Radiosynthesis, cerebral distribution, and binding of [125I]-1-(p-iodophenyl)-3-(1-adamantyl)guanidine, a ligand for sigma binding sites.

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Kimes AS, Wilson AA, Scheffel U, Campbell BG, London ED

Radiosynthesis, cerebral distribution, and binding of [125I]-1-(p-iodophenyl)-3-(1-adamantyl)guanidine, a ligand for sigma binding sites.

J Med Chem. 1992 Dec 11;35(25):4683-9.

PubMed ID
1469697 [ View in PubMed
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Abstract

An analog of 1,3-di-o-tolylguanidine (DTG), [125I]-labeled 1-(p-iodophenyl)-3-(1-adamantyl)guanidine (PIPAG), was synthesized as a potential ligand for cerebral sigma binding sites. Data from in vitro binding experiments and in vivo experiments on brain distribution suggested that PIPAG binds to sigma binding sites with high affinity (Kd in low nanomolar range) as determined by Scatchard analysis and relative potencies of sigma-specific drugs. Haloperidol had the highest potency to inhibit [125I]PIPAG binding. It was followed by DTG, BMY 14802, and (+)-N-allylnormetazocine. Compounds with high affinities for dopamine receptors (but low affinity for sigma binding sites), for opioid receptors, for nicotinic acetylcholine receptors, and for phencyclidine receptors were ineffective inhibitors of [125I]PIPAG binding.

DrugBank Data that Cites this Article

Binding Properties
DrugTargetPropertyMeasurementpHTemperature (°C)
PhencyclidineSigma non-opioid intracellular receptor 1IC 50 (nM)560N/AN/ADetails
PhencyclidineSigma non-opioid intracellular receptor 1IC 50 (nM)1050N/AN/ADetails
PhencyclidineSigma non-opioid intracellular receptor 1IC 50 (nM)1000N/AN/ADetails
PhencyclidineSigma non-opioid intracellular receptor 1IC 50 (nM)868N/AN/ADetails