两亲性纤维素及其自组装纳米胶束的制备与应用研究
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摘要
聚合物胶束在药物传递等领域具有重要的应用前景，然而，基于合成类聚合物纳米胶束存在成本高、潜在生物毒性等缺点。因此，发展基于天然材料的两亲性聚合物成为研究热点，但是由于纤维素的难溶解性，导致迄今为止基于纤维素的两亲性聚合物研究非常有限。本论文以纤维素的高值化转化利用为出发点，重点研究纤维素的两亲性改性与其自组装胶束的制备，并初步探讨了两亲性纤维素基纳米胶束在药物传递、生物成像以及传感等新兴高科技领域的应用，为发展绿色廉价的天然高分子聚合物胶束，实现生物质资源的高值化应用开辟新途径。本论文主要在如下几个方面开展创新性研究工作：
1．在离子液体绿色溶剂反应介质中，分别以具有优良生物可降解性和生物相容性的聚乳酸、聚己内酯和聚对二氧环己酮作为侧链，对纤维素及其水溶性衍生物进行疏水化改性，制得三大类新型纤维素基两亲性聚合物衍生物。制备的纤维素基两亲性共聚物在水溶液中可自组装形成壳核结构的纳米胶束。通过调节衍生物中疏水基团的取代度可以有效控制其自组装行为和纳米胶束的粒径大小。MTT研究显示，此三类纤维素基两亲性聚合物对细胞无明显生物毒性。
2．在DMSO体系中，羟乙基纤维素与高级脂肪酸经CDI活化催化后，室温下即可发生酯化反应。改性后的衍生物具有良好的自组装性能，临界胶束浓度低至0.0019mg/mL和0.0016mg/mL，具有很强的抗稀释稳定性。此类纳米胶束可高效负载疏水性抗氧化剂β-胡萝卜素，并表现出良好的缓释效果，有望在化妆品辅料或功能食品领域获得应用。
3．采用长碳链酰氯对纤维素分子链直接进行疏水酯化改性，制得一系列具备不同碳链长度的纤维素疏水化衍生物。此类衍生物在水溶液中自组装形成单分散球形纳米粒子，且纳米粒子的粒径可通过改变疏水碳链长度进行调控。此外，通过HEC与溴代十二烷之间的醚化反应，合成了HEC的疏水改性衍生物，其可在水溶液中自组装形成20～30nm球形胶束。
4．纤维素基纳米胶束包载毒性大、不溶解、生物利用率低的抗癌药物紫杉醇（PTX），具有高包埋效率（>90%）和良好的缓释效果，深入探讨纤维素基纳米胶束与药物传递之间的“构-效关系”。体外细胞实验结果表明，负载PTX的纳米胶束对肿瘤细胞Hepg2和Hela具有与商业化产品Taxol相近的抗肿瘤活性。而且，负载PTX纳米胶束的抗肿瘤活性随作用时间延长而明显增强，具有延长的治疗效果。细胞流式和DAPI染色结果表明纳米胶束中的PTX主要通过细胞凋亡作用来抑制肿瘤细胞生长。
5．利用纤维素基纳米胶束包载共轭聚合物荧光染料和量子点，制备新型纤维素基高效荧光纳米材料，并考察其在生物成像领域的应用。实验发现，纤维素基纳米胶束可高效包载疏水性荧光染料和量子点，包载后染料未出现明显的荧光猝灭现象，荧光纳米胶束于室温下可稳定保存一周以上。荧光纳米胶束对小鼠干细胞无明显生物毒性，且可通过吞噬作用进入细胞内部，成功实现疏水性荧光染料于水相体系中的细胞成像。
6．成功实现了纤维素基纳米胶束对商业化疏水性荧光共轭聚合物9,9-二辛基聚芴（PFO）的高效包载，为普通疏水性荧光共轭聚合物的水相应用开辟了一条新的途径。包载PFO的纤维素基荧光纳米胶束对水相中痕量硝基苯类爆炸物（DNT、苦味酸等）具有优异的荧光传感检测性能，传感系数比相同染料在有机相中的传感系数增强50～200倍。该现象的发现对于开发新型纳米胶束传感器和拓展荧光共轭聚合物的应用具有非常重要的意义。
The polymeric micelles, which are commonly composed by synthetic block amphiphliccopolymers, have been established great potential application in the field of drug or genedelivery. However, the large-scale application of many synthetic block copolymers is limitedby their high prices and potential biotoxicity. Therefore, there has been a growing interest indeveloping amphihilic copolymers from natural polysaccharies. It’s well known that celluloseis one of the most abundant natural polysaccharides in the world. However, thecellulose-based amphiphilic derivatives have not been efficiently exploited due to itsinsolubility in water and common organic solvents. In respond to the need of efficientlyconversing cellulose to value-added products, this thesis is mainly focused on the design andpreparation of amphiphilic cellulose polymers and their self-assembled nanomicelles.Additionally, the potential application of cellulose-based nanomicelles in the fields of drugdelivery, bioimaging and sensing was also investigated. This work would not only develop thegreen and cheap micelle-forming materials from natural resources, but also offer analternative way for the value-added conversion of agricultural and forest waste biomass. Aseries of innovative researches were carried out as follows:
1. The amphiphilic cellulose copolymers with excellent biodegradable and biocompatibleproperties were homogeneously prepared in the green solvent of ionic liquids. Three kinds ofhydrophobic aliphatic polyesters, polylactide (PLA), polycaprolactone (PCL) andpolydioxanone (PPDO) were grafted onto the backbone of cellulose and cellulose’swater-soluble derivatives through the ring opening polymerization, respectively. It was foundthat the cellulose-based amphiphilic copolymers could self-assemble into core-shell structuredmicelles in aqueous water. The hydrophobic core was formed by the biodegradable sidechains such as PLA, PCL and PPDO, while the outer shells were formed by the main-chain ofcellulose. The self-assembly behavior of these amphiphilic cellulose derivatives in aqueouswater was found to be affected by their molecular structure, especailly the degree ofsubstitution of hydrophobic groups. The MTT assay showed that these amphphilic cellulosemicelles were safe to be applied in biological system.
