CN116440327A - 一种聚氨酯/s-亚硝基化角蛋白复合多孔涂层的合成方法及其应用 - Google Patents
一种聚氨酯/s-亚硝基化角蛋白复合多孔涂层的合成方法及其应用 Download PDFInfo
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Abstract
本发明公开了一种聚氨酯/S‑亚硝基化角蛋白复合多孔涂层的合成方法及其应用,该合成包括如下步骤:将四氢呋喃和二甲基亚砜混合,加入S‑亚硝基化角蛋白,搅拌均匀后加入聚氨酯继续搅拌,得到聚氨酯/S‑亚硝基化角蛋白涂层溶液;将处理后的基材浸没在聚氨酯/S‑亚硝基化角蛋白涂层溶液中,形成聚氨酯/S‑亚硝基化角蛋白复合多孔涂层。本发明合成的聚氨酯/S‑亚硝基化角蛋白复合多孔涂层可涂覆于PET膜片、玻璃、硅胶管以及不锈钢管材等多种材料表面,具有良好的细胞相容性,血液相容性和抗菌性;在一定条件下被催化并缓慢释放出NO,有望于制备可释放一氧化氮的仿生涂层,如制备心血管支架、人造血管或作为伤口敷料的药物或材料。
Description
技术领域
本发明属于可释放一氧化氮涂层,具体涉及一种聚氨酯/S-亚硝基化角蛋白复合多孔涂层的合成方法及其应用。
背景技术
一氧化氮是人体内一种重要的气体信号小分子,一直是科学界和医学界众多研究者关注的焦点。在心血管系统中,NO负责调节血压、血管扩张,可以抑制血小板的粘附与聚集、介导心肌细胞凋亡,在心血管疾病的防治和干预治疗过程中扮演重要的角色。小分子一氧化氮药物治疗方式多为口服或静脉注射,易产生释放速率不稳定以及药物生物利用度较差等弊端。
涂层是提高聚合物材料表面生物相容性最便捷的手段之一。而多孔涂层的结构为细胞的容纳和生长,血管的快速入侵,组织的向内生长以及营养物和代谢物之间的相互交换提供了合适的空间。单纯的聚合物涂层生物相容性和血液相容性较差,临床应用受限。相反,单一的生物大分子涂层机械强度差,且涂层的粘附性不强。高分子聚合物和大分子药物混合制备的涂层有利于提高涂层的生物安全性,机械强度以及药物的利用率。且利用涂层溶液的挥发性不同,可产生不同孔径梯度,满足多种细胞生长需求。此外,具有NO释放性能的血管支架涂层具有抗凝血性能好、促内皮化等特性,在体内植入后可以更快实现受损部位内膜功能修复。
发明内容
发明目的:针对单一聚合物涂层生物相容性差,生物功能性较弱,以及药物利用率不高等技术问题,本发明提供一种聚氨酯/S-亚硝基化角蛋白复合多孔涂层的合成方法,本发明合成的聚氨酯/S-亚硝基化角蛋白复合多孔涂层延长了一氧化氮释放的时间,促进细胞的粘附与增殖。本发明利用两种混合溶剂的挥发性不同,制备出具有不同孔径的高聚物和S-亚硝基化角蛋白生物大分子复合涂层,既可以提高药物的稳定性,丰富涂层的生物功能性,并且可被涂覆于多种基材满足多种生物医用需求。
本发明还提供所述的聚氨酯/S-亚硝基化角蛋白复合多孔涂层及其应用。
技术方案:为了实现上述目的,本发明所述一种聚氨酯/S-亚硝基化角蛋白复合多孔涂层的合成方法,包括如下步骤:
(1)将四氢呋喃和二甲基亚砜混合得到溶液A;
(2)将S-亚硝基化角蛋白加入到溶液A中,搅拌均匀至S-亚硝基化角蛋白溶解完全后得反应液B;
(3)向反应液B中加入聚氨酯继续搅拌,得到聚氨酯/S-亚硝基化角蛋白涂层溶液C;
(4)将处理后的基材浸没在聚氨酯/S-亚硝基化角蛋白涂层溶液C中,采用浸涂法风干成膜在基材上形成聚氨酯/S-亚硝基化角蛋白复合多孔涂层。
其中,步骤(1)所述四氢呋喃和二甲基亚砜的质量比9-7:1-2。
作为优选,所述四氢呋喃和二甲基亚砜的质量比9:1,8:2,7:2。
更优选地,所述四氢呋喃和二甲基亚砜的质量比9:1。
