臺灣博碩士論文加值系統

目前偵測磺胺的方法主要有質譜、層析等，而在電化學分析上也有利用分子印或活化碳材進行檢測，但質譜與層析的成本高，在先前的電化學方法中也有著電流訊號不明顯、電極製作繁瑣的的問題。本研究先將羧酸官能化奈米碳管(carboxylic acid functionalized multi-walled carbon nanotube, 以MWCNT 表示) 修飾於網版印刷碳電極 (screen-printed carbon electrode, 以SPCE 表示) 上，接著將SPCE/MWCNT進行氧化還原處理，即成功製備氧化還原碳管修飾電極(SPCE/MWCNTRD)，並針對磺胺 (sulfanilamide, SAA)進行微量的定量分析。
利用循環伏安法(cyclic voltammetry, CV)偵測磺胺時，在 -0.2V ~ +0.8V的電位中觀測不到任何電流訊號，而在酸性環境下額外添加鄰苯二酚 (catechol, CA) 於分析溶液中後，CA會被電極表面氧化，促使醌胺聚合物(quinone-amine polymers , QAPs)生成，且能在+0.13V形成新的氧化還原對，且能利用QAPs的氧化電流來間接定量磺胺類藥物。利用差式脈衝伏安法(differential pulse voltammetry, DPV)進行磺胺的定量分析，線性範圍分別介於0.5-10 M 和10-50M，且此分析方法的最低極限檢測值為19.2 nM ，本研究利用簡單的修飾
方法，有效的降低偵測成本，並能大幅提前偵測電位。

The sulfonamide detection method mainly includes mass spectrometry and chromatography. In electrochemical detection, molecular imprinting technology and activated carbon materials are also used. However, mass spectrometry and chromatography are expensive, and the previous electrochemical methods also have a drawback that the current signal is not obvious and the electrode modification is complicated. In this study, carboxylic acid-functionalized multi-walled carbon nanotubes were first modified on a screen-printed carbon electrode, followed by electrochemical treatment, and then an activated carbon nanotubes modified electrode
(SPCE/MWCNTRD) was successfully prepared.
When using cyclic voltammetry to examine sulfanilamide in the presences of the potential range of -0.2V to +0.8V in an acidic environment, catechol will be oxidized on the surface of the electrode to promote the formation of quinone-amine polymers, and a new redox pair can be observed at +0.13V, which can be was use for quantification of the sulfonamide by differential pulse voltammetry (DPV). Two linear ranges of 0.5-10 μM and 10-50 μM were obtained. The lowest detection limit of this method was 19.2 nM. In this study, we use a simple modification method
to effectively determine sulfanilamide.

目次
摘要 i
Abstract ii
目次 iv
表目次 vii
圖目次 viii
第一章 簡介 1
1.1 磺胺類藥物介紹 1
1.2 Quinone-amine polymers (QAPs) 11
1.3 過氧化電極 14
1.4 奈米碳管 17
1.5 研究目的 19
第二章 實驗方法 20
2.1 藥品 20
2.2 實驗溶液配置 22
2.2.1 Buffer 製備 22
2.2.2 分析物溶液 22
2.3 SPCE/MWCNTRD 電極製備 23
2.4 偵測SAA方法 25
2.5 產物收集方法 26
2.6 儀器和設備 27
第三章 結果與討論 29
3.1 SPCE/MWCNTRD 的表面鑑定 29
3.1.1 SEM (Scanning electron microscopy) 29
3.1.2 AFM 31
3.1.3 拉曼光譜(Raman spectroscopy) 32
3.1.4 水接觸角儀(contact angle meter) 33
3.1.5 XPS (X-ray photoelectron spectroscopy) 34
3.2 機制探討 36
3.2.1 pH 影響 36
3.2.2 反應機制 40
3.3 產物鑑定 44
3.3.1 UV-Vis 44
3.3.2 FTIR 45
3.4 比較不同磺胺衍生物 47
3.5 SPCE/MWCNTRD 修飾條件最佳化 49
3.5.1 改變redox電位 49
3.5.2 改變浸泡時間 52
3.6 DPV定量 54
3.7 干擾物 56
3.8 真實樣品中SAA之定量分析 57
3.9 電化學方法偵測SAA文獻比較 60
第四章 結論 61
第五章 未來展望 62
參考文獻 63

 
表目次

Table 1.1 Effect of the interferents on DPV response corresponding to the detection of 10 μM Sulfonamides using MIP/PGE. 6
Table 1.2 Characteristics of sulfonamides calibration plots LOD, limits of detection; LOQ, limits of quantification; RSD, relative standard deviation 8
Table 2.1 Chemicals 20
Table 3.1 Difference kinds of Sulfonamides with CA measure by SPCE/MWCNTRD in pH = 5 48
Table 3.2 parameter of DPV 54
Table. 3.3 Interference effects on the determination of Sulfanilamide 56
Table 3.4 Result of recovert for SAA in real samples 59
Table. 3.5 Comparison of the analytical performance for the electrochemical determination different kinds of sulfonamides. 60

