功能化纳米纤维素的设计、构建及其在药物缓控释中的应用研究
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摘要
纳米纤维素（Cellulose nanocrystals, CNCs）具有生物活性、生物相容性、生物可降解性和低毒性等优异性能，是一种理想的新型药物载体。针对目前纳米纤维素制备条件繁杂、环境不友好、结晶度低，及其功能化修饰步骤多和收率低等问题，本论文对功能化纳米纤维素的设计、构建及其在药物缓控释中的应用进行了研究。采用绿色环保的离子交换树脂催化水解法制备了纳米纤维素；研究利用机械力化学作用的机械力、热力和化学力的协同效应作用下，一方面，基于“一锅法反应”原理，在无有机溶剂条件下，不经中间体的分离，开发定向合成马来酸酐酯化纳米纤维素（MA-CNCs）的新路线，为高效、绿色功能化修饰纳米纤维素提供了新思路；另一方面基于Fischer酯化反应原理，控制价键形成的化学选择性，使纤维素降解与酯化反应同步进行，为研制纤维素功能材料提供了科学基础。在此基础上，进一步设计研发了基于功能化纳米纤维素的药物载体，分析了其作为结肠靶向给药和口腔黏附缓释膜类药物载体的可行性。论文具体开展的主要结论及创新点如下：
1．采用离子交换树脂催化水解法制得尺寸较均一的棒状纳米纤维素，这种方法操作方便、过程绿色低碳环保，且CNCs结晶度高（84.26%）。在超声波辅助作用下，基于Fischer酯化反应原理，使纤维素水解与酯化反应同步进行，制得乙酸酯化纳米纤维素（Esterified cellulose nanocrystals, E-CNCs）。研究发现超声波处理对纤维素的降解和酯化反应起着重要作用，XRD和NMR结果表明在实验条件下，酯化反应主要发生于无定形区，而对纤维素晶区结构破坏较小，E-CNCs取代度为0.47时，结晶度仍能达到80.16%。
2．基于“一锅法”（one-pot）反应机理，在无有机溶剂下，使纤维素在机械力、热力与化学力的协同作用下，不经中间体的分离，直接获得马来酸酐酯化修饰纳米纤维素（Maleic anhydride functionalized cellulose nanocrystals, MA-CNCs）。通过改变球磨时间、超声波温度和超声时间研究了反应体系中球磨和超声处理所引起的机械力化学效应对产物得率和取代度的影响，阐明了其中的内在机理。反应过程中无有机溶剂使用、反应条件温和、MA-CNCs得率高和结晶度高等结果表明，将这两种机械力化学技术联合使用，可以高效、绿色地实现纤维素的纳米化与功能化修饰。通过对CNCs、E-CNCs和MA-CNCs的流变行为进行研究，发现这三者均为假塑性流体，并且在较高浓度、温度，以及强酸、强碱条件下分散系黏度较大。
3．为了将纳米纤维素用于靶向药物载体，且具有荧光探测性，论文设计与研发了L-亮氨酸修饰接枝纳米纤维素（A-CNCs）的方法，通过将其与荧光素通过共价结合研制了荧光标记物（F-A-CNCs），研究了荧光素修饰接枝纳米纤维素的方法。采用傅里叶变换红外光谱（FTIR）、核磁共振波谱仪（NMR）、X射线光电子能谱仪（XPS）、荧光分光光度计和共聚焦激光扫描显微镜（CLSM）等表征技术验证了氨基酸和荧光素在CNCs表面的成功修饰接枝，且具有较好的光响应特性，同时研究探讨了氨基酸和荧光素在CNCs表面修饰接枝的机理。
4．基于纳米纤维素优异的生物理化特性，以MA-CNCs为载体，通过酯化反应引入氨基酸间隔臂，再与妥舒沙星（TFLX）偶联得到TFLX-A-MA-CNCs药物轭合物。为判断药物轭合物的成功构建以及观察靶向释药过程，进一步设计合成了具有荧光性的F-TFLX-A-MA-CNCs前药。对TFLX-A-MA-CNCs药物轭合物在模拟胃液、小肠液和结肠液中的释药行为，以及荧光标记前药在这三种介质中的荧光变化机制进行分析与研究。研究表明MA-CNCs载体对药物具有良好的包载性，且可实现结肠靶向释药。
5．采用天然树脂紫胶作为背衬层，以不同配比的E-CNCs、紫胶和PEG复合膜作为药物载体，研制备了基于E-CNCs载体的口腔黏附缓释膜。研发了纳米纤维素与天然树脂复合的方法。研究结果表明E-CNCs作为口腔黏附膜载体，可以较好地包覆药物，同时在口腔粘膜中具有良好的黏附性，缓释效果明显，作为缓释药物载体材料时具有明显的优势。
As an ideal drug carrier, cellulose nanocrystals (CNCs) are interesting nanoscalebiomacromolecular building blocks due to their biological activity, biocompatibility,biodegradability and low toxicity. Much work has been considered as an ideal drug carriers.An extensive number of works have been devoted to isolation and modification of cellulosenanocrystals, but these methods have drawbacks such as harsh conditions,environmentally-unfriendly, low crystallinity, multiple reaction steps and low yield. Toovercome these boundaries, the design and construction of functionalized cellulosenanocrystals and their applications in controlled drug release were studied in this dissertation.The cellulose nanocrystals were manufactured by exchange resin-catalyzed hydrolysis in anenvironmentally-friendly way. To utilize the mechanical, chemical and thermal effects ofmechanochemistry, we developed two approaches to manufacture functionalized CNCs. Asimple and environmentally benign approach was developed for manufacturing maleicanhydride functionalized cellulose nanocrystals (MA-CNCs) via one-pot tandem reactionsunder solvent-free conditions. On the other hand, by utilizing of the mechanism of Fischeresterification, the acetic acid esterified cellulose nanocrystals (E-CNCs) were manufactured insynchronous reaction in which the degradation and esterification of cellulose took placealmost simultaneously. This work will provide a new route to design functionalized CNCs. Inaddition, the functionalized CNCs drug carriers were designed and their feasibility on colonicdrug delivery and mucoadhesive buccal films drug delivery systems were evaluated. The mainachievements and innovative points obtained in this dissertation are as follows.
