐作为载体的活性成分递送系统，该活性成分递送系统包含(i)活性成分和(ii)载体组分，其中载体组分包含无定形金属盐，并且活性成分至少部分地固定到载体组分并部分地为载体组分所包封。活性成分可以是苦味多酚例如类黄酮。
Description
技术领域
本发明涉及一种活性成分递送系统，一种制备该递送系统的方法以及该递送系统掩蔽苦味的应用。
背景技术
众所周知，食品、饮料和药品工业中的某些消费品包含不利于被食用产品总体味道效果的某些苦味物质。为了解决该问题，制造商已竭尽全力去掩蔽或甚至去除该令人不愉快的产物。
在饮料例如啤酒、咖啡和软饮料中，该问题特别严重，据信其中存在多酚例如绿原酸内酯或类黄酮，明显导致消费者的苦味感觉。
尽管如此，在食品中发现的多种多酚或类黄酮是有益的抗氧化剂，食用时，其可清除所谓的“自由基”或调节人或动物基因表达，从而提供给消费者以营养或健康益处。欲更详细了解类黄酮的有益效果，可参见例如Nijveldt等的“Flavonoids：A review ofprobable mechanisms of action and potential applications”，Am J Clin Nutr 2001；74：418-25。
因此，期望掩蔽或抑制这样的成分所赋予的不希望的味道，而不会不利地影响它们的有益效果。
可知还可从食品中提取这些有益成分，获得其分离的形式，例如营养补充剂，其可用于食用得到直接的益处。然而，在这种浓缩的形式中，由于产品苦味而导致消费者拒绝的风险更大。
对于这样的产品，还期望以具有令人不愉快的苦味明显减少或甚至完全除去的感觉的更可口形式提供它们。
使用这样的活性成分的另一个问题是它们对氧化高度敏感。因此，还期望提供一种能保护活性成分耐受所述降解的系统。
JP 2003-128664描述了为减少苦味，将多酚中和为相应的钠盐、钙盐、镁盐或钾盐。该方法产生了明显改变饮料(例如茶)外观的大颗粒，甚至还产生了不希望的沉淀物。
在JP 2003-366456(Taiyo Kagaku KK)中，据说通过添加酪蛋白减少了饮料和食品中的苦味和涩味。
在JP 04-103771(Unitika KK)中，通过将茶叶与几丁质混合制备茶叶提取物，从而消除苦味和涩味。
US-A1-2002/0188019(Bayer Corporation)描述了包含某些据说能掩蔽苦味或金属味感觉的羟基黄烷酮的制剂。
US-A-5741505(Mars)描述了使用无机涂层以提供隔氧层来增加食品和药品的保存期。该涂层不与所包封的产品相互作用。
US 2004/0180097(Lin等)提及一种稳定和/或味道掩蔽的药物剂形式，其包含多孔磷灰石颗粒和陷入孔中的药物。该产品是通过将通常以浆液形式存在的坯料多孔磷灰石颗粒与药物溶液接触，并蒸发溶液的溶剂使得药物陷入多孔磷灰石颗粒中而生成的。因此，在颗粒表面或近表面处存在高浓度的药物，颗粒与陷入的药物之间几乎不存在络合作用。
最后，多种产品可为公众所用，该产品中液体活性成分例如大蒜油被包封入透明外壳中。这些胶囊非常大，通常具有高达5～10mm的直径。
还期望提供具有直径至多用肉眼勉强可见的颗粒。这样的颗粒因而适合于掺入不希望存在可见颗粒的产品特别是饮料中。例如，茶通常以一种透明饮料存在(在非强制性选择地添加牛奶之前)，其中可见颗粒的存在将会对消费者的吸引力造成损害。
多项研究已显示归因于例如多酚的对健康的有益效果可通过将完整的活性分子递送到消化系统而得以增加。
因此，期望以通过胃或消化系统中存在的、而常规贮藏期间或口腔中不存在的物理条件触发释放的这种方式来保护活性成分。
本发明寻求解决一个或多个上述问题和/或提供一种或多种上述益处。
发明内容
因此，本发明提供了一种活性成分递送系统，该系统包含：
(i)活性成分，和
(ii)载体组分，
其中载体组分包含无定形金属盐，并且活性成分至少部分地固定到载体组分并部分地为载体组分所包封。
为了使活性成分部分地固定以及部分地包封入载体组分中，本发明还提供了一种制备活性成分递送系统的方法，包括步骤：
(i)提供第一金属离子源，
(ii)提供独立的第二抗衡阴离子源，
(iii)提供独立的第三活性成分源，
(iv)在混合区中将三种来源组合，和
(v)在混合区中进行混合步骤。
另一方面，本发明提供了如上定义的载体材料的掩蔽、抑制或减少由如上定义的活性成分所引起的消费者的苦味感觉的应用。
又一方面，本发明提供了一种包含上述定义的递送系统的食品或饮料产品。
