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研究生: 朱仕騏
JHU, SHIH-CI
論文名稱: 利用分子印記磁性聚合物搭配液相層析串聯質譜進行雜環胺類化合物分析
Analysis of Heterocyclic Amines using Selective Extraction Magnetic Molecularly Imprinted Polymers and LC-MS
指導教授: 陳頌方
Chen, Sung-Fang
學位類別: 碩士
Master
系所名稱: 化學系
Department of Chemistry
論文出版年: 2020
畢業學年度: 108
語文別: 中文
論文頁數: 84
中文關鍵詞: 雜環胺類化合物分子印記磁性聚合物固相萃取法高效液相層析串聯質譜
英文關鍵詞: Heterocyclic, Magnetic molecularly imprinted polymers, Solid-phase extraction, LC-MS/MS
DOI URL: http://doi.org/10.6345/NTNU202001239
論文種類: 學術論文
相關次數: 點閱:130下載:0
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  • 謝辭 I 中文摘要 II Abstract III 縮寫表 IV 目錄 V 圖目錄 IX 表目錄 XI 第一章 緒論 1 1-1 前言 1 1-2 雜環胺化合物 (Heterocyclic amines, HCAs) 3 1-3 分子印記技術 (Molecularly Imprinted Technology, MIT) 6 1-3-1 分子印記聚合物的起源與概述 6 1-3-2分子印記聚合物的重要組成 8 1-3-3 分子印記聚合物的合成方法 11 第二章 實驗方法概述 14 2-1 液-液相萃取法 (Liquid-Liquid Extraction, LLE) 14 2-2 固相萃取法 (Solid-Phase Extraction, SPE) 15 2-3 高效液相層析 (High Performance Liquid Chromatography, HPLC) 16 2-4 質譜分析系統 (Mass Spectrometry, MS) 18 2-5 液相層析串聯式質譜分析 (HPLS-MS/MS) 21 2-5-1 多重反應監測 (Multiple Reaction Monitoring, MRM) 22 2-5-2 高效液相層析儀參數 24 2-5-3 串聯式質譜儀參數 25 第三章 實驗方法與步驟 26 3-1 實驗儀器與器材 26 3-2 實驗試劑與藥品 27 3-3 製備四氧化三鐵奈米珠 (Fe3O4 nanoparticles) 29 3-4 製備二氧化矽修飾奈米鐵珠 (Fe3O4@SiO2 nanoparticles) 29 3-5 製備表面修飾奈米鐵珠 (Fe3O4@SiO2-NH2 nanoparticles) 29 3-6 製備磁性分子印記聚合物 (MMIPs) 30 3-7 靜態吸附實驗 (Static adsorption) 32 3-8 動態吸附實驗 (Dynamic adsorption) 34 3-9 選擇性吸附實驗 (Selectivity of MMIPs) 36 3-10 利用液相萃取法進行樣品前處理 37 3-11 利用MMIPs-SPE進行真實樣品分析 38 第四章 實驗結果與討論 40 4-1 高效液相層析參數優化 40 4-2 離子對參數優化 42 4-3 分子印記聚合物合成條件優化 43 4-3-1 吸附能力評價 43 4-3-2 合成條件優化 44 4-4 分子印記聚合物之結構鑑定與性質探討 49 4-4-1 官能基鑑定 49 4-4-2 晶相解析與鑑定 50 4-4-3 電子顯微鏡圖像與粒徑分析 51 4-5 靜態吸附研究 52 4-5-1 弗羅因德利希方程式 (Freundlich equation) 52 4-5-2 朗繆耳方程式 (Langmuir equation) 52 4-5-3 等溫吸附曲線 53 4-6 動態吸附研究 55 4-6-1 動力學模型 55 4-6-2 動態吸附曲線 56 4-7 選擇性吸附研究 58 4-8 MMIPs-SPE 條件優化 60 4-9 方法驗證 64 4-9-1 定義空白基質與分析樣品 64 4-9-2 建立檢量線 65 4-9-3 精確度 (Accuracy) 與精密度 (Precision) 68 4-9-4 基質效應評估 71 4-9-5 同日間 (Intra-day) 與異日間 (Inter-day) 回收率 73 4-10 檢測市售肉類加工品 74 4-11 HCAs與 MISPE相關文獻探討與比較 75 第五章 結論與未來展望 78 參考文獻 80

    (1) Sugimura, T.; Wakabayashi, K.; Nakagama, H.; Nagao, M. Cancer science 2004, 95, 290-299.
