開發二硒雙親媒性共聚物的多功能藥物遞送系統用於靶向癌症治療

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研究生：	Hailemichael Tegenu Gebrie Hailemichael Tegenu Gebrie
論文名稱：	開發二硒雙親媒性共聚物的多功能藥物遞送系統用於靶向癌症治療 Multi-responsive drug delivery systems based on di-selenium-containing amphiphilic copolymer for targeting cancer therapy
指導教授：	蔡協致 Hsieh-Chih Tsai
口試委員:	高震宇 Chen-Yu Kao 陳奕君 Yi-Chun Chen 陳玉暄 Yu-Shuan Chen 何明樺 Ho Ming-Hua 蔡協致 Hsieh-Chih Tsai
學位類別：	博士 Doctor
系所名稱：	應用科技學院 - 應用科技研究所 Graduate Institute of Applied Science and Technology
論文出版年：	2023
畢業學年度：	111
語文別：	英文
論文頁數：	186
中文關鍵詞：	氧化還原反應、二硒化物鍵、核心交聯、生物素、酸鹼敏感型
外文關鍵詞：	Redox- responsive, Diselenide bond, Core cross-linked, Biotin, pH-sensitive
相關次數：	點閱：307 下載：0
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癌症為一種細胞不受控制且持續增殖的疾病，而癌細胞的病變是因健康細胞中的遺傳物質受到傷害所引發的現象。目前在癌症治療中，手術及化學療法為最常使用的治療方式，但在化學療法中，藥物釋放的調節為目前需要改善的問題之一。為了解決這項問題，人們正在努力設計和製造環境刺激影響的奈米材料，而此舉能將藥物長時間的釋放於目標器官進而達到治療效果。在本論文的第一部分中，研究了由甲氧基聚乙二醇嵌段聚己內酯共對二氧雜環己酮 (Bi(PPCD)-Se2) 構建的熱/氧化還原敏感可注射水凝膠的開發。在1H-NMR、13C-NMR 和 FTIR 分析中，證實了 Bi(PPCD)-Se2 的形成，並且研究了 Bi(PPCD)-Se2 水膠的流變特徵、溶膠-凝膠轉變機制和體外降解特性，也在流變數據中表現水膠具有明顯的黏度 (45 Pa.s)。水膠包覆DOX顯示出 1.3% 的載藥量和 93% 的藥品包覆率，DOX@Bi(PPCD)-Se2 水膠在 37°C 和pH 7.4 及10mM GSH 和 5mM H2O2 的環境刺激下，在經過 22 天後釋放了 81.6% 和 85.4%的藥物總量。在MTT 實驗中，水膠的釋放對於HeLa細胞及HaCaT細胞皆沒有毒性的產生。相比之下，在最大濃度為 10 µg/mL 時，DOX/水膠活性在 HeLa 細胞中產生了 31.3 ± 2.2% 的細胞活化效果。由於其出色的氧化還原誘導降解性所生成的 Bi(PPCD)-Se2水膠，可用作潛在的藥物遞送生物材料。在本論文的第二個部分中，為了減輕高分子微胞的熱力不穩定性並可提高藥品承載率，我們通過開環聚合和點擊反應，製備了含有 DOX 綴合的 pH 敏感聚合物Methoxy Poly (ethylene oxide)-b-Poly (Aspartate-Hydrazide) Bi(mPEG-P[Asp-(Hyd-DOX)])-Se2 CCMs。在1H-NMR、13C-NMR、拉曼和 FTIR 分析證實了合成材料的形成，並透過 DLS 測量了微胞顆粒大小及zeta 電位鑑定。根據DLS非交聯微胞 (NCM) 顯示出比 CCM (~72.63 nm) 更大的顆粒尺寸 (~96.43 nm)。在FE-SEM中研究及觀察了高分子微胞的形態並使用 HeLa 細胞以及斑馬魚胚胎測試合成材料的細胞毒性。結果顯示與 DOX/SN-38@NCM不同，DOX/SN-38@CCMs 在體外顯示出受控制的釋放現象。在最大藥物濃度 (10 µg/mL) 的作用下，HeLa 細胞的抑制率比HaCaT(14.25%) 高 50.90%。使用螢光顯微鏡觀察了 SN-38/DOX 負載高分子微胞的細胞攝取和細胞間藥物釋放的現象。此外利用 3D 腫瘤球體，研究了腫瘤生長侵襲活動。總結來說，結合上述的這些優勢，合成具pH 敏感的二硒化物的 CCMs 對於 DOX/SN-38 向癌細胞的調節遞送更具有吸引力。我們將含有二硒化物的Biotin -PEG-SeSe-PBLA製備成含生物素介導的高分子微胞，此微胞具氧化還原敏感性且幾乎完全釋放所包覆之 DOX 特性。Biotin-PEG-SeSe-PBLA 會產生均勻分散的高分子微胞，其流體動力學直徑 (Dh) 為 81.54 nm。高分子微胞中DOX藥物包覆率(EE) 和藥物於載體之攜帶率( DLC)分別為 74.325% 和 5.983wt%。在與 0.1% H2O2 和 10 mM GSH 培養 8 小時後，未攜帶藥物載體也具氧化還原反應性。此外DOX@Biotin-PEG-SeSe-PBLA微胞在模擬腫瘤氧化還原環境中表現出最佳的 DOX 釋放，在 0.1% H2O2 和 10 mM GSH 中 72 小時分別為 ~74% 和 ~ 89%。在最大藥物濃度 (5 µg/mL) 下，HeLa 細胞的抑制率比 HaCaT (11%) 高 76%。二硒化物連接的Biotin-PEG-SeSe-PBLA 產生生理穩定、循環、癌症特異性和智能高分子微胞，需要進行進一步研究。總體來說，氧化還原敏感的含硒高分子微胞對於調節腫瘤細胞中化學藥物的釋放至關重要。

Cancer is a disease that is defined by unchecked cell proliferation and the absence of cell death, and it is brought on by harm and/or alterations to the genetic material of healthy cells. Surgery, radiation, and chemotherapy are the most often utilized types of cancer therapies. One of the main difficulties with chemotherapy is the controlled release of medicines. To solve this problem, efforts are being made to design and create stimuli-responsive nanomaterials, which will allow for the prolonged controlled release of medications at the site of action. In this dissertation, the first section examined, the development of thermo/redox-sensitive injectable hydrogels constructed from methoxy poly (ethylene glycol)-block poly(-caprolactone-co-p-dioxanone) (Bi(PPCD)-Se2). 