具應答性高分子奈米載體於腫瘤標的藥物傳遞及硫化氫治療之應用

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研究生：	Le Trong Nghia Trong-Nghia Le
論文名稱：	具應答性高分子奈米載體於腫瘤標的藥物傳遞及硫化氫治療之應用 RESPONSIVE POLYMERIC NANOCARRIERS FOR TUMOR-TARGETED DRUG DELIVERY AND HYDROGEN SULFIDE THERAPY
指導教授：	李振綱 Cheng-Kang Lee Neralla Vijayakameswara Rao Neralla Vijayakameswara Rao
口試委員:	李振綱 Cheng-Kang Lee Neralla Vijayakameswara Rao Neralla Vijayakameswara Rao 蕭偉文 Wei-Wen Hsiao 張家耀 Jia-Yaw Chang 黃志清 Chih-Ching Huang 邱信程 Hsin-Cheng Chiu Raja Shunmugam Raja Shunmugam
學位類別：	博士 Doctor
系所名稱：	工程學院 - 化學工程系 Department of Chemical Engineering
論文出版年：	2022
畢業學年度：	110
語文別：	英文
論文頁數：	138
外文關鍵詞：	anticancer, responsive polymer, stimuli-release, ROS-responsive, hypoxia-responsive, cancer-targeted, doxorubicin, hyaluronic acid, hydrogen sulfide
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癌症是由異常細胞生長與分化而引發之疾病，為導致死亡的主要原因之一。癌症治療的方法中，化學治療藥物必須在有效性與安全性之間取得平衡才能使用成功。然而，傳統的化療方法可因其非鏢靶定位治療、藥物代謝快速、副作用等原因而損害正常細胞。刺激應答型奈米載體因可以響應外部刺激（特別是腫瘤微環境，例如弱酸環境、特定酶的過度表達、高濃度的活性氧化物質等），而達成控制藥物釋放的目的，目前此方法已經獲得相當大的注意。於此論文中，我們將探討多種高分子奈米粒子為載體，並結合缺氧應答、酸鹼性應答與活性氧化物質應答之特性做為抗癌藥物遞送系統。
首先，利用固態腫瘤共同缺氧性（hypoxia）的特徵，研究以抗癌治療之缺氧應答型透明質酸結合黑洞猝滅劑3（HA-BHQ3）為奈米粒子載體。HA-BHQ3是由易放大單步反應製備而成，其可透過獨特之缺氧條件以達到藥物釋放。由於阿黴素（doxorubicin, DOX）與BHQ3間之π-π交互作用，可使得抗癌藥物阿黴素以高藥物包覆效率加載至HA-BHQ3奈米粒子中。阿黴素在正常生理環境下釋放緩慢；相形之下，在缺氧環境中，因BHQ3中之偶氮鍵裂解而顯著地提高阿黴素之釋放效率。例如，在正常條件下24小時後，DOX釋放了25%；然而在缺氧條件下則可達74%。新型之HA-BHQ3具低生物毒性、有效之細胞內化、體外之抗癌活性、並體內針對乳腺癌之腫瘤標靶性。
其次，一種多重刺激響應之PEG-b-PCL高分子微胞也被研究用以有效地釋放阿黴素，其具酸鹼控制電荷可逆性，與硫縮酮為基底之活性氧化物質(ROS)應答(BA-P(CL-co-DCL)-ATK-mPEG, or ATK-ROS-pH)之特性。在嵌段共聚高分子中，對酸不穩定之b-羧酸酰胺可使奈米微胞粒子表面電性依酸鹼值而反轉。同時，在奈米粒子中的ROS敏感性連接子，會因癌細胞中的ROS異質性而降解，而導致在細胞內能有效地釋放藥物。此外，另一種π共軛硫縮酮連接鍛(9FTK)也被用來製備9FTK-ROS-pH，因其與抗癌藥物DOX間之π-π重疊作用與疏水作用，因此具有高藥物裝載率與藥物傳輸率之潛力。嵌段共聚高分子可以自組裝成穩定且具有高載藥量之奈米粒子。在不同pH與ROS環境下，此種具多重刺激響應之奈米粒子在ROS環境下會被觸發釋放，其中ATK-ROS-pH奈米粒子是屬於突發控制釋放；而9FTK-ROS-pH奈米粒子可有望作為長放緩釋之藥物載體。
