Rhodamine-Labeled 2β-Carbomethoxy-3β-(3,4-dichlorophenyl)tropane Analogues as High-Affinity Fluorescent Probes for the Dopamine Transporter
- 5 November 2005
- journal article
- letter
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 48 (24) , 7513-7516
- https://doi.org/10.1021/jm050431y
Abstract
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.Keywords
This publication has 14 references indexed in Scilit:
- Fluorescent Cocaine Probes: A Tool for the Selection and Engineering of Therapeutic AntibodiesJournal of the American Chemical Society, 2005
- Fluorescent Pirenzepine Derivatives as Potential Bitopic Ligands of the Human M1 Muscarinic ReceptorJournal of Medicinal Chemistry, 2004
- A Novel, High-Affinity, Fluorescent Progesterone Receptor Antagonist. Synthesis and in Vitro StudiesBioconjugate Chemistry, 2004
- Synthesis and Characterization of the First Fluorescent Antagonists for Human 5-HT4ReceptorsJournal of Medicinal Chemistry, 2003
- Fluorescence resonance energy transfer to probe human M1 muscarinic receptor structure and drug binding propertiesJournal of Neurochemistry, 2003
- Creating new fluorescent probes for cell biologyNature Reviews Molecular Cell Biology, 2002
- Probes for the dopamine transporter: New leads toward a cocaine‐abuse therapeutic—A focus on analogues of benztropine and rimcazoleMedicinal Research Reviews, 2002
- Synthesis and Characterization of Fluorescent and Photoactivatable MIP-1α Ligands and Interactions with Chemokine Receptors CCR1 and CCR5Journal of Medicinal Chemistry, 2000
- Intracellular Trafficking of Angiotensin II and its AT1and AT2Receptors: Evidence for Selective Sorting of Receptor and LigandMolecular Endocrinology, 1997
- Spectroscopic and immunochemical studies with nitrobenzoxadiazolealanine, a fluorescent dinitrophenyl analogBiochemistry, 1977