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研究生：	周信宏 Chou, Hsin-Hung
論文名稱：	製備亞硝酸根離子電化學感測電極以檢測臨床尿液檢體 Preparation of electrochemical electrode for the detection of nitrite in clinical urine samples
指導教授：	許梅娟 Syu, Mei-Jywan
學位類別：	碩士 Master
系所名稱：	工學院 - 化學工程學系 Department of Chemical Engineering
論文出版年：	2016
畢業學年度：	104
語文別：	中文
論文頁數：	64
中文關鍵詞：	電化學、電位式感測、臨床尿液檢體、亞硝酸根離子、亞硝酸鹽
外文關鍵詞：	nitrite, open-circuit potential
相關次數：	點閱：249 下載：0
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亞硝酸根離子是做為泌尿道感染重要指標之一，目前臨床上是以試紙定性檢測尿液檢體含有亞硝酸根離子與否，在檢測上較為簡易，本研究以電化學方式取代傳統試紙呈色法，能精確定量檢測出臨床尿液檢體中亞硝酸根離子濃度。分別將cysteamine、p-arsanilic acid (p-AsA) 和N-naphthyl-ethylenediamine (NED) 修飾於電極上進行比較。
藉由cysteamine的thiol官能基與金電極表面形成共價鍵結固定於電極上。由於cysteamine須在酸性環境下，才可使 NH2轉變為 NH3+，並與亞硝酸根離子進行重氮反應形成偶氮染料，但人體尿液pH為6~7且酸鹼度不因病變而有大的變化，因此在實際檢測時以cysteamine修飾之電極對於亞硝酸根離子敏感度低、穩定性不佳且電位平衡時間較長。
p-AsA溶於液相中可由自身提供氫離子使 NH2轉變為 NH3+，與亞硝酸根離子進行重氮反應，不會受限於酸性環境下，且含有NED時可快速形成偶氮染料，在亞硝酸根離子感測應用中是優良的功能性材料，p-AsA與NED分別以物理吸附或包埋法固定於金電極上。物理吸附法可固定較多的p-AsA和NED於電極上，因此對於亞硝酸根離子敏感度較高，但由於乾燥後p-AsA和NED會形成結晶，在檢測時導致不同電極間再現性較低，因此對於臨床尿液檢體的準確度不高易受干擾。
包埋法是藉由pyrrole和pyrrole-3-caboxylic acid (P3CA) 共聚合將p-AsA和NED固定於電極上，包埋法修飾之電極在檢測時電位變化穩定、再現性佳、對於臨床尿液檢體檢測準確度高，且達電位平衡所需時間最短。經由干擾測試得知包埋法修飾之電極對於亞硝酸根離子有足夠的專一性。

The presence of nitrite in urine is an important indicator of urinary tract infection. In this work, we report the fabrication and detection of nitrite sensor based on the use of p-AsA/ NED composition. p-AsA/NED reacts with nitrite to form azo dye over a wide range of pH. Both UV/Vis spectra and Raman spectroscopy analysis revealed that the azo dye was successfully produced by the reaction with nitrite. Besides the surface morphology observed from scanning electron microscope (SEM) exhibited a well-modified electrode. Additionally, the prepared p-AsA/NED electrodes were examined for the electrochemical detection of nitrite by using open-circuit potential (OCP). The linear calibration curve of nitrite concentration in urine was established successfully. The calibrated nitrite concentration from patients's urine samples were compared with the measured nitrite values from Combur-10 test strips. In conclusion, the signal corresponding to nitrite concentration is confirmed to be feasible for clinical applications.