1. Exchange resin-catalyzed hydrolysis of cellulose can be an excellent method formanufacturing of cellulose nanocrystals (CNCs) in a simple and environmentally-friendlyway. The regular short rod-like CNCs with a high crystallinity of84.26%was obtained byexchange resin hydrolysis. The esterified cellulose nanocrystals (E-CNCs) were prepared withthe aid of ultrasonication in synchronous reaction, in which the degradation of cellulose pulpand esterification took place simultaneously. The results show ultrasonication treatment iseffective in the degradation of cellulose amorphous regions and esterification of hydroxylgroups. As the crystalline structures of E-CNCs by XRD and NMR revealed the degree ofsubstitute (DS) reaches0.47and E-CNCs still have high crystallinity of80.16%, indicatingthe maintenance of crystalline region of cellulose.
2. We disclose a simple and versatile method to manufacture maleated cellulose nanocrystals (MA-CNCs) by conjunction of ball milling and ultrasonication in tandem mode,in which the nanocrystallization and maleation of cellulose take place simultaneously undersolvent-free conditions. In order to investigate the mechanochemical effects induced by ballmilling and ultrasonication on the yields and DS, some factors, such as the ball-milling time,ultrasonication temperature and ultrasonication time, were taken into consideration. The highyield and crystallinity, solvent-free conditions, as well as relative mild conditions make thisprocess a valuable and environmentally friendly alternative to the currently available methodsfor the preparation of functionalized cellulose nanocrystals in industry. The rheologicalbehaviors of CNCs, E-CNCs and MA-CNCs dispersions were tested. The results show that alldispersions are pseudoplastic fluid. The viscosity can be influenced by the concentration,temperature, pH values and the salt concentration.
3. For the potential practical applications as drug delivery carriers for the fluorescentdetection of the drug release process, the amino modified cellulose nanocrystals (A-CNCs)and fluorescent labled nanoparticles (F-A-CNCs) were designed and constructed. Thesuccessful modifications of CNCs and photo responsive of F-A-CNCs were detected by FTIR,NMR, XPS, fluorescence spectrophotometer and CLSM. The functional mechanism of aminoand fluorescent modification of CNCs was explored.
4. With exquisite biological physical and chemical properties of CNCs, a novel prodrugwas prepared by the covalent attachment of the tosufloxacin tosylate (TFLX) onto the surfaceof MA-CNCs with L-leucine as a spacer. The fluorescent labeled prodrug(F-TFLX-A-MA-CNCs) was designed for monitoring the process of drug release. The releasebehaviors of TFLX-A-MA-CNCs and F-TFLX-A-MA-CNCs in simulated gastric fluid (SGF),simulated intestinal fluid (SIF) and simulated colonic fluid (SCF) were investigated. Therelationship between the accumulative drug release and the fluorescence responsive has beenevaluated. The results show that the drug was efficiently entrapped by MA-CNCs carrier andpresents excellent behavior for colon specificity and may be considered as a potential materialfor a colon-specific drug delivery system.
