Title

A novel photoaffinity ligand for the dopamine transporter based on pyrovalerone

DOI

10.1016/j.bmc.2009.04.057

Document Type

Journal Article

Publication Date

6-1-2009

Publication Title

Bioorganic and Medicinal Chemistry

Volume

17

Issue

11

First Page

3770

Last Page

3774

ISSN

9680896

Keywords

Cocaine, Dopamine transporter, Photoaffinity labeling, Pyrovalerone

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 (Ki = 78 ± 18 nM), suggesting the potential utility of a radioiodinated version in structure-function studies of this protein. © 2009 Elsevier Ltd. All rights reserved.

Open Access

Green Accepted

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