目錄
中文摘要	I
Extended Abstract	II
致謝	V
表目錄	IX
第一章 緒論	1
1.1 前言	1
1.2 泌尿道感染 (Urinary tract infection, UTI )	1
1.3 研究動機與目的	2
第二章 文獻回顧	3
2.1 化學呈色	3
2.1.1 偶氮染料 (Azo dye)	3
2.1.2 比色法 (Colorimetric assay)	3
2.1.3 化學變色試紙	4
2.2 常見電極修飾方法	6
2.2.1 介紹	6
2.2.2 物理吸附 (Physical adsorption)	6
2.2.3 共價鍵結 (Covalent binding)	7
2.2.4 錨固 (Anchoring)	7
2.2.5 包埋 (Entrapment)	8
2.2.6 奈米碳管 (Carbon nanotube) 與石墨烯 (graphene)	8
2.3 常用在亞硝酸根離子的感測材料	9
2.3.1 金屬奈米粒子 (Metal nanoparticles)	9
2.3.2 酵素 (Enzyme)	9
2.3.3 偶氮結構	10
2.4感測方法	11
2.4.1 化學發光 (Chemiluminescence, CL)	11
2.4.2 螢光 (Fluorescence)	12
2.4.3 分光光度法 (Spectrophotometry)	13
2.4.4表面增強拉曼光譜 (Surface enhanced Raman spectroscopy, SERS)	13
2.5 電化學感測 (Electrochemical detection)	14
2.5.1 介紹	14
2.5.2 循環伏安法 (Cyclic voltammetry, CV)	14
2.5.3 安培法 (Amperometric method)	16
2.5.4 微分脈衝伏安法 (Differential pulse voltammetry, DPV)	19
2.5.5 開路電位 (Open circuit potential, OCP)	19
第三章 實驗方法、材料與儀器	22
3.1 主要感測材料	22
3.2 使用UV/Vis分光光度分析	22
3.2.1 以分光光度計分析cysteamine	23
3.2.2 以分光光度計測量cysteamine在不同亞硝酸根離子濃度下的吸光度	23
3.2.3 以分光光度計分析p-AsA	23
3.2.4 以分光光度計測量p-AsA在不同亞硝酸根離子濃度下的吸光度	23
3.3 對於偶氮染料的變色情形拍照紀錄	23
3.3.1 拍攝cysteamine在不同pH下的變色情形	23
3.3.2 拍攝p-AsA/NED在不同pH下與亞硝酸根離子反應的變色情形	23
3.3.3 拍攝p-AsA在含有及未含有NED條件下之變色情形	24
3.4 使用Raman光譜進行分析	24
3.4.1 以Raman光譜分析p-AsA	24
3.4.2 以Raman光譜分析p-AsA/NED溶液與亞硝酸根離子之反應	24
3.5 以Gaussian 09W溶體模擬p-AsA的Raman光譜圖	24
3.6 網印電極之前處理	24
3.7 循環伏安法之分析	25
3.7.1 p-AsA之循環伏安圖譜	25
3.7.2 NED之循環伏安圖譜	25
3.8 電位式分析	25
3.8.1 Cysteamine電位式特性分析	26
3.8.2 固定cysteamine	26
3.8.3 以cysteamine鋪覆金電極以測量亞硝酸根離子	26
3.8.4 p-AsA電位式特性分析	26
3.8.5 以包埋法固定p-AsA	26
3.8.6 以包埋法修飾後的電極測量亞硝酸根離子	26
3.8.7 以物理吸附方式固定p-AsA於金電極	27
3.8.8 以物理吸附方式修飾後電極測量亞硝酸根離子	27
3.9 以製作的電極進行尿液檢體之亞硝酸根離子檢測	27
3.10 干擾測試	27
3.11 穩定性測試	28