再一方面，本发明提供了一种包含上述定义的递送系统的营养、保健或药物产品。
具体实施方式
本发明涉及一种包含载体组分的递送系统，该载体组分包含无定形金属盐。不希望受理论约束，人们相信金属盐作为混合固定-包封剂，使得活性成分部分地与之反应并部分地包埋于其中。
封装领域技术人员容易理解的是，混合载体组分完全不同于常规包封产品，因为后者通常包含完全包裹活性成分的包封外壳(所谓的“核-壳”排列)或包封产物遍布的基质(参见例如US 3704137)。
已经发现这种混合载体组分还能通过在消化道中机械消化断裂(defragmentation)和/或通过胃中pH改变来释放活性成分，从而提供一种用于将活性成分例如营养或健康产品完整地递送至它们最有效的地方的有效机制。
活性成分递送系统可以胶体混合物形式存在。
已发现这样的胶体混合物具有大的比表面积。这是有利的，因为当条件适合于释放所包封的成分(如由于胃中酸性pH)时，存在更大的可利用的反应表面积，加速了载体组分的破裂/溶解，从而能使活性成分在期望位置处更快地释放。
载体组分
载体组分包含无定形金属盐。
当提及无定形金属盐时，为了简明在此使用术语“载体组分”，其表示一种能同时固定和包封活性物质的物质。
“固定”意思是载体与活性成分最好形成键例如络合物。当然，尽管优选配位，但本领域技术人员可设想其他类型的键。
“包封”意思是载体组分在活性成分周围至少部分地形成保护层或外壳。
可以相信通过固定和包封活性成分，该成分就均匀地分布在载体中，而不同于当载体为多孔的且活性成分简单地陷入孔中时所预料的非均匀分布。在后一种例子中，可预料到活性成分会浓缩在载体表面或载体表面附近。
金属盐具有无定形结构。如在此所定义的，“无定形的”用于意指至少部分非结晶性的(即化合物的主要部分缺少明显的晶体结构)。
因此，应当理解的是用作混合载体组分的无定形的金属盐可含有允许量的微晶物质，该物质不会对这些物质的总物理特性或对它们提供的增强的络合-包封益处产生有意义的影响。
在本发明的上下文中，基于无机盐的总重量，如果金属盐按重量计算含有小于约50％，优选小于约40％，更优选小于约30％，还更优选小于10％，最优选小于5％，如小于2％的结晶物质，则其是无定形的。
金属盐优选是基本上不溶于水的。“基本上不溶于水的”在此定义指的是当在20℃和pH 3～7下测量时，小于10-3g/cc、更优选小于10-4g/cc和最优选小于10-5g/cc的溶解度。
因此，在贮藏期间所通常遇到的pH下，金属盐优选以固体的形式存在。
优选地，金属盐是在酸性pH下可溶解的。更优选地，当在37℃和pH 2或更低下测量时，无机盐具有大于10-3g/cc、更优选大于10-2g/cc和最优选大于10-1g/cc的溶解度。
换句话说，通常见于消费者胃中的pH会引起载体组分的破裂/溶解，并最终释放包封在其中的活性成分。
适用于混合载体组分的金属阳离子的例子包括钙、镁、铁(II)、铁(III)、锌或它们的混合物。
更优选地，金属阳离子为钙(II)、镁(II)或它们的混合物。最优选地，其为钙(II)。
适用于混合载体组分的抗衡阴离子的例子包括磷酸盐和碳酸盐。
优选的抗衡离子为磷酸盐，因为已发现其产生具有利于盐与要待包封的物质结合的疏水性分裂面的无定形金属盐。
无定形磷酸钙(在此称为“ACAP”)是最优选的金属盐。其是一种不溶于水和可溶于酸的盐，可在中性pH下制备具有高胶体稳定性的该盐的颗粒。这就提供了如上所讨论的胶体混合物的益处。
根据pH条件，ACAP能既与结构中羟离子的包含物又与该结构中的质子沉淀，中和点通常为pH 4.5。因此，在约pH 7的标准条件下，可沉淀出通常为羟基磷灰石的无定形的金属混合物(metallic cross)。
根据进入混合区的相对反应物流，ACAP还可以富含钙离子或富含磷酸盐离子。
于是大多数的电荷错配为羟基或质子所分别抵消。这种针对化学计量比的不敏感性给予ACAP以巨大的结构自由性，使得粒度、折射率、沉淀物中残留水量以及机械塑性都可得到控制。
钙离子与磷酸盐离子的摩尔比优选为3∶1～1∶3，更优选2∶1～1∶3，还更优选1∶1～1∶3，最优选1∶1.5～1∶3。
优选载体包含过量的阴离子，原因在于最后所得到的带负电荷的载体具有更高的胶体稳定性和/或更易于在含水液体制剂例如茶、咖啡、软饮料和无酒精甜饮料中分散。
