Biodegradable and pH-Responsive Nanoparticles for the Triggered Release of Antibiotics to Infected Wounds

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姓名

林妙玲(Lam Dieu Linh) 查詢紙本館藏

畢業系所

生醫科學與工程學系

論文名稱

(Biodegradable and pH-Responsive Nanoparticles for the Triggered Release of Antibiotics to Infected Wounds)

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摘要(中)

傷口感染已成為全球性的經濟負擔。目前，傷口照護方法以使用抗生素為主，然而過度使用抗生素容易導致細菌產生抗藥性，且新抗生素研發的速度趕不上抗藥性產生的速度。因此，本研究使用聚琥珀酰亞胺(Polysuccinimide, PSI)開發出具酸鹼應答性且生物可降解性之奈米粒子，並以酸鹼調控抗生素釋放。本研究使用酸鹼應答性之11-氨基十一酸(11-aminoundecanoic acid, AUA)官能化部分的PSI，形成隨機兩性共聚物 (random amphiphilic copolymers, PA)。PA以奈米沉澱法於水溶液中形成奈米粒子，並裝載疏水性的抗生素-立放黴素(Rifampicin, Rif)於疏水性的核心中。AUA上的羧基之酸解離常数(pKa)為4.55。因此，於微酸性無感染傷口中，AUA上的羧基為非離子型，此時PA的碳氫鏈緊密地排列將藥物包埋於奈米粒子中。然而由於細菌增生，導致傷口表面的酸鹼值高於7時，AUA被去質子化導致奈米粒子拆解，同時PSI上的疏水結構也被水解，導致抗生素釋放。最終，殘餘水溶性且具生物可降解性的聚（天冬氨酸）(poly(aspartic acid))衍生共聚物於傷口中。
本研究合成三種PA奈米粒子，PA5、PA10、PA25，對應5%、10%、25%莫爾濃度的AUA官能化於PSI，並藉由混濁度與滴定法進行PA奈米粒子的酸鹼響應性鑑定，結果顯示抗生素於酸鹼值5有最低釋放量，而抗生素於酸鹼值7.5增加釋放量。為了證實PA對環境的友善性，PA的可降解性以化學需氧量(Chemical oxygen demand, COD)與凝膠層析滲透儀(Gel Permeation Chromatography, GPC)進行評估。除此之外，本研究將PA與傷口敷料結合，結果顯示結合PA的傷口敷料具有優秀的酸鹼調控抗生素釋放特性，且具有顯著的殺菌效果。因此，本研究開發以酸鹼值調控抗生素釋放之奈米粒子可減緩抗生素濫用的情況，並對治療傷口感染做出貢獻。
關鍵字: 奈米粒子、生物可降解性、酸鹼觸發釋放、抗生素、傷口敷料

摘要(英)

Wound infection has become a health economic burden in the world. Current wound treatment approaches are mostly achieved by using antibiotics. However, the widespread and excessive using antibiotics even without evidence of infection easily causes antibiotic resistance. The new antibiotic productions decline while the elevated antibiotic resistance. Here, we introduce the pH-responsive and biodegradable nanoparticles (NPs) for the pH-triggered release of antibiotics using polysuccinimide (PSI), a forerunner of biodegradable poly(aspartic acid) was functionalized with a pH-responsive amine, 11-aminoundecanoic acid (AUA), to produce random amphiphilic copolymers (PA). The nanoparticle of PA copolymer was formed by the nanoprecipitation method in an aqueous solution and was loaded with hydrophobic antibiotic Rifampicin (Rif) in hydrophobic cores. pKa (COOH) of 4.55 has been determined for 11-aminoundecanoic acid. Therefore, at a slightly acidic pH value of non-infected wounds, the carboxylic groups exist in non-ionic form, the hydrocarbon chains were packed tighter, then the nanoparticles remain and keep the drugs inside. When wound pH value elevates above pH 7 due to proliferation of bacteria, AUA segments were deprotonated leading to disassemble and release drug component, also the hydrolysis of the PSI’s hydrophobic succinimide parts. Finally, the residue was the water-soluble and biodegradable poly(aspartic acid) (PASP) derivative copolymer.
In this study, we synthesized PA5, PA10, and PA25 corresponding to 5%, 10%, and 25% AUA functionalized molarity to PSI. The pH-responsive properties were reviewed by turbidity and titration methods. The drug release from the release test displayed that a minimal at acidic pH = 5.0 but amplified at alkaline pH = 7.5. To demonstrate the environmentally friendly property, their degradation assays were conducted using the Chemical oxygen demand and GPC measurements. Moreover, the coordination with wound dressing materials has been carried out. The results revealed the outstanding selected pH-responsive release of drugs after combination with wound dressing with excellent antibacterial properties. Therefore, this material has become a potential candidate for antibiotic stimulus-responsive release in infected wound treatments, contributing mitigation of exessive using antibiotics.
Keywords: Nanoparticles, biodegradable, pH-triggered release, antibiotics, wound dressing combination.