3.11.1 電極保存穩定性測試	28
3.12 掃描式電子顯微鏡 (Scanning electron microscopic, SEM)	28
3.13 實驗藥品	29
3.14 實驗儀器	30
第四章 結果與討論	31
4.1 cysteamine偶氮染料形成分析	31
4.2 p-AsA/NED偶氮染料形成分析	33
4.2.1 p-AsA/NED偶氮染料變色情形	33
4.2.2 NED對反應之影響	36
4.3 p-AsA之Raman光譜分析	37
4.4 Cysteamine電位式感測	40
4.5 CV之聚合分析	43
4.6 SEM圖譜分析	46
4.6.1 上視圖	46
4.6.2 側視圖	47
4.7 p-AsA電位式感測	48
4.7.1 CV聚合圈數	48
4.7.2 不同NED濃度的影響	50
4.7.3 以物理吸附修飾電極之電位式感測	51
4.7.4 以物理吸附修飾電極之病患尿液檢體檢測	52
4.7.5 以包埋法修飾電極之電位式感測	53
4.7.6 以包埋法修飾電極之病患尿液檢體檢測	55
4.7.7 穩定性測試	55
4.7.8 干擾測試	57
第五章 結論	58
參考文獻	59
 
表目錄
表2-1-1市面上檢測亞硝酸根離子的試紙	5
表2-3-1 人體內的酵素分佈	10
表2-5-1 常用於安培法檢測的分析物	18
表4-2-1顏色變化	36
表4-7-1 電極感測前後之電阻變化	54
表4-7-2 電極穩定性測試	56
表4-7-3 干擾測試	57
圖目錄
圖1-2-1 泌尿系統	1
圖2-1-1 偶氮結構	3
圖2-1-2 Griess reaction	4
圖2-1-3 亞硝酸根離子檢測試紙示意圖	4
圖2-2-1 參考電極修飾方法。(a) 物理吸附；(b) 錨固；(c) 共價鍵結；(d) 交聯鍵結；(e) 包埋	6
圖2-2-2 錨固法。(a) nitrilotriacetic acid/Ni2+/histidine；(b) biotin/avidin/biotin；(c) pho-sphonate/Mg2+/phosphate；(d) adamantane/β-cyclodextrin；(e) nitrilotriacetic acid/Cu2+ /biotin	7
圖2-2-3 包埋	8
圖2-2-4 氧化石墨烯共價鍵結	9
圖2-3-1 歷年奈米粒子發表數	9
圖2-3-2 對胺基苯化合物。(a) 對胺基苯磺醯胺；(b) 4-胺基苯硫酚	11
圖2-3-3偶氮結構的使用方式	11
圖2-4-1 亞硝酸根離子與過氧化氫的反應機制	12
圖2-4-2 螢光與磷光	12
圖2-4-3 不同濃度亞硝酸根離子的吸收光譜	13
圖2-4-4拉曼增強機制 (a) 電磁增強機制；(b) 化學增強機制	14
圖2-5-1 循環伏安圖的整理。(a) 不同電極在赤血鹽溶液的CV圖；(b) 不同電極在含有亞硝酸鹽溶液的CV圖；(c) 不同掃速下的CV圖；(d) 依不同掃速對應電流做圖；(e) 同一電極以相同掃速掃100圈	15
圖2-5-2 電極表面微觀示意圖	16
圖2-5-3亞硝酸根離子的安培法檢測。(a) 不同濃度亞硝酸根離子的電流響應；(b) 電流響應與不同濃度亞硝酸根離子做檢量線	17
圖2-5-4 不同電訊號變化圖。(a) 常規脈衝伏安法；(b) 微分脈衝伏安法；(c) 方波伏安法	19
圖3-1-1 可與亞硝酸根離子進行反應的化合物。(a) cysteamine；(b) p-arsanilic acid	22
圖3-2-1亞硝酸根離子與兩種化合物的反應機制。(a) 與cysteamine；(b) 與p-arsanilic acid反應機制	22
圖3-8-1 電化學分析示意圖	25
圖4-1-1常見液體之pH值	31
圖4-1-2 不同pH下cysteamine顏色變化	31
圖4-1-3 不同pH下cysteamine之UV/Vis光譜圖	32
