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研究生：	高彰隆 Kao, Chang-Long
論文名稱：	一鍋化合成具螢光功能左多巴拓印奈米粒子於控制釋放與相似分子感測之應用 One-Pot Synthesis of L-DOPA Imprinted Nanoparticles with Fluorescent Functionality for Controlled Release and Sensing Similar Molecules
指導教授：	桂椿雄 Kuei, Chun-Hsiung
學位類別：	博士 Doctor
系所名稱：	理學院 - 化學系 Department of Chemistry
論文出版年：	2015
畢業學年度：	103
語文別：	英文
論文頁數：	67
中文關鍵詞：	螢光共振能量轉移、一鍋化反應、功能性多孔洞材料
外文關鍵詞：	Fluorescence resonance energy transfer, Functionalized molecular imprinting materials
相關次數：	點閱：98 下載：1
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本研究開發一鍋化反應製備功能性中孔洞與多孔式拓印高分子奈米粒子，預期於不破壞生物檢體下，增加生物相容性，提高材料本身於生物生理環境下穩定度與專一性，且藉由螢光共振能量轉移機制增加偵測靈敏度。拓印高分子如同分子探針可應用於藥物開發前導分子篩選、生物檢體、和生物仿生檢測。此技術可藉由紫外-可見光吸收及螢光光譜儀、或氣相或液相層析質譜儀分析鑑定分析物，並開發分析定性及定量分析方法。本研究至今已開發重要及新穎技術列舉如下: 1.一鍋化反應製備功能性中孔洞、多孔洞式拓印高分子與功能性奈米粒子、 2..調適分子結合能力。目前技術預期可以延伸其生物體作用機制相關應用價值；希望未來應用拓展至藥物開發前導分子篩選、生物檢體與生物仿生檢測之應用層面延伸，未來希望發展高靈敏度與專一性的藥物開發前導分子(lead molecule)篩選、生物檢體與生物仿生檢測之大量快速化篩選(high throughput screening, HTS) 分子辨識平台。

The major goal of this dissertation is develop fluorescence resonance energy transfer tag and biomimetic materials for molecular recognition. The molecular recognition platform is based on molecular imprinting technology, micro-processes and nanotechnology, which can be applied to lead molecules, proteins and biological specimens screening, bio-imaging, on-line concentration, qualitatively and quantitatively analytical methods.
The major study will be to synthesize fluorescent tag and modify all functionalized molecular imprinting materials to biocompatible materials. Those biocompatible materials are molecular probes and can friendly bind with lead molecules, proteins and biological specimens. Qualitative and quantitative analysis will be evaluated by ultraviolet-visible spectrometer, fluorescence spectrometer, flow cytometer, gas and liquid chromatography coupled with mass spectrometer. The fluorescence resonance energy transfer tag will assist the sensing system for high throughput screening by integrating our methodologies with combinatorial chemistry in the future. All development in this project is to expand its potential in analytical chemistry.

Content
摘要	I
Abstract	II
Acknowledgements	III
Chapter 1 Introduction	1
1.1 Molecularly imprinted polymer: historical perspectives and concepts	1
1.2 Approaches of preparing molecularly imprinted polymer	3
1.2.1 Non-covalent imprinting method	4
1.2.2 Covalent imprinting method	5
1.2.3 Semi-covalent imprinting method	6
1.3 Polymerization and removing of template molecules	7
1.4 Characteristics and evaluation methods of molecularly imprinted polymer	8
1.4.1 Properties of molecularly imprinted polymer	8
1.4.2 Evaluation methods for molecularly imprinted polymers	9
1.5 Adsorption and kinetic aspects for molecularly imprinted polymers	10
1.5.1 Adsorption isotherms for molecularly imprinted polymers	10
1.5.2 Kinetic aspects of molecularly imprinted polymers	12
1.6 Applications of molecularly imprinted polymers	13
1.6.1 Stationary phase in chromatography and solid phase extraction	13
1.6.2 Biomimetic sensors	14
1.6.3 Plastic antibodies	15
1.7 Design and scopes of this study	16
References	18
Chapter 2 One-pot Synthesis of L-DOPA Imprinted Silica Nanospheres for Chiral Separation and in vitro Controlled Release	25
2.1 Introduction	25
2.2 Experiments	27
2.2.1 Reagents	28
2.2.2 Instrumentations	28
2.2.3 Fabrication of L-DOPA or D-DOPA imprinted hollow and mesoporous nanospheres	29