關鍵字(中)

★ 奈米粒子
★ 生物可降解性
★ 酸鹼觸發釋放
★ 抗生素
★ 傷口敷料

關鍵字(英)

★ Nanoparticles
★ biodegradable
★ pH-triggered release
★ antibiotics
★ wound dressing combination

論文目次

TABLE OF CONTENTS
CHINESE ABSTRACT I
ABSTRACT II
TABLE OF CONTENTS IV
LIST OF FIGURES VIII
LIST OF TABLES XII
LIST OF ABBREVIATIONS XIII
CHAPTER I: INTRODUCTION 1
1.1. Overview. 1
1.2. Wounds. 4
1.2.1. Skin structure. 4
1.2.2. Wounds and wound infections. 5
1.3. Driving forces for nanoparticle formation. 8
1.3.1. Electrostatic interactions. 9
1.3.2. Hydrophobic effect. 9
1.3.3. Hydrogen bonding. 9
1.3.4. Van der Waals forces. 10
1.3.5. Coordination interactions. 10
1.3.6. π−π interactions. 10
1.4. Nanoparticle preparation strategies. 11
1.4.1. Self-assembly. 11
1.4.1.1. Nanoprecipitation. 11
1.4.1.2. Coordination. 13
1.4.1.3. Thin-Film Hydration. 14
1.4.2. Microemulsion. 15
1.4.3. Particle Replication in Nonwetting Templates (PRINT). 16
1.4.4. Electrospraying. 17
1.4.5. Microfluidics. 18
1.5. Nanomaterials employed for wound therapy. 19
1.5.1. Nanoparticles in wound therapy. 19
1.5.1.1. Non-polymeric nanoparticles. 19
1.5.1.2. Polymeric nanomaterials. 20
1.5.1.2.1. Natural polymers 21
1.5.1.2.2. Synthetic polymers. 21
1.5.2. Stimulus factors for the intelligent response of nanoparticles in wound therapy. 22
1.5.2.1. Bacterial toxins and enzymes. 22
1.5.2.2. pH changes. 23
1.5.2.3. Light. 23
1.5.3. Nanoparticle-based scaffolds: combination strategies. 24
1.5.3.1. Nanoparticle-based nanofibrous structures. 24
1.5.3.2. Nanoparticle-based hydrogels. 24
1.5.3.3. Nanoparticle-based films or membranes. 25
1.5.3.4. Nanoparticle-based multi-components. 25
1.6. Polysuccinimide and functional polyaspartamide based materials. 26
1.6.1. Overview. 26
1.6.2. Polysuccinimide (PSI) synthesis. 28
1.6.3. Functionalization of Polysuccinimide. 28
1.6.3.1. Thiols modification. 30
1.6.3.2. Long alkyl chain combinations. 30
1.6.3.3. Combination with imaging agents. 31
CHAPTER II: RESEARCH OBJECTIVES 32
CHAPTER III. MATERIALS AND METHODS 34
3.1. Materials. 34
3.1.1. Chemicals. 34
3.1.2. Instruments. 35
3.2. Synthesis. 35
3.2.1. Polysuccinimide (PSI) synthesis procedure. 35
3.2.2. Synthesis of AUA-functionalized polysuccinimide copolymers (PAs). 36
3.3. Experimental method. 37
3.3.1. Characterizations. 37
3.3.1.1. Hydrogen-1 Nuclear Magnetic Resonance Spectrometer (1H-NMR). 37
3.3.1.2. Attenuated Total Reflectance-Fourier Transform Infrared spectrum (ATR-FTIR) measurement. 37
3.3.1.3. Gel permeation chromatography (GPC) measurement. 37
