製備含雙硒之氧化還原應答型高分子微胞作為阿黴素抗癌藥物之輸送: 載體之安定性及藥物控制釋放之研究

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研究生：	Yihenew S Birhan Yihenew Simegniew Birhan
論文名稱：	製備含雙硒之氧化還原應答型高分子微胞作為阿黴素抗癌藥物之輸送: 載體之安定性及藥物控制釋放之研究 Fabrication of Diselenide-Containing Redox-Responsive Polymeric Micelles for Doxorubicin Delivery: Stability of the Carrier and Controlled Release of Drug
指導教授：	蔡協致 Hsieh-Chih Tsai
口試委員:	楊禎明 Jen-Ming Yang 李榮和 Rong-Ho Lee 何明樺 Ming-Hua Ho 楊銘乾 Ming-Chien Yang
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：	2021
畢業學年度：	109
語文別：	英文
論文頁數：	209
中文關鍵詞：	雙硒鍵、氧化還原應應性、核交聯、核殼結構高分子微胞
外文關鍵詞：	Diselenide bond, redox-responsive, core crosslinked, shell-sheddable micelles
相關次數：	點閱：230 下載：0
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上一筆

近年來，大量研究項目集中在高分子微胞(PMs)的製備上，但由於載體中藥物洩漏與材料毒性問題，只有很少的製劑進到臨床開發階段，因此，製備能夠在體內穩定的PMs是抗癌藥物傳遞研究的重點，也將引起了廣泛的關注。本文第一項研究成功地以DMAP和DCC的存在下，通過酯化反應，成功將雙團聯共聚物mPEG-PLGA鍵結上DSeDPA，此含二硒化物的Bi(mPEG-PLGA)-Se2共聚物 (CPs) 是對於氧化還原環境應答行為，此材料在水溶液中可自組裝成水利直徑 (Dh) 為123.9 ± 0.85 奈米的球形微胞。PMs包裹阿黴素 (DOX) 之藥物含量和藥物包覆效率分別為6.61 wt.%與54.9 wt.%。在pH 7.4和37℃的6 mM GSH (還原環境) 和0.1% H2O2 (氧化環境) 的水溶液中環境中下72小時，攜帶DOX的PMs分別釋放出74％(還原環境)和70％ (氧化環境)。利用螢光顯微鏡和MTT檢測HeLa細胞觀察到明顯的內化作用，說明攜帶DOX的藥物載體能誘導癌細胞凋亡。接著，為了改善PMs的熱力學不穩定性，在本文第二項研究中藉由三嵌段共聚物mPEG-P(LA-DSeDEA)-PCL製備了更穩定的核交聯微胞 (CCMs)，該微胞通過可見光引發的DSeDEA基團間的Se-Se鍵交換反應聚集並進行核交聯。CCMs粒徑大小為156.57 ± 4.42奈米，藥物包覆率為42.23%，藥物於載體之含量為7.31 wt.%。CCMs和DOX@CCMs在牛血清白蛋白(BSA)環境下時顯示出高的穩定性與設計的目標一致。此外，在模擬的癌細胞氧化還原環境中，DOX展現持續釋放行為:10 mM GSH使71.7%的DOX在72h內擴散。在DOX@CCMs共培養的HeLa細胞上進行的螢光顯微鏡和流式細胞術實驗均明確表明細胞內吞作用和胞質氧化還原池引起了DOX的釋放。mPEG-P(LA-DSeDEA)-PCL的生物相容性(濃度為600 μg/ mL)藉由MDCK、HaCaT和HeLa細胞共培養24小時後的代謝活性中得到≥82％；相反的，當DOX@CCMs在10 μg/mL的DOX濃度下，有49% HeLa細胞會有選擇性的誘導凋亡。我們進一步從含有星形的3s-PCL-SeSe-PEG-Biotin (s-PMs)的的離子酰胺中構建生物素功能化的可脫殼微胞，由於共聚物支鏈段的纏繞，使其血清穩定性增強，且DOX釋放效能接近完全。3s-PCL-SeSe-PEG-Biotin進行自導向聚集，形成水動力直徑76.27奈米均勻分佈的s-PMs，s-PMs負載阿黴素淨含量(DLC)和封裝效率(EE)分別為5.83 wt.%和71.02%。將s-PMs與DOX負載的s-PMs在FBS與100倍PBS培養7天後，依舊保持其結構完整性，可證明微胞的高穩定性。DOX@3s-PCL-SeSe-PEG-Biotin微胞在10 mM GSH和0.1% H2O2的模擬癌症氧化還原液中72小時分別釋放93%和79%的DOX。DOX@3s-PCL-SeSe-PEG-Biotin微胞在5 μg/mL時抑制77% HeLa癌細胞與62% MDA-MB-231癌細胞而同時只抑制12% HaCaT正常細胞。總體而言，二硒化物連接的3s-PCL-SeSe-PEG-Biotin生物素形成生理穩定、長循環、癌症特異性和智慧的s-PMs，值得進一步的體內研究。一般而言，不同結構的氧化還原反應Se-PMs具有理想的血清穩定性，同時氧化還原所誘導藥物載體中DOX於癌細胞釋放，從實驗中也觀察到很好的效果。

In recent years, an enormous number of research projects focused on the fabrication of polymeric micelles (PMs), yet only a few formulations reach the clinical development stage due to drug leakage and associated systemic toxicities. Thus, fabrication of in vivo stable PMs is of great priority in the anticancer drug delivery research and attracted significant attention in recent years. In our first project, we succeeded in synthesizing redox stimuli sensitive, diselenide-containing Bi(mPEG-PLGA)-Se2 copolymers (CPs) from DSeDPA and mPEG-PLGA through ester coupling “click” reaction in the presence of DMAP and DCC which spontaneously self-assembled into spherical micelles of desirable hydrodynamic diameter (Dh), 123.9 nm, in aqueous solution. The PMs experienced sensible DOX-loading capacity and EE, 6.61 wt.