 
圖目次
Fig. 1.1 General structures of sulfonamide derivatives (sulfa drugs); R is a heterocyclic ring.[7] 1
Fig. 1.2 The structure of sulfa drugs. 2
Fig. 1.3 Cyclic voltammograms of BR buffer solution at bare GCE (curve a), 7.0×10-5 mol/L sulfonamide at bare GCE (curve b), 7.0×10-5 mol/L sulfonamide at carboxyl/DMF/MWCNTs/GCE (curve c), 1.0×10-4 mol/L sulfonamide at carboxyl/DMF/MWCNTs/GCE (curve d) in pH 1.80 BR buffer solution with the scan rate of 100 mV/s.[17] 3
Fig. 1.4 (a) Cyclic voltammograms for different concentrations of sulfonamide on the carboxyl/DMF/MWCNTs/GCE in pH 1.80 of BR buffer solution with the scan rate of 100 mV/s. Curve a to g corresponds to the concentrations of sulfonamide：1.0×10-4mol/L; 7.0×10- 5 mol/L; 5.0×10-5 mol/L; 3.0×10-5 mol/L; 1.0×10-5 mol/L; 7.0×10-6 mol/L; 1.0×10-6 mol/L, respectively. (b) Calibration curve between oxidation peak currents and the concentrations of sulfonamide. [17] 4
Fig. 1.5 Schematic representation of the proposed sensor for electrochemical detection of SN using molecularly imprinted PPy films on PGEs. 5
Fig. 1.6 DPV measurements obtained for the oxidation of SN at the MIP modified PGE for the following concentrations (a) blank (b) 5×10-8 M (c) 4.0×10-7 M (d) 7.98×10-7 M (e) 1.10×10-6 M (f) 10.90×10-6M (g) 20.48×10-6 M (h) 29.87×10-6 M (i) 39.07×10-6 M (j) 48.00×10-6 M of SN respectively. Measurement conditions: B-R buffer of pH 2.0, scan rate=80 mV s-1, 6
Fig. 1.7 Effects of acetonitrile/water ratio and pH on the OPPy electrode response for 0.10 mM (a) SAD, (b) SDZ, (c) SMZ, (d) SMM, (e) SMX in Britton– Robinson buffer solutions. 7
Fig. 1.8 The ionization process of the sulfonamides. 8
Fig. 1.9 TEM micrographs for: (A) MWCNT and (B) MWCNT-SbNPs nanocomposite. 9
Fig. 1.10 Cyclic voltammograms of the paraffin/MWCNT-SbNPs composite electrodein 0.2 mol L-1B-R buffer solution at pH 7.0 in absence of SMX and TMP (dotted line)and in the presence of 1.0 × 10-3mol L-1of SMX and TMP (solid line). 10
Fig. 1.11 DPV voltammograms for paraffin/MWCNT-SbNPs composite electrode, withthe optimised parameters. The SMX and TMP concentrations in μmol L−1are: (a)0.1, (b) 0.2, (c) 0.3, (d) 0.4, (e) 0.5, (f) 0.6 and (g) 0.7. Inset: linear dependence of the peaks current with SMX and TMP concentrations. 10
Fig. 1.12 Preparation of QAPs[36] 11
Fig. 1.13 Mechanism for the Formation of QAP polymer[37] 12
Fig. 1.14 Cyclic voltammograms in 0.10 mol L L-1 phosphate buffer (pH 7.0) containing 50 (dashed) and 0 (solid) mmol L-1 NADH at Au electrodes modified with QAP (a), MWCNTs (b), QAP-MWCNTs film (c) and the nanocomposite (d), respectively. Inset shows the response at a bare Au electrode in 0.10 mol L-1 phosphate buffer (pH 7.0) containing 1 mmol L-1 NADH. Scan rate: 50 mV s -1. 13
Fig. 1.15 Amperometric I – t curve for the detection of NADH on the Au electrodes modified with QAP (a), MWCNTs (b), and the nanocomposite (c) in the stirred 0.1 mol L-1 phosphate buffer. Operating potential: 0.25 V vs. SCE. Inset shows the calibration plot. 13
Fig. 1.16 High-resolution XPS responses for (A) C1s, O1s and (C) Conceptional representation for the surface characteristics[40]. 14
Fig. 1.17 XPS and ECL spectra of (A) SPCE*/NaOH, (B) SPCE and (C) SPCE*/H2SO4. The conditions of ECL detection system: flow rate, 1 mL/min; scan rate, 50 mV/s; scan range, 0.6–1.3 V vs. Ag/AgCl; electrolyte, 0.1 M PBS (pH 7); [Ru(bpy)3 +2]=100 μM. 15
Fig. 1.18 The effect of preanodization potential on the ratio of (A) C-OH/C-C and (B)C=O/C-C for SPCE_ and the relationship between the Epa of 10 ppm 4HP and theratio of (A) C-OH/C-C and (B) C=O/C-C for SPCE*. 16
