Journal
INORGANIC CHEMISTRY
Volume 45, Issue 24, Pages 9748-9757Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ic061137e
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Funding
- NCRR NIH HHS [1S10RR13886-01] Funding Source: Medline
- NIGMS NIH HHS [GM65519, R01 GM065519-01, R01 GM065519] Funding Source: Medline
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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. These sensors each contain an aniline-based ligand moiety functionalized with a pyridyl-amine-pyrrole group and have dissociation constants for Zn(II) in the sub-micromolar (ZP9) and low-micromolar (ZP10) range, which we define as midrange. They give similar to 12- (ZP9) and similar to 7- fold (ZP10) fluorescence turn-on immediately following Zn(II) addition at 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 permeable and Zn(II) responsive in vivo.
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