2. Through activation of carbonyldiimidazole, the acylation between hydroxyethylcellulose and long-chain fatty acid were successfully carried out in the solvent of DMSO atroom temperature. The obtained derivatives have excellent self-assembly behavior and theircritical micelle concentrations were as low as0.0019mg/mL and0.0016mg/mL, respectively, indicating that these kinds of micelles have good anti-dilution stability. It was also found thatthe cellulose-based micelles could efficiently encapsulate the hydrophobic functional moietiesof β-carotene and make them slowly released in the aqueous medium, which means thenanocarriers may be used as cosmetics or food additives.
3. A series of cellulose-based hydrophobic associating polymers with different DS valuesand chain lengths were successfully prepared by homogeneous acylation of microcrystallinecellulose with long-chain acyl chloride. It was found that these cellulose derivatives couldself-assemble into monodispersed nanoparticles with spherical shapes in aqueous solution andtheir diameters can be controlled by adjusting the chain length of hydrophobic groups.Additionally, the hydrophobic modified hydroxyethyl cellulose derivatives (HMHEC) wereeasily synthesized by introducing hydrophobic moieties (long-chain alkyl groups) into thebackbone of HEC. The HMHEC could form near spherical particles with diameters in therange of20-30nm.
4. The novel and biodegradable cellulose-based nanomicelles were used to encapsulatethe hydrophobic anticancer drug of paclitaxel (PTX) to overcome its drawbacks such astoxicity, insolubility in aqueous water, and low biological availability. It was found that thecellulose-based nanomicelles can uptake PTX with high encapsulation efficiency up to90%,and the release behavior of PTX was in a steady and slowly pattern. The in vitro anti-tumoractivity was assessed using the Human Cervix Carcinoma cells (Hela) and hepatoma cell(Hepg2) by MTT test and was compared to the commercial formulation Taxol. ThePTX-loaded nanomicelles have a similar cell inhibition rate to that of Taxol. Furthermore, cellinhibition of PTX-loaded nanomicelles was dependent on the treated time, increasing withprolonging of the treated time. The results from flow cytometry and DAPI staining indicatedthat PTX from nanomicelles could induce cell apoptosis to achieve tumor inhibition.
5. The novel fluorescent amphiphilic cellulose nanoaggregates were successfullyprepared by encapsulation of hydrophobic fluorescent conjugated polymers (CPs) or quantumdots (QD) in the amphiphilic cellulose nanomicelles and their application in the field ofbioimaging was also evaluated. It was found that CPs or QD can be encapsulated into thecores of micelles with high efficiency and no obvious fluorescence quenching was observed.This fluorescent cellulose-based nanomicelles were kept stable after stored for7days at roomtemperature. The fluorescent nanomicelles were observed to be non-toxicity, and can beinternalized and imaging in live cells via cell endocytosis. Potentially, this method proposedin this part may be applied in biological cells imaging in aqueous solution.
