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研究生：	江翊生 Jiang, Yi-Sheng
論文名稱：	透過加入小分子開發和應用聚癸二酸甘油酯類似物 Development and application of poly(glycerol sebacate) analog by incorporation of small molecules
指導教授：	詹正雄 Jan, Jeng-Shiung
學位類別：	博士 Doctor
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2024
畢業學年度：	112
語文別：	英文
論文頁數：	171
中文關鍵詞：	聚癸二酸甘油酯、高分子膜、奈米顆粒、細菌、鐵離子依賴性細胞死亡
外文關鍵詞：	Poly (glycerol-sebacate), polymer film, nanoparticles, bacteria, ferroptosis
ORCID：	https://orcid.org/0000-0002-5461-0897
相關次數：	點閱：42 下載：1
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聚癸二酸甘油酯(Poly(glycerol-sebacate)，PGS)具有高生物相容性和可調整的機械性質。為了擴大其應用的可能性，在合成過程中引入其他化合物來修改PGS是其中一種製備改質PGS類似物的方法。因此我們使用幾個小分子，包括L-谷氨酸（L-glutamic acid，Glu）、Boc-L-谷氨酸-OH（Boc-Glu-OH）、Z-L-谷氨酸-OH（Z-Glu-OH）、二硫二醇酸（DTG）和二硫二丙酸（DTP）在合成PGS的反應液中被加入。合成出的高分子被進一步製成高分子膜或奈米顆粒（NPs）。我們的結果表明在引入這些成分後，PGS類似物顯示出不同的機械和物化特性。為了瞭解改質的PGS類似物組成的高分子膜和NPs的生物應用。我們進一步分析聚合物膜和NPs的生物相容性和生物活性。結果顯示，NIH / 3T3細胞在與聚（癸二酸甘油谷氨酸酯）（PGSE）共孵化後可以生長。此外，聚（癸二酸甘油二硫二醇酸酯）（PGSDTG）作為鐵離子納米載體並在癌細胞中引發鐵離子依賴性細胞死亡(Ferroptosis)。此外，PGSDTG和聚（癸二酸甘油二硫二丙酸酯）（PGSDTP）對細菌展示了抗菌活性。綜上所述，我們預期這些改質的PGS類似物將成為可以用於各種應用的多功能生物材料。

PGS is known for its high biocompatibility and tunable mechanical properties. To broaden its applications, Modification of PGS by incorporation of other compounds during synthesis is one method to prepare modified PGS analog. Herein, small molecules, including L-glutamic acid (Glu), Boc-L-glutamic acid-OH (Boc-Glu-OH), Z-L-glutamic acid-OH (Z-Glu-OH), dithiodiglycolic acid (DTG) and dithiodipropionic acid (DTP) were incorporated into PGS and were further fabricated into polymeric films or nanoparticles (NPs). Our results demonstrated that PGS analog showed different mechanical and physicochemical properties after incorporation of these components. To understand bio-application of polymeric films and NPs, which composed of modified PGS analogs. The bio-compatibility and bio-activity of polymeric films and NPs were investigated. The results showed that NIH/3T3 cells could grow after co-incubation with poly(glycerol-sebacate-glutamate) (PGSE). Also, poly(glycerol-sebacate dithiodiglycolate) (PGSDTG) served as an iron ion nano-carrier and induced ferroptosis in cancer cells. Additionally, PGSDTG and poly(glycerol-sebacate-dithiodipropionate) (PGSDTP) exhibited anti-bacterial activity against bacteria. In conclusion, we anticipate that these modified PGS analogs would become multi-functional biomaterials that can be used in a variety of applications.

