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

Analysis of the IQ- and IQx-type Heterocyclic Amines by Molecularly Imprinted Technology and LC-MS/MS

周秉毅(Jhou Bing-Yi)

指導教授 ： 陳頌方

國立臺灣師範大學/理學院/化學系/碩士(2018年)

https://doi.org/10.6345/THE.NTNU.DC.042.2018.B05

摘要

雜環胺化合物是指在其化學結構中含有兩種以上不同元素和至少一個胺基（-NRR'）的環狀結構化合物。許多文獻和臨床研究已指出雜環胺化合物具有高度致癌性和致突變性。分子模印技術是基於“抗原－抗體結合理論”的延伸性應用，該技術提供對目標分析物極佳的特異性和識別能力，而利用該技術合成的高分子材料則稱為分子模印聚合物（MIPs）。本篇研究目的為開發具有高度選擇性的分子模印聚合物，並使用液相層析－串聯式質譜技術定量複雜基質中的雜環胺化合物。本研究選擇IQ作為模板分子，並使用兩種官能基單體AMPS和MAA，以及交聯劑EGDMA分別透過總體聚合和沉澱聚合的方式合成分子模印聚合物，並搭配使用掃描式電子顯微鏡觀察兩種分子模印聚合物的表面特徵。之後透過對模板分子IQ的吸附能力來評估與優化合成比例，結果顯示當模板分子：官能基單體：交聯劑的比例為1：8：40時具有最好的吸附效果。此外，我們將兩種分子模印聚合物與固相萃取法結合並優化其萃取條件。實驗結果為使用MAA作為官能基單體所製備的分子模印聚合物不僅對 IQ具有高度選擇性，且MeIQ和8-MeIQx兩個雜環胺也可以被有效地偵測。最後，本實驗開發的方法可以成功應用於真實樣品的分析。

關鍵字

雜環胺化合物 ； 分子模印聚合物 ； 2-丙烯醯胺基-2-甲基丙磺酸 ； 甲基丙烯酸 ； 液相層析－串聯式質譜儀 ； 固相萃取技術

並列摘要

Heterocyclic amines (HCAs) refer to compounds that have ring structure which contains more than two different elements and at least one amine group (-NRR') in their chemical structures. Many studies and literature have pointed out that HCAs are highly carcinogenic and mutagenic. Molecularly imprinted technology is an extending application based on the "antigen-antibody binding theory". This technology provides excellent specificity and recognition ability, and the material synthesized by this method called molecularly imprinted polymers (MIPs).  The aim of this study was to develop the highly specific molecularly imprinted polymers for the purification and quantification of heterocyclic amine compounds in complex matrices using liquid chromatography-tandem mass spectrometry. In this study, IQ was selected as a template molecule, and two functional monomers, AMPS and MAA were used with cross-linking agent EGDMA for the synthesis of molecularly imprinted polymers by means of bulk polymerization and precipitation polymerization. The characteristics and surface of the MIPs were investigated through the scanning electron microscope. Afterwards, the synthesis ratios were evaluated and optimized by their adsorption capacity to the template molecules and the selectivity to other HCAs. As a result, template/functional monomer/cross-linking agent at a ratio of 1:8:40 gave better adsorption effect. Furthermore, two kinds of molecularly imprinted polymers were incorporated with solid-phase extraction and optimized the extraction conditions. The results indicated that excellent selectivity for IQ was obtained using MAA as functional monomer, while MeIQ and 8-MeIQx could also be effectively detected. Finally, our method was successfully applied to the real samples.

並列關鍵字

Heterocyclic amines ； Molecularly imprinted polymers ； AMPS ； MAA ； LC-MS/MS ； Solid-phase extraction

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