PMID: 8940718Aug 1, 1996Paper

Synthesis, in vitro validation and in vivo pharmacokinetics of [125I]N-[2-(4-iodophenyl)ethyl]-N-methyl-2-(1-piperidinyl) ethylamine: a high-affinity ligand for imaging sigma receptor positive tumors

Nuclear Medicine and Biology
C S JohnW D Bowen

Abstract

N-[2-(4-iodophenyl)ethyl]-N-methyl-2-(1-piperidinyl)ethylamine, IPEMP, and the corresponding bromo derivative, BrPEMP, have been synthesized and characterized. Both BrPEMP and IPEMP were evaluated for sigma-1 and sigma-2 subtype receptor affinities and found to possess very high affinities for both receptor subtypes. The precursor for radioiodination n-tributylstannylphenylethylpiperidinylethylamine was prepared from its bromo derivative by palladium-catalyzed stannylation reaction. Radioiodinated 4-[125I]PEMP was readily prepared in high yields and high specific activity by oxidative iododestannylation reaction using chloramine-T as oxidizing agent. Sites labeled by 4-[125I]PEMP in guinea pig brain membranes showed high affinity for BD1008, haloperidol, and (+)-pentazocine (Ki = 5.06 +/- 0.40, 32.6 +/- 2.75, and 48.1 +/- 8.60 nM, respectively), which is consistent with sigma receptor pharmacology. Competition binding studies of 4-[125I]PEMP in melanoma (A375) and MCF-7 breast cancer cells showed a high affinity, dose-dependent inhibition of binding with known sigma ligand N-[2-(3,4-dichlorophenyl)ethyl]-N-methyl-2-(1-pyrrolidinyl) ethylamine, BD1008 (Ki = 5, 11 nM, respectively), supporting the labeling of sigma sites in these...Continue Reading

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Citations

Jun 1, 2000·Nuclear Medicine and Biology·K KawamuraM Senda
Mar 9, 2000·Nuclear Medicine and Biology·K KawamuraM Senda
Mar 5, 2016·Journal of Controlled Release : Official Journal of the Controlled Release Society·Yuanke LiJing Yao
Aug 3, 2013·Journal of Receptor and Signal Transduction Research·Michał Skrzycki, Hanna Czeczot
Jun 10, 2015·Journal of Receptor and Signal Transduction Research·Colin G Rousseaux, Stephanie F Greene
Sep 1, 2004·Journal of Clinical Oncology : Official Journal of the American Society of Clinical Oncology·Bieke Van Den Bossche, Christophe Van de Wiele
Feb 8, 2005·The Journal of Biological Chemistry·Amarnath MukherjeeRajkumar Banerjee
Dec 19, 2009·FASEB Journal : Official Publication of the Federation of American Societies for Experimental Biology·Lorena ZentilinMauro Giacca
Jul 25, 2017·European Journal of Organic Chemistry·Lorenzo CavinaFloris P J T Rutjes
Feb 24, 2004·CNS Drug Reviews·Deborah L GilmoreRae R Matsumoto
Dec 12, 2020·Journal of Materials Chemistry. B, Materials for Biology and Medicine·Yijun MeiMin Ren
Aug 4, 2004·Cancer Research·Ebru AydarMustafa B A Djamgoz

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