5. The new mucoadhesive films for topical administration in the oral cavity have beendeveloped, using a natural resin shellac as backing layer for preventing liquid permeation. TheE-CNCs, PEG and shellac composites were used as the drug carrier. The films were evaluated for their weight, thickness, swelling, drug content uniformity, mechanical property, vitro drugrelease and mucoadhesive properties. The films exhibit good swelling, mucoadhesiveproperties and promising controlled drug release, thus it can be selected to develop the buccalfilm for effective therapeutic uses. E-CNCs may be considered as a potential candidate for themucoadhesive film drug carrier.
1．采用离子交换树脂催化水解法制得尺寸较均一的棒状纳米纤维素，这种方法操作方便、过程绿色低碳环保，且CNCs结晶度高（84.26%）。在超声波辅助作用下，基于Fischer酯化反应原理，使纤维素水解与酯化反应同步进行，制得乙酸酯化纳米纤维素（Esterified cellulose nanocrystals, E-CNCs）。研究发现超声波处理对纤维素的降解和酯化反应起着重要作用，XRD和NMR结果表明在实验条件下，酯化反应主要发生于无定形区，而对纤维素晶区结构破坏较小，E-CNCs取代度为0.47时，结晶度仍能达到80.16%。
2．基于“一锅法”（one-pot）反应机理，在无有机溶剂下，使纤维素在机械力、热力与化学力的协同作用下，不经中间体的分离，直接获得马来酸酐酯化修饰纳米纤维素（Maleic anhydride functionalized cellulose nanocrystals, MA-CNCs）。通过改变球磨时间、超声波温度和超声时间研究了反应体系中球磨和超声处理所引起的机械力化学效应对产物得率和取代度的影响，阐明了其中的内在机理。反应过程中无有机溶剂使用、反应条件温和、MA-CNCs得率高和结晶度高等结果表明，将这两种机械力化学技术联合使用，可以高效、绿色地实现纤维素的纳米化与功能化修饰。通过对CNCs、E-CNCs和MA-CNCs的流变行为进行研究，发现这三者均为假塑性流体，并且在较高浓度、温度，以及强酸、强碱条件下分散系黏度较大。
3．为了将纳米纤维素用于靶向药物载体，且具有荧光探测性，论文设计与研发了L-亮氨酸修饰接枝纳米纤维素（A-CNCs）的方法，通过将其与荧光素通过共价结合研制了荧光标记物（F-A-CNCs），研究了荧光素修饰接枝纳米纤维素的方法。采用傅里叶变换红外光谱（FTIR）、核磁共振波谱仪（NMR）、X射线光电子能谱仪（XPS）、荧光分光光度计和共聚焦激光扫描显微镜（CLSM）等表征技术验证了氨基酸和荧光素在CNCs表面的成功修饰接枝，且具有较好的光响应特性，同时研究探讨了氨基酸和荧光素在CNCs表面修饰接枝的机理。
4．基于纳米纤维素优异的生物理化特性，以MA-CNCs为载体，通过酯化反应引入氨基酸间隔臂，再与妥舒沙星（TFLX）偶联得到TFLX-A-MA-CNCs药物轭合物。为判断药物轭合物的成功构建以及观察靶向释药过程，进一步设计合成了具有荧光性的F-TFLX-A-MA-CNCs前药。对TFLX-A-MA-CNCs药物轭合物在模拟胃液、小肠液和结肠液中的释药行为，以及荧光标记前药在这三种介质中的荧光变化机制进行分析与研究。研究表明MA-CNCs载体对药物具有良好的包载性，且可实现结肠靶向释药。
5．采用天然树脂紫胶作为背衬层，以不同配比的E-CNCs、紫胶和PEG复合膜作为药物载体，研制备了基于E-CNCs载体的口腔黏附缓释膜。研发了纳米纤维素与天然树脂复合的方法。研究结果表明E-CNCs作为口腔黏附膜载体，可以较好地包覆药物，同时在口腔粘膜中具有良好的黏附性，缓释效果明显，作为缓释药物载体材料时具有明显的优势。
As an ideal drug carrier, cellulose nanocrystals (CNCs) are interesting nanoscalebiomacromolecular building blocks due to their biological activity, biocompatibility,biodegradability and low toxicity. Much work has been considered as an ideal drug carriers.An extensive number of works have been devoted to isolation and modification of cellulosenanocrystals, but these methods have drawbacks such as harsh conditions,environmentally-unfriendly, low crystallinity, multiple reaction steps and low yield. Toovercome these boundaries, the design and construction of functionalized cellulosenanocrystals and their applications in controlled drug release were studied in this dissertation.The cellulose nanocrystals were manufactured by exchange resin-catalyzed hydrolysis in anenvironmentally-friendly way. To utilize the mechanical, chemical and thermal effects ofmechanochemistry, we developed two approaches to manufacture functionalized CNCs. Asimple and environmentally benign approach was developed for manufacturing maleicanhydride functionalized cellulose nanocrystals (MA-CNCs) via one-pot tandem reactionsunder solvent-free conditions. On the other hand, by utilizing of the mechanism of Fischeresterification, the acetic acid esterified cellulose nanocrystals (E-CNCs) were manufactured insynchronous reaction in which the degradation and esterification of cellulose took placealmost simultaneously. This work will provide a new route to design functionalized CNCs. Inaddition, the functionalized CNCs drug carriers were designed and their feasibility on colonicdrug delivery and mucoadhesive buccal films drug delivery systems were evaluated. The mainachievements and innovative points obtained in this dissertation are as follows.
