Rhodamine-labeled 2β-carbomethoxy-3β-(3, 4-dichlorophenyl) tropane analogues as high-affinity fluorescent probes for the dopamine transporter

JH Cha, MF Zou, EM Adkins… - Journal of medicinal …, 2005 - ACS Publications
JH Cha, MF Zou, EM Adkins, SGF Rasmussen, CJ Loland, B Schoenenberger, U Gether
Journal of medicinal chemistry, 2005ACS Publications
Novel fluorescent ligands were synthesized to identify a high-affinity probe that would
enable visualization of the dopamine transporter (DAT) in living cells. Fluorescent tags were
extended from the N-or 2-position of 2β-carbomethoxy-3β-(3, 4-dichlorophenyl) tropane,
using an ethylamino linker. The resulting 2-substituted (5) and N-substituted (9) rhodamine-
labeled ligands provided the highest DAT binding affinities expressed in COS-7 cells (K i=
27 and 18 nM, respectively) in the series. Visualization of the DAT with 5 and 9 was …
Novel fluorescent ligands were synthesized to identify a high-affinity probe that would enable visualization of the dopamine transporter (DAT) in living cells. Fluorescent tags were extended from the N- or 2-position of 2β-carbomethoxy-3β-(3,4-dichlorophenyl)tropane, using an ethylamino linker. The resulting 2-substituted (5) and N-substituted (9) rhodamine-labeled ligands provided the highest DAT binding affinities expressed in COS-7 cells (Ki = 27 and 18 nM, respectively) in the series. Visualization of the DAT with 5 and 9 was demonstrated by confocal fluorescence laser scanning microscopy in stably transfected HEK293 cells.
ACS Publications