CN101790542B - 经可调交联的透明质酸组合物 - Google Patents
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Abstract
本发明涉及生物相容的交联透明质酸凝胶组合物,它们的制备方法和使用方法,以及用于制备它们的交联剂。在本发明的一个方面中,描述了一种用于交联透明质酸的聚乙二醇交联剂,优选多官能交联剂如四臂星形PEG。在本发明的另一个方面中,描述了包含两个以上官能团的交联剂。这些多官能交联剂可单独使用以使透明质酸交联,或者它们可以不同比例与双官能交联剂结合使用以制备具有可调节的机械强度和硬度的透明质酸。本发明还公开了用聚乙二醇包覆的透明质酸组合物以及它们的使用方法。
Description
相关申请
本申请要求2007年7月30日提交的60/952,770号美国临时专利申请的优先权,该临时专利申请全文以引用的方式纳入本说明书。
发明背景
a.技术领域
本发明涉及新的生物相容性多糖凝胶组合物,它们的制备和使用方法,以及用于制备它们的新的交联剂。更具体而言,本发明涉及用一种新的多功能交联剂交联的透明质酸凝胶的新组合物,并涉及制备这种交联透明质酸凝胶的方法。
b.背景技术
透明质酸是一种广泛分布在整个人体的结缔、上皮和神经组织中的非硫酸化的糖胺聚糖。透明质酸还是皮肤的一种主要成分,其在皮肤中参与组织修复。随着皮肤的老化和反复暴露在太阳的紫外线下,皮肤细胞减少透明质酸产生并加快透明质酸的降解。同样,老化的皮肤丢失胶原——保持皮肤年轻和具有弹性所必需的另一种天然物质。随着时间的推移,透明质酸和胶原的丢失使皮肤出现细纹、皱纹和褶皱。
在过去的几年中,透明质酸组合物已被用于化妆品以填充皱纹、细纹、褶皱、伤疤,并用于提升皮肤组织例如使嘴唇饱满。因为透明质酸对人体是天然的,因此它是一种耐受性通常良好并且风险非常低的皮肤填充产品(skin augmentation product)。
最初,透明质酸组合物含有悬浮在凝胶中的透明质酸颗粒或微球体。这些组合物现仍处于商业应用,其往往在注射后的几个月之内降解并因此需要非常频繁的注射以维持它们的皮肤填充作用。尤其是,透明质酸在其天然状态下是高度可溶的,并通过酶促自由基代谢而快速周转。
最近,交联透明质酸的组合物已被用于皮肤填充。这些透明质酸组合物通常用双官能交联剂如丁二醇二缩水甘油醚(BDDE)交联,所述交联剂通常以双醚键与HA分子连接以形成一种较不易溶于水的聚合水凝胶网络,与非交联的透明质酸组合物相比,所述聚合水凝胶网络更不易降解并因此仅需较低频率的再注射。一些如此交联的组合物包含悬浮在凝胶中的非常大的透明质酸颗粒,每个大约50-1000μm。其他的是稠度非常均一的透明质酸凝胶基质。
尽管这些已知的交联透明质酸组合物存在的时间比非交联透明质酸组合物要长,然而它们的存在时间通常为12个月或更短,因此仍然需要非常频繁的再注射。因此,希望开发一种生物相容的、可用作皮肤填充物的、但在注射后具有更长可使用寿命的透明质酸组合物。具体而言,希望开发这样一种生物相容的且可注射的透明质酸组合物,其比现有可获得组合物具有更高的机械强度、更强的酶促降解抗性和更高的保水性。
发明概要
本发明涉及交联透明质酸组合物、它们的制备方法和它们的使用方法。更具体而言,本发明涉及一种制备交联透明质酸的方法,所述方法包括使透明质酸与一种聚乙二醇(PEG)基交联试剂相接触。所述聚乙二醇(PEG)基交联试剂(或交联剂)可为双官能的,即其PEG骨架带有两个与透明质酸链连接的反应基团。或者,所述聚乙二醇(PEG)基交联试剂(或交联剂)可为“多官能”的,即其PEG骨架带有两个以上与透明质酸链连接的反应基团。所述方法还可包括将所述透明质酸与一种非聚乙二醇基交联剂相接触,此种交联剂包括但不限于BDDE或二乙烯基砜(DVS)。根据本发明制备交联透明质酸的某些方法,所述聚乙二醇基交联剂可为四官能的,并且可使所述透明质酸与该四官能交联剂以及一种双官能交联剂如BDDE相接触。
