綜觀人類對抗癌症數十年來的歷史，癌症治療從手術切除、放射治療、化學治療到標靶藥物，科學家一直戮力於開發更有效並更安全的藥物。硼元素是過去在藥物開發上較被忽視的硼元素，但近年來在抗菌、抗病毒以及抗癌上都開始出現以硼元素為核心的藥物設計。此外硼也是硼中子捕獲治療上所必須的元素。本論文將以硼簇及碳硼烷這兩種特殊的硼立體結構做為研究主題；在第一章節中，將探討硼簇在硼中子捕獲治療中的可能性，除了合成硼簇分子外，也透過對硼的修飾使其能以溫和的反應條件與短肽、金奈米粒子及缺氧標靶分子接合。此外為了以非侵入性的方式進行生物分佈的評估，具放射性的碘原子也被接在我們合成的產物上，並在以金奈米粒子為載體的腫瘤造影上取得不錯的成果；儘管另一個缺氧標靶分子的造影結果並不理想，但也揭示了硼簇分子在生物體內有其它未知的機制存在。在第二章節裡，我透過微波輔助縮合反應來合成天然物leucettamine B的類似物，我選擇了多個六環及五環雜環來檢證微波輔助合成的效果；此外多個支鏈末端包含哌啶、吡咯及嗎啉結構的分子也被用來對上述合成產物的氨基進行烷基化反應。其中一個支鏈尾端替換被我們替換成碳硼烷，藉以研究碳硼烷分子在藥物設計上的潛力。最終我們合成的25個類似物對乳腺癌、肝癌及大腸癌等癌細胞株做生物活性測試，其中化合物31與48對腸癌細胞株都顯示出不錯的抑制效果，化合物48更是對乳腺癌、肝癌細胞株都有著明顯的抑制能力，這些初步的研究能協助我們進一步改良藥物，來開發出更具活性的抗癌藥物。

Looking at the history of cancer treatments for decades, it ranged from surgical resection, radiation therapy, chemotherapy to targeted drugs. Scientists have been working to develop more effective and safer drugs. Boron has been neglected in drug development in the past. But in recent years, antibacterial, antiviral, and anticancer drugs have begun to appear in boron-based drug designs. In addition, boron is an essential element for boron neutron capture therapy (BNCT). In this thesis, two special boron clusters, boron clusters, and carboranes are used as research topics. In the first chapter, the possibility of boron clusters in BNCT will be explored. Different boron cluster molecules were synthesized. The modification of boron allows it to bind to short peptides, gold nanoparticles, and hypoxic target molecules under mild reaction conditions. To evaluate the biodistribution in a non-invasive manner, radioactive iodine atoms are also attached to our synthetic products. Good results were obtained on tumor imaging using gold nanoparticles as carriers; although the effect of hypoxic targeting molecule is not ideal, it also revealed that boron cluster molecules have other unknown mechanisms in vivo. In the second chapter, I use microwave-assisted condensation to synthesize the analog of natural leucettamine B. I select several 5- and 6-membered heterocyclic rings to verify the effect of microwave-assisted synthesis. The alkyl branches of pyridine, pyrrole, and morpholine are also using to undergo the N-alkylation of synthetic products. One of them is replaced by carborane to study its potential in drug design. In the end, we synthesize 25 analogs to test the biological activity of cancer cell lines such as breast cancer, liver cancer, and colorectal cancer. Among them, compounds 31 and 48 show good inhibitory effects on intestinal cancer cell lines, and compound 48 also shows inhibitory effects against breast cancer and liver cancer cell lines. These preliminary studies can help us further improve the drug structure to develop more active anticancer drugs.