2.2.4 Optimization of reaction	29
2.2.5 Static, kinetic, specific binding and in vitro controlled release tests	30
2.3 Results and Discussions	31
2.3.1 FT-IR spectrum and solid-state NMR of synthetic materials	31
2.3.2 Morphology of synthetic materials	34
References	43
Chapter 3 One-Pot Synthesis of L-DOPA Imprinted Nanoparticles with Fluorescent Functionality for Sensing Chiral and Similar Molecules	47
3.1 Introduction	47
3.2 Experimental section	49
3.2.1 Reagents	50
3.2.2 Instrumentations	50
3.2.3 Fabrication of L-DOPA or D-DOPA imprinted with FRET pairs	51
3.2.4 Optimization of reaction	51
3.2.5 Molecules recognition tests	52
3.3 Characteristics of fluorescent L- or D-DOPA imprinted silica nanoparticles	52
3.3.1 FT-IR spectrum and solid-state NMR of synthetic materials	52
3.3.2 Morphology of synthesized materials	53
3.3.3 Rebinding and molecules recognition test on similar structure	56
References	62
Chapter 4 Conclusions, Continued and Future Works	65
4.1 Conclusions	65
4.2 Continuous works	65
4.3 Future works	66
References	67





Tables
Table 3.1 R2 for different isotherms of INSs and NINSs in Chapter 2 and 3	57



















Figures
Fig 1.1 Process of imprinted polymers	4
Fig. 2.1 Fluorescence spectrum during the reaction	30
Fig. 2.2 FTIR spectra of (a) as-synthesized INSs, (b) INSs after extraction, and (c) NINSs	32
Fig. 2.3 13C solid-state NMR of INSs	33
Fig. 2.4 TEM of morphologies and DLS of the size distributions of spheres (a) INSs and (b) NINSs. All scale bars are 100 nm in TEM images.	34
Fig. 2.5 SAX patterns of (a) INSs and (b) NINSs (c) zoom in	35
Fig. 2.6 Surface areas of INSs and NINSs characterized by BET adsorption–desorption isotherms.	36
Fig. 2.7 Distributions of pore size of INSs and NINSs characterized by BET adsorption–desorption isotherms.	36
Fig. 2.8 Mobile phase: 80:20 v/v, ACN /20 mM sodium phosphate buffer(pH=7.4). Flow rate:1 mL/min: Detection UV at 280 nm.	37
Fig. 2.9 Binding isotherm of INSs and NINSs. Values represent the mean of three independent measurements. Error bars are indicated. Concentration of template (L-DOPA): 0-4mM; solvent: H2O; volume: 10 ml; adsorption time: 24 hrs.	38
Fig. 2.10 Kinetic binding profile of INSs and NINSs. Values represent the mean of three independent measurements. Error bars are indicated. Solvent: H2O; volume: 10 ml; adsorption time: 1400 minutes	39
Fig. 2.11 Controlled release of pH dependent profiles of INSs with L-DOPA as template.	40
Fig. 2.12 Binding selectivity of INSs and NINSs. (a) L-DOPA as the template. (b) D-DOPA as the template.	41
Fig. 3.1 Fluorescence spectrum during the reaction.	52
Fig. 3.2. TEM and DLS of (a) INSs and (b) NINSs with FRET pairs	54
Fig. 3.3. Surface area of INSs and NINSs with FRET pairs.	55
Fig.3.4 Distributions of pore size of INSs and NINSs with FRET pairs.	56
Fig.3.5 Binding isotherm of INSs and NINSs with FRET pairs.	57
Fig.3.6 Kinetics of INSs and NINSs with FRET pairs.	58
Fig.3.7 Fluorescence binding selectivity (pB) of INSs and NINSs with FRET pairs: L- for L-DOPA as template and D- for D-DOPA as template.	60
Fig.3.8 Fluorescence binding selectivity (pY) of INSs and NINSs with FRET pairs: L- for L-DOPA as template and D- for D-DOPA as template.	60
Fig.3.9 The quantity of rebinding capacity and selectivity of INSs and NINSs with FRET pairs: L- for L-DOPA as template and D- for D-DOPA as template.	60
