1997•Bioorganic & Medicinal Chemistry LettersOpen access

A novel photoaffinity label for the dopamine transporter based on N-substituted 3α-[bis(4′-fluorophenyl)methoxy]tropane

Gregory E. Agoston, Roxanne A. Vaughan, John R. Lever, Sari Izenwasser, Phyllis D. Terry, Amy Hauck Newman

Abstract

A novel photoaffinity label for the dopamine transporter (DAT) based on N-substituted 3α-[bis(4′-fluorophenyl)methoxy]tropane has been synthesized in five steps and has been characterized. Preliminary binding studies indicated this ligand bound irreversibly to the dopamine transporter. Preparation of the 125I analog and its photoactivation in the presence of membrane bound DAT demonstrated it covalently binds to the DAT.

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Key concepts: Tropane, Dopamine transporter, Chemistry, Dopamine Plasma Membrane Transport Proteins, Dopamine, Stereochemistry, Transporter, Ligand (biochemistry)