本发明还涉及一种制备交联透明质酸的方法,所述方法包括使透明质酸与一种多官能交联剂相接触。所述多官能交联剂可为三、四、五、六官能等(带有两个以上的反应官能基团)。在本发明的一个实施方案中,所述方法包括使透明质酸与一种四官能交联剂接触,例如一种在本文中被进一步描述的四臂星形(4-Arm Star)PEG环氧化物。所述方法还可包括使透明质酸也与一种双官能交联剂相接触。透明质酸可与多种双官能和多官能交联剂接触,并且这种接触可以任意顺序相继发生,或者透明质酸可在一个步骤中与多种交联剂反应。
本发明的方法还可包括用聚乙二醇基悬膜(pendant)包覆透明质酸组合物。所述聚乙二醇基包覆可用于交联或非交联的透明质酸。在一个优选的实施方案中,还将根据本发明制备的交联透明质酸组合物用聚乙二醇基悬膜包覆起来。
本发明还包括根据本发明方法制备的用于软组织填充——特别是用于皮肤填充物——的组合物。更具体而言,本发明包括包含用至少一种类型的聚乙二醇交联剂交联的透明质酸的用于软组织填充——特别是用于皮肤填充物——的组合物。所述聚乙二醇基交联剂可为双官能的、多官能的或它们的组合。在一个实施方案中,本发明的透明质酸组合物用一种四臂星形PEG环氧化物交联。本发明的组合物也可包括用一种类型以上的PEG交联剂制备的交联透明质酸组合物。例如,可用一种官能基团数量可变和/或聚合物链或臂上的聚乙二醇长度可变的聚乙二醇基交联剂的结合物制备本发明的组合物。本发明的组合物还可包含一种聚乙二醇基涂层。
本发明还涉及包含用至少一种多官能交联剂交联的透明质酸的皮肤填充物组合物。所述多官能交联剂可为一种多官能聚乙二醇基交联剂,例如一种四官能聚乙二醇基交联剂,包括但不限于四臂星形PEG环氧化物。本发明的皮肤填充物也可包括用一种多官能交联剂(如一种四官能聚乙二醇)以及一种双官能交联剂(如BDDE、DVS或一种双官能聚乙二醇)交联的透明质酸。
在另一个方面,本发明涉及修复或填充患者软组织的方法,其包括以下步骤:选择要修复或填充的软组织并将如本文所述的一种包含本发明的交联透明质酸的组合物注射到所选择的软组织中。
通过阅读下面的描述和权利要求书以及通过观察附图,可清楚地理解本发明的前述和其他方面、特性、细节、效用和优点。
附图说明
图1示出了两条透明质酸链与一种双官能交联剂的交联。
图2示出了四条透明质酸链与一种多官能交联剂的交联。
图3示出了本发明的四官能聚乙二醇基交联剂及其前体这两种物质的化学分子式。
图4示出了一种用BDDE交联的透明质酸组合物样品与一种本发明的用BDDE及四臂星形PEG环氧化物交联剂交联的透明质酸组合物之间的机械强度差异的图表。
具体实施方式
本发明总的来说涉及使用一种多官能交联剂交联的透明质酸组合物,使用这种组合物的方法,并涉及用于制备这种透明质酸组合物的新的交联剂。这种交联透明质酸组合物可用于软组织填充,尤其用作皮肤填充剂。
本发明的一个方面涉及用于透明质酸交联的新的催化剂。在一个实施方案中,本发明的交联剂是聚乙二醇(PEG)基交联剂。PEG是一种亲水且惰性的生物相容性聚合物。由于其自身是一种聚合物,因此其大小(长度)可被改变。因此,所述PEG基交联剂的大小可根据期望所述交联透明质酸所具有的性质进行调整。如图1所示,在本发明的一个实施方案中,PEG基交联剂200是双官能的,所述聚合物链的两个末端都是反应活性的(通常具有环氧化物末端)并因此能够与透明质酸100的链结合。在本发明的另一个实施方案中,所述PEG基交联剂包括多种链长的PEG。所述PEG基交联剂可根据任何为本领域技术人员所已知的PEG合成方法制备。