可以本领域技术人员所知的任何一种合适的方法制备供使用的包含无定形无机盐的载体组分。通常，其在结合和包封活性成分的同时被原位制备。例如，可通过在含活性成分(如多酚)的液体溶液存在下沉淀无机盐来制备递送系统。
对于不溶于水的活性成分，可通过将无机盐和活性成分共沉淀来制备递送系统。通常通过将不同来源的金属阳离子、抗衡阴离子和待包封的活性物质导入混合区并使沉淀-包封过程在该区中发生来进行该沉淀。
可存在附加原料并与无定形金属盐一起制备络合的载体材料。有机材料是特别优选的。例如，还可存在碳水化合物如麦芽糖糊精、环糊精和化学改性淀粉以致形成络合的载体材料。
活性成分
活性成分可以是任何期望待固定或待包封的化合物或组合物。
尽管如此，本发明已显示在掩蔽不希望的味道的同时使得它们被完整地递送以在消费者的消化道或胃中释放上作用惊人的好。
尤其是，已显示混合载体组分能特别有效地掩蔽苦味或涩味。
还已显示能阻止对氧化降解特别敏感的活性成分的不希望的氧化。
优选的活性成分包括多酚、共轭多酚、多酚聚合物、香豆素、多糖、脂质、有机硫化合物、共轭维生素、肽、类胡萝卜素、蛋白质或它们的混合物。
在一方面，活性物质优选是多酚。
特别优选的多酚是非强制性选择地与一个或多个甲基、硫酸酯、配糖物、磷酸酯、醋酸酯和酯共轭的苷元。
适合的多酚的例子包括类黄酮族化合物。
类黄酮包括(i)黄酮，例如白杨黄素、莰非醇、芸香苷、五羟黄酮、木樨草素和芹菜素，(ii)黄烷醇，例如五羟黄酮、莰非醇、杨梅黄酮、异鼠李素、藿香黄酮醇、甲基鼠李黄素，(iii)黄烷酮，例如非瑟酮、柚苷、柚苷配基、橙皮素、柚苷配基、毛纲草酚，(iv)黄烷-3-醇，例如(+)-儿茶素、(+)-没食子儿茶素、(-)-表儿茶素、(-)-*表没食子儿茶素、(-)-表儿茶素3-没食子酸酯、(-)-表没食子儿茶素3-没食子酸酯、茶黄素、茶黄素-3-没食子酸酯、茶黄素3’-没食子酸酯、茶黄素3，3’二没食子酸酯，(v)茶玉红精，(vi)异黄酮，例如染料木黄酮、黄豆苷原、黄豆黄素，(vii)花色素，例如花青素、花翠素、二甲花翠素、花葵素、甲基花青素和矮牵牛苷配基，(viii)多甲氧基黄酮，(ix)黄烷，(x)酚性类黄酮，(xi)原花色素和(xii)异类黄酮。
如Adam Drewnowski和Carmen Gomez-Carneros 2000，在The AmericanJournal of Clinical Nutrition所描述的，在多种天然消费品例如葡萄柚汁、绿茶、红茶和咖啡中发现了多酚活性成分。当与这样的食品或它们的提取物共同使用时，载体组分是特别有效的。例如，包含绿茶提取物或发酵茶提取物的活性成分是特别适合的。
另一方面，活性成分可以是着色剂，更优选类胡萝卜素。适合的类胡萝卜素的例子包括β-胡萝卜素、视黄醇、虾青素、叶黄素、番茄红素、隐黄质和玉米黄质。例如这样的着色剂通常用于半透明饮料中。贮藏时，着色剂有时会沉降从而在整个饮料中产生不希望的色泽差异。此外，之后需要用力摇动以在整个饮料中均匀地再分散着色剂。使用混合试剂去络合-包封着色剂，即使在贮藏条件下非常小的被包封的颗粒也能持久均匀地混悬在整个饮料中。
其他适合的活性成分包括酚酸、维生素E磷酸酯、维生素E醋酸酯、芪、白藜芦醇、姜黄素、维生素、6-姜醇、呋喃香豆素、香柠檬素、三萜(柠檬苦素类化合物)、丹宁酸、安石榴甙、石榴多酚(punicocides)、鞣花酸、木酚素、原花青素、碧萝芷(pycnogenol)、植物甾醇、硫代葡萄糖苷、水解硫代葡萄糖苷、异硫氰酸酯、异硫氰酸4-(甲基亚磺酰)丁酯(sulphoraphane)、谷胱甘肽、麦角硫因、硫辛酸、鞘脂和丁酸酯。
活性成分可以是油类。
可包封在本发明活性成分递送系统中的优选的油类是例如富含多不饱和脂肪酸的油类。基于油类的总重量，这样的油类通常包含至少5wt.％，优选至少10wt.％，更优选至少25wt.％和最优选至少35wt.％的多不饱和脂肪酸。
富含多不饱和脂肪酸的油类优选是富含Ω-3脂肪酸的油类。
更优选地，多不饱和脂肪酸选自二十碳五烯酸(EPA)、二十二碳六烯酸(DHA)、花生四烯酸(ARA)、α-亚麻酸、亚油酸和它们中至少两种的混合物。DHA和EPA是最优选的。
油类优选与植物油衍生物例如甘油三酯油混合。特别优选的市售油类是以
(来自Stepan)名称进行销售的油类。
富含多不饱和脂肪酸的油类与植物油衍生物优选的重量比为70∶30～99∶1，更优选80∶20～95∶5。
