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

Eyup Akgün; Philip S. Portoghese; Munawwar Sajjad; Hani A. Nabi

doi:10.1002/jlcr.1216

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

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

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

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 language	English (US)
Pages (from-to)	165-170
Number of pages	6
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	50
Issue number	3
DOIs	https://doi.org/10.1002/jlcr.1216
State	Published - Mar 2007

Keywords

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

Publisher link

10.1002/jlcr.1216

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@article{e2a9bc66fca3449f9b070b5adc3c232c,

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 Akg{\"u}n and Portoghese, \{Philip S.\} and Munawwar Sajjad and Nabi, \{Hani A.\}",

year = "2007",

month = mar,

doi = "10.1002/jlcr.1216",

language = "English (US)",

volume = "50",

pages = "165--170",

journal = "Journal of Labelled Compounds and Radiopharmaceuticals",

issn = "0362-4803",

publisher = "John Wiley and Sons Ltd",

number = "3",

}

TY - JOUR

T1 - Synthesis and 124I-labeling of m-iodophenylpyrrolomorphinan as a potential PET imaging agent for delta opioid (DOP) receptors

AU - Akgün, Eyup

AU - Portoghese, Philip S.

AU - Sajjad, Munawwar

AU - Nabi, Hani A.

PY - 2007/3

Y1 - 2007/3

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

UR - https://www.scopus.com/pages/publications/34248598915

UR - https://www.scopus.com/pages/publications/34248598915#tab=citedBy

U2 - 10.1002/jlcr.1216

DO - 10.1002/jlcr.1216

M3 - Article

AN - SCOPUS:34248598915

SN - 0362-4803

VL - 50

SP - 165

EP - 170

JO - Journal of Labelled Compounds and Radiopharmaceuticals

JF - Journal of Labelled Compounds and Radiopharmaceuticals

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