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研究生:林泓倫
研究生(外文):Hong-lun Lin
論文名稱:(1)用同位素稀釋氣相層析質譜法分析人體尿液中1,N2-乙烯基鳥糞嘌呤和(2)DNA上無鹼基位置之分析
論文名稱(外文):(1)Quantitative Analysis of 1,N2-Ethenoguanine in Human Urine by Isotope Dilution GC/NICI/MS and(2) Measurement of Apurinic Sites on DNA
指導教授:陳皓君
學位類別:碩士
校院名稱:國立中正大學
系所名稱:化學所
學門:自然科學學門
學類:化學學類
論文種類:學術論文
論文出版年:2005
畢業學年度:93
語文別:中文
論文頁數:85
中文關鍵詞:乙烯基加成產物同位素稀釋氣相層析質譜儀
外文關鍵詞:isotope dilutionGC/NICI/MSetheno adduct
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1,N2-ethenoguanine (1,N2-eGua)是高度突變性的DNA傷害,它可由體內DNA與體內脂質過氧化形成的化學物質反應形成。其中1,N2-eGua 可經由人體酵素alkylpurine-DNA-N-glycosylase 從組織切除修復排至尿液。我們開發了一個高靈敏度和高特異性的同位素稀釋氣相層析負離子化學游離質譜法來分析人體尿液中1,N2-eGua。在樣品前處理部分,先使用強陽離子交換和C18-OH兩種固相萃取管柱濃縮樣品後,以親電性衍生化試劑(PFB-Br)衍生,再以Si固相萃取管柱純化樣品PFB2-1,N2-eGua,接著以氣相層析負離子化學游離質譜搭配選擇離子追蹤分析;並以結構相同但分子量較高的穩定同位素[13C1,15N2] 1,N2-eGua作為內標準物。此方法在0.5 mL人體尿液樣品中偵測到1,N2-eGua的存在,並準確地定量。本研究也提供了一個可信的方法來測量人體尿液中1,N2-eGua作為脂質過氧化和氧化壓力的生化指標。
無鹼基位置(apurinic/apyrimidinic sites)是體內鹼基切除修復機制切除由外來環境污染物和內生性化學物質所修飾之鹼基,但未接上正常鹼基前的過渡狀態。也會因硝化性修飾鹼基,在生理條件下醣苷鍵水解而硝化鹼基自發性的掉落而生成。我們在此描述兩個定量DNA中無鹼基位置的方法:螢光和表面電漿共振(LSPR)。以具專一性之胺氧官能基和DNA上無鹼基位置之開環去氧核醣醛類反應形成穩定的oxime ether,在含胺氧官能基之探針另一端接上螢光集團後以螢光定量分析。第二個方法為合成一端含胺氧基,另一端含硫醇的化合物。硫醇可與金奈米結合成奈米探針,當它與DNA上無鹼基位置之醛基反應成oxime ether,會有LSPR訊號增加產生。
1,N2-Ethenoguanine (1,N2-eGua) is promutagenic DNA lesions, known to derive from endogenous lipid peroxidation. Moreover, 1,N2-eGua is reported to be a primary substrate of human alkylpurine-DNA-N-glycosylase. Thus, this DNA lesion could be excised from tissue DNA and released into urine. In this study, a highly sensitive and quantitative assay based on isotope dilution gas chromatography/ negative ion chemical ionization/ mass spectrometry (GC/NICI/MS) was developed for analysis of 1,N2-eGua in human urine. The assay involved adduct enrichment by consecutive strong cation exchange and reversed phase solid phase extraction columns. The enriched sample was derivatized by pentafluorobenzyl bromide (PFB-Br) and PFB2-1,N2-eGua was analyzed by GC/NICI/MS after a Si SPE clean-up. The stable isotope of the analyte, [13C1,15N2] 1,N2-eGua, was used as internal standard for accurate quantification of urinary 1,N2-eGua in as little as 0.5 mL of human urine samples. This assay provides a valuable tool for measuring urinary 1,N2-eGua as a potential biomarker of DNA damage and repair derived form lipid peroxidation and oxidative stress in general.
Apurinic (AP) sites are important DNA repair intermediates in mutagenesis and carcinogenesis. These lesions are generated by hydrolysis of the N-glycosidic bonds. We have described two methods for quantification of DNA apurinic sites, i.e. fluorescence and localized surface plasma resonance (LSPR). Based on the specific reaction of the amionooxy group and the aldehyde moiety of the open ring deoxyribose of DNA apurinic sites, a stable oxime ether is formed. A fluorescence probe is synthesized with an aminooxy group at one end to react with the apurinic sites of DNA. Another approach is to synthesize a nano-probe with an aminooxy group on one end and thiol group on the other. The thiol is attached to gold nanoparticles. When it reacts with the aldehydic group of DNA apurinic sites, formation of the oxime ether should lead to signal enhancement in LSPR.
目錄
目錄 Ⅰ
圖表目錄 IV
附圖目錄                   V

第一章 序論 1
1-1 去氧核醣核酸(DNA)的簡介 1
1-2 DNA加成產物的種類 3
1-3 外環性乙烯基加成產物對生物體的影響 4
1-4 外環性乙烯基加成產物的來源 6
1-5 DNA加成產物的生化意義 12
1-6 DNA上無嘌呤位置的形成 15
1-7 負離子化學游離質譜法(negative ion chemical
ionization Mass Spectrometry, NICI/MS) 17
1-8 研究動機 18

