A rhodamine-labeled citalopram analogue as a high-affinity fluorescent probe for the serotonin transporter.

Article Details

Citation

Copy to clipboard

Zhang P, Jorgensen TN, Loland CJ, Newman AH

A rhodamine-labeled citalopram analogue as a high-affinity fluorescent probe for the serotonin transporter.

Bioorg Med Chem Lett. 2013 Jan 1;23(1):323-6. doi: 10.1016/j.bmcl.2012.10.089. Epub 2012 Nov 1.

PubMed ID

23168018 [ View in PubMed

]

Abstract

A novel fluorescent ligand was synthesized as a high-affinity, high specificity probe for visualizing the serotonin transporter (SERT). The rhodamine fluorophore was extended from an aniline substitution on the 5-position of the dihydroisobenzofuran ring of citalopram (2, 1-(3-(dimethylamino)propyl)-1-(4-fluorophenyl)-1,3-dihydroisobenzofuran-5-carboni trile), using an ethylamino linker. The resulting rhodamine-labeled ligand 8 inhibited [(3)H]5-HT uptake in COS-7 cells (K(i)=225 nM) with similar potency to the tropane-based JHC 1-064 (1), but with higher specificity towards the SERT relative to the transporters for dopamine and norepinephrine. Visualization of the SERT with compound 8 was demonstrated by confocal microscopy in HEK293 cells stably expressing EGFP-SERT.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Citalopram	Sodium-dependent serotonin transporter	Ki (nM)	16	N/A	N/A	Details