在一个非常优选的实施方案中，油混合物随后可使用任何合适的乳化剂进行乳化。乳化剂优选为食品级乳化剂，更优选为糖酯。发现乳化油能更容易地与载体系统混合，从而提供了更稳定的产物。
由于其混合特性，本发明的递送系统容许在载体组分之上和之中负载很多活性成分，与此同时如消费者感知到的仍惊人地保持高度的苦味掩蔽。
因此，活性成分可占递送系统总重量的高达70重量％，更优选10～65重量％，最优选20～55重量％递送系统。
其优点在于当与传统的包封系统比较时，为递送所需量的活性成分只需较少的载体组分，从而增加了成本效益。
递送系统结构
递送系统可以是固体、半固体或液体形式的。
如果是固体形式的，则其优选以颗粒形式存在。
递送系统粒度优选为10～1000μm，更优选20～500μm，最优选50～300μm。
在本发明的上下文中，“粒度”定义为通过常规的光散射实验所测定的算术平均直径。
在粒度决定颗粒是否能用于不希望看见这样的颗粒的食品或饮料产品的情况下，其是特别重要的。已发现与使用常规包封产品所通常可能制备的颗粒相比，根据本发明的递送系统能制备更小的颗粒。
优选总共至少90％，更优选至少95％和最优选97％，如99％(以数量计)的颗粒具有10～1000μm，更优选20～500μm和最优选50～300μm的粒度。
已发现与传统包封系统相比，本发明递送系统中的颗粒通常具有更加均匀的大小。从美学观点来看以及还考虑到更加均匀的活性成分剂量，期望均匀大小的颗粒。
如果递送系统是液体形式的，则其优选作为水分散体提供。
活性成分递送系统可进一步被包封。由于能增加在贮藏时递送系统的抗氧化稳定性，因此非常期望对活性成分递送系统的进一步包封。
第一优选的包封系统是活性成分递送系统居于其中的玻璃状基质。更优选地，包封系统为玻璃状碳水化合物基质。该碳水化合物基质成分优选包含糖衍生物，更优选麦芽糖糊精。
特别优选的麦芽糖糊精是那些具有10～30，更优选15～25，最优选17～19的DE的麦芽糖糊精。
通常，将活性成分递送系统与碳水化合物基质材料以及适量的增塑剂如水混合，在螺杆挤出机中加热混合物至高于基质材料的玻璃化转变温度的温度，以致形成能通过模口挤出的熔融体，然后利用诸如现有技术中所描述的既有方法将该熔融体挤出。参见例如2002年5月11日公开的专利申请WO 00/25606或2001年3月15日公开的专利申请WO 01/17372，以及其中引用的文献，其内容特此并入作为参考。
如果需要的话，可存在更多的碳水化合物基质成分以更进一步改善抗氧化剂防护性能。
其他合适的包封系统描述于例如US 4,610,890或US4,707,367中，其内容并入作为参考。
制备
活性成分递送系统的制备通常包括将分别提供的(i)金属离子源，(ii)抗衡阴离子源和(iii)活性成分源共同混合。
尽管如此，已发现有可能将源(i)和(iii)组合。例如，在活性成分以水溶液、水/有机溶剂溶液、分散乳状液或水包油乳状液形式存在的情况下，可使用乳化剂(优选食品级乳化剂)将源(i)和(iii)组合。
实施例
现将根据下列实施例描述本发明。可以知道的是实施例在于举例说明本发明，本发明的范围并非因此而受限。
根据本发明的样品以数字方式表示，比较实施例以字母方式表示。除非另外指出，所有的量均为重量计的百分比。
实施例1
用ACAP包封柚苷
使用可以间歇方式和连续方式操作的常规的双喷射沉淀法。首先将活性成分(柚苷)溶解在乙醇或乙醇/水介质中。制备包含Ca2+离子(由氯化钙溶液提供)的第一液流和包含PO4 3-离子(由磷酸钠提供)的第二液流，以便提供含10g/L ACAP溶液的合成载体组分。然后制备包含标准溶液(2g/L的柚苷的30％乙醇溶液)的第三液流。
使用标准的Y-混合器，将这三种液流分别喷射入混合室中进行反应，喷入相同体积时停止，即将10ml Ca2+储液加10ml PO4 3-储液喷入10ml柚苷中。在用30wt％乙醇溶液标准化稀释(1∶12)后，测定吸光系数(在280nm处的强酚带，略微酸性条件)，并与ACAP添加前后进行比较。
结果显示E-值从3.75降低到1.5，并据此计算出至少70％的柚苷为ACAP所俘获。
实施例2
天然消费品的评价
制备下列样品：
表1
| 样品 | 成分 |
| A | 绿茶 |
| 1 | 绿茶+ACAP |
| B | 红茶 |
| 2 | 红茶+ACAP |
| C | 葡萄柚汁 |
| 3 | 葡萄柚汁+ACAP |