其中,步骤(2)中加入S-亚硝基化角蛋白时需避光,室温下搅拌10-12h。。
作为优选,步骤(2)中加入S-亚硝基化角蛋白时需避光搅拌12h。
其中,步骤(3)中加入的聚氨酯与S-亚硝基化角蛋白的为质量比为9-7:1:3。
作为优选,所述聚氨酯与S-亚硝基化角蛋白的为质量比为9:1、8:2、7:3。
更优选地,所述聚氨酯与S-亚硝基化角蛋白的为质量比为9:1,其生物相容性更好。
其中,步骤(3)中加入聚氨酯搅拌至溶液呈均一状态。
其中,步骤(3)中加入聚氨酯后;S-亚硝基化角蛋白和聚氨酯的总质量占整份混合溶液总质量的10-15wt%。
其中,步骤(4)中基材为PET膜片、玻璃、硅胶管或者不锈钢管材;所述处理方法为先用足量的无水乙醇浸泡,接着在去离子水和无水乙醇中依次超声清洗,最后风干,裁剪为长方形备用。
作为优选,步骤(4)中PET膜片的处理方法为先用足量的无水乙醇浸泡24h,接着在去离子水和无水乙醇中依次超声清洗30min,最后风干,裁剪为4.8cm长度、1.6cm宽度的长方形备用。
其中,步骤(4)中将PET膜片浸泡到聚氨酯/S-亚硝基化角蛋白涂层溶液C中3-5min后取出晾干再次浸泡后取出晾干。
本发明所述的合成方法所合成的聚氨酯/S-亚硝基化角蛋白复合多孔涂层。
本发明所述的聚氨酯/S-亚硝基化角蛋白复合多孔涂层在制备心血管支架、伤口敷料中的应用。
本发明合成的聚氨酯/S-亚硝基化角蛋白复合多孔涂层,通过将聚氨酯与S-亚硝基化角蛋白按一定比例混合并溶于易挥发的四氢呋喃和二甲基亚砜混合溶液中,形成多孔涂层。本发明合成方法简单易行、无毒且成本低,且制备的涂层可稳定释放一氧化氮,可稳定存在。有望于用于生物组织工程支架的制备。
本发明将聚氨酯与S-亚硝基化角蛋白混合后溶于四氢呋喃和二甲基亚砜的混合溶液搅拌得到均匀的涂层溶液。本发明制备得到的聚氨酯/S-亚硝基化角蛋白复合涂层溶液可涂覆于硅胶管、玻璃、PET膜片,不锈钢管材等多种基材,应用广泛。通过浸涂晾干法制备得到的涂层为多孔涂层,有利于细胞的粘附,同时S-亚硝基化角蛋白的存在使涂层可稳定释放一氧化氮从而具有促进细胞增殖,抗菌,抗血小板粘附等作用。
本发明的重点在于解决单一高聚物涂层生物相容性差,以及药物利用不充分,不能长久稳定存在从而影响治疗效果等问题。通过两种特定的混合溶剂(四氢呋喃和二甲亚枫)的使用是利用溶剂挥发快慢不同,导致涂层形成尺寸不一的孔,利于细胞在涂层表面的粘附与生长。通过改变聚氨酯PU和S-亚硝基化角蛋白KSNO的特定比例(9:1,8:2,7:3),使得药物KSNO能够稳定存在于涂层中,且KSNO特定的比例使得相应的一氧化氮释放含量增加(释放时间可以达到200h),细胞增殖效果也更好,本发明通过特定PU和KSNO比例能够稳定长期释放一氧化氮,发挥抗菌和促细胞生长的作用。而现有涂层多为无孔涂层,不仅制备方法不同,其使用的材料与药物与本发明完全不同,涂层的功能也有所不同。本发明中的聚氨酯/S-亚硝基化角蛋白复合多孔涂层,重点在于形成的一个多孔涂层,可以利于细胞粘附生长并可缓慢释放一氧化氮。本发明中使用了两种特定比例的有机溶剂,沸点不同,由于挥发快慢不同,使得形成的涂层孔径不同。本发明不仅制备方法简单,且涂层粘附效果好,并可涂覆于多种基材,应用更广泛,具有普适性。
有益效果:与现有技术相比,本发明具有如下优点:
(1)本发明合成制备的聚氨酯/S-亚硝基化角蛋白复合多孔涂层,利于细胞的粘附与增殖,生物毒性低。
(2)本发明合成制备的聚氨酯/S-亚硝基化角蛋白复合多孔涂层,可稳定释放一氧化氮,解决了一氧化氮半衰期短,释放速率不可控的问题。
(3)本发明所采用的方法操作简便,反应条件温和,易于实现,并且四氢呋喃和二甲基亚砜两种溶液的混合可通过相分离产生复合多孔涂层。