1H-NMR, 13C-NMR, and FTIR analysis confirmed the formation of Bi(PPCD)-Se2. The rheological features, sol-gel transition mechanisms, and in vitro degradation characteristics of Bi(PPCD)-Se2 hydrogels were studied. The rheological data show that the hydrogel has a noticeable viscosity. The hydrogel showed 1.3% of Drug loading content and 93% encapsulation efficiency of Doxorubicin. The DOX@Bi(PPCD)-Se2 hydrogel released 81.6% and 85.4% of its payload after 22 days at 37°C and pH 7.4 with 10mM GSH and 5mM H2O2 stimuli. In HeLa and HaCaT cells, the MTT study revealed no toxicity. In contrast, the DOX/hydrogel activity produced 31.3 ± 2.2% of cell viability in HeLa cells at the maximal concentrations of 10 µg/mL. Due to its excellent redox induced degradability, the generated Bi(PPCD)-Se2 hydrogel may be used as a potential drug delivery biomaterial with a focus on local drug distribution in a sustained way. In our second project in order to alleviate thermodynamic instability of Polymeric micelles and enhancing drug control releasing capacity, we were prepared diselenide containing DOX-conjugated pH-sensitive polymeric prodrug Methoxy Poly (ethylene oxide)-b-Poly(Aspartate-Hydrazide) Bi(mPEG-P[Asp-(Hyd-DOX)])-Se2 CCMs via ring-opening polymerization and click reaction. 1H-NMR, 13C-NMR, Raman, and FTIR analysis confirmed the formation of the synthesized material while the micelle size and zeta potential were measured by DLS. According to DLS, the non-cross-linked micelle (NCMs) displayed a larger (~96.43 nm) particle size than the CCMs (~72.63 nm). Unlike the DOX/SN-38@NCMs, the DOX/SN-38@CCMs displayed a controlled release outline in vitro. At the maximal drug concentration (10 µg/mL), HeLa cells were inhibited 50.90% more than HaCaT (14.25%). Using fluorescence imaging, the cellular uptake and intercellular drug discharge of SN-38/DOX-loaded PMs were studied. Additionally, utilizing 3D tumor spheroids, the tumor growth inhibition activity was investigated. Overall, the combination of all these attractive features makes the synthesized pH-sensitive diselenide containing CCMs attractive for regulated delivery of DOX/SN-38 to cancer cells. We intensified our efforts to produce biotin-mediated PMs from Biotin-PEG-SeSe-PBLA that contain diselenide and have improved redox triggered and nearly complete DOX-releasing property. The self-assembly biotin-PEG-SeSe-PBLA would result in uniformly dispersed PMs with a hydrodynamic diameter (Dh) of 81.54 nm. Significant DOX EE and DLC, 74.325% and 5.983wt%, respectively, were observed in the PMs. The blank PMs micelles showed improved redox reactivity following an 8 h incubation with 0.1% H2O2 and 10 mM GSH. Additionally, DOX@Biotin-PEG-SeSe-PBLA micelles demonstrated optimal DOX release in mimicked tumor redox environment, at ~74% and ~ 89%, in 0.1% H2O2 and 10 mM GSH 72 h, respectively. At the maximal drug concentration (5 µg/mL), HeLa cells were inhibited 76% more than HaCaT (11%). In conclusion, the diselenide-linked Biotin-PEG-SeSe-PBLA produced physiologically stable, long-circulating, cancer-specific, and intelligent PMs that warrant additional in vivo research. Overall, redox sensitive Selenium-containing PMs are essential for the regulated discharge of chemo drug in tumor cells.