本发明的PEG基交联剂可单独使用,或者与任何适于制备交联透明质酸的另一种交联剂结合使用。在本发明的一个实施方案中,本发明的PEG基交联剂和BDDE的组合用于制备交联透明质酸组合物。
在另一个实施方案中,本发明的交联剂是一种多官能交联剂。本文中使用的多官能是指在所述交联剂上具有两个以上反应活性位点。如图2所示,与双官能交联剂相比,多官能交联剂300能够将透明质酸100的更多条链相互连接起来。因此,所述多官能交联剂生成具有更高机械强度(G′)的透明质酸组合物。本发明的多官能交联剂还能改善所生成透明质酸组合物的降解。此外,本发明的多官能交联剂增加每个交联分子与至少一条透明质酸链反应的可能性,从而有利于纯化以及从最终的透明质酸组合物中去除未反应的交联剂。
在本发明的一个实施方案中,所述多官能交联剂是三官能的(含有3个活性位点)。在另一个实施方案中,所述多官能交联剂是四官能的。在另一个实施方案中,所述多官能交联剂是五官能的。在另一个实施方案中,所述多官能交联剂是六官能或更多官能的。实际上,本发明交联剂上官能位点的数目只受到透明质酸链与交联剂上所产生反应活性位点(例如由于几何和空间阻碍)的结合能力的限制。在本发明的另一个实施方案中,一种交联剂组合物包括至少两种不同官能度的多官能交联剂(例如四官能交联剂与六官能交联剂的结合物)。在另一个实施方案中,一种多官能交联剂以可变比例与一种双官能交联剂组合以形成具有可变机械强度的透明质酸组合物。表1示出了几种样品的双官能与多官能交联剂的比例和所生成的透明质酸凝胶的机械强度。
在另一个方面,本发明的多官能交联剂可为一种多官能PEG基交联剂。本发明的一种四官能PEG基交联剂示于图3。如图3所示,在一个实施方案中,本发明涉及一种四官能PEG交联剂前体。还如图3所示,所述四官能PEG交联剂前体还可与一种环氧化物反应以形成一种新的四臂星形PEG环氧化物交联剂。图3所示的环氧化物四官能PEG交联剂可通过使一种碱性多元醇分子(如季戊四醇)连接环氧基并与具有所需长度和支化的羟基-PEG链反应而制备。环氧基可通过将所述羟基基团去质子化并与氯甲基代氧丙环反应而连接所述碱性多元醇分子。然后所述环氧环在碱性条件下可与PEG链的羟基反应。在交联剂制备的最后一步中,环氧基可连接至PEG的各个末端,从而能使交联剂与多糖分子反应。
与上面所述双官能PEG基交联剂一样,四官能PEG基交联剂(包括四臂星形PEG环氧化物)的大小可调节。如图3所示,所述交联剂的臂可具有多种聚合长度,从而影响它们的机械特性。此外,通过将本发明的四官能PEG基交联剂与一种双官能交联剂——例如本发明的双官能PEG交联剂、BDDE、DVS和/或1,2,7,8-二环氧辛烷——以可变比例混合,最终的透明质酸组合物的机械强度和硬度可按需调节。
本发明还涉及使用本发明交联剂制备的交联透明质酸组合物。在一个实施方案中,本发明的透明质酸组合物包含一种PEG基交联剂。在另一个实施方案中,本发明的透明质酸组合物包含一种多官能PEG基交联剂。在另一个实施方案中,所述透明质酸组合物包含一种四官能PEG基交联剂。在另一个实施方案中,所述透明质酸组合物包含一种四臂星形PEG环氧化物交联剂。在其他实施方案中,所述透明质酸组合物包含多官能交联剂以及双官能交联剂。本发明的透明质酸组合物可为相当均匀的凝胶或它们可被研磨成可进一步悬浮在凝胶中的颗粒。在本发明的一个实施方案中,所述透明质酸组合物包含用一种多官能交联剂制备然后研磨成颗粒的透明质酸,以及所述颗粒悬浮于其中的用一种多官能和/或双官能交联试剂制备的透明质酸凝胶。