3.3.2. Preparation of PA Nanoparticles (PA-NPs) and Rifampicin-Loaded PA Nanoparticles (Rif-PA-NPs). 37
3.3.3. Dynamic light scattering (DLS) and zeta-potential measurement. 39
3.3.4. Turbidity study. 39
3.3.5. Titration study. 39
3.3.6. pH-responsive casting test. 40
3.3.7. In vitro release study. 40
3.3.8. Antimicrobial activity test. 40
3.3.8.1. Bacterial minimum inhibitory concentration (MIC) determination and minimum bactericidal concentration (MBC). 40
3.3.8.2. Antibacterial plate counting assay. 41
3.3.8.3. Antibacterial release test. 42
3.3.9. Biodegradability test. 42
3.3.9.1. Degradation evaluation by Gel permeation chromatography (GPC). 42
3.3.9.2. Chemical demand oxygen (COD) measurement. 43
3.3.10. Cytotoxicity test. 44
3.3.11. Modification of gauze bandages with PA copolymers containing rifampicin (Rif-PA-Ban). 44
3.3.11.1. The combination PAs containing drugs on the gauze bandages. 44
3.3.11.2. In vitro release study of drug-loaded gauze bandages. 45
3.3.11.3. Antibacterial assay. 46
CHAPTER IV: RESULTS AND DISCUSSION 47
4.1. Polysuccinimide (PSI) synthesis and characterization. 47
4.2. Synthesis and characterization of AUA-functionalized polysuccinimide copolymers (PA). 48
4.3. Characteristics of the PA nanoparticles (PA-NPs). 53
4.3.1. Dynamic light scattering (DLS) and zeta-potential measurement. 53
4.3.2. Turbidity study. 56
4.3.3. Titration study. 58
4.3.4. pH-responsive casting test. 59
4.3.5. Rifampicin-Loaded PA Nanoparticles (Rif-PA-NPs). 61
4.4. In vitro release study. 62
4.5. Antimicrobial activity test. 64
4.5.1. Bacterial minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) determination. 64
4.5.2. Antibacterial plate counting assay. 65
4.5.3. Antibacterial release test. 68
4.6. Biodegradability test. 69
4.6.1. Degradation evaluation by Gel permeation chromatography (GPC). 69
4.6.2. Chemical demand oxygen (COD) measurement. 71
4.7. Cytotoxicity test. 73
4.8. Modification of gauze bandages with PA copolymers containing rifampicin. 74
4.8.1. The combination PAs containing drugs on the gauze bandages (Rif-PA-Ban). 74
4.8.1.1. Scanning Electron Microscopy (SEM) analysis. 74
4.8.1.2. Drug loading capacity of the gauze bandages. 75
4.8.2. In vitro release study of drug-loaded gauze bandages. 76
4.8.3. Antibacterial assay. 78
CHAPTER V: CONCLUSION 80
CHAPTER VI: FUTURE PERSPECTIVES 81
REFERENCES: 82

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指導教授

黃俊仁李宇翔

審核日期

2022-1-19

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