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研究生：	蔡軒昂 Tsai, Hsuan-Ang
論文名稱：	分子模版材料之製備與對肌酸酐之特異性吸附 Synthesis of Molecularly Imprinted Materials for the Specific Binding of Creatinine
指導教授：	許梅娟 Syu, Mei-Jywan
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：	2005
畢業學年度：	93
語文別：	中文
論文頁數：	118
中文關鍵詞：	4-乙烯吡啶、溶膠-凝膠法.肌酸酐、肌酸、模印因子、分子辨識系統、分子模版高分子、β-環糊精
外文關鍵詞：	creatine, creatinine, 4-vinylpyridine, β-cyclodextrin, molecularly imprinted polymer, molecular recognition, imprinting factor
相關次數：	點閱：85 下載：4
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　　分子辨識系統在生化界上的應用相當廣泛，但由於天然的分子辨識系統常因為外在因素的影響，如：pH 值、有機溶劑和溫度的影響下而造成分子辨識系統無法達到預期的效果。近十幾年來分子模版高分子(molecularly imprinted polymer) 的理論已被廣泛的應用在分子辨識系統上。所謂的分子模版高分子主要是利用官能基單體與目標物或目標物之相似物即分子模版進行共價或非共價鍵鍵結，之後再利用交聯劑來進行交聯聚合。當聚合完成後以適當溶劑將高分子中的分子模版洗出。洗出模版後的高分子本身則具有與分子模版形狀相近或具互補作用力的孔洞。具這樣特性的孔洞即可作為分子辨識系統的最主要依據。

　　在本論文中，嘗試利用各種不同的分子模版高分子製備方法，包括：(1) 以β-環糊精(β−cyclodedxtrin, β−CD) 作為官能基單體，環氧氯丙烷(Epichlorohydrin, EPI) 為交聯劑所製備之分子模版高分子、(2) 以4-乙烯吡啶(4-vinylpyridine, 4-Vpy) 為官能基單體，二乙烯基苯(divinylbenzene, DVB) 為交聯劑所製備之分子模版高分子、(3) 利用溶膠-凝膠法(sol-gel) 所製備之分子模版高分子對於肌酸酐進行作辨識能力測試。

　　製備之分子模版高分子利用掃描式電子顯微鏡(SEM)、FT-IR 以及Solid state NMR 鑑定其化學結構，並且判定肌酸酐是否包埋於高分子中。同時利用N-羥基丁二硫亞氨(N-hydroxysuccinimide) (相似物)、咯烷酮(2-pyrrolidinone) (相似物)、肌酸(creatine) (共存物)和肌酸酐(creatinine)以雙成份或三成份共存混合後，測試上述之模版高分子在不同成份之混合液中對肌酸酐之辨識能力。而在此外，希望製備的分子模版吸附材料能進一步應用在臨床上，本論文中也將分子模版高分子應用在人血清中，以測試其在血清中辨識肌酸酐的能力。

　　由結果中可以觀察並得到在以β-環糊精為官能基單體所製備的高分子中，當製備條件β-環糊精/環氧氯丙烷=1/10 (molar ratio) 和β-環糊精/肌酸酐=3/2 (molar ratio) 時可得到最佳的模印因子(imprinting factor) 為4.06 ± 0.98。而在雙成份與三成份的混合液分析中對於肌酸酐的最佳選擇性則分別為2.43 ± 0.20 與2.87 ± 0.39。在鹽類影響以及遮蓋(capping) 修飾實驗中得到此分子模版高分子之氫鍵作用力會影響對於肌酸酐的專一辨識能力。在以4-乙烯吡啶為官能基單體所製備的高分子中，利用其較微弱的氫鍵作用力用以突顯其分子模版孔洞效應，最後得到最佳的模印因子為3.25。為探求其此分子模版高分子在混合液中對於肌酸酐的辨識能力，分別選用了與肌酸酐在結構上相似物質以及其在血清中的共存物當作競爭吸附的一個模式，其結果可得到對於肌酸酐最佳的選擇性為3.90± 0.01。再進一步的測試中了解此分子模版高分子在人血清之複雜成份環境下亦具有辨識肌酸酐的能力。最後經由上述實驗的結果分析後，採用無機溶膠-凝膠法(sol-gel) 所製備之分子模版高分子希望能藉此提高其專一辨識肌酸酐的能力。經實驗結果顯示在以水為溶劑下吸附肌酸酐的效果為最好，其模印因子可高達7.18 ± 0.05。在定濃度混合液的分析結果中，分子模版高分子對於肌酸酐最佳的選擇性則分別為8.75 ± 0.38 (雙成份混合液) 和5.19 ± 0.54 (三成份混合液)。

　　由以上所有的製備與測試結果中可以結論出對於分子量較小且為極性之肌酸酐分子模版，於分子模版高分子的製備方法上，顯示是以無機方法製備出的材料較有機製備法，與模版性質與分子專一辨識能力兩方面有較佳的表現，但因模版材料之製備條件中變數相當多，因此僅就本系統之結果做此結論，至於模版無機材料是否優於模版有機材料則尚待進一步確認。