    (2) Oz, F. Food chemistry 2011, 126, 2010-2016.
    (3) Turesky, R. J.; Taylor, J.; Schnackenberg, L.; Freeman, J. P.; Holland, R. D. Journal of agricultural and food chemistry 2005, 53, 3248-3258.
    (4) Toribio, F.; Busquets, R.; Puignou, L.; Galceran, M. T. Food and Chemical Toxicology 2007, 45, 667-675.
    (5) Poole, C. F. TrAC Trends in Analytical Chemistry 2003, 22, 362-373.
    (6) González-Curbelo, M.; Socas-Rodríguez, B.; Herrera-Herrera, A.; González-Sálamo, J.; Hernández-Borges, J.; Rodríguez-Delgado, M. TrAC Trends in Analytical Chemistry 2015, 71, 169-185.
    (7) Jian, S.-H.; Yeh, P.-J.; Wang, C.-H.; Chen, H.-C.; Chen, S.-F. journal of food and drug analysis 2019, 27, 595-602.
    (8) 周秉毅. 利用分子模印技術搭配液相層析串聯式質譜儀分析IQ及IQx型的雜環胺類. 國立臺灣師範大學, 台北市.
    (9) Sugimura, T. Mutation Research 1997, 376, 211-219.
    (10) Ellis, G. In Advances in carbohydrate chemistry; Elsevier, 1959, pp 63-134.
    (11) Alaejos, M. S.; Afonso, A. M. Comprehensive Reviews in Food Science and Food Safety 2011, 10, 52-108.
    (12) Jägerstad, M.; Skog, K.; Grivas, S.; Olsson, K. Mutation Research/Genetic Toxicology 1991, 259, 219-233.
    (13) Hsu, K.-Y.; Chen, B.-H. Food Research International 2020, 131, 109004.
    (14) Chevolleau, S.; Bouville, A.; Debrauwer, L. Food Chemistry 2020, 316, 126327.
    (15) Wu, Y.; Chen, L.; Xian, Y.; Hou, X.; Liang, M.; Dong, H.; Chen, J. Food chemistry 2019, 298, 125048.
    (16) Mohammadi, A.; Barzegar, F.; Kamankesh, M.; Mousavi Khaneghah, A. Food Science & Nutrition 2020, 8, 88-96.
    (17) Pauling, L. Journal of the American Chemical Society 1940, 62, 2643-2657.
    (18) Alexander, C.; Andersson, H. S.; Andersson, L. I.; Ansell, R. J.; Kirsch, N.; Nicholls, I. A.; O'Mahony, J.; Whitcombe, M. J. Journal of Molecular Recognition: An Interdisciplinary Journal 2006, 19, 106-180.
    (19) Whitcombe, M. J.; Kirsch, N.; Nicholls, I. A. Journal of molecular recognition 2014, 27, 297-401.
    (20) Tokonami, S.; Shiigi, H.; Nagaoka, T. Analytica chimica acta 2009, 641, 7-13.
    (21) Farooq, S.; Nie, J.; Cheng, Y.; Yan, Z.; Li, J.; Bacha, S. A. S.; Mushtaq, A.; Zhang, H. Analyst 2018, 143, 3971-3989.
    (22) Wulff, G. Angewandte Chemie International Edition in English 1995, 34, 1812-1832.
    (23) Mosbach, K. Trends in biochemical sciences 1994, 19, 9-14.
    (24) Grabowski, S. J. Hydrogen bonding: new insights; Springer, 2006; Vol. 3.
    (25) Whitcombe, M. J.; Rodriguez, M. E.; Villar, P.; Vulfson, E. N. Journal of the American Chemical Society 1995, 117, 7105-7111.
    (26) Xie, C.; Gao, S.; Guo, Q.; Xu, K. Microchimica Acta 2010, 169, 145-152.
    (27) Ye, L.; Haupt, K. Analytical and bioanalytical chemistry 2004, 378, 1887-1897.
    (28) Santos, H.; Martins, R. O.; Soares, D. A.; Chaves, A. R. Analytical Methods 2020.
    (29) Feás, X.; Seijas, J.; Vázquez-Tato, M.; Regal, P.; Cepeda, A.; Fente, C. Analytica chimica acta 2009, 631, 237-244.