% 54.9%, respectively. Upon incubation with 6 mM GSH and 0.1% H2O2, the DOX-loaded PMs released ⁓74% and ⁓70% of DOX, respectively, in 72 h at pH 7.4 and 37 ℃. The fluorescent microscope images and MTT assays on HeLa cells revealed the efficient cellular internalization and efficient apoptotic potential of DOX-loaded PMs. To ameliorate the thermodynamic instability of PMs, we also prepared a more stable core crosslinked micelles (CCMs) in our second project from the triblock copolymer, mPEG-P(LA-DSeDEA)-PCL, which would aggregate and undergo core crosslinking via visible light-triggered Se-Se bond exchange reactions among pendant DSeDEA groups. The CCMs with 156.57 nm in diameter were shown to encapsulate 42.23% of initial DOX with a net content of 7.31 wt.%. In line with our objective, CCMs and DOX@CCMs unveiled trustworthy stability when co-incubated with bovine serum albumin (BSA). Moreover, a therapeutically sufficient quantity of DOX was release persistently from DOX@CCMs in a simulated cancer cell redox pool; 10 mM GSH caused 71.7% of the loaded DOX to diffuse in 72 h. The fluorescent microscopy and flow cytometry experiments executed on HeLa cells co-cultured with DOX@CCMs asserted the endocytosis and cytosolic redox pool initiated DOX release. The biocompatibility of mPEG-P(LA-DSeDEA)-PCL was drawn from the metabolically active (≥ 82%) profiles of MDCK, HaCaT, and HeLa cells after 24 h at 600 µg/mL. In contrast, DOX@CCMs selectively induce an apoptotic effect in ⁓49% of HeLa at an equivalent DOX concentration of 10 µg/mL. We further extend an effort to engineer biotin-functionalized shell-sheddable micelles from diselenide containing star-shaped 3s-PCL-SeSe-PEG-Biotin (s-PMs) with enhanced serum stability due to the entanglement of the branched segments of the CP. 3s-PCL-SeSe-PEG-Biotin would undergo self-directed clustering to form uniformly distributed s-PMs with a hydrodynamic diameter (Dh) of 76.27 nm. The s-PMs experienced appreciable doxorubicin (DOX)-loading content (DLC) and EE, 5.83 wt.%, and 71.02%, respectively. The blank and DOX-loaded s-PMs (DOX@3s-PCL-SeSe-PEG-Biotin) micelles maintained their structural integrity under 50% FBS and 100-fold PBS confirming their colloidal stability. Moreover, DOX@3s-PCL-SeSe-PEG-Biotin micelles unveiled desirable DOX release in simulated cancer redox pool, ⁓93%, and ⁓79% in 10 mM GSH and 0.1% H2O2, respectively in 72 h. In contrast to blank micelles, DOX@3s-PCL-SeSe-PEG-Biotin selectively suppressed the proliferation of ⁓77% HeLa and ⁓62% MDA-MB-231 cells as compared to ⁓12% of HaCaT cells at 5 µg/mL. Overall, we succeeded in fabricating physiologically stable, long-circulating, cancer-specific, smart, and redox-responsive Se-PMs in the entire project, especially mPEG-P(LA-DSeDEA)-PCL CCMs and 3s-PCL-SeSe-PEG-Biotin s-PMs, that deserve further in vivo investigations in tumor-bearing mice models.