　The approach of molecular recognition based on synthetic materials has beenwidely applied in the biological research. To utilize nature molecular ecognitionbiological system exists many problems, such as variation of pH environment,organic solvents and high temperature effects, which will then result in anunstable system. One approach known as molecular imprinting was developed to overcome the above-mentioned disadvantages occurred in nature molecularrecognition systems. Molecularly imprinted polymer (MIP), a kind of molecular recognition materials, is generally synthesized from using certain functional monomer to copolymerize with a cross-linking agent in the presence of a targetmolecule (template). The functional monomer forms a complex with the template molecule first and then the polymerization is propagated under proper condition. After the polymerization, a proper solvent is applied to wash out the imprinted templates so that specific cavity is formed. The polymer is then expected to be able to provide the specific recognition sites for the template molecule.

　In this study, by using creatinine as the template molecule, three different molecularly imprinted materials were prepared including the imprinted poly(β-cyclodextrin-co-epichlorohydrin), the imprinted poly(4-vinylpyridine-co-divinylbenzene) and the imprinted sol-gel. Using these molecularly imprinted materials respectively, we expected that the specific recognition of creatinine in different mixture solutions under the interference of the other compounds could be accomplished.FT-IR, SEM, and Solid state NMR were applied to identify the chemical structures and imprinting effect of the synthetic polymers.Creatinine and other three compounds, N-hydorxysuccinimide, 2-pyrrolidinone and creatine, were used to comprise the mixture solutions for the investigation of the selectivity factors of the molecularly imprinted polymers thus repared. For the further evaluation of medical application, serum samples of different creatinine concentrations were employed in the adsorption experiments with molecularly imprinted polymers as the adsorbents to test the feasibility of MIP for clinical use.

　From the experimental results of imprinted poly(β-cyclodextrin-co-epichlorohydrin), it indicated that with a molar ratio of monomer to template, 3:2, and monomer to cross-linking agent, 1:10, the imprinted polymer was successfully prepared. The imprinting factor was 4.06 ± 0.98. In the adsorption results from mixtures, the best selectivity for creatinine by MIP in binary and ternary solutions were 2.43±0.20 and 2.87±0.39,respectively.According to the results of salt effect and capping effect, it was pointed out that hydrogen binding played an important factor for specific recognition of creatinine.

　From the experimental results of imprinted poly(4-vinylpyridine-co-divinylbenzene), best imprinting factor of 3.25 was achieved. In the multi-component adsorption results, the best selectivity for creatinine by MIP were 3.90 ± 0.01. Furthermore, this MIP was also applied to human seum for the recognition of creatinine.

　From the results of sol-gel MIP, it could be seen that water was the better solvent compared to methanol. The imprinting factor was 7.18±0.05. In the multi-component adsorption results, the best selectivity for creatinine by MIP in binary and ternary mixture solutions were 8.75±0.38 and 5.19±0.54, respectively. Comparing the results between inorganic sol-gel MIP and synthesized organic MIP, it could be seen that inorganic sol-gel MIP may have better recognition ability for small size template, such as creatinine.

