本研究中利用循環伏安法、安培法、方波伏安法等電化學分析技術配合流注式分析系統探討腐胺(putrescine)、屍胺(cadaverine)、精胺(spermine)與亞精胺(spermidine)等多胺(polyamine)與鍍銅白金電極間可能存在的電化學反應機制。為了確認鍍銅電極對多胺的電訊號如何產生，研究中在流注式分析系統中連續流注多胺溶液並使用雙工作電極加以偵測，利用上游鍍銅電極進行氧化偵測、下游白金電極進行陰極沉積的工作模式確認在偵測時會溶出銅離子；並進一步利用多胺溶液浸泡銅氧化物，使用方波伏安法確認浸泡液中含有銅離子存在，藉以上實驗結果證實鍍銅電極對於多胺的電訊號源自於銅電極表面惰性氧化層溶解後由內部零價銅再生而產生。
    在確認鍍銅電極偵測多胺之機制後，研究中進一步探討得知在流注式分析統(FIA)中偵測多胺之最佳條件如下：偵測電位為0.25V、載體溶液為0.1 M磷酸緩衝溶液、環境pH值為10、載體流速為0.5 ml/min、樣品迴路體積為50μl。對於腐胺、屍胺、精胺與亞精胺等之偵測極限與線性範圍分別為：23.50 μM、32.58 μM - 1mM；381.6 μM、529.1 μM - 10mM；456.0 nM、0.6323μM - 100μM；337.7 nM、0.4682μM - 100 μM，其相關係數均在0.99以上，連續偵測各種多胺之相對標準偏差均在5%以下，並可以避免常見之人體干擾物之訊號干擾。

Cyclic voltammetry, amperometry, and square wave voltammetry were used in this research to discuss the electrochemical mechanism might exist between electrodeposited copper electrodes and polyamines, such as putrescine, cadaverine, spermine, and spermidine. Continuous flow of polyamine solution was injected and detected by dual electrode in flow injection analysis system for assuring how the current response on electrodeposited electrode was produced by polyamines, it shows that cupric ion dissolves from the electrodeposited copper electrode surface when detecting polyamines while using upstream electrode to perform anodic detection and downstream electrode for cathodic electrodeposition. Then, after immersing copper oxides in polyamine solution, cupric ion was found by square wave voltammetry. It can be concluded that the anodic current response produced by polyamines on the electrodeposited copper electrode is produced by the oxidization of Cu(0) to regenerate the passive oxide layer dissolved by polyamines passing through the electrode surface.
      After the detection mechanism was certified, the optimization of flow injection(FIA) system was done and it show that the best conditions are 0.25 V as detection voltage, 0.1 M pH 10 phosphate buffer as carrier solution, 0.5 ml/min as flow rate and the sample loop is 50μl. The detection limit of putrescine, cadaverine, spermine, and spermidine were 23.50 μM,32.58 μM - 1mM; 381.6 μM, 529.1 μM - 10mM; 456.0 nM, 0.6323μM - 100μM, 337.7 nM, 0.4682μM - 100 μM, respectively, the RSD of sequential detection were all below 5%, and the common interference in human body can be avoided.

論文提要內容...............................................................................................I
Abstract........................................................................................................II
符號及單位、縮寫對照表..........................................................................III
目錄............................................................................................................VI
圖表目錄.................................................................................................VIII
第一章 緒論................................................................................................1
1-1 銅電極的性質及應用...........................................................................1
1-1-1 金屬銅的性質 ...........................................................................1
1-1-2 金屬電極的特性.........................................................................3
1-1-3 銅電極的應用.............................................................................4
1-2流注式分析系統..................................................................................14
1-3 與多胺相關的研究.............................................................................18
1-3-1 多胺在人體內扮演的角色.......................................................19
1-3-2 多胺與癌症的相關性...............................................................22
1-3-3 多胺與食品的相關性...............................................................24
1-4多胺之偵測方式.................................................................................26
1-4-1多胺分析方式簡介....................................................................26
  1-4-1-1 光譜學分析........................................................................26
  1-4-1-2 質譜分析............................................................................30
  1-4-1-3 其他分析方法....................................................................32
1-4-2 電化學分析...............................................................................32
  1-4-2-1生化感測器........................................................................32
  1-4-2-2非生化感測器.....................................................................34
1-5 本研究的目的....................................................................................39
第二章 實驗.............................................................................................40
2-1儀器.....................................................................................................40
  2-1-1 電化學分析部分.........................................................................40
  2-1-2 流注式分析系統部分.................................................................40
  2-1-3 高效式液相層析儀部分.............................................................42
  2-1-4 其他.............................................................................................42
2-2 藥品....................................................................................................43
2-3 實驗前處理........................................................................................44
  2-3-1 電極前處理.............................................................44
  2-3-2 樣品配製...............................................................45
2-4 實驗設計............................................................................................45
2-4-1 測機制探討...............................................................................45
2-4-2 偵測操作條件探討...................................................................46
2-4-2-1分析物特性探討......................................................46
2-4-2-2 偵測電位探討....................................................................46
2-4-2-3 環境酸鹼度之探討............................................................46
2-4-2-4 緩衝溶液種類之探討........................................................47
2-4-2-5 緩衝溶液濃度之探討........................................................47
2-4-2-6 載體流速之探討................................................................47
2-4-2-7 載體迴路容積探討............................................................47
2-4-2-8 分析特性............................................................................48
第三章 結果與討論.................................................................................49
3-1 電化學偵測機制探討........................................................................49
3-1-1 白金鍍銅電極之電化學性質探討......................................49
3-1-2 白金鍍銅電極與多胺間的電化學反應機制探討..................60
3-2 偵測操作條件最佳化............................................................82
3-2-1 分析物特性探討............................................................82
3-2-2 偵測電位探討..............................................................82
3-2-3 環境酸鹼度之探討.........................................................86
3-2-4 緩衝溶液種類之探討....................................................88
3-2-5 緩衝溶液濃度之探討.....................................................90
3-2-6 載體流速之探討...........................................................92
3-2-7 樣品迴路容積探討........................................................95
3-2-8 分析特性....................................................................97
3-5 結論...........................................................................107


