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

Research output: Contribution to journalArticlepeer-review

6 Scopus citations


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.

Original languageEnglish (US)
Pages (from-to)3770-3774
Number of pages5
JournalBioorganic and Medicinal Chemistry
Issue number11
StatePublished - Jun 1 2009
Externally publishedYes


  • Cocaine
  • Dopamine transporter
  • Photoaffinity labeling
  • Pyrovalerone

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry


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