Fig. 1.19 The structure of CNTs 17
Fig. 1.20 Hydrodynamic amperometric results for 3 mg/mL of each SAA. The average peak current obtained from injections (n = 4) of SDZ, SMZ, SAA, SGN, STZ and SXZ in 0.05 M KH2PO4 pH = 3: ACN : MeOH (80 : 15 : 5) solution at (A) MWCNTs-GCE and (B) GCE[54]. 18
Fig. 2.1 Schematic illustration for the preparation of modified electrodes. 24
Fig. 2.2 Schematic illustration of the assay for the determination of SAA. 25
Fig. 2.3 Schematic illustration of extract SAA sample 26
Fig. 3.1 Scanning electron micrographs of (A) bare SPCE, (B) SPCE/MWCNT, (C) SPCE/MWCNT after 2V 300s, and (D) SPCE/MWCNTRD Magnification of 50 K. 30
Fig. 3.2 AFM images of (A) SPCE/MWCNT and (B )SPCE/MWCNTRD 31
Fig. 3.3 Raman image of (a)SPCE/MWCNT and (b)SPCE/MWCNTRD 32
Fig. 3.4 Water contant angle of (A) bare SPCE (B) SPCE/MWCNT (C) SPCE/MWCNTRD 33
Fig. 3.5 ESCA spectra of (a) SPCE/MWCNT and (b) SPCE/MWCNTRD 34
Fig. 3.6 C1s XPS spectra of (A) SPCE/MWCNT and (B) SPCE/MWCNTRD 35
Fig. 3.7 CV curve of (a)bare SPCE ,(b)SPCE/MWNCT, (c)SPCE/MWCNTRD in pH 5 buffer solution containing (A) 1.0 mM CA (B)1.0 mM CA and 0.05mM SAA. Immsersion time: 7min Scan rate:0.10Vs-1 37
Fig. 3.8 CV curve of (a)bare SPCE ,(b)SPCE/MWCNT, (c)SPCE/MWCNTRD in pH 7 buffer solution containing (A) 1.0 mM CA (B)1.0 mM CA and 0.05mM SAA. Immsersion time: 7min Scan rate:0.10Vs-1 38
Fig. 3.9 CV curve of (a)bare SPCE, (b)SPCE/MWCNT, (c)SPCE/MWCNTRD in pH 9 buffer solution containing (A) 1.0 mM CA (B)1.0 mM CA and 0.05mM SAA. Immsersion time: 7min Scan rate:0.10Vs-1 39
Fig. 3.10 CV curve of (a) SPCE/MWCNT and (b) SPCE/MWCNTRD in blank solution (pH = 5) 40
Fig. 3.11 CV curve of (a)SPCE/MWCNT and (b)SPCE/MWCNTRD detect CA after immerse 7min in (A) original solution (B) in blank solution 41
Fig. 3.12 CV curve of (a)SPCE/MWCNT and (b)SPCE/MWCNTRD detect (A) SAA and (B) CA+SAA mixture after immerse 7min (pH = 7) 42
Fig. 3.13 Mechanism for the formation of QAP 43
Fig. 3.14 UV-vis spectrum of CA(10ppm) , SAA(5ppm) CA+SAA sample in ACN:H2O(6:4) 44
Fig. 3.15 FTIR spectra of (A)CA,SAA, CA+SAA and (B) CA+SAA 46
Fig. 3.16 CV cruve of difference kinds of Sulfonamides with CA by SPCE/MWCNTRD in pH = 5 47
Fig. 3.17 CV curve (A) and bar chart (B) of SPCE/MWCNT when redox with different final potential detect Catechol(1mM), SAA(50mM) in pH = 5 50
Fig. 3.18 CV curve (A) and bar chart (B) of SPCE/MWCNT when redox with different initial potential detect Catechol(1mM), SAA(50mM) in pH = 5 51
Fig. 3.19 CV cruve (A) and bar chart (B) of SPCE/MWCNTRD after immersion in the 50 mM sulfanilamide and 1mM catechol pH 5.0 solution. Scan rate = 0.10 V/s. Immersion time 3~15 min. 53
Fig. 3.20 DPV curve of SPCE/MWCNTRD immers in 1mM CA and (0.5, 0.1, 0.5, 1, 5, 10, 20, 30, 40, 50μM) of SAA in pH = 5 with immersion time = 7min 55
Fig. 3.21 Calibration plot of concentration 0.5μM~50μM (Insert:0.5μM~10μM of SAA). 55
Fig. 3.22 (A)DPV responses for SAA containing milk sample spiked with various concentration of 0, 1, 2, 5 and 10 μM of SAA (from a to e) in 0.1M pH 5.0 CA at SPCE/MWCNTRD . Immersion time = 7 min. (B) Calibration plot of concetration 0~10μM. 58
Fig. 3.23 (A)DPV responses for SAA containing lake water spiked with various concentration of 0, 1, 2, 5 and 10 μM of SAA (from a to e) in 0.1M pH 5.0 CA at SPCE/MWCNTRD . Immersion time = 7 min. (B) Calibration plot of concetration 0~10μM. 58

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