6. The common commercially available light-emitting conjugated polymers of poly(9,9-dioctylfluorene (PFO) were easily dispersed into water by efficiently encapsulatedthem in the amphiphilic cellulose nanomicelles, which could offer an alternative way to usethose common hydrophobic CPs in aqueous solution. The PFO-containing cellulose-basedmicelles were successfully used to detect trace amounts of nitroaromatics (2,4-dinitrotoluene,picric acid) in aqueous solution and the sensitivity of PFO in nanomielles was50～200higherthan that of the chromophores in organic solvent, which means the cellulose nanomicelles canbe used to develop the novel nanocarriers for sensoring and extending the application regionof CPs.
1．在离子液体绿色溶剂反应介质中，分别以具有优良生物可降解性和生物相容性的聚乳酸、聚己内酯和聚对二氧环己酮作为侧链，对纤维素及其水溶性衍生物进行疏水化改性，制得三大类新型纤维素基两亲性聚合物衍生物。制备的纤维素基两亲性共聚物在水溶液中可自组装形成壳核结构的纳米胶束。通过调节衍生物中疏水基团的取代度可以有效控制其自组装行为和纳米胶束的粒径大小。MTT研究显示，此三类纤维素基两亲性聚合物对细胞无明显生物毒性。
2．在DMSO体系中，羟乙基纤维素与高级脂肪酸经CDI活化催化后，室温下即可发生酯化反应。改性后的衍生物具有良好的自组装性能，临界胶束浓度低至0.0019mg/mL和0.0016mg/mL，具有很强的抗稀释稳定性。此类纳米胶束可高效负载疏水性抗氧化剂β-胡萝卜素，并表现出良好的缓释效果，有望在化妆品辅料或功能食品领域获得应用。
3．采用长碳链酰氯对纤维素分子链直接进行疏水酯化改性，制得一系列具备不同碳链长度的纤维素疏水化衍生物。此类衍生物在水溶液中自组装形成单分散球形纳米粒子，且纳米粒子的粒径可通过改变疏水碳链长度进行调控。此外，通过HEC与溴代十二烷之间的醚化反应，合成了HEC的疏水改性衍生物，其可在水溶液中自组装形成20～30nm球形胶束。
4．纤维素基纳米胶束包载毒性大、不溶解、生物利用率低的抗癌药物紫杉醇（PTX），具有高包埋效率（>90%）和良好的缓释效果，深入探讨纤维素基纳米胶束与药物传递之间的“构-效关系”。体外细胞实验结果表明，负载PTX的纳米胶束对肿瘤细胞Hepg2和Hela具有与商业化产品Taxol相近的抗肿瘤活性。而且，负载PTX纳米胶束的抗肿瘤活性随作用时间延长而明显增强，具有延长的治疗效果。细胞流式和DAPI染色结果表明纳米胶束中的PTX主要通过细胞凋亡作用来抑制肿瘤细胞生长。
5．利用纤维素基纳米胶束包载共轭聚合物荧光染料和量子点，制备新型纤维素基高效荧光纳米材料，并考察其在生物成像领域的应用。实验发现，纤维素基纳米胶束可高效包载疏水性荧光染料和量子点，包载后染料未出现明显的荧光猝灭现象，荧光纳米胶束于室温下可稳定保存一周以上。荧光纳米胶束对小鼠干细胞无明显生物毒性，且可通过吞噬作用进入细胞内部，成功实现疏水性荧光染料于水相体系中的细胞成像。
6．成功实现了纤维素基纳米胶束对商业化疏水性荧光共轭聚合物9,9-二辛基聚芴（PFO）的高效包载，为普通疏水性荧光共轭聚合物的水相应用开辟了一条新的途径。包载PFO的纤维素基荧光纳米胶束对水相中痕量硝基苯类爆炸物（DNT、苦味酸等）具有优异的荧光传感检测性能，传感系数比相同染料在有机相中的传感系数增强50～200倍。该现象的发现对于开发新型纳米胶束传感器和拓展荧光共轭聚合物的应用具有非常重要的意义。
The polymeric micelles, which are commonly composed by synthetic block amphiphliccopolymers, have been established great potential application in the field of drug or genedelivery. However, the large-scale application of many synthetic block copolymers is limitedby their high prices and potential biotoxicity. Therefore, there has been a growing interest indeveloping amphihilic copolymers from natural polysaccharies. It’s well known that celluloseis one of the most abundant natural polysaccharides in the world. However, thecellulose-based amphiphilic derivatives have not been efficiently exploited due to itsinsolubility in water and common organic solvents. In respond to the need of efficientlyconversing cellulose to value-added products, this thesis is mainly focused on the design andpreparation of amphiphilic cellulose polymers and their self-assembled nanomicelles.Additionally, the potential application of cellulose-based nanomicelles in the fields of drugdelivery, bioimaging and sensing was also investigated. This work would not only develop thegreen and cheap micelle-forming materials from natural resources, but also offer analternative way for the value-added conversion of agricultural and forest waste biomass. Aseries of innovative researches were carried out as follows:
1. The amphiphilic cellulose copolymers with excellent biodegradable and biocompatibleproperties were homogeneously prepared in the green solvent of ionic liquids. Three kinds ofhydrophobic aliphatic polyesters, polylactide (PLA), polycaprolactone (PCL) andpolydioxanone (PPDO) were grafted onto the backbone of cellulose and cellulose’swater-soluble derivatives through the ring opening polymerization, respectively. It was foundthat the cellulose-based amphiphilic copolymers could self-assemble into core-shell structuredmicelles in aqueous water. The hydrophobic core was formed by the biodegradable sidechains such as PLA, PCL and PPDO, while the outer shells were formed by the main-chain ofcellulose. The self-assembly behavior of these amphiphilic cellulose derivatives in aqueouswater was found to be affected by their molecular structure, especailly the degree ofsubstitution of hydrophobic groups. The MTT assay showed that these amphphilic cellulosemicelles were safe to be applied in biological system.