Declaration    i
Acknowledgment    ii
摘要    iii
Abstract    v
List of tables    xvi
List of schemes    xvii
List of Acronyms    xviii
CHAPTER ONE    1
Background    1
1. Anticancer drug delivery    1
2. Redox-responsive nanocarriers for anticancer drug delivery    2
3. Current trends in redox-responsive nanocarriers    2
CHAPTER TWO    4
Literature Review    4
1. Etiology and treatment of cancer    4
2. Nanomedicine and cancer treatment    6
3. Polymeric nanocarriers for drug delivery applications    7
4. Stimuli-responsive polymeric nanocarriers for drug delivery    8
5. Redox sensitive polymeric nanocarriers for anticancer drug delivery    9
6. Selenium-containing redox-responsive polymeric nanocarriers    10
7. Selenium-containing polymeric micelles as drug delivery vehicles    14
7.1. Noncleavable selenium-containing polymeric micelles    15
7.2. Monocleavable diselenide-containing polymeric micelles    17
7.3. Multicleavable selenium-containing polymeric micelles    19
7.4. Selenium-containing crosslinked polymeric micelles    21
8. Research gaps and motivation of the study    24
9. Objectives and outline of the study    26
CHAPTER THREE    28
Fabrication of Redox-Responsive Bi(mPEG-PLGA)-Se2 Micelles for Doxorubicin Delivery    28
1. Introduction    28
2. Materials and Methods    30
2.1. Materials    30
2.2. Methods    31
2.2.1. Synthesis of 3,3'-diselanediyldipropanoic acid (DSeDPA)    31
2.2.2. Synthesis of mPEG-PLGA diblock copolymer    31
2.2.3. Synthesis of Bi(mPEG-PLGA)-Se2 conjugate    32
2.2.4. Characterization    33
2.2.5. Bi(mPEG-PLGA)-Se2 micelle formation and drug loading    33
2.2.6. Determination of critical micelle concentration (CMC)    35
2.2.7. Redox-responsive drug release study    36
2.2.8. Cellular uptake study    37
2.2.9. In vitro cytotoxicity and cell viability study    37
3. Results and Discussion    38
3.1. Synthesis of DSeDPA, mPEG-PLGA, and Bi(mPEG-PLGA)-Se2    38
3.2. Preparation and characterization of Bi(mPEG-PLGA)-Se2 micelles    43
3.3. Critical micelle concentration (CMC) of the copolymer    45
3.4. Stability and redox-responsiveness of micelles    47
3.5. Drug loading behavior of Bi(mPEG-PLGA)-Se2 micelles    48
3.6. Drug releasing trends of DOX-loaded Bi(mPEG-PLGA)-Se2 micelles    49
3.7. In vitro cytotoxicity study of Bi(mPEG-PLGA)-Se2 micelles    51
3.8. Cellular uptake of DOX-loaded Bi(mPEG-PLGA)-Se2 micelles    52
3.9. In vitro cell viability of DOX-loaded micelles    56
4. Conclusion    58
CHAPTER FOUR    60
Fabrication of Core Crosslinked Polymeric Micelles as Nanocarriers for Doxorubicin Delivery: Self-Assembly, In Situ Diselenide Metathesis and Redox-Responsive Drug Release    60
1. Introduction    60
2. Materials and methods    63
2.1. Materials    63
2.2. Methods    63
2.2.1. Synthesis of BLA-NCA    63
2.2.2. Synthesis of mPEG-PBLA    65
2.2.3. Synthesis of mPEG-PBLA-PCL    66
2.2.4. Synthesis of mPEG-PLA-PCL    66
2.2.5. Synthesis of mPEG-P(LA-DSeDEA)-PCL    67
2.2.6. Characterization    67
