Midrange Affinity Fluorescent Zn(II) Sensors of the Zinpyr Family: Syntheses, Characterization, and Biological Imaging Applications

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• 作者：Elizabeth M. Nolan ; Jacek Jaworski ; Maryann E. Racine ; Morgan Sheng ; Stephen J. Lippard
• 刊名：Inorganic Chemistry
• 出版年：2006
• 出版时间：November 27, 2006
• 年：2006
• 卷：45
• 期：24
• 页码：9748 - 9757
• 全文大小：329K
• 年卷期：v.45,no.24(November 27, 2006)
• ISSN：1520-510X

文摘

The syntheses and photophysical characterization of ZP9, 2-{2-chloro-6-hydroxy-3-oxo-5-[(2-{[pyridin-2-ylmethyl-(1H-pyrrol-2-ylmethyl)amino]methyl}phenylamino)methyl]-3H-xanthen-9-yl}benzoic acid, and ZP10, 2-{2-chloro-6-hydroxy-5-[(2-{[(1-methyl-1H-pyrrol-2-ylmethyl)pyridin-2-ylmethylamino]methyl}phenylamino)methyl]-3-oxo-3H-xanthen-9-yl}benzoic acid, two asymmetrically derivatized fluorescein-based dyes, are described. Thesesensors each contain an aniline-based ligand moiety functionalized with a pyridyl-amine-pyrrole group and havedissociation constants for Zn(II) in the sub-micromolar (ZP9) and low-micromolar (ZP10) range, which we define as"midrange". They give ~12- (ZP9) and ~7-fold (ZP10) fluorescence turn-on immediately following Zn(II) additionat neutral pH and exhibit improved selectivity for Zn(II) compared to the di-(2-picolyl)amine-based Zinpyr (ZP)sensors. Confocal microscopy studies indicate that such asymmetrical fluorescein-based probes are cell permeableand Zn(II) responsive in vivo.