2. Through activation of carbonyldiimidazole, the acylation between hydroxyethylcellulose and long-chain fatty acid were successfully carried out in the solvent of DMSO atroom temperature. The obtained derivatives have excellent self-assembly behavior and theircritical micelle concentrations were as low as0.0019mg/mL and0.0016mg/mL, respectively, indicating that these kinds of micelles have good anti-dilution stability. It was also found thatthe cellulose-based micelles could efficiently encapsulate the hydrophobic functional moietiesof β-carotene and make them slowly released in the aqueous medium, which means thenanocarriers may be used as cosmetics or food additives.
3. A series of cellulose-based hydrophobic associating polymers with different DS valuesand chain lengths were successfully prepared by homogeneous acylation of microcrystallinecellulose with long-chain acyl chloride. It was found that these cellulose derivatives couldself-assemble into monodispersed nanoparticles with spherical shapes in aqueous solution andtheir diameters can be controlled by adjusting the chain length of hydrophobic groups.Additionally, the hydrophobic modified hydroxyethyl cellulose derivatives (HMHEC) wereeasily synthesized by introducing hydrophobic moieties (long-chain alkyl groups) into thebackbone of HEC. The HMHEC could form near spherical particles with diameters in therange of20-30nm.
4. The novel and biodegradable cellulose-based nanomicelles were used to encapsulatethe hydrophobic anticancer drug of paclitaxel (PTX) to overcome its drawbacks such astoxicity, insolubility in aqueous water, and low biological availability. It was found that thecellulose-based nanomicelles can uptake PTX with high encapsulation efficiency up to90%,and the release behavior of PTX was in a steady and slowly pattern. The in vitro anti-tumoractivity was assessed using the Human Cervix Carcinoma cells (Hela) and hepatoma cell(Hepg2) by MTT test and was compared to the commercial formulation Taxol. ThePTX-loaded nanomicelles have a similar cell inhibition rate to that of Taxol. Furthermore, cellinhibition of PTX-loaded nanomicelles was dependent on the treated time, increasing withprolonging of the treated time. The results from flow cytometry and DAPI staining indicatedthat PTX from nanomicelles could induce cell apoptosis to achieve tumor inhibition.
5. The novel fluorescent amphiphilic cellulose nanoaggregates were successfullyprepared by encapsulation of hydrophobic fluorescent conjugated polymers (CPs) or quantumdots (QD) in the amphiphilic cellulose nanomicelles and their application in the field ofbioimaging was also evaluated. It was found that CPs or QD can be encapsulated into thecores of micelles with high efficiency and no obvious fluorescence quenching was observed.This fluorescent cellulose-based nanomicelles were kept stable after stored for7days at roomtemperature. The fluorescent nanomicelles were observed to be non-toxicity, and can beinternalized and imaging in live cells via cell endocytosis. Potentially, this method proposedin this part may be applied in biological cells imaging in aqueous solution.
6. The common commercially available light-emitting conjugated polymers of poly(9,9-dioctylfluorene (PFO) were easily dispersed into water by efficiently encapsulatedthem in the amphiphilic cellulose nanomicelles, which could offer an alternative way to usethose common hydrophobic CPs in aqueous solution. The PFO-containing cellulose-basedmicelles were successfully used to detect trace amounts of nitroaromatics (2,4-dinitrotoluene,picric acid) in aqueous solution and the sensitivity of PFO in nanomielles was50～200higherthan that of the chromophores in organic solvent, which means the cellulose nanomicelles canbe used to develop the novel nanocarriers for sensoring and extending the application regionof CPs.
引文
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