論文最後設計並合成一具S-芳酰硫基肟S-aroylthiooxime (SATO)之硫化氫(H2S)提供者，用以產生硫化氫氣體之高分子聚合物，並研究提升硫化氫之治療效果。此種可將硫化氫釋放之高分子微胞是由聚乙二醇(PEG)與S-芳酰硫基肟S-aroylthiooxime (SATO)之硫化氫(H2S)提供者所組成，其在聚降冰片烯骨架上(PNEG-b-PNSATO)經開環易位聚合反應，與第二代Grubbs催化劑輔助下製備而成。此種高分子微胞大小分佈於41~57奈米之間，與小分子SATO相比，可在延長對半胱氨酸應答釋放硫化氫氣體之速率（尖峰時間為60~70分鐘）。體外細胞毒性結果顯示PNEG-b-PNSATO高分子微胞，具有極佳的生物相容性。透過螢光顯微影像可觀察細胞內硫化氫氣體釋放的情況。此外，PNEG-b-PNSATO高分子微胞對由過氧化氫(H2O2) 之致死劑量所誘導出的氧化損害具有保護之功效，這顯示可將PNEG-b-PNSATO高分子微胞用在生物系統中，而實現此有潛力之硫化氫治療方法。

Cancer, one of the leading causes of death, is a group of diseases that results from abnormal cell growth and division. For cancer treatment, chemotherapeutic drugs must be administered successfully by striking a balance between their effectiveness and safety. However, conventional chemotherapy may harm normal cells due to its non-targeted site curing, rapid drug metabolism, and side effects. Stimuli-responsive nanocarriers have garnered considerable interest due to their ability to respond to external stimuli, most notably the tumor microenvironment (weakly acidic environment, overexpression of specific enzymes, and high level of reactive oxygen species), in order to achieve controlled drug release. In this thesis, several polymeric nanoparticles systems were developed for anticancer drug delivery with the features of hypoxia-responsive pH-responsive and ROS-responsive.
Firstly, hypoxia, a common feature of the solid tumor, was utilized to develop a hypoxia-responsive hyaluronic acid conjugated black hole quencher 3 (HA-BHQ3) for anticancer therapy. The HA-BHQ3 was prepared as a single-step reaction with easy scale-up for drug delivery by using the unique hypoxic conditions. The anticancer drug doxorubicin (DOX) is loaded into the HA-BHQ3 nanoparticles (NPs) with high drug loading efficiency due to the π-π interaction between DOX and BHQ3. In the physiological environment, DOX is released slowly. In contrast, under hypoxic conditions, the azo bond in BHQ3 is cleaved, thus significantly enhancing the DOX release rate. For instance, after 24 h, 25% of DOX is released under normal conditions, while 74% of DOX is released under hypoxic conditions. The designed HA-BHQ3 showed low toxicity, effective cellular internalization, in vitro anticancer activity as well as in vivo tumor targetability against breast cancer.
