Design and Synthesis of A Caged Zn2+ Probe, 8-Benzenesulfonyloxy-5-N,N-dimethylaminosulfonylquinolin-2-ylmethyl-pendant 1,4,7,10-Tetraazacyclododecane, and Its Hydrolytic Uncaging up

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• 作者：Shin Aoki ; Kazusa Sakurama ; Ryosuke Ohshima ; Nanako Matsuo ; Yasuyuki Yamada ; Ryoko Takasawa ; Sei-ichi Tanuma ; Kei Takeda ; Eiichi Kimura
• 刊名：Inorganic Chemistry
• 出版年：2008
• 出版时间：April 7, 2008
• 年：2008
• 卷：47
• 期：7
• 页码：2747 - 2754
• 全文大小：1101K
• 年卷期：v.47,no.7(April 7, 2008)
• ISSN：1520-510X

文摘

8-Benzenesulfonyloxy-5-N,N-dimethylaminosulfonylquinolin-2-ylmethyl-pendant cyclen (BS-caged-L⁴, BS = benzenesulfonyl) was designed and synthesized as a “caged” derivative of a previously described Zn²⁺ fluorophore, 8-hydroxy-5-N,N-dimethylaminosulfonylquinolin-2-ylmethyl-pendant cyclen (L⁴) (cyclen = 1,4,7,10-tetraazacyclododecane). In the absence of metal ions and in the dark, BS-caged-L⁴ (10 µM) showed negligible fluorescence emission at pH 7.4 (10 mM HEPES with I = 0.1 (NaNO₃)) and 25 °C (excitation at 328 nm). Addition of Zn²⁺ induced an increase in the UV/vis absorption of BS-caged-L⁴ (10 µM) at 258 nm and a significant increase in fluorescence emission at 512 nm. These responses are results from the formation of Zn(H₋₁L⁴) by the hydrolysis of the sulfonyl ester at the 8-position of the quinoline unit promoted by the Zn²⁺-bound HO⁻. Improvement of cell membrane permeation in comparison with L⁴ is also described.