CN108815529B - 季铵盐功能化的球型共轭聚合物纳米粒子及其抗菌应用 - Google Patents
季铵盐功能化的球型共轭聚合物纳米粒子及其抗菌应用 Download PDFInfo
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Abstract
Description
技术领域
本发明属于纳米粒子抗菌技术领域,具体涉及一类新型的共轭聚合物纳米粒子,以及该纳米粒子作为抗菌材料的应用。
背景技术
随着近年来耐药型细菌的出现,发展不受细菌抗性影响并具有高效抗菌性能的新型抗菌剂以及抗菌方法具有重大意义。纳米抗菌材料由于尺寸小、比表面积大等优势大大提高了抗菌活性。而且和传统的抗菌剂相比,纳米抗菌材料具有不易产生耐药性、可持久抗菌和广谱抗菌等优点。目前常见抗菌纳米材料虽然抗菌性能好,但大多需要光催化并且对哺乳动物细胞具有生物毒性,尤其是重金属纳米粒子,因此限制了它们在生物医学方面的应用。
共轭聚合物纳米粒子(CPNs)是近年来发展迅速的新型纳米材料,基于共轭聚合物制备得到的纳米粒子普遍具有明亮的荧光、胶体稳定性好、生物相容性高以及细胞毒性低等优点,因此被广泛应用于生物成像、诊断、治疗等方面。
发明内容
本发明所要解决的技术问题在于提供一种新型的季铵盐功能化的球型共轭聚合物纳米粒子,以及该共轭聚合物纳米粒子在抗菌方面的应用。
解决上述技术问题所采用的季铵盐功能化的球型共轭聚合物纳米粒子是将疏水性共轭聚合物和季铵盐功能团分子通过疏水作用形成的以疏水性共轭聚合物为内核、季铵盐功能团分子为外壳的纳米球。
上述疏水性共轭聚合物的结构式如下所示:
其中R选自C1~C20烷基、中任意一种,m为1~19的整数,X1代表Br或I,n代表聚合度;该疏水性共轭聚合物的数均分子量为10000~50000,制备方法为:将式I化合物与式II化合物、醋酸钯按摩尔比为1:1:0.036加入二甲基甲酰胺和三乙胺的混合溶剂中,在100℃下反应4小时,分离纯化产物,得到疏水性共轭聚合物。
上述季铵盐功能团分子的结构式如下所示:
式中X代表Cl或Br,p为3、4、6、8、9、10、12、14、16或18。
本发明共轭聚合物纳米粒子的制备方法为:该纳米粒子是将疏水性共轭聚合物与季铵盐功能团分子在超声冰浴条件下均匀分散于四氢呋喃中,所得溶液快速注入去离子水中,继续超声10~20分钟,然后除去四氢呋喃和部分去离子水,即得球型共轭聚合物纳米粒子。
上述制备方法中,所述疏水性共轭聚合物与季铵盐功能团分子的摩尔比为1:1~5,加入的四氢呋喃与去离子水的体积比为1:1~3。
本发明共轭聚合物纳米粒子作为抗菌材料的用途,所述的菌为大肠杆菌、金黄色葡萄球菌等。
本发明共轭聚合物纳米粒子以疏水性共轭聚合物作为内核,带季铵基团的阳离子表面活性剂通过疏水作用在表面形成外壳,最终得到球型的共轭聚合物纳米粒子。本发明通过控制疏水性共轭聚合物和季铵盐功能团分子的摩尔比、水相和四氢呋喃的体积比以及疏水性共轭聚合物和季铵盐功能团分子在体系中的浓度,调控生成的纳米粒子的粒径。本发明纳米粒子在避光条件下,无需光源或其他能量即可实现广谱高效抗菌,其抗菌率远远高于相同浓度季铵盐功能团分子的抗菌率,并不易产生耐药性,为未来抗菌纳米材料的开发提供了新的思路。
附图说明
图1是实施例1制备的共轭聚合物纳米粒子的透射电镜图。
图2是避光条件下实施例1制备的共轭聚合物纳米粒子对大肠杆菌的杀菌活性。
图3是避光条件下实施例1制备的共轭聚合物纳米粒子对金黄色葡萄球菌的杀菌活性。
具体实施方式
下面结合附图和实施例对本发明进一步详细说明,但本发明的保护范围不仅限于这些实施例。
实施例1
在超声冰浴条件下,将0.1mg疏水性共轭聚合物c-1与0.1mg十六烷基三甲基溴化铵加入5mL四氢呋喃中,超声分散均匀,将所得混合溶液快速倒入装有15mL二次水的烧瓶中,轻摇使其混匀,继续超声15分钟。超声完成后,恢复至室温,分别用针头鼓氮气在室温条件下除去混合溶液中的四氢呋喃、在加热条件下除去部分去离子水,使溶液浓缩至5mL,得到共轭聚合物纳米粒子。由图1可见,所得纳米粒子的粒径为为50nm左右。
