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

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Lapinsky DJ, Aggarwal S, Huang Y, Surratt CK, Lever JR, Foster JD, Vaughan RA

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

Bioorg Med Chem. 2009 Jun 1;17(11):3770-4. doi: 10.1016/j.bmc.2009.04.057. Epub 2009 May 3.

PubMed ID

19442525 [ View in PubMed

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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.

DrugBank Data that Cites this Article

Binding Properties

Drug	Target	Property	Measurement	pH	Temperature (°C)
Bupropion	Sodium-dependent dopamine transporter	Ki (nM)	441	N/A	N/A	Details
Bupropion	Sodium-dependent dopamine transporter	IC 50 (nM)	1567	N/A	N/A	Details