Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/5717
標題: 同步分析人類血清白蛋白中萘及雌性激素醌類代謝物之蛋白質胼合物
Simultaneous analysis of naphthalene and estrogen quinone derived-protein adducts in human serum albumin
作者: 魏子翰
Wei, Hz-han
關鍵字: protein adducts
蛋白質胼合物
human serum albumin
hemoglobin
albumin
人類血清白蛋白
人類血紅蛋白
白蛋白
出版社: 環境工程學系所
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摘要: 本研究之主旨係運用蛋白質胼合物(protein adduct)作為生物指標(biomarker),以雌性激素及萘之醌類化物與蛋白質形成之共價鍵結產物-蛋白質胼合物,作為推估雌性激素及萘之醌類化物於標的器官之組織劑量。並探討於多環芳香族碳氫化合物(Polycyclic aromatic hydrocarbons, PAHs)及影響雌性激素代謝活化之干擾物質,例如戴奧辛(2,3,7,8-tetrachlorodibenzo-p-dioxin, TCDD)之環境暴露下,對萘及雌性激素醌類化物與蛋白質反應形成蛋白質胼合物之影響。本研究係以TFAA (trifluoroacetic acid anhydride) 作為衍生劑,並於強酸環境下移除雌性激素及萘之醌類化物與蛋白質上cysteine之硫原子鍵結產生之胼合物,並經由溶劑萃取濃縮,再利用氣相層析負離子化學離子化質譜儀 (GC/NICI/MS),進行定量分析。此外運用高效能液相層析儀純化雌性激素及萘之醌類化物與N-acetyl-L-cysteine反應形成之胼合物,以製備定量所需之標準品;同時利用同位素內標準品,對待測物進行定性及定量分析。首先在萘醌類蛋白質胼合物之分析結果顯示,自美國Sigma-Aldrich公司購買之人類血紅蛋白(Hemoglobin)、人類血清白蛋白 (human serum albumin, HSA)、台灣台南捐血中心提供之人類血清白蛋白及懷孕婦女和嬰兒臍帶血之血清白蛋白分析結果中,測得萘醌類化物蛋白質胼合物之背景值,1,2-NPQ-Alb及1,4-NPQ-Alb分別為67-1679及38-449 pmol/g;萘醌類(1,2-NPQ及1,4-NPQ)於人體血清中二階反應速率常數(kr, Lg-1h-1)經推估分別為0.0044及0.0002 Lg-1h-1;組織劑量則為20.6-144及217-957 nM-h。在雌性激素醌類蛋白質胼合物之分析結果顯示,於Hb、HSA、台南捐血中心及國家衛生研究院之四種血清白蛋白中均測得雌性激素醌類之蛋白質胼合物4-OHE2-2-Alb 及2-OHE2-4-Alb分別為14.6-59.7及70.2-440 pmol/g,且均無測得2-OHE2-1-Alb之生成。將所測得之1,2-NPQ-Alb與2-OHE2-4-Alb及4-OHE2-2-Alb的背景值取自然對數作線性迴歸,結果指出1,2-NPQ-Alb與2-OHE2-4-Alb及4-OHE2-2-Alb具高度的相關性 (p<0.001)。所以當暴露在PAHs的環境下亦可能會提高內生性雌性激素醌類代謝物質的產生。進一步以統計分析台南捐血中心樣本與健康懷孕婦女萘醌類胼合物及雌性激素醌類胼合物背景值與年齡之相關性,結果指出均無明顯的相關。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PAHs及雌性激素代謝活化之干擾物質長期暴露族群之研究。
The objective of this research is to develop a biochemical assay using protein adducts as biomarker of environmental exposure to polycyclic aromatic hydrocarbons (PAHs) and modulators of estrogen homeostasis, such as 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD). This methodology ultilizes trifluoroacetic acid (TFAA) and methanesulfonic acid (MSA) as catalysts to cleave cysteinyl adducts of naphthalene- and estrogen-derived quinones on proteins. The cleaved adducts are recovered by organic solvent extractions and analyzed by gas chromatography- negative-ion-chemical-ionization-mass spectrometer (GC-NICI-MS). The isomeric forms of cysteinyl adducts of naphthoquinones, including 1,2-naphthoquinone (1,2-NPQ) and 1,4-naphthoquinone (1,4-NPQ) as well as estrogen quinones, including estrogen-2,3-quinones (2-OHE2) and estrogen-3,4-quinones (4-OHE2), are characterized by using isotopically-labelled bound internal standards after adducts cleavage by the TFAA/MSA derivatization procedure. We applied this method to analyze the background levels of cysteinyl adducts of estrogen- and naphthalene-derived quinones on Hemoglobin(Hb), human serum albumin(HSA) (purchased from Sigma-Aldrich), human serum albumin derived from unexposed blood donors in Taiwan, and serum albumin derived from healthy pregnant women and their respective umbilical cord. Results showed that the background levels of cysteinyl adducts of 1,2-NPQ and 1,4-NPQ on human serum albumin derived from Sigma and from blood donors in Taiwan at levels ranging from 67-1679 and 38-449 pmol/g, respectively. Further investigation indicated that the second-order reaction rate constants of 1,2-NPQ and 1,4-NPQ with human serum were estimated to be 0.0044 and 0.0002 Lg-1h-1, respectively, whereas tissue dose of naphthoquinones in human serum derived from blood donors were estimated to be between 20.6-144 and 217-957 nM-h for 1,2-NPQ and 1,4-NPQ, respectively. In addition, cysteinyl adducts of 4-OHE2-2-Alb and 2-OHE2-4-Alb were detected in all four types of proteins at levels ranging from 14.6-59.7 and 70.2-440 pmol/g, respectively. We noticed that logged levels of 1,2-NPQ-Alb highly correlated with logged levels of 2-OHE2-4-Alb and 4-OHE2-2-Alb (p<0.001). This evidence suggests that environmental exposure to PAHs may enhance the production of reactive quinone species of endogenous estrogen in human. Further, we noticed that among the samples derived from blood donors in Taiwan and from healthy pregnant women, levels of naphthalene and estrogen quinone-derived adducts were not associated with age. Overall, we conclude that the methodology developed in this study may be applied to epidemiological study to serve as biomarkers of environmental exposure to PAHs and other modulators of estrogen homeostasis.
URI: http://hdl.handle.net/11455/5717
其他識別: U0005-2907200911455500
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