Design and Synthesis of A Caged Zn super(2+) Probe, 8-Benzenesulfonyloxy-5-N,N-dimethylaminosulfonylqu inolin-2-ylmethyl-pendant 1,4,7,10-Tetraazacyclododecane, and Its Hydrolytic Uncaging upon Complexation with Zn super(2+)

• Published in: Inorganic chemistry Vol. 47; no. 7; pp. 2747 - 2754
• Main Authors: Aoki, Shin, Sakurama, Kazusa, Ohshima, Ryosuke, Matsuo, Nanako, Yamada, Yasuyuki, Takasawa, Ryoko, Tanuma, Sei-ichi, Takeda, Kei, Kimura, Eiichi
• Format: Journal Article
• Language: English
• Published: 07.04.2008
• Subjects: Chemical compounds; Complexation; Derivatives; Emission; Esters; Fluorescence; Hydrolysis; Quinoline
• ISSN: 0020-1669
• DOI: 10.1021/ic702002m

8-Benzenesulfonyloxy-5-N,N-dimethylaminosulfonylquino lin-2-ylmethyl-pendant cyclen (BS-caged-L super(4), BS = benzenesulfonyl) was designed and synthesized as a "caged" derivative of a previously described Zn super(2+) fluorophore, 8-hydroxy-5-N,N-dimethylaminosulfonylquinolin-2-yl methyl-pendant cyclen (L super(4)) (cyclen = 1,4,7,10-tetraazacyclododecane). In the absence of metal ions and in the dark, BS-caged-L super(4) (10 [mu]M) showed negligible fluorescence emission at pH 7.4 (10 mM HEPES with l = 0.1 (NaNO sub(3))) and 25 [degrees]C (excitation at 328 nm). Addition of Zn super(2+) induced an increase in the UV/vis absorption of BS-caged-L super(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 sub(-1),L super(4)) by the hydrolysis of the sulfonyl ester at the 8-position of the quinoline unit promoted by the Zn super(2+)-bound HO-. Improvement of cell membrane permeation in comparison with L super(4) is also described.