Abstract	iii
摘要	iv
誌謝	v
目錄	vi
List of Tables	x
List of Figures	xi
Abbreviation	xvii
Chapter 1 Introduction	1
1 Background	1
2 Poly(glycerol-sebacate)	3
3 Current modifications of preparing PGS analog	4
4 Motivation	5
Chapter 2 Experimental methods	7
1 Materials	7
2 Synthesis and purification of poly(glycerol-sebacate) and poly(glycerol sebacate) analog	9
2.1 Characterization of prepolymers	12
3 Preparation and characterization of polymer films	13
3.1 FTIR spectroscopy	14
3.2 Thermal properties	14
3.3 Mechanical testing	15
3.4 Measurement of water contact angle	15
4 Preparation and characterization of NPs	16
4.1 Nanoprecipitation	16
4.2 Dynamic Light Scattering (DLS)	17
4.3 Transmission electron microscopy (TEM)	17
5 Statistical analysis	18
Chapter 3 Incorporation of Glutamic Acid or Amino-Protected Glutamic Acid into Poly(glycerol-sebacate): Synthesis and Characterization	19
1 Chapter abstract	19
2 Chapter introduction	20
3 Materials and method	23
3.1 Materials	23
3.2 In vitro enzymatic degradation	23
3.3 Cytocompatibility	24
4 Results and Discussion	25
5 Chapter conclusion	34
Chapter 4. Poly(glycerol-sebacate) analog acquires lipase resistant and anti-bacterial activity through incorporation of DTG	35
1 Chapter abstract	35
2 Chapter introduction	35
3 Materials and method	39
3.1 Materials	39
3.2 Swelling test	39
3.3 In vitro degradation test	40
3.4 Bio-compatibility and bio-activity analysis	40
3.4.1 Cytotoxicity test	41
3.4.2 Antibacterial activity analysis	42
4 Results and Discussion	44
4.1 Chemical structure of PGSDTG prepolymers	44
4.2 Chemical structure of PGSDTG polymer film	46
4.3 Incorporation of DTG reduced thermal stability of film specimen	47
4.4 Mechanical properties of PGSDTG	50
4.5 Incorporation of DTG increased hydrophilicity of film specimen	51
4.6 The film specimens showed tunable lipase resistance and were disintegrated by GSH after incorporation of DTG	52
4.7 The film specimens acquired antibacterial activity after introduction of DTG	56
5 Chapter conclusion	62
Chapter 5 GSH/pH-sensitive poly(glycerol-sebacate-dithiodiglycolate) nanoparticle as a ferroptotic inducer through cooperation with Fe3+	64
1 Chapter abstract	64
2 Chapter introduction	65
3 Materials and method	68
3.1 Materials	68
3.2 Degradation properties of NPs in neutral or acidic condition with GSH	69
3.3 Preparation and characterization of metal ion in NPs	69
3.3.1 ICP-MS	70
3.3.2 Quantification of Fe3+ in NPs	70
3.4 Biocompatibility of NPs	71
3.4.1 Hemolysis assay	71
3.4.2 Cytocompatibility assay	72
3.5 Anti-bacterial effect of PGSDTG6 NPs against S. aureus in vitro and vivo	72
3.6 Ferroptotic effects analysis in vitro and vivo	74
3.6.1 Cytotoxicity assay	75
3.6.2 Examination of ROS level	76
3.6.3 Iron staining	76
3.6.4 GSH, GSSG level and GSH/GSSG ratio analysis	76
3.6.5 Expression of ferroptosis markers	77
3.6.6 Ferroptotic effect in organoid.	78
3.6.7 Aversion test in C. elegans	78
3.6.8 Lifespan analysis in C. elegans	78
3.6.9 Iron staining in C. elegans	79
4 Results and Discussion	79
4.1 Successful incorporation of DTG into PGS analogs	79
4.2 PGSDTG formed NPs in aqueous solution	83
4.3 PGSDTG6 NPs were sensitive to GSH and pH in solution	86
4.4 PGSDTG6 NPs were biocompatible and showed anti-bacterial activity against S. aureus	87
4.5 PGSDTG6 NPs were promised metal ion nanocarrier	90
4.6 Cell death induced by NPs was inhibited by ferroptotic inhibitors in vitro	95
4.7 NPs induced ferroptosis	97
4.8 NPs increased intracellular GSSG levels and reduced GPX4 expression in cells	104
4.9 NPs induced ferroptosis in cell organoid and C. elegans	107
5 Chapter Conclusion	111
Chapter 6 Fe2+/Poly(glycerol-sebacate-dithiodipropionate-sulfone)  showed anti-bacterial activity against Klebsiella pneumoniae	112
1 Chapter abstract	112
2 Chapter introduction	113
3 Materials and method	114
3.1 Materials	114
3.2 Modification of PGSDTP	115
3.3 Measurement of encapsulated metal element in NPs	115
3.4 Bio-compatibility and activity analysis	115
3.4.1 Hemolysis assay	115
3.4.2 Anti-bacterial activity analysis in vitro	116
3.4.3 Anti-bacterial activity analysis in vivo by using C. elegans	117
4 Results and Discussion	118
4.1 DTP was successfully incorporated into PGS	118
4.2 Modification of PGSDTP by sodium hypochlorite solution promoted the encapsulation of ferrous ions	119
4.3 Hemocompatibility of NPs on erythrocytes	124
4.4 Fe2+/PGSDTPSO NPs showed antibacterial activity against K. pneumoniae	125
5 Chapter conclusion	128
Chapter 7 Conclusion and Recommendation	130
Chapter 8 Reference	131
Chapter 9 Appendix	145
                                    

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