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通过取代模式识别 Cu 和 S 的丹磺酰基取代的 N-杂环。

A dansyl-appended N-heterocycle for Cu and S recognition via a displacement mode.

机构信息

Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002, PR China.

Hubei Key Laboratory of Pollutant Analysis and Reuse Technology, College of Chemistry and Chemical Engineering, Hubei Normal University, Huangshi 435002, PR China.

出版信息

Spectrochim Acta A Mol Biomol Spectrosc. 2019 Mar 5;210:98-104. doi: 10.1016/j.saa.2018.11.017. Epub 2018 Nov 13.

Abstract

A novel l-proline based heterocycle 3 of C symmetry has been designed and synthesized for cation and anion recognition in aqueous solution. Ligand 3 shows a strong affinity to Cu ion, and their interaction induces a remarkable fluorescence quenching in DMSO:HO=9:1 (HEPES buffer, 0.01M, pH7.4) among various metal ions. Both the in-situ generated and isolated 3-Cu complex exhibit specific fluorescence recovery upon addition of S, even in the presence of SO, L-histidine, and thiol-containing amino acids. For this dual functional switch, a combination of H NMR titration, ESI mass and FT-IR spectra suggest that its sensing behavior is via a displacement mode. Sequential "on-off-on" fluorescence bio-imaging of the heterocycle 3 to Cu and S was carried out in HeLa cells.

摘要

一种新型的 C2 对称的 l-脯氨酸衍生杂环 3 已被设计和合成用于水溶液中的阳离子和阴离子识别。配体 3 对 Cu 离子表现出很强的亲和力,其相互作用在 DMSO:HO=9:1(HEPES 缓冲液,0.01M,pH7.4)中诱导各种金属离子的显著荧光猝灭。在存在 SO、L-组氨酸和含巯基氨基酸的情况下,即使在原位生成和分离的 3-Cu 配合物中,加入 S 也会导致特定的荧光恢复。对于这种双功能开关,H NMR 滴定、ESI 质谱和 FT-IR 光谱的组合表明其传感行为是通过置换模式。杂环 3 对 Cu 和 S 的顺序“开-关-开”荧光生物成像在 HeLa 细胞中进行。

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