Stimuli-Responsive Polymers Based Therapeutic Approaches for Enhanced Anti-Metastasis, Antitumor and Wound Healing

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研究生：	Abegaz Tizazu Andrgie Abegaz Tizazu Andrgie
論文名稱：	Stimuli-Responsive Polymers Based Therapeutic Approaches for Enhanced Anti-Metastasis, Antitumor and Wound Healing Stimuli-Responsive Polymers Based Therapeutic Approaches for Enhanced Anti-Metastasis, Antitumor and Wound Healing
指導教授：	蔡協致 Hsieh-Chih Tsai
口試委員:	陳建光 Jem-Kun Chen 邱信程 Hsin-Cheng Chiu 何明樺 Ming-Hua Ho 游佳欣 Jiashing Yu 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：	2020
畢業學年度：	108
語文別：	英文
論文頁數：	186
中文關鍵詞：	肝素、水膠、轉移、前驅藥物、刺激應答、熱敏性
外文關鍵詞：	heparin, hydrogel, metastasis, prodrugs, stimuli-responsive, thermo-sensitive
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摘要
癌症是一個細胞異常增生且不受控制所衍生之疾病，而對於癌症病患而言有90%的死亡是因癌細胞轉移。另外傷口是由於受傷或是手術，造成組織之結構與功能之破壞。傷口癒合不良與癌症轉移在臨床治療上常導致嚴重後果。也因此經有已有針對上述病因問題所開發出治療方法。為了達到長效之治療目的，設計可控制的藥物釋放載體在治療上是不可或缺的。目前已經有多種生物材料被設計為控制藥物釋放的載體。由於癌症附近的高滲透性，可藉由水膠與奈米粒子作為輸送蛋白質，多肽、藥物小分子和細胞至腫瘤區，高分子奈米顆粒已廣泛研究用於抗腫瘤藥物輸送，而水膠所包覆之藥劑並可以用作長時間持續釋放之載體。水膠可根據對人體的傳遞途徑而形成巨觀材料或微米及奈米之尺寸粒子。而水膠可透過外科植入、局部或全身注射而被引入體內。手術植入會引起患者不適和與手術相關的風險，而全身性注射可能使藥物載體暴露於免疫系統及降解酶中。為了獲得預期的治療結果並克服上述問題，人們越來越關注於局部水膠遞送系統和奈米藥物載體的應用。本文製備了原位熱敏性聚合物和氧化還原反應奈米粒子前驅藥物，以用於增強抗腫瘤，抗轉移和傷口癒合活性的藥物的傳遞。
第一項研究中我們使用一非抗凝肝素(heparin)作為前藥，並使用(poly‐(ε‐caprolactone‐co‐lactide) ‐b‐poly (ethylene glycol) ‐b‐poly(ε‐caprolactone‐co‐lactide)高分子水膠包覆藥物，設計了感溫型生物降解水膠，預期透過注射的方式來局部抑制癌細胞擴散。高分子水膠會透過酯化反應和肝素結合，並透過肝素的水解來達到長時間釋放藥物的效果，此高分子水溶液於25℃時會呈溶液狀，並在人體溫度37℃時凝膠。本研究設計了體內與體外實驗來觀察水膠的抗轉移效用，結果顯示，注射此水膠可有效的抑制癌細胞的轉移。第二項研究中，我們開發一款由肝素與聚（N-異丙基丙烯酰胺）(Poly(N-isopropylacrylamide),PNIPAM) 形成共軛結構的聚合物，具有注射後於原位形成凝膠及促進傷口癒合的特性，利用此水膠包覆非類固醇消炎藥布洛芬(ibuprofen)，以減輕傷口癒合過程中所產生的疼痛和抑制炎症反應。透過體外實驗證實，由此藥物載體可抑制RAW264.7巨噬細胞株中的促炎介質(NO、PGE2、TNF-α)的產生，來推斷水膠釋放的布洛芬可抑制脂多醣進而抑制炎症，體內實驗則設計控制組及對照組(磷酸鹽緩衝溶液)，透過將水膠覆蓋於傷口，並記錄傷口癒合程度等概況，而包覆布洛芬的組別相較於對照組具有更佳的癒合狀況，結果表明，包覆布洛芬的原位注射水膠有望應用於促進傷口癒合的治療。第三項研究中，我們設計並合成了氧化還原應答含雙硫鍵之雙親性肝素-苯丁酸氮芥(chlorambucil)共軛聚合物前藥，以增強抗腫瘤和抗轉移活性。該共軛前藥可自組裝形成球形囊泡，接枝效率為61.33%。細胞活性測試結果表明，該前藥與正常細胞(HaCaT)具有生物相容性，並選擇性殺死腫瘤細胞（HeLa細胞）。證實了前藥對HeLa細胞的攝取與時間成正比。因此，設計的前藥可以是癌細胞中苯丁酸氮芥的傳遞和控制釋放的潛在候選物。

