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研究生:Yitayal Admassu Workie
研究生(外文):Yitayal Admassu Workie
論文名稱:用於治療氣體和多種藥物遞送系統的碳聚合物納米複合材料的合成與表徵
論文名稱(外文):Synthesis and Characterization of Carbon-Polymer Nanocomposites for Therapeutic Gas and Multidrug Delivery Systems
指導教授:今榮東洋子
指導教授(外文):Toyoko Imae
口試委員:今榮東洋子氏原真樹吳嘉文詹正雄何明樺
口試委員(外文):Toyoko ImaeMasaki UjiharaChia-Wen WuJeng-Shiung JanMing-Hua Ho
口試日期:2019-10-22
學位類別:博士
校院名稱:國立臺灣科技大學
系所名稱:應用科技研究所
學門:自然科學學門
學類:其他自然科學學類
論文種類:學術論文
論文出版年:2019
畢業學年度:108
語文別:英文
論文頁數:176
中文關鍵詞:碳聚合物靶向藥物輸送系統奈米複合材料治療氣體一氧化氮氧化石墨烯氟化聚乙二醇OH封端的樹枝狀大分子五氟丙酸抗菌活性大腸桿菌金黃色葡萄球菌載體藥物釋放單壁奈米角吉西他濱阿黴素熱重分析
外文關鍵詞:Carbon-polymerTargeted drug delivery systemNanocompositesTherapeutics gasNitric oxideGraphene oxideFluorinated poly(ethylene glycol)OH terminated dendrimerPentafluoropropionic acidAnti-bacterial activityEscherichia coliStaphylococcus aureusOxygenLoadingReleasingSingle walled nanohornGemcitabineDoxorubicin
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靶向藥物遞送系統(Targeted drug delivery system)是一種新穎且具有用途的技術,已被用於通過增加生物利用度(bioavailability),藥物在特定部位的蓄積並減少副作用來克服當前治療的局限性。目前,迫切且未滿足的對奈米載體的需求,以有效並安全地輸送治療性氣體和藥物。這項研究評估用於治療性氣體和多種藥物的輸送系統基於碳聚合物的奈米複合材料的合成,表徵及其各自的應用。總結了三個主要的研究領域。

在第一項研究工作中,我們準備了有效的一氧化氮(NO)節約型氧化石墨烯(GO)平台,並通過非共價官能化將其與氟化聚乙二醇(F-PEG)製成複合材料。 當研究摻雜在GO和F-PEG@GO上的NO氣體的持久性3小時後,保守的NO氣體載體分別從49.00±7.06降至2.17±1.36 nmol/mg,從58.51±6.02降至4.58±2.22 nmol/mg 。F-PEG在GO上的吸附以及NO在GO和F-PEG@GO上的摻雜可以通過GO片之間的距離增加來確定,而NO的摻雜也可以通過紅外吸收和X射線光電子能譜來闡明。守恆NO的F-PEG@GO抗菌效果比守恆NO 的GO高,並且對金黃色葡萄球菌(Staphylococcus aureus)的抗藥性相較於大腸桿菌(Escherichia coli)更有效。顯然,在GO上塗覆F-PEG對於提高NO氣體的負載效率,穩定性和生物醫學功效是優良的。
此研究的第二部分是用單壁碳奈米角(SWCNH),氧化石墨烯(GO),氮摻雜單壁碳官能化功能化氟化聚乙二醇(F-PEG)和五氟丙酸附著的樹枝狀聚合物(F-Den)奈米角(N-SWCNH),以製備F-PEG@SWCNH,F-PEG @ GO,F-PEG@N-SWCNH,F-Den@N-SWCNH和F-PEG@F-Den@N-的複合材料SWCNH作為有效的氧氣輸送系統。測量SWCNH,F-PEG@SWCNH,GO,F-PEG@GO的氧氣保留效率24小時,最大保留量分別為26.64μg/mg,58.67μg/mg,30.16μg/mg,54.62μg/mg。此外,N-SWCNH(37.43μg/mg),F-PEG@SWCNH(59.15μg/mg),F-Den@N-SWCNH(52.44μg/mg)和F-PEG@F-Den@N-SWCNH(79.22μg/ mg)的攝氧能力在48小時的測量中觀察。參數中研究了載體(SWCNH,F-PEG@SWCNH,GO和F-PEG@GO)的體外釋氧行為。由於F-PEG的氣體溶解作用和表面形態變化的結果,複合材料F-PEG@SWCNH和F-PEG@GO顯示出較慢的氧釋放行為。所製備的製劑可能具有用於氧氣輸送系統的潛力,顯示出隨著時間的推移緩慢地存儲和釋放氣體的能力。

在最後一項研究工作中,聚乙二醇與酸處理的單壁碳奈米角(SWCNH-COOH)共價官能化,作為吉西他濱(GCT)和阿黴素(DOX)的新型pH響應共遞送系統(co-delivery system)。有趣的是結果顯示SWCNH-COOH和PEG@SWCNH分別可以裝載GCT(32.26%和43.43%)和DOX(40.91%和59.10%)。這顯示了透過通過強大的π-π*堆積和氫鍵結合顯示出高載藥效率。(GCT@DOX)載藥SWCNH-COOH(18.41%&30.85%)和PEG@SWCNH(30.85%&40.95%)。展現SWCNH-COOH和PEG@SWCNH是共遞送系統的GCT和DOX的潛在載體。但是,由於PEG鏈上存在其他藥物,因此與SWCNH-COOH相比,複合PEG@SWCNH具有更高的載藥能力。體外藥物釋放實驗表明,SWCNH-COOH和PEG@SWCNH對GCT和DOX均表現出控制釋放的方式,並且兩種藥物在腫瘤環境(pH 5.5)和生理(pH 7.4)下同時釋放。此外,SWCNH-COOH和PEG@SWCNH的藥物釋放方式幾乎相同。因此,該共同遞送系統可以提供雙重療法與封裝的藥物協同治療癌症的協同遞送的新方法。