VI
總目錄
中文摘要............................................................................................................ I
英文摘要..........................................................................................................III
誌謝...................................................................................................................V
總目錄............................................................................................................ VI
表目錄..............................................................................................................X
圖目錄........................................................................................................... XII
第一章緒論......................................................................................................1
1.1 分子辨識系統.............................................................................................1
1.1.1 抗體-抗原反應.................................................................................1
1.1.2 酵素催化反應..................................................................................1
1.2 分子模版高分子.................................................................................3
1.2.1 單體..................................................................................................5
1.2.2 交聯劑..............................................................................................7
1.2.3 起始劑..............................................................................................7
1.2.4 溶劑..................................................................................................7
1.2.5 聚合方式..........................................................................................7
1.2.6 分子模版高分子的應用..................................................................9
1.3 以β-環糊精(β-cyclodextrin, β-CD) 為單體之分子模版高分子.12
1.3.1 環糊精............................................................................................12
1.3.2 藥物釋放系統................................................................................12
1.3.3 分離純化........................................................................................12
1.3.4 分子模版β-環糊精(β-CD) 高分子............................................12
1.4 以4-乙烯吡啶(4-vinylpyridine, 4-Vpy) 為單體之分子模版高分子..14
1.4.1 固相萃取........................................................................................14
1.5 溶膠-凝膠(Sol-gel) 分子模版高分子...................................................15
1.6 肌酸酐(Creatinine)................................................................................ 16
1.6.1 光學測量法(又稱為Jaffe reaction)............................................ 16
1.6.2 酵素法............................................................................................16
VII
1.6.3 高效能液相層析(HPLC) 法.......................................................17
1.6.4 分子模版高分子............................................................................18
1.7 研究動機與目的...............................................................................21
第二章實驗方法、藥品、儀器與原理........................................................22
2.1 肌酸酐模版高分子之製備、定性和吸附................................................22
2.1.1 β-環糊精(β-Cyclodextrin)-co-環氧氯丙烷(epichlorohydrin)
肌酸酐模板高分子之製備.........................................................22
2.1.2 以不同單體/分子模板比例製備之β-環糊精-co-環氧氯丙烷子
模版高分子其模印因子(imprinting factor) 之探討...............21
2.1.3 以不同單體/交聯劑比例製備β-環糊精-co-環氧氯丙烷分子模
版高分子吸附肌酸酐之探討.....................................................25
2.1.4 β-環糊精-co-環氧氯丙烷分子模版高分子對肌酸酐於混合溶
液之特異性吸附探討.................................................................25
2.1.5 鹽類對於β-環糊精-co-環氧氯丙烷分子模版高分子特異性吸
附之影響效應.............................................................................25
2.2.1 4-乙烯吡啶(4-Vinylpyridine)-co-二乙烯基苯(divinylbenzene)
肌酸酐模版高分子之製備…………………………………….26
2.2.2 4-乙烯吡啶-co-二乙烯基苯分子模版高分子之定性分析……26
2.2.3 4-乙烯吡啶-co-二乙烯基苯分子模版高分子之模印因子
(imprinting factor) 之探討…………………………………….26
2.2.4 4-乙烯吡啶-co-二乙烯基苯分子模版高分子對肌酸酐混合溶液
之特異性吸附探討......................................................................28
2.2.5 4-乙烯吡啶-co-二乙烯基苯分子模版高分子對肌酸酐於人血清
之特異性吸附探討……………………………………….……28
2.3.1 溶膠-凝膠(Sol-gel) 肌酸酐模版高分子之製備......................28
2.3.2 溶膠-凝膠分子模版高分子之定性分析...................................28
2.3.3 以掃瞄式電子顯微鏡(SEM) 觀察溶膠-凝膠分子模版高分
子.................................................................................................30
2.3.4 溶膠-凝膠分子模版高分子在不同溶劑溶劑下其模印因子
(imprinting factor) 的探討..........................................................30
VIII
2.3.5 溶膠-凝膠分子模版高分子在不同溶劑下對肌酸酐混合溶液之
特異性吸附探討..........................................................................30
2.4 分析方法...........................................................................................30
2.4.1 利用HPLC 分析分子模版高分子在單一溶液或混合溶液中對
肌酐之特異性吸附......................................................................30
2.5 藥品...................................................................................................37
2.6 實驗儀器...........................................................................................38
第三章結果與討論........................................................................................39
3.1 β-環糊精-co-環氧氯丙烷分子模版高分子..............................................39
3.1.1 不同單體：交聯劑之比例所製備之β-環糊精-co-環氧氯丙烷分子
模版高分子對肌酸酐吸附之影響..................................................39
3.1.2 不同單體：分子模板之比例所製備之β-環糊精-co-環氧氯丙烷分
子模版高分子對肌酸酐其模印因子(Imprinting factor) 之影響40
3.1.3 β-環糊精-co-環氧氯丙烷分子模版高分子之動力學分析...........41
3.1.4 β-環糊精-co-環氧氯丙烷分子模版高分子對肌酸酐於混合溶液之
特異性吸附.......................................................................................41
3.1.5 鹽類對於β-環糊精-co-環氧氯丙烷分子模版高分子其特異性吸附
之影響結果.......................................................................................44
3.1.6 遮蓋修飾-β-環糊精-co-環氧氯丙烷分子模版高分子對肌酸酐於
混合溶液之特異性吸附之結果......................................................44
3.2 4-乙烯吡啶-co-二乙烯基苯分子模版高分子..........................................62
3.2.1 4-乙烯吡啶-co-二乙烯基苯分子模版高分子之製備結果.............62
3.2.2 4-乙烯吡啶-co-二乙烯基苯分子模版高分子高分子其對吸附肌酸
之模印因子(Imprinting factor)的探討............................................64
3.2.3 4-乙烯吡啶-co-二乙烯基苯分子模版高分子對肌酸酐於混合溶液
之特異性吸附探討..........................................................................66
3.2.4 4-乙烯吡啶-co-二乙烯基苯分子模版高分子對肌酸酐於人體血清
之特異性吸附探討..........................................................................68
3.3 溶膠-凝膠(Sol-gel) 分子模版高分子...................................................83
3.3.1 溶膠-凝膠分子模版高分子之製備結果討論.................................83
3.3.2 溶膠-凝膠分子模版高分子在不同溶劑下對肌酸酐之吸附探討.84
3.3.3 溶膠-凝膠分子模版高分子在不同溶劑溶劑下其模印因子
(imprinting factor) 之結果..............................................................84
3.3.4 溶膠-凝膠分子模版高分子在不同溶劑下對肌酸酐於混合溶液之
特異性吸附結果..............................................................................86
3.3.5 遮蓋修飾-溶膠-凝膠分子模版高分子於混合溶液中對於肌酸酐
之特異性吸附結果..........................................................................88
第四章結論..................................................................................................100
IX
參考文獻........................................................................................................106
                                    

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