Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/5882
標題: 研發一化學分析法測定人類血液蛋白雌酮醌類代謝物之胼合物
Development of a chemical assay to analyze the protein adducts of estrone (E1) quinone adducts on human blood proteins
作者: 鍾國炫
Chung, Kuo-Suan
關鍵字: 雌性激素;Protein adducts;醌;生物指標;Estrogen;Quinone;Biomarker
出版社: 環境工程學系所
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摘要: 
雌酮-2,3-醌類代謝物 (E1-2,3-Q) 和雌酮-3,4-醌類代謝物 (E1-3,4-Q) 為雌性激素之活性代謝產物,並且雌性激素認為會誘發遺傳毒性。本研究為建立一化學分析方法,將雌性激素之雌酮 (estrone, E1) 醌類化合物,作為環境暴露累積組織劑量之生物指標。本研究以TFAA (trifluoroacetic anhydride) 作為衍生劑,在強酸環境下催化,將雌性激素之醌類化物與蛋白質上之Cysteine之硫原子鍵結產生之胼合物,自蛋白質結構中切除,並經由溶劑萃取濃縮,再利用氣相層析電子撞擊與負離子化學離子化質譜儀 (GC/EI/MS及GC/NICI/MS),進行定性與定量分析。運用此分析方法,在時間效應實驗結果顯示, E1-3,4-Q-2-S-Alb和E1-2,3-Q-4-S-Alb之蛋白質胼合物都會迅速在五分鐘即達到最大鍵結量,而隨著時間加長並沒有顯著之差異。運用此分析方法,對小牛血清白蛋白和人類血清白蛋白分析其背景值。實驗結果顯示,人類血清白蛋白 (n=5) 之E1-3,4-Q-2-S-Alb和E1-2,3-Q-4-S-Alb蛋白質胼合物平均值分別為71.5及265 pmol/g,而小牛血清白蛋白 (n=5) 之E1-3,4-Q-2-S-Alb以及E1-2,3-Q-4-S-Alb 蛋白質胼合物平均值46.4及118 pmol/g。將人類乳癌細胞株MCF-7以TCDD預處理(10 nM, 72小時)後,添加雌性激素及共同添加COMT抑制劑。實驗結果顯示,共同添加COMT抑制劑相較於單獨暴露於雌性激素之實驗組,其結果發現前者比後者增加3倍之雌性激素醌類蛋白質胼合物。進一步的分析台灣女性乳癌患者 (n=10) 與健康婦女 (n=10) 血清白蛋白胼合物之背景值。研究結果顯示乳癌患者相較於健康人控制組之背景值約高出2倍左右。本研究預期此一蛋白質胼合物分析法,將能作為一高效率之生物指標,提供流行病學中評估雌性激素代謝活化之干擾物質長期暴露族群之研究。

Both estrone-2,3-quinone (E1-2,3-Q) and estrone-3,4-quinone (E1-3,4-Q) are reactive metabolites of estrogen that are thought to be responsible for the estrogen-induced genotoxicity. The objective of this research is to develop a biochemical assay using estrone (estrone, E1) quinone adducts as biomarker of exposure to assess the cumulative body burden of estrogen-derived quinones in target organs. This method ultilizes trifluoroacetic anhydride (TFAA) as catalysts to cleave cysteinyl adducts of estrogen-derived quinones on proteins. The cleaved adducts are recovered by organic solvent extractions and analyzed by gas chromatography-electron-impact/negative-ion-chemical-ionization-massspectrometer (GC-EI-MS/GC-NICI-MS). Time-course experiments suggested that both E1-2,3-Q-4-S-Alb and E1-3,4-Q-2-S-Alb rapidly reached maximum values at 5 min mark and remained constant thereafter. We applied this methodology to analyze the background levels of estrone quinone-derived adducts on bovine serum albumin (BSA) and human serum albumin (HSA). Results showed that cysteinyl adducts of E1-2,3-Q-4-S-Alb and E1-3,4-Q-2-S-Alb were detected in HSA (n=5) with mean levels at 71.5 and 265 (pmol/g), respectively. Similarily, we detected these adducts in BSA (n=5) with mean levels at 46.4 and 118 pmol/g for E1-2,3-Q-4-S-Alb and E1-3,4-Q-2-S-Alb, respectively. In human MCF-7 breast cancer cells, with 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) pretreatment (10 nM for 72 h), production of estrogen quinone-derived protein adducts was detected in cells exposed to E1. Co-treatment of a catechol-o-methyl transferase (COMT) inhibitor further enhanced the production of estrogen quinone-derived adducts (~3 fold). Further investigation indicated that the background levels of these adducts in human albumin (Alb) derived from female breast cancer patients (n=10) were ~2 fold greater than those of healthy controls (n=10). Overall, we concluded that the methodology developed in this study may be applied to epidemiological study to serve as biomarkers of environmental exposure to modulators of estrogen homeostasis.
URI: http://hdl.handle.net/11455/5882
其他識別: U0005-1908201311175500
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