Fig.3.10 Fluorescence binding selectivity (pB and pY) of INSs with FRET pairs from 10-9 M to 10-4 M of L-DOPA.○:L-DOPA, △:Catechol◇:L-Tyrosine, ▽:D-DOPA, □:Hydroquinone	61
















Schemes
Scheme 1.1. Flow chart of this research	17
Scheme 2.1 Schematic procedure for synthesizing the L-DOPA imprinted silica nanospheres with built-in interactions between L-DOPA and functional groups.	27
Scheme 3.1 Schematic procedure for synthesizing the L-DOPA imprinted silica nanoparticles with proposed interactions between L-DOPA and functional groups.	49



                                    

Chapter 1 References
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(4) Yu Hoshino, Hiroyuki Koide, Takeo Urakami, Hiroaki Kanazawa, Takashi Kodama,| Naoto Oku, and Kenneth J. Shea, “Recognition, Neutralization, and Clearance of Target Peptides in the Bloodstream of Living Mice by Molecularly Imprinted Polymer Nanoparticles: A Plastic Antibody”, Journal of the American Chemical Society, 132(29), 6644–6645, 2010.
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(29) Jun Matsui, Kuniyuki Fujiwara, Satoshi Ugata, and Toshifumi Takeuchi, “Solid-phase extraction with a dibutylmelamine-imprinted polymer as triazine herbicide-selective sorbent”, Journal of Chromatography A, 889 (1-2),25-31, 2000.
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(34) Serena Ambrosini, Sudhirkumar Shinde, Ersilia De Lorenzi, and Borje Sellergren, “Glucuronide directed molecularly imprinted solid-phase extraction: isolation of testosterone glucuronide from its parent drug in urine”, Analyst, 137, 249-254, 2012.
(35) Andrea Speltini, Michela Sturini, Federica Maraschi, and Antonella Profumo, “Fluoroquinolone antibiotics in environmental waters: Sample preparation and determination”, Journal of Separation Science, 23 (8), 1115-1131, 2010.
(36) Francisco Barahona, Esther Turiel, Peter A. G. Cormack, and Antonio Martín-Esteban, “Synthesis of core-shell molecularly imprinted polymer microspheres by precipitation polymerization for the inline molecularly imprinted solid-phase extraction of thiabendazole from citrus fruits and orange juice samples”, Journal of Separation Science, 34 (2), 217-224, 2011.
(37) Javier L. Urraca, Andrew J. Hall, Maria C. Moreno Bondi, and Börje Sellergren, “A Stoichiometric Molecularly Imprinted Polymer for the Class-Selective Recognition of Antibiotics in Aqueous Media”, Angewandte Chemie, 118 (31), 5282 –5285, 2006.
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(40) Sergey A. Piletsky, and Anthony P. F. Turner, “Electrochemical Sensors Based on Molecularly Imprinted Polymers”, Electroanalysis, 14 (5), 317-323, 2002.
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(43) Masanobu Matsuguchi, and Toshiyuki Uno, “Molecular imprinting strategy for solvent molecules and its application for QCM-based VOC vapor sensing”, Analytical Communications, 36, 391-393, 1999.
(44) Karsten Haupt, Krzysztof Noworyta and Wlodzimierz Kutner, “Imprinted polymer-based enantioselective acoustic sensor using a quartz crystal microbalance”, Sensors and Actuators B: Chemical, 113 (1), 94-99, 2006.
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(55) Yu Hoshino, Hiroyuki Koide, Takeo Urakami, Hiroaki Kanazawa, Takashi Kodama, Naoto Oku and Kenneth J. Shea, “Recognition, Neutralization, and Clearance of Target Peptides in the Bloodstream of Living Mice by Molecularly Imprinted Polymer Nanoparticles: A Plastic Antibody”, Journal of the American Chemical Society, 132 (19), 6644–6645, 2010.