Secondly, a multi-stimuli poly(ethylene glycol)-block-poly(ε-caprolactone) (PEG-b-PCL) polymeric micelle with pH charge-reversible and thioketal-based ROS-responsive (BA-P(CL-co-DCL)-ATK-mPEG, or ATK-ROS-pH) was developed for efficient DOX release. The acid-labile b-carboxylic amides in the block copolymers provided the pH-dependent charge-conversional feature to the NPs, which resulted in the transform surface charge of the NPs depending on the environment acidity. Meantime ROS sensitive linkers of those NPs preferentially degraded at ROS heterogeneity of cancer cells leading to efficient intracellular drug release. Additionally, a π-conjugated thioketal linker (9FTK) was also used to prepare 9FTK-ROS-pH for its potential to enhance drug loading and delivery efficiency owing to its π-π stacking and hydrophobic interactions with the anti-cancer drug DOX. The block copolymer can self-assemble into stable NPs with higher drug loading capacity. The multi-stimuli responsive NPs against various pH and ROS condition was obtained to be able to trigger release under ROS condition, in which ATK-ROS-pH NPs provided burst controlled-release while 9FTK-ROS-pH NPs is promising as a sustained release nanocarrier.
Finally, a hydrogen sulfide (H2S) gas generation copolymer with S-aroylthiooxime (SATO) H2S-donor was designed and synthesized, which have great opportunity for further studies to enhance the therapeutic effect of H2S. The H2S releasing polymeric micelles consisting of PEG and S-aroylthiooxime (SATO) H2S donor was prepared on the polynorbornene backbone (PNEG-b-PNSATO) via ring-opening metathesis polymerization (ROMP) assisted by second-generation Grubbs’ catalyst. The polymeric micelles were observed with the size various from 41 – 57 nm and can release H2S in response to cysteine at a prolonged release rate (peak time of 60 – 70 min) compared to the small molecule SATO. The in vitro cytotoxicity indicated that the PNEG-b-PNSATO polymeric micelles exhibited excellent biocompatibility. The H2S release in cells was observed by fluorescent imaging. Moreover, the protective effect of the PNEG-b-PNSATO polymeric micelles against oxidative damage induced by a lethal dose of H2O2 was demonstrated, indicating the potential use of the PNEG-b-PNSATO polymeric micelles to achieve H2S therapeutic effect in biological systems.

Abstract        i
摘要        iii
Acknowledgment    v
Abbreviations    xi
Index of Figures    xiii
Index of Schemes    xvi
Index of Tables    xvii
Chapter 1    INTRODUCTION    1
1    Preface        1
2    Nanocarriers for tumor therapy    1
2.1    pH-responsive    2
2.2    Hypoxia-responsive    3
2.3    ROS-responsive    4
3    Hydrogen sulfide (H2S) generation    4
4    Motivation and research objectives    5
4.1    Hyaluronic acid derived hypoxia-sensitive nanocarrier for tumor-targeted drug delivery        5
4.2    Multi-stimuli PEG-PCL polymeric nanoparticles with charge conversion and thioketal-based ROS-responsive for doxorubicin drug delivery    6
4.3    Norbornene block copolymer micelles with capacity of hydrogen sulfide generation                8
Chapter 2    LITERATURE REVIEW    9
1    Steglich esterification    9
2    Ring-opening polymerization (ROP)    11
3    Ring-opening metathesis polymerization (ROMP)    14
Chapter 3    GENERAL MATERIALS AND METHODS    17
1    Cell lines    17
2    Cell subculture medium    17
3    Reagents    18
4    Apparatus    19
5    Characterization Methods    20
5.1    1H-NMR spectroscopy    20
5.2    Fourier transform infrared spectra (FTIR)    20
5.3    Gel permeation chromatograpy (GPC)    20
5.4    Dynamic light scattering (DLS)    20
5.5    Field Emission Scanning Electron Microscopy (FE-SEM)    20