样品A、B和C制备如下：如实施例1，使用搅拌用的Y-混合器生成10g/L基础浓度的ACAP。将该原位产生的胶体喷射入三种不同的含天然多酚的溶液中，即泡过10分钟的红茶、泡过10分钟的绿茶和葡萄柚汁。添加的最终量为每100ml含多酚液体100mg粗制起始产品(相应于约50mg ACAP)，即以0.1％浓度添加。
然后如下进行苦味感觉的评价：
让受过训练的7人评审团去比较样品A和样品1，并回答问题“样品对中哪一个更苦？”。然后对样品B和2重复该过程。
以下表中给出了结果：
表2
| 样品 | 结果 |
| A和1 | 6个人认为样品A更苦 |
| B和2 | 6个人认为样品B更苦 |
| C和3 | 4个人认为样品C更苦 |
这证明了递送系统提供了显著的苦味掩蔽益处。
实施例3
鱼油的包封
通过通氮气1小时对鱼油(金枪鱼油)样品脱气。然后使用
均质器在24000rpm下，将脱气鱼油与中链甘油三酯油(Neobee，来自Stepan)混合并与糖酯(Ryoto S-1670，来自Mitsubishi)一起乳化。在3-吗啉代丙磺酸缓冲液(MOPS)中制备钙和磷酸盐离子溶液，以达到7.2的pH。添加阿拉伯树胶到钙溶液中以避免磷酸钙颗粒结晶。
使用双喷射沉淀法将鱼油俘获入无机混合基质中。制备包含2％Ca2+离子(由氯化钙溶液提供)和0.2％阿拉伯树胶的第一液流以及包含2％PO4 3-离子(由磷酸钠提供)的第二液流，以便提供含10g/L ACAP溶液的合成载体组分。然后如上所述制备包含25％鱼油/Neobee(90∶10的重量比)乳状液的第三液流。乳状液中Ryoto糖酯S-1670的浓度为0.3％。使用标准的Y-混合器，将这三种液流分别喷射入混合室中进行反应，喷入相同体积时停止。通过除去水相，对所得到的样品进行浓缩。最终的样品是均匀的并发现具有26％的鱼油含量。
Claims (12)
1.一种活性成分递送系统，该系统包含：
(i)活性成分，和
(ii)载体组分，
其中载体组分包含无定形磷酸钙，其中钙离子与磷酸盐离子的摩尔比为1:1.5~1:3，并且活性成分至少部分地固定到载体组分并部分地为载体组分所包封。
2.根据权利要求1的递送系统，其中活性成分为多酚、香豆素、多糖、脂质、有机硫化合物、肽、类胡萝卜素或蛋白质。
3.根据权利要求1的递送系统，其中活性成分为多酚聚合物。
4.根据权利要求1或2的递送系统，其中活性成分为多酚。
5.根据权利要求4的递送系统，其中多酚为类黄酮。
6.根据权利要求1或2的递送系统，其中活性成分为类胡萝卜素。
7.根据权利要求1的递送系统，其中活性成分为富含多不饱和脂肪酸的乳化油。
8.根据权利要求1或2的递送系统，其中该系统被进一步包封。
9.一种制备活性成分递送系统的方法，包括步骤：
(i)提供第一金属离子源，
(ii)提供独立的第二抗衡阴离子源，
(iii)提供独立的第三活性成分源，
(iv)在混合区中将三种来源组合，和
(v)在混合区中进行混合步骤，
使得活性成分部分地固定到载体组分并部分地包封入载体组分中，
其中所述金属离子源为钙离子，所述抗衡阴离子源为磷酸盐离子，并且钙离子与磷酸盐离子的摩尔比为1:1.5~1:3。
10.一种包含权利要求1~5任一项的递送系统的营养、保健或药物产品。
11.一种包含权利要求1~7任一项的递送系统的食品产品。
12.一种包含权利要求1~7任一项的递送系统的饮料产品。
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| PCT/IB2007/054975 WO2008072155A1 (en) | 2006-12-12 | 2007-12-07 | Active ingredient delivery system with an amorphous metal salt as carrier |
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| CN101557720B true CN101557720B (zh) | 2013-05-29 |
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| EP (1) | EP2106217B1 (zh) |
| JP (3) | JP5468386B2 (zh) |