Targeted drug delivery system is a new and promising technique which has been used to overcome the present therapeutic limitation by increasing bioavailability, accumulation of drug at a specific site and reduce side effect. Currently, there is an urgent and unmet need of nanocarrier for delivery of therapeutics gas and multidrug efficiently and safely. This study, evaluates synthesis, characterization and their respective application of carbon polymer based nanocomposites for therapeutics gas and multidrug delivery system. There are three major areas of study undertaken as summarized below.

In the first work, we prepared effective nitric oxide (NO) conserving platforms of graphene oxide (GO) and it’s composite with fluorinated poly (ethylene glycol) (F-PEG) by non-covalent functionalization. When the persistence of NO gas doped on GO and F-PEG@GO was investigated for 3 h, the conserved NO gas decreased from 49.00±7.06 to 2.17±1.36 nmol/mg carrier and from 58.51± 6.02 to 4.58±2.22 nmol/mg carrier, respectively. The adsorption of F-PEG on GO and the doping of NO on GO and F-PEG@GO were declarative by the increase of distance between GO sheets, and the NO-doping was also clarified by infrared absorption and X-ray photoelectron spectroscopies. The anti-bacterial effect was higher for NO-conserved F-PEG@GO than for NO-conserved GO and more effective against Staphylococcus aureus than against Escherichia coli. It is evident that the coating of F-PEG on GO is preferable for advancing the loading efficiency, the stability and the biomedical efficacy of NO gas.

On the second part of the study, F-PEG and fluorinated dendrimer (F-Den) were functionalized with single walled carbon nanohorn (SWCNH), graphene oxide (GO), nitrogen doped SWCNH (N-SWCNH), to prepare the composites of F-PEG@SWCNH, F-PEG@GO, F-PEG@N-SWCNH, F-Den@N-SWCNH and F-PEG@F-Den@N-SWCNH as an effective oxygen delivery system. The maximum oxygen conservation of SWCNH, F-PEG@SWCNH, GO and F-PEG@GO at 24 h was 26.64 μg/mg, 58.67 μg/mg, 30.16 μg/mg and 54.62 μg/mg respectively. Moreover, the oxygen uptake capacity of N-SWCNH (37.43 μg/mg), F-PEG@N-SWCNH (59.15μg/mg), F-Den@N-SWCNH (52.44 μg/mg) and F-PEG@F-Den@N-SWCNH (79.22 μg/mg) was observed during 48h. The existence of F-PEG and dendrimer in the composite, F-PEG@SWCNH, F-PEG@GO, F-PEG@N-SWCNH, F-Den@N-SWCNH and F-PEG@F-Den@N-SWCNH cause to intensify the oxygen uptake efficiency. The prepared formulations might be potential used for oxygen gas delivery system showing the ability to store and release gas slowly over time.