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Chapter 2 References
(1) Chang-Long Kao, Yan-Fu Chen, Ping-Chih Huang, Ching-Yun Hsu and Chun-Hsiung Kuei, “A facile one-pot synthesis of L-DOPA imprinted silica nanospheres for chiral separation and in vitro controlled release”, RSC Advances, 5, 15511-15514, 2015.
(2) Lingxin Chen, Shoufang Xu and Jinhua Li, “Recent advances in molecular imprinting technology: current status, challenges and highlighted applications”, Chemical Society Reviews, 40, 2922–2942, 2011.
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(4) (a) Yaniv Ben-Amram, Michael Riskin and Itamar Willner, “Selective and enantioselective analysis of mono- and disaccharides using surface plasmon resonance spectroscopy and imprinted boronic acid-functionalized Au nanoparticle composites”, Analyst, 135, 2952–2959, 2010.
(b)Lin Peng , Yuzhi Wang, Huan Zeng and Ya Yuan, “Molecularly imprinted for of in complicated traditional Chinese medicines”, Analyst, 136, 756-763, 2011.
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(7) (a)Marco Frasconi, Ran Tel-Vered, Michael Riskin, and Itamar Willner, “Surface Plasmon Resonance Analysis of Antibiotics Using Imprinted Boronic Acid-Functionalized Au Nanoparticle Composites”, Analytical Chemistry, 82, 2512–2519, 2010.
(b) Qing-Qing Gai, Feng Qu, Zong-Jian Liu, Rong-Ji Dai, and Yu-Kui Zhang, “Superparamagnetic lysozyme surface-imprinted polymer prepared by atom transfer radical polymerization and its application for protein separation”, Journal of Chromatography A, 31,5035–5042, 2010.
(c) Jin-Qun Xue, Da-Wei Li, Lu-Lu Qu, and Yi-Tao Long, “Surface-imprinted core–shell Au nanoparticles for selective detection of bisphenol A based on surface-enhanced Raman scattering”, Analytica Chimica Acta, 13, 7–62, 2013.
(8) Byung Mun Jung, Min Soo Kim, Woo Jin Kim, and Ji Young Chang, “Molecularly imprinted mesoporous silica particles showing a rapid kinetic binding”, Chemical Communications, 46, 3699–3701, 2010.
(9) (a)Wendong Wang, Jennifer E. Lofgreen, and Geoffrey A. Ozin, “Why PMO? Towards Functionality and Utility of Periodic Mesoporous Organosilicas”, small, 6, 2634–2642, 2010.
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(10) (a) Bernadette Tse Sum Bui, and Karsten Haupt, “Molecularly imprinted polymers: synthetic receptors in bioanalysis”, Analytical and Bioanalytical Chemistry, 398, 2481–2492, 2010.
(b)Michael J. Whitcombe, Iva Chianella, Lee Larcombe, Sergey A. Piletsky, James Noble, Robert Porter and Adrian Horgan, “The rational development of molecularly imprinted polymer-based sensors for protein detection”, Chemical Society Reviews, 40, 1547–1571, 2011.
(c)Junfa Yin, Yue Cui, Gengliang Yang and Hailin Wang, “Molecularly imprinted nanotubes for enantioselective drug delivery and controlled release”, Chemical Communications, 46, 7688–7690, 2010.
(d) Saman Azodi-Deilamia, Majid Abdoussa, and S. Rezvaneh Seyedi, “Synthesis and characterization of molecularly imprinted polymer for controlled release of tramadol”, Central European Journal of Chemistry, 8 (3), p 687–695, 2010.
(11) Johann Kecht, Axel Schlossbauer, and Thomas Bein, “Selective Functionalization of the Outer and Inner Surfaces in Mesoporous Silica Nanoparticles”, Chemistry of Materials, 20(23), 7207–7214, 2008.
(12) (a) Jennifer E. Lofgreen, Igor L. Moudrakovski, and Geoffrey A. Ozin, “Molecularly Imprinted Mesoporous Organosilica”, ACS Nano, 5 (3), 9788–9798, 2011.
(b)Yu Gao,Yu Chen, Xiufeng Ji,Xinyu He, Qi Yin, Zhiwen Zhang, Jianlin Shi, and Yaping Li , “Controlled Intracellular Release of Doxorubicin in Multidrug-Resistant Cancer Cells by Tuning the Shell-Pore Sizes of Mesoporous Silica Nanoparticles”, ACS Nano, 5 (12), 9788–9798, 2011.