在本发明的另一个方面,透明质酸组合物还被包覆在PEG基悬膜中。作为一种生物相容的、惰性且亲水的聚合物,PEG使透明质酸具有良好的降解抗性。交联的或非交联的透明质酸颗粒可用PEG基悬膜包覆以提高它们在体内的寿命。在一个实施方案中,本发明的交联透明质酸组合物被研磨成颗粒且该颗粒用PEG基悬膜包覆。所述颗粒通常为约100μm-1000μm且所述涂层的厚度通常可为2nm-50nm。
本发明还涉及制备用PEG基交联剂交联的透明质酸组合物的方法。在一个实施方案中,将透明质酸与一种双官能PEG基交联剂接触并使其反应。在另一个实施方案中,将透明质酸与一定量的双官能交联剂接触,然后与一定量的多官能交联剂接触。所述透明质酸可与一种以上的交联剂逐步反应,先与较低官能度的交联剂接触或者先与较高官能度的交联剂接触。或者,所述透明质酸可在一个步骤中与多种交联剂反应。
本发明的另一个方面为使用本发明的新的透明质酸组合物填充软组织的方法。在一个实施方案中,本发明的新的透明质酸组合物被用作皮肤填充物以填充患者皮肤上不想要的细纹、皱纹和/或褶皱。
下面的实施例提供了关于本发明某些实施方案的更多细节。
实施例1
本发明的一种多官能交联剂可由一种基础多元醇制备。例如,136mg的季戊四醇(即四官能PEG交联剂)可与100mg的氢化钠反应并随后与370mg的氯甲基代氧丙环反应以连接环氧基。5000mg的羟基PEG链(即MW=1.25k)可与环氧化物封端的多元醇在碱性条件下(如在NaOH溶液中)反应生成一种四官能PEG羟基封端的交联剂前体。所述前体可如上所述与等摩尔量的氯甲基代氧丙环反应生成所述四官能交联剂。
实施例2
本发明一个实施方案的透明质酸凝胶可如下制备。
将1g透明质酸钠纤维(NaHA,Mw=0.5-3MDa)与5-10g 0.01-1%的氢氧化钠溶液混合且将所述混合物进行水合1-5小时。然后将20-200mg的1,4-丁二醇二缩水甘油醚(BDDE)和0.05-2g四臂星形PEG环氧化物(Mw=200-10,000Da)加入所述NaHA凝胶中。将所述混合物机械匀化,然后置于40-70℃烤箱中1-10小时。所得交联水凝胶用等摩尔量的盐酸中和,并溶胀于磷酸盐缓冲液(PBS,pH=7.4)中。然后可将这种水凝胶机械匀化。
实施例3
为比较本发明的交联透明质酸与现有技术类型的交联透明质酸的特性,使用实施例2中所公开的方法制备一批新的可调节交联的透明质酸。用一种类似方法制备一批已知交联透明质酸,其中使用BDDE作为唯一的交联剂(不添加任何新的四臂星形PEG环氧化物)并使HA与交联剂的摩尔比与实施例2中相同。
然后通过使用应变扫描试验测定凝胶硬度,作为每种样品交联程度的指示来比较获自所述两批产品的样品。所述应变扫描试验在ARES流变仪上使用50mm平行板装置进行。将大约2-3ml的每种样品置于较低盘的中央并将间隙(gap)设为1mm。所述试验在5Hz频率下进行,范围为1-250%应变。在应变低值,用弹性或储能模量G’中的平顶来量化凝胶硬度。
图4图示了与现有技术的水凝胶相比在根据本发明制备的填充凝胶上所进行测量的结果。如图4所示,本发明水凝胶的G’平顶明显高于现有技术凝胶。本发明的水凝胶比现有技术的凝胶更硬并具有更高的交联程度。
实施例4
用双官能PEG和四臂星形PEG环氧化物交联剂制备六个交联透明质酸的样品。在每个样品中,改变双官能PEG与四臂星形PEG环氧化物的比例,从而使所有六个样品中HA与总交联剂的摩尔比保持相同。每个样品的机械强度用上述相同方法进行检测。低应变值下的G’平顶示于下表1。如表1所示,当双官能交联剂被等摩尔量的四官能交联剂替换时,低应变下的平顶G’值增加,这表明交联程度增加。
表1
%双官能PEG | %四臂星形PEG环氧化物 | G’(Pa) |
100 | 0 | 180 |
90 | 10 | 190 |
85 | 15 | 205 |
75 | 25 | 252 |
