Progressive structural modification to a zinc-actuated photoinduced electron transfer (PeT) switch in the context of intracellular zinc imaging

Photoinduced electron transfer (PeT)-type fluorescent molecular switches are often applied in ion-selective sensors. Zinc-targeting sensors that contain an anilino-based electron donor (aka, the PeT 'switch') have multiple advantages over those with an aliphatic amino switch. In addition t...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2017, Vol.15 (43), p.9139-9148
Main Authors: Macias-Contreras, Miguel, Daykin, Kirsten L, Simmons, J Tyler, Allen, John R, Hooper, Zachary S, Davidson, Michael W, Zhu, Lei
Format: Article
Language:English
Subjects:
Aliphatic amines
Aniline
Chemical compounds
Electron transfer
Electrons
Fluorescence
Fluorophores
Intracellular
Ligands
Molecular machines
Oxidation
Sensors
Switches
Zinc
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Summary:Photoinduced electron transfer (PeT)-type fluorescent molecular switches are often applied in ion-selective sensors. Zinc-targeting sensors that contain an anilino-based electron donor (aka, the PeT 'switch') have multiple advantages over those with an aliphatic amino switch. In addition to the lower pK value of an aniline than that of a comparably substituted aliphatic amine, which reduces the interference of pH on the spectral properties of the attached fluorophore, the oxidation potentials of anilino groups are lower than those of aliphatic amino counterparts, which make them better electron donors in PeT. The effectiveness of anilino as a PeT switch is evaluated in a series of zinc-sensitive sensors that contain different fluorophores, zinc-binding ligands, and alkyl linkers between ligand and fluorophore. The abilities of these compounds to distinguish high and low intracellular zinc concentrations in living cells are demonstrated.
ISSN:1477-0520
1477-0539
DOI:10.1039/c7ob02235b