(13) (a) Souad A. Elfeky, Stephen E. Flower, Naoko Masumoto, Francois D’Hooge, Ludivine Labarthe, Wenbo Chen, Christophe Len, Tony D. James, and John S. Fossey, “Diol Appended Quenchers for Fluorescein Boronic Acid”, Chemistry – An Asian Journal, 5, 581 – 588, 2010.
(b)Ryuhei Nishiyabu, Yuji Kubo, Tony D. James, and John S. Fossey, “Boronic acid building blocks: tools for sensing and separation”, Chemical Communications, 47, 1106–1123, 2011.
(c)Ryuhei Nishiyabu, Yuji Kubo, Tony D. James, John S. Fossey, “Boronic acid building blocks: tools for self assembly”, Chemical Communications, 47, 1124–1150, 2011.
(14) Shoufang Xu, Lingxin Chen, Jinhua Li,a Wei Qina, and Jiping Ma, “Preparation of hollow porous molecularly imprinted polymers and their applications to solid-phase extraction of triazines in soil samples”, Journal of Materials Chemistry, 21, 12047-12053, 2011.
(15) John W. Tomsho, Stephen J. Benkovic, “Elucidation of the Mechanism of the Reaction between Phenylboronic Acid and a Model Diol, Alizarin Red S”, The Journal of Organic Chemistry, 77, 2098−2106, 2012.

Chapter 3 References
(1) G. Guan, B. Liu, Z. Wang and Z. Zhang, “Imprinting of Molecular Recognition Sites on Nanostructures and Its Applications in Chemosensors”, Sensors, 2008, 8, 8291–8320, 2008.
(2) M. J. Whitcombe, I. Chianella, L. Larcombe, S. A. Piletsky, J. Noble, R. Porter and A. Horgan, “The rational development of molecularly imprinted polymer-based sensors for protein detection”, Chemical Society Reviews, 40, 1547–1571, 2011.
(3) Po-Yen Chen, R Vittal, Po-Chin Nien, Guey-Sheng Liou, and Kuo-Chuan Ho “A novel molecularly imprinted polymer thin film as biosensor for uric acid”, Talanta, 80 (3), 1145-1151, 2010.
(4) Tian-Ying Guo, Yong-Qing Xia, Jin Wang, Mou-Dao Song, and Bang-Hua Zhang, “Chitosan beads as molecularly imprinted polymer matrix for selective separation of proteins”, Biomaterials, 26 (28), 5737-5745, 2005.
(5) Alexandra Molinelli, Robert Weiss, and Boris Mizaikoff, “Advanced solid phase extraction using molecularly imprinted polymers for the determination of quercetin in red wine”, Journal of Agricultural and Food Chemistry, 50 (7), 1804-10808, 2002.
(6) JM Lin, T Nakagama, K Uchiyama, and T Hobo, “Molecularly imprinted polymer as chiral selector for enantioseparation of amino acids by capillary gel electrophoresis”, Chromatographia, 43 (11-12), 585-591, 1996.
(7) Richard J Ansell, Dario Kriz, and Klaus Mosbach, “Molecularly imprinted polymers for bioanalysis: chromatography, binding assays and biomimetic sensors”, Current Opinion in Biotechnology, 7 (1), 89-94, 1996.
(8) Jun-qiu Liu, and Günter Wulf, “Molecularly Imprinted Polymers with Strong Carboxypeptidase A-Like Activity: Combination of an Amidinium Function with a Zinc-Ion Binding Site in Transition-State Imprinted Cavities”, Angewandte Chemie International Edition, 43, 1287-1290, 2004.
(9) Xiaobin Hu, Qi An, Guangtao Li, Shengyang Tao, and Jian Liu, “Imprinted Photonic Polymers for Chiral Recognition”, Angewandte Chemie International Edition, 45, 8145-8148, 2006.
(10) Lingxin Chen, Shoufang Xuab and Jinhua Li, “Recent advances in molecular imprinting technology: current status, challenges and highlighted applications”, Chemical Society Reviews, 40, 2922-2942, 2011.