Abstract
Cancer is a group of diseases characterized by the uncontrolled growth of abnormal cells. The serious and devastating problem in cancer is metastasis, which accounts for 90% of cancer‐associated death. A wound is a break in the integrity of tissues by injury or operation, which may be associated with disruption of the structure and function. From this view, restores the structural integrity of injured tissues is referred to as wound healing. Both cancer and wound healings are major public issues and clinical burden. Especially, impaired healing wounds and metastasis cancer may cause serious complications and difficult for treatment. Different clinical and research efforts have been made to succeed in a convenient treatment formulation for these kinds of problems. Long-acting, controlled, and pathophysiologic specific drug release formulations are much desired and essential in clinical practice. Various biomaterials have been designed as controlled release drug delivery vehicles. Hydrogels and nanoparticles have received special consideration as sustained-release formulation. Polymeric nanoparticles have been widely investigated as promising antitumor-drug vehicles due to enhanced permeability and retention (EPR) effect of the cancerous environments. As the type of delivery approach, hydrogels can also encapsulate and maintain a sustained release of various therapeutic agents, like drugs, protein, polypeptide, other small molecules, and cells. Hydrogels can be formed as macro, micro, and nano sizes according to the requirements of the delivery route into the human body. Hydrogels can be administered into the body through surgical implantation, local or systemic injection. Surgical implantation causes the patient discomfort and the risks associated with surgery whereas, the systemic injection may expose the drugs and carriers to potentially degradative enzymes that degrade both drugs and carriers. To succeed in the desired therapeutic outcomes and overcome these challenges, there has been increasing attention to the employment of hydrogels for localized delivery systems and nanoparticle prodrugs. In this dissertation, in situ gelling thermo-responsive polymers and redox-sensitive nanoparticle prodrugs were fabricated for the delivery of drugs for enhanced antitumor, anti-metastasis and wound healing activity. In the first work, non‐anticoagulant heparin prodrugs were synthesized for metastasis treatment with a localized treatment system using temperature-sensitive, injectable, and biodegradable (poly‐(ε‐caprolactone‐co‐lactide) ‐b‐poly (ethylene glycol) ‐b‐poly(ε‐caprolactone‐co‐lactide) polymeric hydrogel. The esterification conjugation of heparin and polymers was ensured the sustained release of heparin through hydrolysis and followed by polymeric biodegradation. Below 25 ℃ an aqueous solution of the polymers was existed in the sol state but transformed to gel in human body temperature (37 °C.) that is suitable for injection. The anti‐metastasis effect of the hydrogels is investigated both in vitro and in vivo. The results demonstrated that local administration of injectable heparin‐loaded hydrogels effectively promotes an inhibitory effect on cancer metastasis. In the second study, Heparin-conjugated PNIPAM, an injectable, in situ gel-forming polymer were developed and applied to induce wound healing. The non-steroidal anti-inflammatory drug, ibuprofen was encapsulated into the hydrogel to reduce pain and excessive inflammation during healing. An in vitro assay confirmed that the ibuprofen released from the hydrogel were dramatically reduced lipopolysaccharide-induced inflammation by suppressing the production of the proinflammatory mediators NO, PGE2, and TNF-α in RAW264.7 macrophages. An in vivo wound healing assay was conducted out by applying hydrogels to induced wounds. It was verified that ibuprofen-loaded hydrogel improved healing relative to the control group (phosphate-buffered saline). This study indicates that ibuprofen loaded in an injectable hydrogel is a promising candidate for wound healing therapy. In the third work, redox-responsive disulfide bond containing amphiphilic heparin–chlorambucil conjugated polymeric prodrugs were designed and synthesized to enhance antitumor and anti-metastasis activity. The conjugated prodrug can be self-assembled to form spherical vesicles with 61.33% chlorambucil grafting efficiency. The cell viability test results showed that the prodrug was biocompatible with normal cells (HaCaT) and selectively killed tumor cells (HeLa cells). It was confirmed that cellular uptake of prodrugs against HeLa cells increases with time. Therefore, the designed prodrugs can be a potential candidate for the delivery and controlled release of chlorambucil in cancer cells.