Table of Contents
Declaration    i
Acknowledgment    ii
摘要xx    Error! Bookmark not defined.
Abstract    vi
List of Tables    xiv
List of Figures    xv
List of Schemes    xix
List of Abbreviations    xx
CHAPTER 1    1
   Background    1
1. Anticancer drug delivery    1
2.  Delivery of anticancer drug via a redox-responsive polymeric nanocarriers    2
3. Redox sensitive polymeric nanocarrier recent trends    3
CHAPTER 2    5
Literature review    5
1. Treatment of cancer    5
2. Nanomedicine and cancer treatment    6
3. Polymer nanocarriers for drug delivery applications    7
4. Stimuli-responsive polymeric nanocarriers for drug delivery    8
4.1. pH-Responsive Polymer nanocarriers    9
4.2. Thermo-responsive polymeric nanocarriers    10
4.3. Multi-Stimuli Responsive Polymeric nanocarrier    12
4.4. Redox-sensitive polymeric nanocarrier for delivery of anticancer drug    13
4.5. Selenium-containing redox-responsive polymeric nanocarriers    14
4.6. Selenium-containing polymeric micelles as drug carrier    15
4.6.1. Non-cleavable selenium-containing polymeric micelles    16
4.6.2.  Mono-cleavable diselenide-containing polymeric micelles    18
4.6.3 Multicleavable selenium-containing polymeric micelles    20
4.7. Selenium-containing crosslinked polymeric micelles    22
5. Research gaps and motivation of study    25
6. Objective and outline of study    26
CHAPTER 3    29
Development of thermo/redox‑responsive diselenide linked methoxy poly (ethylene glycol) block‑poly(ε‑caprolactone‑co‑p‑dioxanone) hydrogel for localized control drug release    29
1. Introduction    29
2. Material and methods    33
2.1. Materials    33
2.2. Methods    33
2.2.1. Synthesis of PPCD    33
2.2.2. Synthesis of 3,3’-diselanediyldipropanoic acid (DSeDPA)    34
2.2.3. Synthesis of Bi(PPCD)‑Se2    35
2.2.4. Characterization    36
2.2.5. Morphology    36
2.2.6. Sol-gel phase transition and rheological behavior    36
2.2.7. In vitro H2O2 / GSH‑triggered hydrogel degradation    37
2.2.8. The Bi(PPCD)Se2 copolymer in vitro biocompatibility    38
2.2.9. Drug loading and in vitro redox-triggered release of drug    39
2.2.10. DOX anti-cancer action released from the hydrogel    40
3. Results and Discussion    41
3.1. Synthesis and Characterization of Bi(PPCD)-Se2    41
3.2. Sol-gel phase transition temperature and rheological properties    45
3.3. Hydrogels in vitro redox-triggered degradation    47
3.4. Morphology of the hydrogel    49
3.5. In vitro cytotoxicity test (MTT Assay)    50
3.6. Drug loading and in vitro release    50
3.7. DOX-loaded hydrogel in vitro anti-cancer activity    51
4. CONCLUSIONS    53
CHAPTER 4    54
pH/redox-responsive core cross-linked based prodrug micelle for enhancing micellar stability and controlling delivery of chemo drugs: An effective combination drug delivery platform for cancer therapy    54
1. Introduction    54
2. Material and methods    58
2.1. Materials    58
2.2. Methods    59
2.2.1. Synthesis of β-Benzyl-L-aspartates N-carboxy anhydride (BLA-NCA)    59
2.2.2. Synthesis of methoxy poly (ethylene oxide) b-poly(β-Benzyl-L-aspartate)    61
(mPEG-PBLA) amphiphilic diblock copolymer    61
2.2.3. Synthesis of methoxy poly (ethylene oxide)-b-poly (aspartate-hydrazide)    61
(mPEG-P(Asp-Hyd)    61
2.2.4. Synthesis of doxorubicin conjugated polymeric prodrug Methoxy poly(ethylene oxide)-b-poly(aspartate-hydrazide) (mPEG-P[Asp-(Hyd-DOX)])    62