參考資料..........................................................................108
圖表目錄
圖1-1 電流響應與各級反應常數及電流響應與胺基酸濃度之關係....12
圖1-2 擴散作用的種類…….................………………………….….….15
圖1-3 分散度的定義………………….................……………….….….16
圖1-4 腐胺的化學結構式………………………………………...…….18
圖1-5 屍胺的化學結構式……………………………………………....18
圖1-6 亞精胺的化學結構式……….................……………………..….18
圖1-7 精胺的化學結構式…….................…………………………..….18
圖1-8 多胺在人體內的代謝途徑……….................………………..….21
圖2-1 FIA 電化學反應槽裝置圖………………….................…….…..41
圖2-2 雙工作電極及電化學反應槽內溶液流向示意圖…....................41
圖3-1 白金電極鍍銅前後之CV 圖譜對照…….................……….…..53
圖3-2 改變掃描區間探討白金鍍銅電極之CV 圖譜(I)…....................54
圖3-3 改變掃描區間探討白金鍍銅電極之CV 圖譜(II)…...................55
圖3-4 改變掃描區間探討白金鍍銅電極之CV 圖譜(III) .................…56
圖3-5 改變掃描區間探討白金鍍銅電極之CV 圖譜(IV) .................…57
圖3-6 白金鍍銅電極之CV 圖譜與氧化還原峰價數判定....................58
圖3-7 白金鍍銅電極在磷酸緩衝溶液中的CV 圖譜.................….…..59
圖3-8 鍍銅電極對於腐胺之CV 圖譜……………………....................61
圖3-9 鍍銅電極對於屍胺之CV 圖譜…….................…………….…..62
圖3-10 鍍銅電極對於亞精胺之CV 圖譜………….................….……63
圖3-11 鍍銅電極對於精胺之CV 圖譜………………..................…….64
圖3-12 鍍銅電極在FIA 中偵測各種多胺的訊號.................…….……65
圖3-13 上下游比對鍍銅電極與白金電極之差異…................…..……66
圖3-14 連續電沉積磷酸緩衝溶液之下游電極CV 圖譜..................….70
圖3-15 連續電沉積精胺溶液之下游電極CV 圖譜…..................……71
圖3-16 電沉積浸泡Cu2O 溶液之方波伏安圖.…………..................…74
圖3-17 電沉積浸泡CuO 溶液之方波伏安圖.………..................….…75
圖3-18 在FIA 系統中偵測各種胺類及鹽類之訊號…..................……78
圖3-19 在FIA 系統中偵測各種雙胺之訊號…………..................……81
圖3-20 分析物特性探討…....................…………………………...……84
圖3-21 偵測電位探討…………………....................……………...……85
圖3-22 環境pH 值探討…….................………………………….…….87
圖3-23 緩衝溶液種類探討……………....................……………..……89
IX
圖3-24 緩衝溶液濃度探討…………………………......................……91
圖3-25 載體流速探討 …………………………………........................94
圖3-26 樣品迴路容積探討………………………………......................96
圖3-27 腐胺偵測之校正曲線………………………………................100
圖3-28 屍胺偵測之校正曲線……………………………....................101
圖3-29 亞精胺偵測之校正曲線…………………………....................102
圖3-30 精胺偵測之校正曲線……………………………....................103
圖3-31 在FIA 系統中以鍍銅電極偵測各種多胺的再現性…..…….104
圖3-31 各種干擾物之干擾程度……................…………………..…..105
圖3-33 分離並偵測真實樣品中的各種多胺....…………………..…..106
表3-1 電沉積浸泡銅氧化物溶液之參數…….................………..….....73
表3-2 最佳化分析條件…………………………………........................97
表3-3 分析特性……………………………………………....................98
表3-4 HPLC 實驗參數…....………………………………………….....99

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