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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 翁啟惠(Chi-Huey Wong) | |
dc.contributor.author | Hsin-Yu Lee | en |
dc.contributor.author | 李信佑 | zh_TW |
dc.date.accessioned | 2021-05-14T17:46:34Z | - |
dc.date.available | 2020-04-20 | |
dc.date.available | 2021-05-14T17:46:34Z | - |
dc.date.copyright | 2015-08-28 | |
dc.date.issued | 2015 | |
dc.date.submitted | 2015-04-24 | |
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dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/4757 | - |
dc.description.abstract | 大部分癌症細胞表面會表現多量的特定醣抗原,Globo H (Fucα1→2Galβ1→ 3GalNAcβ1→ 3Galα1→4Galβ1→ 4Glc)六碳醣是其中一種,以Globo H為基礎的治療疫苗已經在應用在 乳癌、前列腺癌、卵巢癌、胰腺癌、大腸直腸癌及肺癌。在這篇研究中,我們合成一系列Globo H衍生物以提升癌症疫苗的免疫性。Globo H衍生物是由酵素法合成而來並和載體蛋白(CRM) 197 (DT)接合,並搭配C34醣脂類為佐劑(adjuvant)。在注射完Balb/c老鼠實驗,免疫的反應由醣晶片來分析,結果顯示在Globo H還原端六號位上的glucose修飾氟化(F),疊氮基(N3),苯基(phenyl)和在Globo H非還原端六號位上的fucose修飾疊氮基(N3)亦有強烈的IgG免疫球蛋白反應辨認Globo H 和Gb5 和SSEA4。上述的疫苗可以辨認Globo H表現的癌細胞(MCF-7)和具有補體依賴的細胞毒殺能力。由上述資料顯示這樣的化學修飾癌症醣抗原可以促進癌症疫苗的發展。 | zh_TW |
dc.description.abstract | Globo H-based therapeutic cancer vaccines have been tested in clinical trials for the treatment of late stage breast, ovarian and prostate cancers. In this study, we explored Globo H analogue antigens with an attempt to enhance the antigenic properties in vaccine design. The Globo H analogues with modification at the reducing or non-reducing end were synthesized using chemoenzymatic methods, and these modified Globo H antigens were then conjugated with the carrier protein diphtheria toxoid cross-reactive material (CRM) 197 (DT), and combined with a glycolipid C34 as an adjuvant designed to induce a class switch of antibody to form the vaccine candidates. The immune response was studied by a glycan array and the results showed that modification at the C-6 position of reducing end glucose of Globo H with the fluoro, azido or phenyl group elicited robust IgG antibody response to specifically recognize Globo H (GH) and the GH-related epitopes, stage-specific embryonic antigen 3 (SSEA3) (also called Gb5) and stage-specific embryonic antigen 4 (SSEA4). However, only the modification of Globo H with the azido group at the C-6 position of the non-reducing end fucose could elicit strong IgG immune response. Moreover, the antibodies induced by theses vaccines were shown to recognize GH expressing tumor cells (MCF-7) and mediate the complement-dependent cell cytotoxicity against tumor cells. Our data suggest a new potential approach to cancer vaccine development. | en |
dc.description.provenance | Made available in DSpace on 2021-05-14T17:46:34Z (GMT). No. of bitstreams: 1 ntu-104-D99223202-1.pdf: 48081373 bytes, checksum: 9df1504735bf589ef20bb95ac4715f0a (MD5) Previous issue date: 2015 | en |
dc.description.tableofcontents | CONTENTS
論文摘要 I Abstract II Abbreviations III CONTENTS VI CONTENT OF FIGURES VIII CONTENT OF TABLES XI Chapter I General Introduction 1 1.1 Introduction 1 1.2. Carbohydrate-based vaccine 1 1.3. Immune response to carbohydrates 3 1.4. Tumor-associated carbohydrate antigens (TACAs) 5 1.5. Challenges of carbohydrate-based cancer vaccine development 8 1.6. Carbohydrate-based cancer vaccine 8 1.1.1 Classical approach 10 1.1.2. Fully synthetic carbohydrate-based cancer vaccines 14 1.7. Modification of carbohydrate antigens structures (MCAS) and cross-reactivity based immunotherapies 18 1.8. Synthesis of Globo H hexasaccharide 20 1.9. Glycolipids as adjuvants 27 1.10. Glycan arrays are tools for passive immunization 30 Chapter II Immunogenicity study of Globo H analogues with modification at the reducing or non-reducing end of the tumor antigen 32 2.1. Introduction 32 2.2. Results and discussion 36 2.2.1. Chemical synthesis of Globo H and analogues 36 2.2.1.1. Synthesis of lactose building block (18) 36 2.2.1.2. Synthesis of galactose building block (17) 38 2.2.1.3. Synthesis of GalNAc building block (16) 39 2.2.1.4. Synthesis of galactose building block (15) 40 2.2.1.5. Synthesis of fucose building block (12) 41 2.2.1.6. Synthesis of disaccharide (13) and trisaccharide (14) building blocks 42 2.2.1.7. One-pot synthesis and Deprotection of Globo H (11) 43 2.2.2. Chemoenzymatic synthesis of Globo H and analogues 46 2.2.2.1. Synthesis of lactose building blocks (62 - 66) 46 2.2.2.2. Chemoenzymatic synthesis of Globo H-Lac analogues 49 2.2.2.3. Chemoenzymatic synthesis of Globo H-Fuc analogues 51 2.2.3. Synthesis of GH-Lac and GH-Fuc DT-conjugates 53 2.2.4. Glycan array analysis of the immunogenicity of the GH-Lac and GH-Fuc DT-conjugates 54 2.2.5. Binding studies of the mouse antisera induced by GH-Lac and GH-Fuc DT-conjugates to GH–expressing cancer cells 71 2.2.6. Complement-dependent cytoxicity (CDC) of the Mouse Antisera induced by GH-DT conjugates to MCF7 breast cancer cell 73 Chapter III Experiment section 75 References: 125 APPENDIX (1H & 13C NMR spectrums) 133 | |
dc.language.iso | en | |
dc.title | 以化學酵素法合成Globo H衍生物作為癌症疫苗用之研究 | zh_TW |
dc.title | Chemoenzymatic synthesis of Globo H Analogues as haptens for cancer vaccine design | en |
dc.type | Thesis | |
dc.date.schoolyear | 103-2 | |
dc.description.degree | 博士 | |
dc.contributor.coadvisor | 吳宗益(Chung-Yi Wu) | |
dc.contributor.oralexamcommittee | 方俊民(Jim-Min Fang),林國儀(Kuo-I Lin),林俊成(Chun-Cheng Lin),吳世雄(Shih-Hsiung Wu) | |
dc.subject.keyword | 癌症,疫苗,醣,酵素合成, | zh_TW |
dc.subject.keyword | Globo H,TACA,cancer,vaccine,carbohydrate,chemoenzymatic synthesis, | en |
dc.relation.page | 285 | |
dc.rights.note | 同意授權(全球公開) | |
dc.date.accepted | 2015-04-24 | |
dc.contributor.author-college | 理學院 | zh_TW |
dc.contributor.author-dept | 化學研究所 | zh_TW |
顯示於系所單位: | 化學系 |
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