Bioorganic & Medicinal Chemistry 2009-06-01

A novel photoaffinity ligand for the dopamine transporter based on pyrovalerone.

David J Lapinsky, Shaili Aggarwal, Yurong Huang, Christopher K Surratt, John R Lever, James D Foster, Roxanne A Vaughan

Index: Bioorg. Med. Chem. 17(11) , 3770-4, (2009)

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Abstract

Non-tropane-based photoaffinity ligands for the dopamine transporter (DAT) are relatively unexplored in contrast to tropane-based compounds such as cocaine. In order to fill this knowledge gap, a ligand was synthesized in which the aromatic ring of pyrovalerone was substituted with a photoreactive azido group. The analog 1-(4-azido-3-iodophenyl)-2-pyrrolidin-1-yl-pentan-1-one demonstrated appreciable binding affinity for the DAT (K(i)=78+/-18 nM), suggesting the potential utility of a radioiodinated version in structure-function studies of this protein.

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