2.2.7. Preparation of mPEG-P(LA-DSeDEA)-PCL micelles    68
2.2.8. Determination of critical micelle concentration (CMC)    69
2.2.9. Preparation of DOX-loaded mPEG-P(LA-DSeDEA)-PCL micelles    69
2.2.10. Redox-responsiveness DOX releasing behavior of micelles    71
2.2.11. Cellular uptake study    72
2.2.12. Flow cytometry analysis    73
2.2.13. In vitro cytotoxicity study    73
3. Results and Discussion    74
3.1. Synthesis and characterization of copolymers    74
3.2. Self-assembly and preparation of core cross-linked polymeric micelles    79
3.3. Determination of critical micelle concentration (CMC)    81
3.4. Colloidal stability of blank and DOX-loaded micelles    83
3.5. Redox sensitivity of mPEG-P(LA-DSeDEA)-PCL micelles    84
3.6. Drug loading behavior of mPEG-P(LA-DSeDEA)-PCL micelles    86
3.7. Drug releasing trends of mPEG-P(LA-DSeDEA)-PCL of micelles    88
3.8. Cellular uptake and localization study    90
3.9. In vitro cytotoxicity of blank mPEG-P(LA-DSeDEA)-PCL micelles    96
3.10. In vitro cell viability of DOX-loaded micelles    97
CHAPTER FIVE    101
Biotin-Decorated Redox-Responsive Micelles from Diselenide-Linked Star-Shaped Copolymers for The Targeted Delivery and Controlled Release of Doxorubicin in Cancer Cells    101
1. Introduction    101
2. Materials and Methods    104
2.1. Materials    104
2.2. Methods    105
2.2.1. Synthesis of star-shaped PCL (3s-PCL)    105
2.2.2. Synthesis of 3,3'-diselanediyldipropanoic acid (DSeDPA)    105
2.2.3. Synthesis of diselenide functionalized 3s-PCL-SeSe    107
2.2.4. Synthesis of diselenide-linked 3s-PCL-SeSe-PEG    107
2.2.5. Synthesis of diselenide-linked 3s-PCL-SeSe-PEG-Biotin    108
2.2.6. Characterization    108
2.2.7. Preparation of blank and DOX-loaded 3s-PCL-SeSe-PEG-Biotin    109
2.2.8. Determination of critical micelle concentration of 3s-PCL-SeSe-PEG-Biotin    111
2.2.9. Colloidal stability of blank and DOX@3s-PCL-SeSe-PEG-Biotin micelles    112
2.2.10. Redox-responsiveness and DOX releasing studies    112
2.2.11. Cellular uptake study    113
2.2.12. In vitro cytotoxicity study    114
3. Results and Discussion    115
3.1. Characterization of 3s-PCL-SeSe-PEG-Biotin conjugate    115
3.2. Self-assembly of blank and DOX-loaded 3s-PCL-SeSe-PEG-Biotin micelles    119
3.3. Determination of CMC of 3s-PCL-SeSe-PEG-Biotin    122
3.4. Colloidal stability of blank and DOX@3s-PCL-SeSe-PEG-Biotin micelles    123
3.5. Redox-sensitivity of 3s-PCL-SeSe-PEG-Biotin micelles    126
3.6. Redox-responsive DOX releasing trend of DOX@3s-PCL-SeSe-PEG-Biotin    128
3.7. Cellular uptake of DOX@3s-PCL-SeSe-PEG-Biotin micelles    130
3.8. In vitro cytotoxicity and anticancer effects    136
4. Conclusion    138
CHAPTER SIX    140
General summary and future perspectives    140
1. Summary    140
2. Future perspectives and recommendations    142
References:    144
APPENDIX: A    175
APPENDIX: B    182
APPENDIX: C    185


                                

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