In our last work, poly (ethylene glycol) was covalently functionalized with acid treated single wall carbon nanohorn (SWCNH-COOH) as a novel, pH responsive co-delivery system of gemcitabine (GCT) and doxorubicin (DOX). Intriguingly, SWCNH-COOH and PEG@SWCNH could load GCT (32.26% & 43.43%) and DOX (40.91% & 59.10%) respectively. These results indicated a high drug loading efficiency via by strong π-π* stacking and hydrogen bonding. The dual (GCT@DOX) drug-loaded SWCNH-COOH (18.41% & 30.85%) and PEG@SWCNH (30.85% & 40.95%) showed that SWCNH-COOH and PEG@SWCNH were potential carriers for GCT and DOX for co-delivery system. In vitro drug release experiment demonstrated that SWCNH-COOH and PEG@SWCNH exhibited a controlled release manner for both GCT and DOX, and the two drugs were released simultaneously at tumor environment pH 5.5 and physiological pH 7.4. Thus, the release manners of drugs from SWCNH-COOH and PEG@SWCNH were almost same. Therefore, this co-delivery system may provide a new approach for delivery of dual chemotherapeutics with an encapsulated drugs to treat cancer.
Abstract..................................................................................................................................................................iv
Acknowledgements ......................................................................................................................................vii
Table of Contents...............................................................................................................................................x
List of Abbreviations.......................................................................................................................................xvi
List of Figures....................................................................................................................................................xix
List of Schemes................................................................................................................................................xxv
List of Tables...................................................................................................................................................xxvi
Chapter 1: Introduction..................................................................................................................................1
1.1. Nanomedicine...........................................................................................................................................1
1.2. Therapeutics Gas and Drug Delivery Systems..............................................................................4
1.2.1. Therapeutics Gas Drug Delivery Systems...............................................................................6
1.2.1.1. Nitric Oxide Delivery System.......................................................................................................6
1.2.1.1.1. Nitric Oxide Based Gas Therapy.........................................................................................6
1.2.1.1.2. Physiological Role of Nitric Oxide.....................................................................................7
1.2.1.1.3. Nitric Oxide Donors................................................................................................................8
1.2.1.1.3.1. N-Diazeniumdiolates Based Nitric oxide Donor.........................................................8
1.2.1.1.3.2. S-Nitrosothiols Based Nitric Oxide Donor....................................................................9
1.2.1.2. Oxygen Delivery System...............................................................................................................9
1.2.1.2.1. Physiological Role of Oxygen.............................................................................................9
1.2.1.2.2. Oxygen Donor Biomaterials..............................................................................................11
1.2.1.2.2.1. Hyperbaric Oxygen Delivery System (HBO2)..............................................................11
1.2.1.2.2.2. Oxygen Generating Materials...........................................................................................11
1.2.1.2.2.3. Oxygen Carrying Materials................................................................................................12
1.2.2. Multi Drug Delivery Systems.....................................................................................................12
1.2.2.1. Combination Chemotherapy....................................................................................................12
1.2.2.2. Co-delivery of Gemcitabine and Doxorubicin.....................................................................13
1.3. Biomaterials...............................................................................................................................................15
1.4. Carbon Based Nanomaterials.............................................................................................................16
1.4.1. Surface Modification of Carbon Nanomaterials ................................................................17
1.4.1.1. Covalent Surface Functionalization.........................................................................................18
1.4.1.2. Non-covalent Surface Functionalization...............................................................................18
1.4.2. Graphene Oxide (GO)....................................................................................................................19
1.4.2.1. Properties of Graphene Oxide (GO)........................................................................................20
1.4.3. Single Walled carbon nanohorn (SWCNH).........................................................................21
1.4.3.1. Properties of Single Walled Carbon Nanohorn (SWCNH)............................................22
1.5. Perfluorocarbons (PFCs).....................................................................................................................23
1.5.1. Properties of Perfluorocarbons (PFCs).................................................................................24
1.6. Poly (Amido Amine) (PAMAM) Dendrimers (Den (OH)).........................................................24
1.7. Poly (Ethylene Glycol) (PEG)...............................................................................................................26
1.7.1. Properties of Poly (Ethylene Glycol).......................................................................................26
Chapter 2: Challenges and Opportunities in Therapeutic Gas and Multi-drug Delivery Systems................................................................................................................................................................27
2.1. Challenges and Opportunities in the Current Therapeutics Gas Delivery System........27
2.2. Challenges and Opportunities in the Current Multi Drug Delivery System.....................28
2.3. Objectives of the Research Work.....................................................................................................28
Chapter 3: Nitric Oxide Gas Delivery by Fluorinated Poly (Ethylene Glycol) @Graphene Oxide Carrier toward Pharmacotherapeutics......................................................................................31
3.1. Motivation.................................................................................................................................................31
3.2. Experimental.............................................................................................................................................32