1. Exchange resin-catalyzed hydrolysis of cellulose can be an excellent method formanufacturing of cellulose nanocrystals (CNCs) in a simple and environmentally-friendlyway. The regular short rod-like CNCs with a high crystallinity of84.26%was obtained byexchange resin hydrolysis. The esterified cellulose nanocrystals (E-CNCs) were prepared withthe aid of ultrasonication in synchronous reaction, in which the degradation of cellulose pulpand esterification took place simultaneously. The results show ultrasonication treatment iseffective in the degradation of cellulose amorphous regions and esterification of hydroxylgroups. As the crystalline structures of E-CNCs by XRD and NMR revealed the degree ofsubstitute (DS) reaches0.47and E-CNCs still have high crystallinity of80.16%, indicatingthe maintenance of crystalline region of cellulose.
2. We disclose a simple and versatile method to manufacture maleated cellulose nanocrystals (MA-CNCs) by conjunction of ball milling and ultrasonication in tandem mode,in which the nanocrystallization and maleation of cellulose take place simultaneously undersolvent-free conditions. In order to investigate the mechanochemical effects induced by ballmilling and ultrasonication on the yields and DS, some factors, such as the ball-milling time,ultrasonication temperature and ultrasonication time, were taken into consideration. The highyield and crystallinity, solvent-free conditions, as well as relative mild conditions make thisprocess a valuable and environmentally friendly alternative to the currently available methodsfor the preparation of functionalized cellulose nanocrystals in industry. The rheologicalbehaviors of CNCs, E-CNCs and MA-CNCs dispersions were tested. The results show that alldispersions are pseudoplastic fluid. The viscosity can be influenced by the concentration,temperature, pH values and the salt concentration.
3. For the potential practical applications as drug delivery carriers for the fluorescentdetection of the drug release process, the amino modified cellulose nanocrystals (A-CNCs)and fluorescent labled nanoparticles (F-A-CNCs) were designed and constructed. Thesuccessful modifications of CNCs and photo responsive of F-A-CNCs were detected by FTIR,NMR, XPS, fluorescence spectrophotometer and CLSM. The functional mechanism of aminoand fluorescent modification of CNCs was explored.
4. With exquisite biological physical and chemical properties of CNCs, a novel prodrugwas prepared by the covalent attachment of the tosufloxacin tosylate (TFLX) onto the surfaceof MA-CNCs with L-leucine as a spacer. The fluorescent labeled prodrug(F-TFLX-A-MA-CNCs) was designed for monitoring the process of drug release. The releasebehaviors of TFLX-A-MA-CNCs and F-TFLX-A-MA-CNCs in simulated gastric fluid (SGF),simulated intestinal fluid (SIF) and simulated colonic fluid (SCF) were investigated. Therelationship between the accumulative drug release and the fluorescence responsive has beenevaluated. The results show that the drug was efficiently entrapped by MA-CNCs carrier andpresents excellent behavior for colon specificity and may be considered as a potential materialfor a colon-specific drug delivery system.
5. The new mucoadhesive films for topical administration in the oral cavity have beendeveloped, using a natural resin shellac as backing layer for preventing liquid permeation. TheE-CNCs, PEG and shellac composites were used as the drug carrier. The films were evaluated for their weight, thickness, swelling, drug content uniformity, mechanical property, vitro drugrelease and mucoadhesive properties. The films exhibit good swelling, mucoadhesiveproperties and promising controlled drug release, thus it can be selected to develop the buccalfilm for effective therapeutic uses. E-CNCs may be considered as a potential candidate for themucoadhesive film drug carrier.
引文
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