(4)本发明制备的聚氨酯/S-亚硝基化角蛋白复合多孔涂层,可以在一定条件下被催化并缓慢释放出NO,有望于制备可释放一氧化氮的仿生涂层,如制备心血管支架、人造血管或作为伤口敷料的药物或材料。
附图说明
图1是本发明实施例1合成的聚氨酯/S-亚硝基化角蛋白复合多孔涂层的红外光谱图;
图2是本发明实施例1合成的聚氨酯/S-亚硝基化角蛋白复合多孔涂层的微观形貌;
图3是本发明实施例1合成的聚氨酯/S-亚硝基化角蛋白复合多孔涂层促进内皮细胞增殖与迁移的示意图。
图4是本发明实施例1合成的聚氨酯/S-亚硝基化角蛋白复合多孔涂层一氧化氮释放速率曲线示意图;
图5是本发明聚氨酯/S-亚硝基化角蛋白复合多孔涂层的制备示意图。
具体实施方式
根据下述实施例,可以更好地理解本发明。然而,本领域的技术人员容易理解,实施例所描述的内容仅用于说明本发明,而不应当也不会限制权利要求书中所详细描述的本发明。
实施例中所述实验方法,如无特殊说明,均为常规方法;所述试剂和材料,如无特殊说明,均可从商业途径获得。
其中,PET膜购买于sigma;聚氨酯重均分子量Mw=80000。
S-亚硝基化角蛋白的合成参考文献:S-nitrosated keratin composite matswith NO release capacity for wound Healing.Chemical Engineering Journal 400(2020)125964.
实施例1
(1)将一定面积的PET膜先用足量的无水乙醇浸泡24h,接着在去离子水和无水乙醇中依次超声清洗30min,最后风干,裁剪为4.8cm长度、1.6cm宽度的长方形备用。
(2)称取S-亚硝基化角蛋白分散于10mL四氢呋喃(THF)和二甲亚砜(DMSO)的混合溶液中,避光室温下搅拌12h,其中THF与DMSO的质量比为9:1。
(3)待S-亚硝基化角蛋白在溶液中分散均匀后加入聚氨酯继续搅拌12h溶解至溶液呈均一状态,得到聚氨酯/S-亚硝基化角蛋白(PU/KSNO)涂层溶液,其中聚氨酯与S-亚硝基化角蛋白质量比为9:1,S-亚硝基化角蛋白和聚氨酯的总质量占整份混合溶液总质量的10wt%;
(4)将步骤(1)处理后的PET膜片为基材,浸泡到PU/KSNO溶液中5min后取出晾干再次浸泡后取出晾干,在PET膜片上形成PU/KSNO涂层,本发明聚氨酯/S-亚硝基化角蛋白复合多孔涂层的制备示意图和浸涂过程如图5所示。
通过扫描电镜观察制备得到的涂层的微观形貌,以及细胞毒性实验检测图层的生物安全性。图1为聚氨酯/S-亚硝基化角蛋白复合多孔涂层的傅里叶变换衰减全反射红外光谱(ATR-FTIR),证明了涂层的成功制备;图2为涂层的多孔微观结构,本发明制备利用不同溶剂挥发快慢不同得到的多孔涂层结构如图2中扫面电镜图所示,多孔涂层与细胞外基质的多孔结构相近,利于细胞的粘附、生长与迁移,可显著提高涂层的生物安全性。
实施例2
(1)将一定面积的PET膜先用足量的无水乙醇浸泡24h,接着在去离子水和无水乙醇中依次超声清洗30min,最后风干,裁剪为1.6cm宽度的长方形备用。
(2)称取S-亚硝基化角蛋白分散于10mL四氢呋喃(THF)和二甲亚砜(DMSO)的混合溶液中,避光室温下搅拌12h,其中THF与DMSO的质量比为8:2。
(3)待S-亚硝基化角蛋白在溶液中分散均匀后加入聚氨酯继续搅拌12h溶解至溶液呈均一状态,得到聚氨酯/S-亚硝基化角蛋白(PU/KSNO)涂层溶液,其中聚氨酯与S-亚硝基化角蛋白质量比为8:2,S-亚硝基化角蛋白和聚氨酯的总质量占整份混合溶液总质量的10wt%;
(4)将步骤(1)处理后的PET膜片为基材,浸泡到PU/KSNO溶液中5min后取出晾干再次浸泡后取出晾干,在PET膜片上形成PU/KSNO涂层。