5.6    Transmission Electron Microscope (TEM)    20
5.7    UV/Vis spectroscopy    20
5.8    Fluorescence spectroscopy    20
5.9    Fluorescence imaging    20
5.10    In vivo imaging    21
5.11    Determination of drug loading efficiency and drug loading content    21
5.12    Determine H2S concentration via methylene blue method    21
Chapter 4    Hyaluronic Acid Derived Hypoxia-Sensitive Nanocarrier for Tumor Targeted Drug Delivery    23
1    Introduction    23
2    Experimental Section    26
2.1    Materials    26
2.2    Preparation of HA-BHQ3    26
2.3    Preparation of DOX@HA-BHQ3 NPs    27
2.4    Drug release profiles of DOX@HA-BHQ3 NPs    27
2.5    In vitro cell viability assay    27
2.6    In vitro cellular uptake    27
2.7    In vivo biodistribution of HA-BHQ3    28
2.8    Statistical Analysis    28
3    Results and Discussion    28
3.1    Synthesis of HA-BHQ3    28
3.2    Characterization of HA-BHQ3 NPs    29
3.3    In vitro drug release profiles of DOX@HA-BHQ3 NPs    32
3.4    Cell viability    33
3.5    Cellular uptake    34
3.6    In vivo biodistribution of HA-BHQ3 NPs    35
4    Conclusions    36
Chapter 5    Multi-Stimuli PEG-PCL Polymeric Nanoparticles with Charge Conversion and Thioketal-Based ROS-Responsive for Doxorubicin Drug Delivery    37
1    Introduction    37
2    Experimental Section    40
2.1    Materials    40
2.2    Synthesis of mPEG-ATK    41
2.3    Synthesis of BA-P(CL-co-CATCL)    41
2.4    Synthesis of BA-P(CL-co-CATCL)-ATK-mPEG    41
2.5    Deprotection of BA-P(CL-co-ACL)-ATK-mPEG    41
2.6    Synthesis of BA-P(CL-co-DCL)-ATK-mPEG    42
2.7    Preparation of blank and drug loaded nanoparticles    42
2.8    Release profiles of drug loaded NPs    42
2.9    Cell viability    42
2.10    Cellular uptake    43
3    Results and discussion    44
3.1    Synthesis of BA-P(CL-co-DCL)-ATK-mPEG    44
3.2    Preparation and characterization of BA-P(CL-co-DCL)-ATK-mPEG nanoparticles                46
3.3    Charge-conversional properties of BA-P(CL-co-DCL)-ATK-mPEG NPs    48
3.4    pH and ROS sensitivity of BA-P(CL-co-DCL)-ATK-mPEG NPs    49
3.5    DOX loading and releasing    50
3.6    Cell viability    52
3.7    Cellular uptake    53
3.8    π-Conjugated thioketal ROS-responsive linker for enhancing DOX loading efficiency    54
4    Conclusion    58
Chapter 6    Polynorbornene-Derived Block Copolymer Micelles with Capacity of Hydrogen Sulfide Generation    59
1    Introduction    59
2    Materials and methods    62
2.1    Materials    62
2.2    Synthesis of Nor-HBA    63
2.3    Synthesis of Nor-SATO    63
2.4    Synthesis of norbornene grafted methoxypoly(ethyleneglycol) (Nor-mPEG)    64
2.5    Synthesis of block copolymer (PNEG-b-PNSATO)    64
2.6    Preparation of PNEG-b-PNSATO micelles    65
2.7    Determination of critical micelle concentrations    65
2.8    H2S release profile via the methylene blue method    65
2.9    In vitro cytotoxicity    65
2.10    Fluorescence imaging of H2S release in L929 cells    66
2.11    Effect on H2O2-induced damage    66
2.12    Statistical Analysis    66
3    Results and discussion    66
3.1    Synthesis and characterization of PNEG-b-PNSATO    66
3.2    PNEG-b-PNSATO micelles preparation and characterization    69
3.3    H2S release profile    70
3.4    Cell viability    71
3.5    Fluorescence imaging of H2S release in L929 cells    72
3.6    Effect on H2O2-induced damage    73
4    Conclusion    75
Chapter 7    CONCLUSION AND PERSPECTIVES    76
References        79
Appendix A        96
Appendix B        99
Appendix C        105
CURRICULUM VITAE    113

                                

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