    (30) Chen, L.; Xu, S.; Li, J. Chemical Society Reviews 2011, 40, 2922-2942.
    (31) Matyjaszewski, K.; Davis, T. P. Handbook of radical polymerization; John Wiley & Sons, 2003.
    (32) Xia, J.; Matyjaszewski, K. Macromolecules 1997, 30, 7692-7696.
    (33) Yan, H.; Row, K. H. International journal of molecular Sciences 2006, 7, 155-178.
    (34) Beltran, A.; Marcé, R.; Cormack, P.; Borrull, F. Journal of Chromatography A 2009, 1216, 2248-2253.
    (35) Long, C.; Mai, Z.; Yang, Y.; Zhu, B.; Xu, X.; Lu, L.; Zou, X. Journal of Chromatography A 2009, 1216, 2275-2281.
    (36) Jing, T.; Gao, X.-D.; Wang, P.; Wang, Y.; Lin, Y.-F.; Hu, X.-Z.; Hao, Q.-L.; Zhou, Y.-K.; Mei, S.-R. Analytical and bioanalytical chemistry 2009, 393.
    (37) Gao, D.; Zhang, Z.; Wu, M.; Xie, C.; Guan, G.; Wang, D. Journal of the American Chemical Society 2007, 129, 7859-7866.
    (38) Lofgreen, J. E.; Ozin, G. A. Chemical Society Reviews 2014, 43, 911-933.
    (39) Zhang, Y.; Liu, R.; Hu, Y.; Li, G. Analytical Chemistry 2009, 81, 967-976.
    (40) Wang, D.-D.; Gao, D.; Xu, W.-J.; Li, F.; Yin, M.-N.; Fu, Q.-F.; Xia, Z.-N. Talanta 2018, 184, 307-315.
    (41) Wang, A.; Lu, H.; Xu, S. Journal of agricultural and food chemistry 2016, 64, 5110-5116.
    (42) Zhang, Y.; Liu, D.; Peng, J.; Cui, Y.; Shi, Y.; He, H. Talanta 2020, 209, 120555.
    (43) Yao, G.-H.; Liang, R.-P.; Huang, C.-F.; Wang, Y.; Qiu, J.-D. Analytical chemistry 2013, 85, 11944-11951.
    (44) Diltemiz, S. E.; Say, R.; Büyüktiryaki, S.; Hür, D.; Denizli, A.; Ersöz, A. Talanta 2008, 75, 890-896.
    (45) Chen, S.; Fu, J.; Li, Z.; Zeng, Y.; Li, Y.; Su, X.; Jiang, X.; Yang, H.; Huang, L.; Zou, L. Journal of Chromatography A 2019, 1602, 124-134.
    (46) Arabi, M.; Ghaedi, M.; Ostovan, A. ACS Sustainable Chemistry & Engineering 2017, 5, 3775-3785.
    (47) Ashley, J.; Wu, K.; Hansen, M. F.; Schmidt, M. S.; Boisen, A.; Sun, Y. Analytical chemistry 2017, 89, 11484-11490.
    (48) Xu, C.; Uddin, K. M. A.; Shen, X.; Jayawardena, H. S. N.; Yan, M.; Ye, L. ACS applied materials & interfaces 2013, 5, 5208-5213.
    (49) Liu, H.-Y.; Lin, S.-L.; Fuh, M.-R. Talanta 2016, 150, 233-239.
    (50) Hennion, M.-C. Journal of chromatography A 1999, 856, 3-54.
    (51) Unger, K.; Lamotte, S.; Machtejevas, E. Liquid Chromatography: Chapter 3. Column Technology in Liquid Chromatography; Elsevier Inc. Chapters, 2013.
    (52) Sykora, D.; Vozka, J.; Tesarova, E. Journal of separation science 2016, 39, 115-131.
    (53) Žuvela, P.; Skoczylas, M.; Jay Liu, J.; Ba̧czek, T.; Kaliszan, R.; Wong, M. W.; Buszewski, B. Chemical reviews 2019, 119, 3674-3729.
    (54) James, A. T.; Martin, A. J. Biochemical Journal 1952, 50, 679.
    (55) Baldwin, M.; McLafferty, F. Organic Mass Spectrometry 1973, 7, 1111-1112.