实施例3
(1)将一定面积的PET膜先用足量的无水乙醇浸泡24h,接着在去离子水和无水乙醇中依次超声清洗30min,最后风干,裁剪为1.6cm宽度的长方形备用。
(2)称取相应质量的S-亚硝基化角蛋白分散于10mL四氢呋喃(THF)和二甲亚砜(DMSO)的混合溶液中,避光室温下搅拌12h,其中THF与DMSO的质量比为7:3。
(3)待S-亚硝基化角蛋白在溶液中分散均匀后加入相应质量的聚氨酯继续搅拌12h溶解至溶液呈均一状态,得到聚氨酯/S-亚硝基化角蛋白(PU/KSNO)涂层溶液,其中聚氨酯与S-亚硝基化角蛋白质量比为7:3,S-亚硝基化角蛋白和聚氨酯的总质量占整份混合溶液总质量的10wt%;
(4)将步骤(1)处理后的PET膜片为基材,浸泡到PU/KSNO溶液中5min后取出晾干再次浸泡后取出晾干,在PET膜片上形成PU/KSNO涂层。
实施例4
将HUVEC用0.25%的胰蛋白酶消化,配置成细胞悬液浓度为3×104cells/mL。将实施例1-3制备得到的PU/KSNO涂层PET膜片样品打成直径1.5cm的圆片,置于超净工作台紫外照射正反面各1h杀菌,用高温灭菌后的圆片将其固定于24孔板中,每孔中有1mL细胞悬液,将孔板放入37℃且含有5% CO2的细胞培养箱中进行培养3天。对照组分别加入20μL Asc(250μg/mL),每12h补加一次。结束后弃掉原有培养基并用PBS清洗3次,随后向每孔加入1mL新鲜培养基和100μL浓度为0.5mg/mL的MTT溶液。4h后,吸弃孔内溶液,用PBS溶液洗涤,每孔加入500μL DMSO避光反应30min,最后吸取溶液转移到96孔板中,通过酶标仪测量490nm处OD值;其中,对照组(PU涂层PET膜片样品)按实施例1-3任意的制备方法,其中S-亚硝基化角蛋白全部替换成等量的聚氨酯;TCPS为不加样品的空白的细胞培养板对照。
将上述采用实施例1制备得到的PU/KSNO涂层PET膜片样品圆片放置于6孔板中,并用厚度为0.5mm的细胞迁移模具固定。随后将经过染色和胰酶消化的HUVECs细胞悬液(5×104cells/mL)种植于样品膜表面。分别在4h和24h采用荧光显微镜记录细胞迁移变化。
如图3所示,PU/KSNO与PU涂层相比在抗坏血酸Asc的存在下,可显著促进内皮细胞的增殖与迁移。综上,聚氨酯/S-亚硝基化角蛋白复合多孔涂层具有良好的生物相容性。
实施例5
使用Griess试剂法间接测定释放的NO。将实施例1制备的同等质量(50mg)的PU/S-亚硝基化角蛋白涂层PET膜片样品分别浸入于PBS(pH7.4)和Asc(250μg/mL)溶液中,置于37℃震荡器中避光,在设定时间点用移液枪取出50uL溶液于96孔板内,依次加入100μLGriess试剂,避光反应15min,每管样品设定三个平行孔,并更换同等体积新鲜PBS溶液和Asc溶液于对应的玻璃瓶内。按照标准曲线测定方法进行测量,并根据NaNO2标准曲线计算出NO产生量。如图4所示,PU/KSNO涂层可在Asc的催化下缓慢稳定的释放一氧化氮,且释放时间可达200h。
对比例1
对比例1采用实施例1的合方法,不同之处在于:二甲亚砜(DMSO)替换成等量的四氢呋喃(THF)。
对比例2
对比例2采用实施例1的合方法,不同之处在于:四氢呋喃(THF)替换成等量的二甲亚砜(DMSO)。
对比例3
对比例3采用实施例1的合方法,不同之处在于:二甲亚砜(DMSO)替换成等量的六氟异丙醇。
对比例4
对比例4采用实施例1的合方法,不同之处在于:四氢呋喃(THF)替换成等量的甲醇或者二氯甲烷。
对比例5
采用实施例1的合方法,不同之处在于:其中THF与DMSO的质量比为6:4。
对比例6
