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 upon complexation with Zn2+

被引：42

作者：

Aoki, Shin ^{[1
,2
]}

Sakurama, Kazusa ^{[3
]}

Ohshima, Ryosuke ^{[1
]}

Matsuo, Nanako ^{[1
]}

Yamada, Yasuyuki ^{[1
,2
]}

Takasawa, Ryoko ^{[1
]}

Tanuma, Sei-ichi ^{[1
]}

Talkeda, Kei ^{[3
]}

Kimura, Eiichi ^{[4
]}

机构：

[1] Tokyo Univ Sci, Fac Pharmaceut Sci, Noda, Chiba 2788510, Japan

[2] Tokyo Univ Sci, Ctr Drug Delivery Res, Noda, Chiba 2788510, Japan

[3] Hiroshima Univ, Grad Sch Biomed Sci, Div Med Chem, Hiroshima 7348551, Japan

[4] Shizuoka Univ, Dept Chem, Shizuoka 4228529, Japan

来源：

INORGANIC CHEMISTRY | 2008年 / 47卷 / 07期

关键词：

D O I：

10.1021/ic702002m

中图分类号：

O61 [无机化学];

学科分类号：

070301 [无机化学]; 081704 [应用化学];

摘要：

8-Benzenesulfonyloxy-5-N,N-dimethylaminosulfonylquinolin-2-ylmethyl-pendant cyclen (BS-caged-L-4, 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 (L-4) (cyclen = 1,4,7,10-tetraazacyclododecane). In the absence of metal ions and in the dark, BS-caged-L-4 (10 mu M) showed negligible fluorescence emission at pH 7.4 (10 mM HEPES with l = 0.1 (NaNO3)) and 25 degrees C (excitation at 328 nm). Addition of Zn2+ induced an increase in the UV/vis absorption of BS-caged-L-4 (10 mu M) 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 L-4 is also described.

引用

页码：2747 / 2754

页数：8

共 128 条

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