圖4-1-4 pH 1.0下不同濃度亞硝酸鈉之cysteamine溶液的UV/Vis光譜圖。(a) 全範圍；(b) 局部圖	32
圖4-1-5 亞硝酸鈉與吸光值之檢量線	33
圖4-2-1不同pH下p-AsA-NED顏色變化	34
圖4-2-2不同pH下p-AsA/NED之UV/Vis光譜圖	34
圖4-2-3不同濃度亞硝酸鈉之p-AsA/NED溶液的UV/Vis光譜圖	35
圖4-2-4 亞硝酸鈉與吸光值之檢量線	35
圖4-2-5偶氮染料隨時間的顏色變化。(a) t=0 min；(b) t=30 min；(c) t=60 min；(d) t=90 min；(e) t=120 min	37
圖4-3-1 Raman光譜	38
圖4-3-2 局部放大之Raman光譜	39
圖4-3-3 4-ABT光反應情形	39
圖4-4-1 金電極以35 mM cysteamine修飾4小時之OCP。(a) 全範圍；(b) 注入亞硝酸根離子後	40
圖4-4-2 金電極以35 mM cysteamine修飾8小時之OCP。(a) 全範圍；(b) 注入亞硝酸根離子後	41
圖4-4-3 金電極以40 mM cysteamine修飾4小時之OCP。(a) 全範圍；(b) 注入亞硝酸根離子後	41
圖4-4-4 金電極以40 mM cysteamine修飾8小時之OCP。(a) 全範圍；(b) 注入亞硝酸根離子後	42
圖4-4-5 金電極以40 mM cysteamine修飾8小時之亞硝酸根離子對電位變化檢量線	42
圖4-4-6 金電極以40 mM cysteamine修飾8小時之OCP。(a) 全範圍；(b) 注入亞硝酸根離子後	43
圖4-5-1 NED之CV圖	44
圖4-5-2 p-AsA之CV圖	44
圖4-5-3 Pyrrole和P3CA之CV圖	45
圖4-5-4電極製備之CV圖	45
圖4-6-1以不同聚合液修飾金電極之SEM。(a) 未修飾；(b) Pyrrole/P3CA為聚合液；(c) Pyrrole/P3CA/p-AsA/NED為聚合液	46
圖4-6-2以不同聚合條件修飾金電極之SEM側視圖。(a) Pyrrole/P3CA為聚合液，聚合2 segments；(b) Pyrrole/P3CA為聚合液，聚合4 segments；(c) Pyrrole/P3CA/p-AsA/NED為聚合液，聚合4 segments	47
圖4-7-1循環伏安電聚合進行6 segments修飾之電極。(a) CV圖；(b) 全範圍OCP	48
圖4-7-2循環伏安電聚合6 segments修飾之電極。(a) 加入亞硝酸根離子後OCP；(b) 檢量線	49
圖4-7-3循環伏安電聚合4 segments修飾之電極。(a) CV圖；(b) 全範圍OCP	49
圖4-7-4循環伏安電聚合4 segments修飾之電極。(a) 加入亞硝酸根離子後OCP；(b) 檢量線	50
圖4-7-5 不同NED濃度之斜率變化	50
圖4-7-6以物理吸附法修飾金電極之OCP。(a) 全範圍；(b) 注入亞硝酸根離子後	51
圖4-7-7以物理吸附法修飾金電極之 (a) 檢量線；(b) 校正線	52
圖4-7-8 以物理吸附修飾電極之臨床尿液檢測結果。(a) 全檢體比較圖；(b) 局部放大圖	52
圖4-7-9以包埋法修飾金電極之OCP。(a) 全範圍；(b) 注入亞硝酸根離子後	53
圖4-7-10以包埋法修飾金電極之 (a) 檢量線；(b) 校正線	53
圖4-7-11 包埋法修飾電極之檢測示意圖	54
圖4-7-12 以包埋法修飾電極之臨床尿液檢測結果。(a) 全檢體比較圖；(b) 局部放大圖	55
圖4-7-13 電極穩定性測試	56
圖4-7-14 干擾測試	57


                                    

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