Table of Contents
摘要     i
Abstract    iii
Acknowledgment    vi
Table of Contents    vii
List of Figures    xiii
List of Tables    xix
List of Abbreviations    xx
   CHAPTER ONE    1
1.    Introduction    1
2.    Objectives    4
2.1.    General Objective    4
2.2.    Specific Objectives    4
   CHAPTER TWO    5
1.    Literature Review    5
1.1.    Overview of Cancer and Cancer Metastasis    5
1.2.    Wound Healing: An Overview    6
1.3.    Hydrogels    8
1.4.    Classifications of Hydrogels    9
1.5.    Stimuli-Responsive Hydrogels    12
1.6.    Temperature-Responsive    14
1.7.    Types of Thermo-sensitive Hydrogels    16
1.7.1.    Polysaccharide Based Thermo-Sensitive Hydrogels    17
1.7.2.    Heparin and Heparin Derivatives    19
1.7.3.    Polypeptide-Based Hydrogels    21
1.7.4.    Poly (Ethylene Glycol) (PEG)-Polyesters    22
1.7.5.    N-Substituted Acrylamide Based Polymers    24
1.8.    Redox Sensitive Polymers and Nanoparticle Prodrugs    25
1.9.    Biomedical Applications of Thermo-Responsive Hydrogels    26
1.9.1.    Therapeutic Agent Delivery    27
1.9.2.    Cell Therapy and Tissues Regeneration    29
1.9.3.    Postoperative Anti-Adhesive    31
   CHAPTER THREE    33
1.    Non-Anticoagulant Heparin Prodrug Loaded Biodegradable and Injectable Thermo-Responsive Hydrogels for Metastasis Treatment    33
2.    Experimental Section    37
2.1.    Materials    37
2.2.    Synthesis of triBlock Copolymer    38
2.3.    Preparation of Chemically Modified Heparin Derivative    39
2.4.    Synthesis of Hep Conjugated triBLOCK Polymer    40
2.5.    Characterizations of triBLOCK Copolymer and Nac-hep-triBLOCK    41
2.6.    Sol-gel Phase Transition Diagram and Rheological Behavior    41
2.7.    Biodegradation of triBLOCK Polymer    42
2.8.    Release Test of Heparin from Hydrogel    42
2.9.    Cytotoxicity Test    43
2.10.    In vitro Cell Migration Test    44
2.11.    In vivo Anti-Metastasis Model    44
3.    Result and Discussion    45
3.1.    Synthesis of triBLOCK Copolymers    45
3.2.    Preparation of Heparin Derivatives    48
3.3.    Synthesis of Heparin-Conjugated triBLOCK Polymer    50
3.4.    Sol-gel Transition Phase Diagram and Rheological Properties    53
3.5.    Biodegradation of triBLOCK    56
3.6.    Release Test of Heparin from Hydrogel    57
3.7.    In vitro Cytotoxicity Test of Nac-hep-triBLOCK    58
3.8.    Cell Culture Wound Closure Assay    59
3.9.    In vivo Anti-Metastasis Effects    61
4.    Conclusion    64
   CHAPTER FOUR    65
1.    Ibuprofen-loaded injectable hydrogel for inhibiting excessive inflammation and promoting wound healing    65
2.    Experimental Section    69
2.1.    Materials    69
2.2.    NIPAM-NH2 Synthesis    69
2.3.    Heparin-PNIPAM Synthesis    70
2.4.    Characterization of PNIPAM and Hep-PNIPAM Copolymers    71
2.5.    Grafting Efficiency and Ratio    71
2.6.    Hydration Ratio    72
2.7.    Hep-PNIPAM Copolymer Morphology    72
2.8.    Lower Critical Solution Temperature (LCST) and Rheological Behavior    72
2.9.    In Vitro Cytotoxicity Test (MTT Assay)    73
2.10.    Ibuprofen Encapsulation and In Vitro Drug Release    74
2.11.    Anti-Inflammation Assay for Ibuprofen-Loaded Hydrogel    74
2.12.    Animal Experiment    75
3.    Results and Discussion    77
3.1.    Synthesis of Hep-PNIPAM Copolymers    77
3.2.    Grafting Efficiency and Grafting and Hydration Ratios    80
3.3.    Lower Critical Solution Temperature (LCST) and Rheological Behavior    82
3.4.    In Vitro Cytotoxicity Test (MTT Assay)    83
3.5.    Ibuprofen Encapsulation and In Vitro Drug Release    85
3.6.    Effects of IB-Hep-PNIPAM on NO, PGE2, and TNF-Α Production in LPS-Stimulated RAW264.7 Cells    86
3.7.    In Vivo Wound Healing Effects and Healing Rate    88
3.8.    In Vivo Anti-Inflammation Assay on Ibuprofen-Loaded Hydrogel    90
4.    Conclusions    92
   CHAPTER FIVE    93
1.    Redox-Responsive Heparin–chlorambucil Conjugate Polymeric Prodrug for Improved Anti-Tumor Activity    93
2.    Experimental Section    96
2.1.    Materials    96
2.2.    Synthesis of Heparin-Chlorambucil (Hep-Chl)    96
2.3.    Heparin-Chlorbumcil (Hep- Chl) Prodrug Self-Assembled Nanoparticle Preparation  ………………………………………………………………………………………97
2.4.    Characterization of Heparin-Chlorambucil (Hep-Chl) Prodrug    97
2.5.    In Vitro Chlorambucil Release Study    98
2.6.    Cell viability study    98
2.7.    Examination of In Vitro Cellular Uptake Of Hep-Chl Nanoparticles    99
3.    Results and Discussion    100
3.1.    Synthesis of Heparin-Chlorambucil (Hep-Chl)    100
3.2.    Formation of Self-Assembled Prodrugs    105
3.3.    In Vitro Drug Release Studies    108
3.4.    In Vitro Cytotoxicity Study    110
3.5.    In Vitro Cellular Uptake of Hep-Chl Nanoparticles    111
4.    Conclusions    113
   CHAPTER SIX    114
1.    General Summary    114
2.    Recommendation    116
   REFERENCES    118


                                

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