采用实施例1的合方法,不同之处在于:其中THF与DMSO的质量比为1:1。
对比例7
采用实施例1的合方法,不同之处在于:其中THF与DMSO的质量比为1:9。
采用上述对比例1和2均无法形成多孔结构涂层,不利于细胞的粘附、生长与迁移,涂层安全性较差。同时,将四氢呋喃(THF)或者二甲亚砜(DMSO)替换成等量的其他溶剂,也无法形成多孔结构涂层(对比例3-4);而THF与DMSO比例也非常重要,当减少四氢呋喃(THF)的用量时,也无法形成多孔结构涂层(对比例5-7)。本发明采用特定比例的两种混合溶剂(四氢呋喃和二甲亚枫)利用其挥发快慢不同,导致涂层形成尺寸不一的孔,利于细胞在涂层表面的粘附与生长。
对比例8
采用实施例1的合方法,不同之处在于:聚氨酯与S-亚硝基化角蛋白的质量比为6:4。
对比例9
采用实施例1的合方法,不同之处在于:聚氨酯与S-亚硝基化角蛋白的质量比为5:5。
本发明中聚氨酯与S-亚硝基化角蛋白的比例十分重要,保证药物KSNO能够稳定存在于涂层中,且KSNO特定比例的添加一氧化氮释放含量增加,细胞增值效果也更好。此外,虽然KSNO添加可以增加一氧化氮释含量,但是只有本发明特定的比例才能实现一氧化氮释放含量显著增加,对比例8和9中增加S-亚硝基化角蛋白反而会降低一氧化氮含量释放,对比例8和9采用本发明实施例5的方法,其一氧化氮释放时间只能达到100h不到。
Claims (10)
1.一种聚氨酯/S-亚硝基化角蛋白复合多孔涂层的合成方法,其特征在于,包括如下步骤:
(1)将四氢呋喃和二甲基亚砜混合得到溶液A;
(2)将S-亚硝基化角蛋白加入到溶液A中,搅拌均匀至S-亚硝基化角蛋白溶解完全后得反应液B;
(3)向反应液B中加入聚氨酯继续搅拌,得到聚氨酯/S-亚硝基化角蛋白涂层溶液C;
(4)将处理后的基材浸没在聚氨酯/S-亚硝基化角蛋白涂层溶液C中,采用浸涂法风干成膜在基材上形成聚氨酯/S-亚硝基化角蛋白复合多孔涂层。
2.根据权利要求1所述的聚氨酯/S-亚硝基化角蛋白复合多孔涂层的合成方法,其特征在于,步骤(1)所述四氢呋喃和二甲基亚砜的质量比优选为9-7:1-2。
3.根据权利要求1所述的聚氨酯/S-亚硝基化角蛋白复合多孔涂层的合成方法,其特征在于,步骤(2)中加入S-亚硝基化角蛋白时需避光,室温下搅拌10-12h。
4.根据权利要求1所述的聚氨酯/S-亚硝基化角蛋白复合多孔涂层的合成方法,其特征在于,步骤(3)中加入的聚氨酯与S-亚硝基化角蛋白的为质量比优选为9-7:1:3。
5.根据权利要求1所述的聚氨酯/S-亚硝基化角蛋白复合多孔涂层的合成方法,其特征在于,步骤(3)中加入聚氨酯搅拌至溶液呈均一状态。
6.根据权利要求1所述的聚氨酯/S-亚硝基化角蛋白复合多孔涂层的合成方法,其特征在于,步骤(3)中加入聚氨酯后;S-亚硝基化角蛋白和聚氨酯的总质量占整份混合溶液总质量的10-15wt%。
7.根据权利要求1所述的聚氨酯/S-亚硝基化角蛋白复合多孔涂层的合成方法,其特征在于,步骤(4)中基材为PET膜片、玻璃、硅胶管或者不锈钢管材;所述处理方法为先用足量的无水乙醇浸泡,接着在去离子水和无水乙醇中依次超声清洗,最后风干,裁剪为长方形备用。
8.根据权利要求1所述的聚氨酯/S-亚硝基化角蛋白复合多孔涂层的合成方法,其特征在于,步骤(4)中将PET膜片浸泡到聚氨酯/S-亚硝基化角蛋白涂层溶液C中3-5min后取出晾干再次浸泡后取出晾干。
9.一种权利要求1所述的合成方法所合成的聚氨酯/S-亚硝基化角蛋白复合多孔涂层。
10.一种权利要求9所述的聚氨酯/S-亚硝基化角蛋白复合多孔涂层在制备心血管支架、伤口敷料中的应用。
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