3.2.1. Materials and Methods.....................................................................................................................32
3.2.1.1. Synthesis of Graphene Oxide (GO).........................................................................................33
3.2.1.2. Preparation of F-PEG@GO Composites................................................................................34
3.2.1.3. Preparation of Griess Assay Reagents....................................................................................35
3.3.1.4. Quantitative Determination of Doped NO Gas by Griess Assay Method.................36
3.2.1.5. Antibacterial Activity Test............................................................................................................37
3.3. Results and Discussion..........................................................................................................................38
3.3.1. Characterization of Composite..................................................................................................38
3.3.2. Nitric Oxide Conservation Measurement..............................................................................45
3.3.3. Brunauer−Emmett−Teller (BET) of GO and F-PEG@GO..................................................46
3.3.4. Effect of NO on FT-IR, XRD and XPS Spectra of GO and F-PEG@GO.........................47
3.3.5. Anti-Bacterial Effect of NO Doped on GO and F-PEG@GO...........................................52
3.4. Conclusions ..............................................................................................................................................54
CHAPETR 4: Fluorinated Poly (Ethylene Glycol) and Dendrimer Attached Single Walled Carbon Nanohorn and Graphene Oxide Composites as an Effective Oxygen Delivery System..................................................................................................................................................................55
4.1. Motivation..................................................................................................................................................55
4.2. Experimental..............................................................................................................................................57
4.2.1. Materials and Methods......................................................................................................................57
4.2.1.1. Synthesis of Nitrogen-Doped Single Walled Carbon Nanohorn (N-SWCNH).......58
4.2.1.2. Synthesis of F-Den@N-SWCNH Composite........................................................................58
4.2.1.3. Preparation of F-PEG@SWCNH, F-PEG@N-SWCNH and F-PEG@F-Den@N-SWCNH Composites.......................................................................................................................................59
4.2.1.4. Conservation of Oxygen...............................................................................................................60
4.3. Results and Discussion...........................................................................................................................61
4.3.1. Characterization of Composites......................................................................................................61
4.3.2.Oxygen Uptake.......................................................................................................................................68
4.3.3.Adsorption Kinetics of Oxygen on carriers..................................................................................70
4.3.3. Effect of oxygen XPS and XRD Spectra of F-PEG@SWCNH and F-PEG@GO...............75
4.3.4. Oxygen Releasing Study....................................................................................................................79
4.4. Conclusions................................................................................................................................................80
CHAPTER 5: Co-delivery of Gemcitabine and Doxorubicin by Single Wall Carbon Nanohorn Functionalized with Poly (Ethylene Glycol) for Enhanced Anti-Cancer Efficacy .................................................................................................................................................................................81
5.1. Motivation...................................................................................................................................................81
5.2. Experimental..............................................................................................................................................83
5.2.1. Materials and Methods......................................................................................................................83
5.2.1.1. Synthesis of Carboxylated Single Walled Carbon Nanohorn (SWCNH-COOH) ……………………………………………………………………………..............................................................................84
5.2.1.2. Esterification of Poly (Ethylene Glycol) with Single Walled Carbon Nanohorn ……………………………………………………………………………........................................................................…..85
5.2.1.3. In vitro Drug Loading...................................................................................................................85
5.2.1.4. In vitro Co-Drugs Loading...........................................................................................................87
5.2.1.5. In vitro Drug Release ....................................................................................................................89
5.2.1.6. In vitro Co-Drugs Release............................................................................................................90
5.3. Results and Discussion...........................................................................................................................90
5.3.1. Characterization of Composites......................................................................................................90
5.3.2. In vitro Drug Loading.......................................................................................................................103
5.3.3. In vitro Co-Drugs Loading..............................................................................................................105
5.3.4. In vitro Drug Release.........................................................................................................................111
5.4. Conclusions..............................................................................................................................................112
CHAPTER 6: General Conclusions and Future Perspectives..........................................................114
6.1. Conclusions..............................................................................................................................................114
6.2. Future Perspectives..............................................................................................................................116
References........................................................................................................................................................118
List of Publication..........................................................................................................................................146
List of Conferences........................................................................................................................................146
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