    (56) Olivares, J. A.; Nguyen, N. T.; Yonker, C. R.; Smith, R. D. Analytical chemistry 1987, 59, 1230-1232.
    (57) Dempster, A. Physical Review 1918, 11, 316.
    (58) Fenn, J. B.; Mann, M.; Meng, C. K.; Wong, S. F.; Whitehouse, C. M. Science 1989, 246, 64-71.
    (59) Carroll, D.; Dzidic, I.; Stillwell, R.; Haegele, K.; Horning, E. Analytical Chemistry 1975, 47, 2369-2373.
    (60) Karas, M.; Hillenkamp, F. Analytical chemistry 1988, 60, 2299-2301.
    (61) Gaskell, S. J. Journal of mass spectrometry 1997, 32, 677-688.
    (62) Dawson, P. H. Quadrupole mass spectrometry and its applications; Elsevier, 2013.
    (63) Wiley, W.; McLaren, I. H. Review of scientific instruments 1955, 26, 1150-1157.
    (64) Schwartz, J. C.; Senko, M. W.; Syka, J. E. Journal of the American Society for Mass Spectrometry 2002, 13, 659-669.
    (65) Hu, Q.; Noll, R. J.; Li, H.; Makarov, A.; Hardman, M.; Graham Cooks, R. Journal of mass spectrometry 2005, 40, 430-443.
    (66) de Hoffmann, E. Journal of mass spectrometry 1996, 31, 129-137.
    (67) Farnsworth, P. T.; Google Patents, 1934.
    (68) Wiza, J. L. Nucl. Instrum. Methods 1979, 162, 587-601.
    (69) Yost, R.; Enke, C. Journal of the American Chemical Society 1978, 100, 2274-2275.
    (70) CARR, P. W.; Snyder, L.; Dolan, J. W.; Majors, R. E. LC GC North America 2010, 28.
    (71) Jaroniec, M. Surface Science 1975, 50, 553-564.
    (72) Veith, J.; Sposito, G. Soil Science Society of America Journal 1977, 41, 697-702.
    (73) Aeenehvand, S.; Toudehrousta, Z.; Kamankesh, M.; Mashayekh, M.; Tavakoli, H. R.; Mohammadi, A. Food Chemistry 2016, 190, 429-435.
    (74) Hsiao, H.-Y.; Chen, B.-H.; Kao, T.-H. Journal of agricultural and food chemistry 2017, 65, 9360-9368.
    (75) Chang, C.-C.; Zhang, D.; Wang, Z.; Chen, B.-H. Journal of Chromatography A 2019, 1585, 82-91.
    (76) Yan, Y.; Zhang, S.; Tao, G.-j.; You, F.-h.; Chen, J.; Zeng, M.-m. Journal of Chromatography B 2017, 1068, 173-179.
    (77) Chen, J.; He, Z.; Qin, F.; Chen, J.; Zeng, M. Journal of agricultural and food chemistry 2017, 65, 4493-4499.
    (78) Yang, D.; He, Z.; Gao, D.; Qin, F.; Deng, S.; Wang, P.; Xu, X.; Chen, J.; Zeng, M. Food chemistry 2019, 276, 195-201.
    (79) Dong, H.; Xian, Y.; Li, H.; Wu, Y.; Bai, W.; Zeng, X. Food Chemistry 2020, 310, 125937.
    (80) Zhang, X.; Wen, J.; Lian, L.; Ma, X.; Wang, X.; Lou, D. Analyst 2020.
    (81) Liang, R.; Hu, Y.; Li, G. Journal of Chromatography A 2020, 460867.
    (82) Shan, S.; Ma, Y.; Sun, C.; Guo, X.; Zheng, H.; Xu, X.; Qin, L.; Hu, J. Food Chemistry 2020, 127630.
    (83) Vasconcelos, I.; da Silva, P. H. R.; Dias, D. R. D.; de Freitas Marques, M. B.; da Nova Mussel, W.; Pedrosa, T. A.; e Silva, M. E. S. R.; de Souza Freitas, R. F.; de Sousa, R. G.; Fernandes, C. Materials Science and Engineering: C 2020, 111191.
    (84) Gholami, H.; Arabi, M.; Ghaedi, M.; Ostovan, A.; Bagheri, A. R. Journal of Chromatography A 2019, 1594, 13-22.

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