第二章 實驗部分 22
2-1 儀器 22
2-2 材料 22
2-3 藥品 23
2-4 氣相層析儀系統條件 23
2-5 質譜儀系統條件 24
2-6 高效能液相層析儀(HPLC)的分析條件 24
2-7 乙烯基鳥糞嘌呤的合成 24
2-8 尿液中1,N2-乙烯基鳥糞嘌呤之分析 25
2-9 利用SCX固相萃取管柱收集0.5毫升人體尿液中的
1,N2-εGua之條件 26
2-10 利用C18-OH固相萃取管柱收集經由SCX純化之1,N2-εGua之條件 27
2-11 PFB衍生化反應的條件 27
2.-12 Si固相萃取PFB-εGua的條件 28
2-13 利用氣相層析儀搭配負離子化學游離質譜儀對人體尿液中1,N2- εGua含量偵測 29
2-14 1,N2- Gua定量曲線 29
2-15 螢光感測器與金奈米感測器的合成 29
2-16 DNA上無鹼基位置的形成 31
2-17 螢光感測的反應條件 32
2-18 螢光感測的定量曲線 32

第三章 實驗結果 34
3-1-1 合成1,N2-εGua的結果 34
3-1-2 以SCX和C18-OH SPE收集人體尿液中之1,N2-εGua方法之確立 35
3-1-3 以Si SPE收集PFB2-1,N2-eGua方法之最佳化 36
3-1-4 1,N2-εGua定量曲線的確立 36
3-1-5 利用GC/NICI/MS法量測人體尿液中1,N2-eGua含量 37
3-2-1 螢光感測器與金奈米感測器的合成結果 38
3-2-2 DNA上無鹼基位置的形成 40
3-2-3 螢光感測的最佳反應條件 41
3-2-4 螢光感測的定量曲線 41
3-2-5 螢光探針偵測AP-sites DNA  42

第四章 討論 43
第五章 結論 46
參考文獻 48
中英對照表 61
























圖表目錄
圖一. DNA上的鹼基結構和Watson-Crick之DNA中鹼基結構與配對方式 2
圖二.單股DNA之鏈狀結構              3
圖三. 外環乙烯基加成產物結構 5
圖四. vinyl chloride及ethyl carbamate在生物體內的代謝物與DNA之作用 7
圖五. HNE和DNA作用生成etheno adducts 8
圖六. 生物體內氧化壓力生成外環性DNA adducts 9
圖七. 維生素C誘導脂質過氧化產生DNA加成產物示意圖 11
圖八. 3’-乙醛磷酸及CAA和Ade作用,生成εAde的推測機制 11
圖九. 無鹼基位置上的半縮醛與開放形式的醛基與含有胺基親核反應機制 16
圖十. 乙烯基鳥糞嘌呤的合成機制圖 25
圖十一. 人體尿液中的1,N2- eGua 之分析流程圖 26
圖十二. PFB-εGua衍生化反應 28
圖十三. DNA上無鹼基位置分析流程圖 32
圖十四. 螢光探針的合成流程 39
圖十五. 奈米探針的合成流程 40
圖十六. 螢光探針和去氧核糖穩定的oxime ether產物 42
圖十七. 螢光探針偵測AP-sites DNA的線性關係 42
圖十八. 螢光探針偵測DAN螢光圖譜 44
表一. 尿液中1,N2-εGua的含量結果 (尿液樣品量為0.5 mL) 38
表二. 與NO2Cl反應之DNA中8NG和8NX之含量 41

附圖目錄
附圖一. 1,N2- eGua之HPLC-UV層析圖譜 64
附圖二. 1,N2- eGua以PFB-Br衍生化後的層析圖譜
   (a)為HPLC圖譜(b)為GC/MS圖譜 65
附圖三. 1,N2- eGua以PFB-Br衍生化後的層析圖譜HPLC圖譜 65
附圖四. 1,N2- eGua以PFB-Br衍生化後的GC/MS層析圖譜 66
附圖五. GC/NICI/MS分析1,N2- eGua以PFB-Br衍生化後的層析圖譜 67
附圖六. 10pg 1,5-PFB2-1,N2- eGua之GC/NICI/MS質譜圖 68
附圖七. 1,5-PFB2-1,N2- eGua 之GC/NICI/MS的LOD圖 69
附圖八. 1,N2- eGua 之GC/NICI/MS定量曲線 69
附圖九. GC/NICI/MS分析1,N2- eGua的控制組層析圖譜 70
附圖十. GC/NICI/MS分析吸煙者尿液樣品中1,N2- eGua的層析圖譜 71
附圖十一. GC/NICI/MS分析非吸煙者尿液樣品中1,N2- eGua的層析圖譜 72
附圖十二. 螢光探針3 400MHz NMR圖譜 73
附圖十三. 螢光探針3 ESI/MS圖譜 73
附圖十四. 金奈米探針10在有機相中表面電漿共振圖譜(a)為未接上9之金奈米粒子LSPR圖譜;(b)為接上9後之金奈米粒子10 LSPR圖 74
附圖十五. 金奈米探針10在水相中表面電漿共振圖譜(a)為未接上9之金奈米粒子LSPR圖譜;(b)為接上9後之金奈米粒子10 LSPR圖譜 74
附圖十六. pH值對以螢光法偵測AP sites的影響 75
附圖十七. 螢光感測之定量曲線(螢光強度為在激發波長323 nm,
   放射波長525 nm下偵測) 75
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