(11) Petra Turkewitsch, Barbara Wandelt, Graham D. Darling, and William S. Powell, “Fluorescent Functional Recognition Sites through Molecular Imprinting. A Polymer-Based Fluorescent Chemosensor for Aqueous cAMP”, Analytical Chemistry, 70(10), 2025-2030, 1998.
(12) Alexandre Rachkov, a, Scott McNivena, Anna El’skayab, Kazuyoshi Yanoa, and Isao Karubea, “Fluorescence detection of β-estradiol using a molecularly imprinted polymer”, Analytica Chimica Acta, 405 (1-2), 23-29, 2000.
(13) Daniel L Rathbone, Danqing Su, Yongfeng Wang, and David C Billington, “Molecular recognition by fluorescent imprinted polymers”, Tetrahedron Letters, 41 (1), 123-126, 2000.
(14) Yonghui Deng, Chong Liu, Ting Yu, Feng Liu, Fuqiang Zhang, Ying Wan, Lijuan Zhang, Changchun Wang, Bo Tu, Paul A. Webley, Huanting Wang, and Dongyuan Zhao, “Facile Synthesis of Hierarchically Porous Carbons from Dual Colloidal Crystal/Block Copolymer Template Approach”, Chemistry of Materials, 19, 3271-3277, 2007.
(15) T. Hien Nguyen and Richard J. Ansell, “Fluorescent imprinted polymer sensors for chiral amines”, Organic & Biomolecular Chemistry, 7, 1211-1220, 2009.
(16) R. Cody Stringer, Shubhra Gangopadhyay, and Sheila A. Grant, “Detection of Nitroaromatic Explosives Using a Fluorescent-Labeled Imprinted Polymer”, Analytical Chemistry, 82 (10), 4015-4019, 2010.
(17) (a) Jennifer E. Lofgreen, Igor L. Moudrakovski, and Geoffrey A. Ozin, “Molecularly Imprinted Mesoporous Organosilica”, ACS Nano, 5 (3), 9788–9798, 2011.
(b)Yu Gao,Yu Chen, Xiufeng Ji,Xinyu He, Qi Yin, Zhiwen Zhang, Jianlin Shi, and Yaping Li , “Controlled Intracellular Release of Doxorubicin in Multidrug-Resistant Cancer Cells by Tuning the Shell-Pore Sizes of Mesoporous Silica Nanoparticles”, ACS Nano, 5 (12), 9788–9798, 2011.
(18) Robert J. Umpleby, Sarah C. Baxter, Yizhao Chen, Ripal N. Shah, and Ken D. Shimizu, “Characterization of Molecularly Imprinted Polymers with the Langmuir-Freundlich Isotherm”, Analytical Chemistry, 73 (19), 4584-4591, 2001.

Chapter 4 References
(1) A.M Starvin, and T.Prasada Rao, “Solid phase extractive preconcentration of uranium(VI) onto diarylazobisphenol modified activated carbon”, Talanta, 63 (2), 225-232, 2004.
(2) Dhruv K. Singh, and Shraddha Mishra, “Synthesis of a New Cu(II)-Ion Imprinted Polymer for Solid Phase Extraction and Preconcentration of Cu(II)”, Chromatographia, 70 (11-12) 1539–1545, 2009.
(3) Majid Kalate Bojdi, Mohammad Hossein Mashhadizadeh, Mohammad Behbahani, Ali Farahani, Saied Saeed Hosseini Davarani, and Akbar Bagheri, “Synthesis, characterization and application of novel lead imprinted polymer nanoparticles as a high selective electrochemical sensor for ultra-trace determination of lead ions in complex matrixes”, Electrochimica Acta, 136, 59–65, 2014.
(4) Catherine C. Berry, and Adam S. G. Curtis, “Functionalisation of magnetic nanoparticles for applications in biomedicine”, Journal of Physics D: Applied Physics, 36, 198-206, 2003.
(5) Conroy Sun, Jerry S.H. Lee, and Miqin Zhang, “Magnetic nanoparticles in MR imaging and drug delivery”, Advanced Drug Delivery Reviews, 60 (11), 1252-1265, 2008.
(6) Anna A. Volkert, and Amanda J. Haes, “Advancements in nanosensors using plastic antibodies”, Analyst, 139, 21-31, 2014.

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