Synthesis and 124I-labeling of m-iodophenylpyrrolomorphinan as a potential PET imaging agent for delta opioid (DOP) receptors

Eyup Akgun, Philip S Portoghese, Munawwar Sajjad, Hani A. Nabi

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Condensation of phenylazo-β-ketoamide 4 with oxymorphone 5 afforded an m-iodophenylpyrrolomorphinan (m-IPPM) 6 mediated by elemental zinc in acetic acid/sodium acetate buffer. m-IPPM 6 is a novel opioid receptor agonist (K i = 4.53 nM for DOP) with high selectivity for DOP receptors. m-IPPM 6 was converted into the positron emitter m-[124I]PPM 8 via the stannylated intermediate 7. The final yield was 24.5 ± 1.9 % (n = 6) with a specific activity of 2.5 ± 1.2 Ci/μmol.

Original languageEnglish (US)
Pages (from-to)165-170
Number of pages6
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume50
Issue number3
DOIs
StatePublished - Mar 1 2007

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Oxymorphone
Sodium Acetate
delta Opioid Receptor
Opioid Receptors
Positrons
Acetic Acid
Labeling
Opioid Analgesics
Zinc
Condensation
Buffers
Electrons
Imaging techniques

Keywords

  • DOP receptor agonist
  • Iodine-124
  • Positron emission tomography
  • m-IPPM

Cite this

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title = "Synthesis and 124I-labeling of m-iodophenylpyrrolomorphinan as a potential PET imaging agent for delta opioid (DOP) receptors",
abstract = "Condensation of phenylazo-β-ketoamide 4 with oxymorphone 5 afforded an m-iodophenylpyrrolomorphinan (m-IPPM) 6 mediated by elemental zinc in acetic acid/sodium acetate buffer. m-IPPM 6 is a novel opioid receptor agonist (K i = 4.53 nM for DOP) with high selectivity for DOP receptors. m-IPPM 6 was converted into the positron emitter m-[124I]PPM 8 via the stannylated intermediate 7. The final yield was 24.5 ± 1.9 {\%} (n = 6) with a specific activity of 2.5 ± 1.2 Ci/μmol.",
keywords = "DOP receptor agonist, Iodine-124, Positron emission tomography, m-IPPM",
author = "Eyup Akgun and Portoghese, {Philip S} and Munawwar Sajjad and Nabi, {Hani A.}",
year = "2007",
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T1 - Synthesis and 124I-labeling of m-iodophenylpyrrolomorphinan as a potential PET imaging agent for delta opioid (DOP) receptors

AU - Akgun, Eyup

AU - Portoghese, Philip S

AU - Sajjad, Munawwar

AU - Nabi, Hani A.

PY - 2007/3/1

Y1 - 2007/3/1

N2 - Condensation of phenylazo-β-ketoamide 4 with oxymorphone 5 afforded an m-iodophenylpyrrolomorphinan (m-IPPM) 6 mediated by elemental zinc in acetic acid/sodium acetate buffer. m-IPPM 6 is a novel opioid receptor agonist (K i = 4.53 nM for DOP) with high selectivity for DOP receptors. m-IPPM 6 was converted into the positron emitter m-[124I]PPM 8 via the stannylated intermediate 7. The final yield was 24.5 ± 1.9 % (n = 6) with a specific activity of 2.5 ± 1.2 Ci/μmol.

AB - Condensation of phenylazo-β-ketoamide 4 with oxymorphone 5 afforded an m-iodophenylpyrrolomorphinan (m-IPPM) 6 mediated by elemental zinc in acetic acid/sodium acetate buffer. m-IPPM 6 is a novel opioid receptor agonist (K i = 4.53 nM for DOP) with high selectivity for DOP receptors. m-IPPM 6 was converted into the positron emitter m-[124I]PPM 8 via the stannylated intermediate 7. The final yield was 24.5 ± 1.9 % (n = 6) with a specific activity of 2.5 ± 1.2 Ci/μmol.

KW - DOP receptor agonist

KW - Iodine-124

KW - Positron emission tomography

KW - m-IPPM

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