上述疏水性共轭聚合物c-1的合成路线和合成方法如下:
1、向50mL圆底烧瓶中加入7.2mL(50mmol)1-溴己烷、0.33g(1mmol)溴化四丁基铵、20mL质量分数为50%的KOH水溶液,除氧30分钟后,将反应混合物升温至75℃,加入1.62g(5mmol)2,7-二溴芴,继续75℃回流15分钟。反应混合液经萃取、干燥和浓缩后柱层析分离,得到化合物a-1。
2、向25mL圆底烧瓶中加入738.5mg(1.5mmol)化合物a-1、10mL甲苯,除氧30分钟后依次加入1.43mL(4.5mmol)三丁基乙烯基锡、2mg(0.0095mmol)2,6-二叔丁基酚和47.4mg(0.0675mmol)双(三苯基膦)氯化钯,反应混合物在100℃回流7小时,冷却至室温,加入10mL质量分数为10%的KF水溶液搅拌过夜,除去固体残留物后经萃取、干燥和浓缩后柱层析分离,得到化合物b-1。
3、向25mL圆底烧瓶中加入96.7mg(0.25mmol)化合物b-1、1.67mL二甲基甲酰胺、0.83mL三乙胺,除氧30min后依次加入73.5mg(0.25mmol)4,7-二溴-2,1,3-苯并噻二唑、2mg(0.009mmol)醋酸钯、15mg(0.049mmol)磷酸三对甲苯基酯,反应混合物在100℃回流4小时后经萃取、干燥、浓缩后离心沉淀,得到疏水性共轭聚合物c-1。经凝胶渗透色谱检测,疏水性共轭聚合物c-1的Mn=44810,Mw=47827,PDI=1.07。
实施例2
在超声冰浴条件下,将0.1mg疏水性共轭聚合物c-2与0.1mg十六烷基三甲基溴化铵加入5mL四氢呋喃中,超声分散均匀,将所得混合溶液快速倒入装有15mL二次水的烧瓶中,轻摇使其混匀,继续超声15分钟。超声完成后,恢复至室温,分别用针头鼓氮气在室温条件下除去混合溶液中的四氢呋喃、在加热条件下除去部分去离子水,使溶液浓缩至5mL,得到共轭聚合物纳米粒子。
上述疏水性共轭聚合物c-2的合成路线和合成方法如下:
其合成方法中,只需用等摩尔1,6-二溴己烷替换实施1中的1-溴己烷,替他步骤与c-1的合成方法相同,得到疏水性共轭聚合物c-2。经凝胶渗透色谱检测,疏水性共轭聚合物c-2的Mn=13958,Mw=15078,PDI=1.08。
实施例3
在超声冰浴条件下,将0.1mg疏水性共轭聚合物e-3与0.1mg十六烷基三甲基溴化铵加入5mL四氢呋喃中,超声分散均匀,将所得混合溶液快速倒入装有15mL二次水的烧瓶中,轻摇使其混匀,继续超声15分钟。超声完成后,恢复至室温,分别用针头鼓氮气在室温条件下除去混合溶液中的四氢呋喃、在加热条件下除去部分去离子水,使溶液浓缩至5mL,得到共轭聚合物纳米粒子。
上述疏水性共轭聚合物e-3的合成路线和合成方法如下:
1、向100mL圆底烧瓶中加入6mL(75mmol)三乙二醇单甲醚、10mL CH2Cl2,并在冰浴下加入2.07mL(15mmol)三乙胺,将1.42g(7.5mmol)对甲基苯磺酰氯溶于10mL CH2Cl2中并滴加入上述溶液中常温反应过夜后,经萃取、干燥和浓缩后柱层析分离,得到化合物a-3。
2、向100mL圆底烧瓶加入30mL无水丙酮、1.27g(4mmol)化合物a-3,1.4g(16mmol)LiBr,混合溶液升温至85℃,回流反应过夜后,冷却至室温,经萃取、干燥和浓缩后柱层析分离,得到化合物b-3。
3、向50mL圆底烧瓶中加入0.4g(1.76mmol)化合物b-3,0.23g(0.71mmol)2,7-二溴芴、0.02g(0.06mmol)溴化四丁基铵、2mL DMSO、0.56mL质量分数为50%的KOH水溶液,升温至100℃,回流反应过夜后,冷却至室温,经萃取、干燥和浓缩后柱层析分离,得到化合物c-3。
4、向25mL圆底烧瓶中加入924.6mg(1.5mmol)化合物c-3、10mL甲苯,除氧30分钟后依次加入1.43mL(4.5mmol)三丁基乙烯基锡、2mg(0.0095mmol)2,6-二叔丁基酚和47.4mg(0.0675mmol)双(三苯基膦)氯化钯,反应混合物在100℃回流7小时,冷却至室温,加入10mL质量分数为10%的KF水溶液搅拌过夜,除去固体残留物后经萃取、干燥和浓缩后柱层析分离,得到化合物d-3。
