title: Fluorescent neuroactive probes based on stilbazolium dyes.
abstract: 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 via catecholamine 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 via NET was confirmed by imaging uptake in the absence and presence of desipramine, a norepinephrine reuptake inhibitor.
authors.affiliation: Department of Chemistry, University of Miami, 1301 Memorial Drive, Coral Gables, FL 33124, USA.
authors.forename: Adrienne S
authors.initials: AS
authors.lastname: Brown
authors.forename: Lisa-Marie
authors.initials: LM
authors.lastname: Bernal
authors.forename: Teresa L
authors.initials: TL
authors.lastname: Micotto
authors.forename: Erika L
authors.initials: EL
authors.lastname: Smith
authors.forename: James N
authors.initials: JN
authors.lastname: Wilson
mesh_terms: D000818:Animals; D002463:Cell Membrane Permeability; D002470:Cell Survival; D002642:Chick Embryo; D005456:Fluorescent Dyes / Q000737:chemistry* / Q000378:metabolism; D057809:HEK293 Cells; D006801:Humans; D015394:Molecular Structure; D011726:Pyridinium Compounds / Q000737:chemistry* / Q000378:metabolism; D013267:Stilbenes
chemical_list: D005456:Fluorescent Dyes; D011726:Pyridinium Compounds; D013267:Stilbenes