50 | 50 | 360 |
25 | 75 | 400 |
实施例5
被PEG基悬膜包覆的水凝胶颗粒可通过以下方式制备:将380mg的水凝胶颗粒(例如)与0-100mg的环氧化物封端的单官能PEG 2000Da和0.5ml氢氧化钠(0.01-1%wt)混合,并在40-70℃下反应1-10小时。可将得到的被PEG基悬膜包覆的颗粒用等摩尔量的盐酸中和。
可用酶降解试验比较经包覆的颗粒与未包覆的颗粒。可将0.1-10mg量的透明质酸酶在10-250分钟内于37℃下加入所述透明质酸颗粒中,然后加入0.1ml的0.8M的四硼酸钾溶液并在100℃下加热10分钟。可在所述样品中加入3ml 10wt%对二甲氨基苯甲醛的乙酸溶液并在37℃下培养10-120分钟。可使用585nm的吸收值来确定每个样品中透明质酸降解的量。光密度值(OD)示于表2。当更多PEG基悬膜用于包覆所述透明质酸颗粒时,该体系变得更不易于酶促降解。
表2
样品(PEG∶HA比例) | 585nm下的光密度(OD) |
A(0∶1) | 0.750 |
B(2∶1) | 0.400 |
C(10∶1) | 0.260 |
尽管上面只对本发明的几个实施方案进行了一定程度上的具体描述,然而本领域技术人员可在不背离本发明的精神或范围的情况下对所公开的实施方案进行多种改造。上面描述中所包含的或附图中所示的全部内容意欲应解释只作为解释说明而非限制性的。可在不背离如所附权利要求所限定的本发明精神的情况下进行细节上的改变。
Claims (3)
1.一种制备交联透明质酸的方法,所述方法包括将透明质酸与一种聚乙二醇基交联剂接触,还包括将透明质酸与一种非聚乙二醇基交联剂接触,其中所述聚乙二醇基交联剂是四官能的,其中所述透明质酸在一个步骤中与所述多种交联剂反应,其中所述方法还包括用一种聚乙二醇基悬膜涂层包覆所述交联的透明质酸。
2.权利要求1的方法,其中所述方法包括将透明质酸与丁二醇二缩水甘油醚接触。
3.一种由权利要求1的方法获得的用于软组织填充的组合物。
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US20090036403A1 (en) | 2009-02-05 |
MX2010001219A (es) | 2010-03-01 |
US20130023658A1 (en) | 2013-01-24 |
NZ583031A (en) | 2012-05-25 |
NZ599888A (en) | 2013-08-30 |
HK1142917A1 (zh) | 2010-12-17 |
US8318695B2 (en) | 2012-11-27 |
KR20100046038A (ko) | 2010-05-04 |
CA2695179A1 (en) | 2009-02-05 |
CN102850468A (zh) | 2013-01-02 |
AU2008282541A1 (en) | 2009-02-05 |
EP2178923A1 (en) | 2010-04-28 |
JP2010535277A (ja) | 2010-11-18 |
BRPI0815045A2 (pt) | 2015-02-10 |
AU2008282541B2 (en) | 2013-09-26 |
JP5518709B2 (ja) | 2014-06-11 |
CN101790542A (zh) | 2010-07-28 |
WO2009018076A1 (en) | 2009-02-05 |
JP2014194018A (ja) | 2014-10-09 |
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