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Issue 7, 2011
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Fluorescent neuroactive probes based on stilbazolium dyes

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A set of spectrally diverse stilbazolium dyes was identified in an uptake assay using cultured brainstem and cerebellum cells isolated from e19 chicks. Pretreatment of cells with indatraline, a monoamine reuptake inhibitor, allowed identification of dyes that may interact with monoamine transporters. Two structurally related, yet spectrally segregated, probes, (E)-1-methyl-4-[2-(2-naphthalenyl)ethenyl]-pyridinium iodide (NEP+, 3A) and (E)-4-[2-(6-hydroxy-2-naphthalenyl)ethenyl]-1-methyl-pyridinium iodide (HNEP+, 4A), were selected and further investigated using HEK-293 cells selectively expressing dopamine, norepinephrine or serotonin transporters. HNEP+ was selectively accumulated viacatecholamine transporters, with the norepinephrine transporter (NET) giving the highest response; NEP+ was not transported, though possible binding was observed. The alternate modes of interaction enable the use of NEP+ and HNEP+ to image distinct cell populations in live brain tissue explants. The preference for HNEP+ accumulation viaNET was confirmed by imaging uptake in the absence and presence of desipramine, a norepinephrine reuptake inhibitor.

Graphical abstract: Fluorescent neuroactive probes based on stilbazolium dyes

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Article information

07 Oct 2010
13 Dec 2010
First published
15 Dec 2010

Org. Biomol. Chem., 2011,9, 2142-2148
Article type

Fluorescent neuroactive probes based on stilbazolium dyes

A. S. Brown, L. Bernal, T. L. Micotto, E. L. Smith and J. N. Wilson, Org. Biomol. Chem., 2011, 9, 2142
DOI: 10.1039/C0OB00849D

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