Acknowledgement I
Abstract II
中文摘要 III
Table of Contents IV
Figures VIII
Tables XI
Abbreviation table XII
Chapter 1 Synthesis of Tumor-targeting Boron Cluster Derivatives as Boron Neutron Capture Therapy Potential Agents 1
1-1 Literature Review 2
1-1-1 Boron 2
1-1-2 Boron Neutron Capture Therapy (BNCT) 2
1-1-3 Drug development of BNCT 4
1-1-4 Cell apoptosis 12
1-1-5 Marker to apoptosis: Bis(Zinc-Dipicolylamine) 14
1-1-6 Research Incentive 18
1-2 Results and Discussion 20
1-2-1 Chemistry 20
1-2-1-1 Synthesis of the boron agents 20
1-2-1-2 Synthesis of BC-peptide conjugate 22
1-2-1-3 Produce the BC-gold nanoparticles 23
1-2-1-4 Synthesis of BC-Zn-DPA 24
1-2-2 Biological evaluation 29
1-2-2-1 Property of BC-peptide conjugates 29
1-2-2-2 Bioevaluation of BC-gold nanoparticles 30
1-2-2-3 Bioevaluation of IBC-DPA (21) 33
1-2-2-4 Analysis of the DPA molecule imaging results 34
1-2-2-5 Conclusions 37
1-3 Experimental Section 39
1-3-1 Chemistry 39
1-3-1-1 Chemicals and characterization methods 39
1-3-1-2 Synthesis of (Bu4N)2[B12H12] (2) 40
1-3-1-3 Synthesis of (Bu4N)[B12H11O(CH2CH2)2O] (3) 41
1-3-1-4 Synthesis of (Bu4N)2[B12H11O(CH2)2O(CH2)2SH] (4) 41
1-3-1-5 Synthesis of (Bu4N)2[B12H11O(CH2)2O(CH2)2N3] (5) 42
1-3-1-6 Peptide synthesis for (6) and (7) 42
1-3-1-7 Synthesis of boron-peptides of (8) and (9) 43
1-3-1-8 The preparation of boron-containing gold nanoparticles (12) 43
1-3-1-9 Radioiodination of AuNPs (13) 43
1-3-1-10 Antibody conjugation of AuNPs (14) 44
1-3-1-11 Synthesis of DPA-NH2 (15) 44
1-3-1-12 Synthesis of BC-DPA (16) 44
1-3-1-13 Synthesis of BC-Zn-DPA (17) 45
1-3-1-14 Synthesis of (Bu4N)2(B12H11I) (19) 45
1-3-1-15 Synthesis of (Bu4N)(B12H11I)－O(CH2CH2)2O (20) 46
1-3-1-16 Synthesis of IBC-DPA (21) 46
1-3-2 Biology 47
1-3-2-1 Circular dichroism (CD) spectroscopy for (8) and (9) 47
1-3-2-2 Cell cultures and xenograft inoculation 47
1-3-2-3 In vitro cellular uptake and internalization assays 47
1-3-2-4 MicroSPECT/CT imaging of radioiodinated AuNPs 48
1-3-2-5 Assessment of radioactivity accumulation in tissues 48
1-3-2-6 Assessment of boron content in tumor and muscle 49
Chapter 2 Leucettamine B Analogs and its Carborane Derivative as Potential Anti-Cancer Agents: Design, Synthesis, and Biological Evaluation 50
2-1 Literature Review 51
2-1-1 Introduction of leucettamine B 51
2-1-2 Heterocyclic rings application in drug development 51
2-1-3 Potential pharmacophore：Carborane 54
2-1-4 Microwave-assisted synthesis in organic reaction 57
2-1-5 Research Incentive 59
2-2 Results and Discussion 61
2-2-1 Chemistry 61
2-2-2 Biological evaluation 65
2-2-3 Conclusions 70
2-3 Experimental Section 72
2-3-1 Chemistry 72
2-3-1-1 Standard procedures for the synthesis of conjugated derivatives from piperonal and various barbituric acids & 5-membered heterocycles. 73
2-3-1-2 Standard procedures for the synthesis of piperonal-alkylheterocycle derivatives from piperonal derivatives with various alkyl chlorides (30–45). 75
2-3-1-3 Synthesis of (Z)-5-(Benzo[d][1,3]dioxol-5-ylmethylene)-3-(prop-2-yn-1-yl)-thiazolidine-2,4-dione (46). 80
2-3-1-4 Synthesis of (Z)-5-(Benzo[d][1,3]dioxol-5-ylmethylene)-3-(1-closo-carbo-ranyl)-2-thioxothiazolidin-4-one (48). 81
2-3-2 Biology 81
References 83
Appendix 101

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