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| EP2106217B1 (en) * | 2006-12-12 | 2019-03-13 | Firmenich S.A. | Active ingredient delivery system with an amorphous metal salt as carrier |
| BRPI1008764A2 (pt) * | 2009-02-27 | 2018-07-24 | Council Scient Ind Res | microcápsula para liberação controlada para ação osteogênica |
| CN103249405A (zh) * | 2010-08-23 | 2013-08-14 | 哈佛学院院长等 | 用于药物递送和其他应用的颗粒 |
| WO2012027366A2 (en) | 2010-08-23 | 2012-03-01 | President And Fellows Of Harvard College | Acoustic waves in microfluidics |
| GB201319548D0 (en) | 2013-11-05 | 2013-12-18 | Medical Res Council | Amorphous magnesium-substituted calcium phosphate compositions and their uses |
| US10258987B2 (en) | 2014-06-26 | 2019-04-16 | President And Fellows Of Harvard College | Fluid infection using acoustic waves |
| CN104398489A (zh) * | 2014-11-04 | 2015-03-11 | 安徽省农业科学院农产品加工研究所 | 一种纳米化水飞蓟宾羟基磷灰石复合微胶囊的制备方法 |
| CN104398490A (zh) * | 2014-11-04 | 2015-03-11 | 安徽省农业科学院农产品加工研究所 | 一种纳米化水飞蓟宾磷酸钙复合微胶囊的制备方法 |
| WO2017035287A1 (en) | 2015-08-27 | 2017-03-02 | President And Fellows Of Harvard College | Acoustic wave sorting |
| US11701658B2 (en) | 2019-08-09 | 2023-07-18 | President And Fellows Of Harvard College | Systems and methods for microfluidic particle selection, encapsulation, and injection using surface acoustic waves |
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| US8383175B2 (en) | 2013-02-26 |
| WO2008072155A1 (en) | 2008-06-19 |
| US20100055256A1 (en) | 2010-03-04 |
| CN101557720A (zh) | 2009-10-14 |
| JP2017000164A (ja) | 2017-01-05 |
| US20130195929A1 (en) | 2013-08-01 |
| EP2106217B1 (en) | 2019-03-13 |
| EP2106217A1 (en) | 2009-10-07 |
| JP2014097067A (ja) | 2014-05-29 |
| US8808771B2 (en) | 2014-08-19 |
| JP6253425B2 (ja) | 2017-12-27 |
| JP2010512161A (ja) | 2010-04-22 |
| BRPI0716275A2 (pt) | 2015-01-20 |
| JP5468386B2 (ja) | 2014-04-09 |
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