Please use this identifier to cite or link to this item: http://hdl.handle.net/11455/3946
標題: 運用於細胞內生物感測器的研究
Development of Subcellular Biosensor
作者: 黃景同
Huang, Jing-Tong
關鍵字: biosensor
酸鹼指示劑
pH sensor
phenothiazine
吩噻嗪
出版社: 生醫工程研究所
引用: [1] W.T.Mason. Fluorescent and Luminescent Probes for Biological Activity; Academic: San Diego, 1999. [2] D.W.Domaille, E.L.Que, C.J.Chang. Nature Chemical Biology.2008,4,168-175 [3] X.J.Peng, J.J.Du, J.G.Fan. J. Am. Chem. Soc.2007,129,1500-1501 [4] S.G.Yoon, E.W.Miller, Q.W.He, P.H.Do, C.J.Chang. Angew. Chem. Int. Ed.2007, 46, 6658 -6661 [5] K.Komatsu. J. Am. Chem. Soc.2007,129,13447-13454 [6] M.Zhu, M.J.Yuan, X.F.Liu, J.L.Xu, J.Lv, C.S.Huang, H.B.Liu, Y.L.Li. Org. Lett. 2008,10,1481-1484 [7] T.Matsumoto, Y.Urano, T.Shoda, H.Kojima, T.Nagano. Org. Lett. 2007,9, 3375- 3377 [8] S.Girouard, M.Houle. J. Am. Chem. Soc.2005,127,559-566 [9] H.H.Lin, C.C.Chang. Dyes and Pigments.2009,83,230-236 [10] K.Pluta, B.Morak-mlodawsk, M.Jelen. European Journal of Medicinal Chemistry.2011,46,3179-3189 [11] G.Sudeshna, Karmakar.Parimal. European Journal of Pharmacology.2010,648 ,6-14 [12] A.Helal, S.H.Kim, H.S. Kim. Tetrahedron.2010,66,9925-9932. [13] M.Taki. J. Am. Chem. Soc.2004,126,712-713 [14] W.M.Leevy. J. Am. Chem. Soc.2006,128,16476-16477 [15] A.O. J. Am. Chem. Soc.2002,124,6256-6258 [16] Z.Xu, Y.Xiao, X.Qian. Org. Lett.2005,7,889-892 [17] Z.R.Grabowski. Chem. Rev.2003,103,3899-4031 [18] M.O, S.Uchiyama. Org. Lett.2003,5,1459-1461 [19] J.Han, K.Burgess. Chem.Rev.2010,110,2709-2728 [20] E.Deniz. Org. Lett.2008,10,3401-3403 [21] S.Uchiyama. Chem Commun.2009,2646-2648 [22] K.Tram, H.Yan, Hilary.A.Jenkins. Dyes and Pigments.2009,82,392-395 [23] V.R.Donuru et al. Polymer.2010,51,5359-5368 [24] Y.Tian et al. Biomaterials.2010,31,7411-7422 [25] B.Das et al. Tetrahedron Letters.2004,45,6717-6719 [26] M.Taki, J.L.Wolford, T.V.O'Halloran. J. Am. Chem. Soc.2004,126,712-713 [27] Http://www.sunbio.com/peg-shop/peg-shop-pegylation06.asp
摘要: 本篇論文是合成螢光染劑做為螢光感測器(Fluorescent sensors)主要分為兩部分,第一部分是以Phenothiazine(PTZ)為發光團,延伸兩部分位置,其中在第3的位置上以dipicolylamine (DPA)及maleimide的取代基,分別用來與金屬離子及硫醇作用反應;而在7的位置上共振延伸連接不同推拉電子的官能基作為衍生物,經由溶劑效應,加入不同的金屬離子與胺基酸L-cysteine,設計出對稱與不對稱的分子,探討其ICT(Intramolecular charge transfer)與PET(Photon electron transfer)行為機制,挑選出在最適化的條件下,合成之化合物對金屬離子與對硫醇的專一性與靈敏度。 另一部分主要是利用連接兩個發光團,設計出二元系統定量酸鹼螢光指示劑。其中一個發光團以bodipy為核心,在第3、5的位置上,共振延伸出對稱取代基,為紅色螢光;另一個發光團以naphthalimide為核心,在第4的位置上,延伸取代基,為綠色螢光。其中,紅色螢光的發光團不隨著酸鹼濃度的改變造成顏色的改變,然而綠色螢光的發光團會隨著酸鹼濃度的改變造成顏色的改變。因此,藉由添加不同濃度的酸鹼,設計出化合物在不同的酸鹼濃度,肉眼上可以清楚辨識對應的顏色,進一步運用至細胞內並嘗試觀察細胞中胞器的酸鹼值,有利於了解細胞內的運作功能。
The first section of this thesis is development of fluorescent sensors. The 3-position of the phenothiazine (PTZ) core was conjugated with dipicolylamine (DPA) and maleimide, respectively. The former product was designed to be a fluoroionophore and the later product to be a thio-reaction sensor. In the mean time, the 7-position of PTZ core was substituted with donor or acceptor functional groups. Hence, the optimum detection condition and their characters of fluoroionophore and thio-sensor were evaluated with ICT (Intramolecular charge transfer) and PET (Photon electron transfer) effect behaviour. The second section of this thesis is development of quantitative fluorescent pH sensor. This binary conjugate was constructed with a pH-responded green fluorescence enhancement fluorophore and a red fluorescence fluorophore whose emission property was inert to condition and acted as a control color of fluorometers. Furthermore, this fluorometer was used to stain the cell and quantitatively measure the pH value of organs in cell.
URI: http://hdl.handle.net/11455/3946
其他識別: U0005-1808201121044600
文章連結: http://www.airitilibrary.com/Publication/alDetailedMesh1?DocID=U0005-1808201121044600
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