2.2.5. Synthesis of diselenide core cross-linked doxorubicin-conjugated methoxy poly(ethylene oxide)-b-poly(aspartate-hydrazide) (Bi(mPEG-P[Asp-(Hyd-DOX])-Se2)    62
2.2.6. Characterization    63
2.2.7. Formation of critical micelle concentration (CMC)    63
2.2.8. SN-38 loaded NCMs and CCMs preparation    64
2.2.9. The CCMs stability and pH/redox responsiveness    66
2.2.10. In vitro pH/redox triggered DOX/SN-38 releasing behavior of micelles    67
2.2.11. in vitro cytotoxicity Study    68
2.2.12. cellular uptake Study    68
2.2.13. Zebrafish biotoxicity testing of blank mPEG-P(Asp-Hyd) copolymer    69
2.2.14. Development of tumor spheroid models and cell culture    70
2.2.15. Inhibition of tumor spheroids development    70
2.2.16. Study on drug dispersion in tumor spheroids    70
3. Results and Discussion    71
3.1. Synthesis and characterization of Copolymer    71
3.2. Core cross-linked and non-cross-linked polymeric micelle synthesis    75
3.3. mPEG-P[Asp-(Hyd-DOX)] copolymer Critical micelle concentration    78
3.4. Stability and pH and/or redox responsiveness of CCMs    80
3.5. Micelles’ drug-loading and release behavior    81
3.6. in vitro anticancer and Cytotoxicity activity    85
3.7. Zebrafish in vivo biocompatibility    88
3.8. Studying growth inhibition and characterizing spheroid growth    89
3.9. Delivery of DOX/SN-38 in 3D spheroids    93
3.10. Investigation of cellular absorption and localization    94
4. Conclusion    97
CHAPTER 5    98
Multifunctional Drug-Loaded Micelle with Biotin-Mediated Cancer Cell Targeting and Redox-Triggered Drug Releasing for Enhanced Anticancer Efficacy    98
1. Introduction    98
2. Materials and Methods    101
2.1. Materials    101
2.2. Methods    102
2.2.1. β-Benzyl-L-aspartates N-carboxy anhydride Synthesis (BLA-NCA)    102
2.2.2. Synthesis of 3’3’-diselanediydipropanole acid (DSeDPA)    102
2.2.3. Synthesis of Biotin-PEG    103
2.2.4. Synthesis of diselenide functionalized Biotin-PEG-SeSe    104
2.2.5. Synthesis of diselenide-linked Biotin-PEG-SeSe-PBLA    104
2.2.6. Characterization    105
2.2.7. Preparation of blank and DOX-loaded Biotin-PEG-SeSe-PBLA    106
2.2.8. Determination of critical micelle concentration (CMC) of Biotin-PEG-SeSe-PBLA    107
2.2.9. Redox-responsiveness of Biotin-PEG-SeSe-PBLA    108
2.2.10. DOX releasing studies of DOX@Biotin-PEG-SeSe-PBLA    109
2.2.11. In vitro cytotoxicity study    109
2.2.12. Cellular uptake study    110
3. Results and Discussion    111
3.1. Characterization of Biotin-PEG-SeSe-PBLA    111
3.2. Self-assembly of blank and DOX-loaded Biotin-PEG-SeSe-PBLA micelles    115
3.3. Determination of CMC of Biotin-PEG-SeSe-PBLA    117
3.4. Redox-responsiveness of Biotin-PEG-SeSe-PBLA    119
3.5. Redox responsive DOX releasing trend of DOX@Biotin-PEG-SeSe-PBLA    120
3.6. In vitro cytotoxicity and anticancer effect    122
3.7. Cellular uptake of Biotin-PEG-SeSe-PBLA micelles    125
CONCLUSION    128
CHAPTER 6    130
General summary and future perspective    130
1. summary    130
2. Future perspective and recommendations    132
Reference    134
Appendix: A    150
Appendix: B    162
Appendix: C    163


                                

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全文公開日期 2033/01/13 (國家圖書館：臺灣博碩士論文系統)

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