5、向25mL圆底烧瓶中加入127.7mg(0.25mmol)化合物d-3、1.67mL二甲基甲酰胺、0.83mL三乙胺,除氧30min后依次加入73.5mg(0.25mmol)4,7-二溴-2,1,3-苯并噻二唑、2mg(0.009mmol)醋酸钯、15mg(0.049mmol)磷酸三对甲苯基酯,反应混合物在100℃回流4小时后经萃取、干燥、浓缩后离心沉淀,得到共轭聚合物e-3。经凝胶渗透色谱检测,疏水性共轭聚合物e-3的Mn=16589,Mw=23420,PDI=1.41。
实施例4
实施例1制备的共轭聚合物纳米粒子作为抗菌材料的应用
将保存在零下80℃的金黄色葡萄球菌和大肠杆菌以划线法分别转移至TSB琼脂板和LB琼脂平板上,置于37℃的隔水式培养箱中孵育过夜进行第一代活化。挑取琼脂板上的单菌落置于25mL培养基中,放入37℃的摇床中孵育约12小时至其对数生长期。通过离心收集对数生长期的细菌,再用0.9%NaCl溶液洗涤两次,除去上清液,最后加入0.9%NaCl溶液,得到细菌悬浮液。
将共轭聚合物纳米粒子(最终浓度分别为0、0.2、0.5、0.8、1.0、1.5、2.0μg/mL)和细菌悬浮液(终浓度为2×107cfu/mL)混匀后,置于避光环境中分别孵育30分钟和60分钟。孵育完成后,用SYTO 9/PI混合染料染色处理,用流式细胞仪检测细菌的存活率。取样量为100000个信号,信号收集选择FL1(530±15nm)通道收集绿色荧光信号,FL2(585±20nm)通道收集红色荧光信号。同时每个处理做空白对照实验以及相同浓度的十六烷基三甲基溴化铵(CTAB)的抗菌实验。抑菌率结果见图2和图3。
由图2可见,在避光条件下,大肠杆菌与共轭聚合物纳米粒子孵育30分钟和60分钟的抗菌效果几乎一致,说明纳米粒子在30分钟内已经完成与细菌结合并破坏细菌膜的全过程,并且抗菌活性与纳米粒子的浓度呈正相关,当纳米粒子的浓度为0.8μg/mL时,细菌的死亡率达到91%。
由图3可见,共轭聚合物纳米粒子对金黄色葡萄球菌的抗菌过程也能在30分钟内完成,抗菌活性的变化趋势与抗大肠杆菌基本一致,由于革兰氏阳性菌在结构上其细胞壁的强度比革兰氏阴性菌坚韧,但在避光条件下1.0μg/mL的纳米粒子孵育30分钟也可使抗菌率达到96%。并且从图中我们还可以看出0至1.0μg/mL CTAB几乎没有抗菌活性,而此浓度下纳米粒子的抗菌率可以超过90%,说明共轭聚合物纳米粒子的抗菌性能并不是来源于CTAB而是通过与共轭聚合物形成纳米粒子共同作用实现的。这些实验结果表明本发明共轭聚合物纳米粒子在避光条件下具有高效的广谱抗菌活性。
Claims (5)
1.一种季铵盐功能化的球型共轭聚合物纳米粒子,其特征在于:该纳米粒子是将疏水性共轭聚合物和季铵盐功能团分子通过疏水作用形成的以疏水性共轭聚合物为内核、季铵盐功能团分子为外壳的纳米球;
上述疏水性共轭聚合物的结构式如下所示:
上述季铵盐功能团分子的结构式如下所示:
式中X代表Cl或Br,p为3、4、6、8、9、10、12、14、16或18;
该纳米粒子是将疏水性共轭聚合物与季铵盐功能团分子在超声冰浴条件下均匀分散于四氢呋喃中,所得溶液快速注入去离子水中,继续超声10~20分钟,然后除去四氢呋喃和部分去离子水,即得球型共轭聚合物纳米粒子。
2.根据权利要求1所述的季铵盐功能化的球型共轭聚合物纳米粒子,其特征在于:所述疏水性共轭聚合物与季铵盐功能团分子的摩尔比为1:1~5。
3.根据权利要求1所述的季铵盐功能化的球型共轭聚合物纳米粒子,其特征在于:加入的四氢呋喃与去离子水的体积比为1:1~3。
4.权利要求1所述的季铵盐功能化的球型共轭聚合物纳米粒子作为抗菌材料的用途。
5.根据权利要求4所述的季铵盐功能化的球型共轭聚合物纳米粒子作为抗菌材料的用途,其特征在于:所述的菌为大肠杆菌或金黄色葡萄球菌。
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