N1'-(p-[18F]fluorobenzyl)naltrindole (p-[18F]BNTI) as a potential PET imaging agent for DOP receptors

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Abstract

The N1'-(p-fluorobenzyl)naltrindole 5 has been synthesized by reaction of 3-O-benzyl NTI 3 with p-fluorobenzylbromide under phase transfer catalysis. The subsequent 3-O-benzyldeprotection of 4 in HBr/CH3COOH gave the target compound 5 in three steps from naltrindole 2. p-FBNTI 5 is a novel delta opioid receptor antagonist (Ki = 0.00312 nM) and antagonizes the delta opioid (DOP) agonist, DPDPE, with a Ke = 1.55 nM in the mouse vas deferens preparation. Using the same synthetic strategy the synthesis of p-[18F]BNTI 10 was undertaken. The final yield was 4% and the specific activity varied in a range of 250-400 mCi/μmol.

Original languageEnglish (US)
Pages (from-to)857-866
Number of pages10
JournalJournal of Labelled Compounds and Radiopharmaceuticals
Volume49
Issue number10
DOIs
StatePublished - Sep 1 2006

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naltrindole
delta Opioid Receptor
Imaging techniques
D-Penicillamine (2,5)-Enkephalin
Vas Deferens
Narcotic Antagonists
Catalysis
Opioid Analgesics

Keywords

  • Delta opioid receptors
  • FBNTI
  • Fluorine-18
  • Positron emission tomography

Cite this

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title = "N1'-(p-[18F]fluorobenzyl)naltrindole (p-[18F]BNTI) as a potential PET imaging agent for DOP receptors",
abstract = "The N1'-(p-fluorobenzyl)naltrindole 5 has been synthesized by reaction of 3-O-benzyl NTI 3 with p-fluorobenzylbromide under phase transfer catalysis. The subsequent 3-O-benzyldeprotection of 4 in HBr/CH3COOH gave the target compound 5 in three steps from naltrindole 2. p-FBNTI 5 is a novel delta opioid receptor antagonist (Ki = 0.00312 nM) and antagonizes the delta opioid (DOP) agonist, DPDPE, with a Ke = 1.55 nM in the mouse vas deferens preparation. Using the same synthetic strategy the synthesis of p-[18F]BNTI 10 was undertaken. The final yield was 4{\%} and the specific activity varied in a range of 250-400 mCi/μmol.",
keywords = "Delta opioid receptors, FBNTI, Fluorine-18, Positron emission tomography",
author = "Eyup Akgun and Munawwar Sajjad and Portoghese, {Philip S}",
year = "2006",
month = "9",
day = "1",
doi = "10.1002/jlcr.1095",
language = "English (US)",
volume = "49",
pages = "857--866",
journal = "Journal of Labelled Compounds and Radiopharmaceuticals",
issn = "0362-4803",
publisher = "John Wiley and Sons Ltd",
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TY - JOUR

T1 - N1'-(p-[18F]fluorobenzyl)naltrindole (p-[18F]BNTI) as a potential PET imaging agent for DOP receptors

AU - Akgun, Eyup

AU - Sajjad, Munawwar

AU - Portoghese, Philip S

PY - 2006/9/1

Y1 - 2006/9/1

N2 - The N1'-(p-fluorobenzyl)naltrindole 5 has been synthesized by reaction of 3-O-benzyl NTI 3 with p-fluorobenzylbromide under phase transfer catalysis. The subsequent 3-O-benzyldeprotection of 4 in HBr/CH3COOH gave the target compound 5 in three steps from naltrindole 2. p-FBNTI 5 is a novel delta opioid receptor antagonist (Ki = 0.00312 nM) and antagonizes the delta opioid (DOP) agonist, DPDPE, with a Ke = 1.55 nM in the mouse vas deferens preparation. Using the same synthetic strategy the synthesis of p-[18F]BNTI 10 was undertaken. The final yield was 4% and the specific activity varied in a range of 250-400 mCi/μmol.

AB - The N1'-(p-fluorobenzyl)naltrindole 5 has been synthesized by reaction of 3-O-benzyl NTI 3 with p-fluorobenzylbromide under phase transfer catalysis. The subsequent 3-O-benzyldeprotection of 4 in HBr/CH3COOH gave the target compound 5 in three steps from naltrindole 2. p-FBNTI 5 is a novel delta opioid receptor antagonist (Ki = 0.00312 nM) and antagonizes the delta opioid (DOP) agonist, DPDPE, with a Ke = 1.55 nM in the mouse vas deferens preparation. Using the same synthetic strategy the synthesis of p-[18F]BNTI 10 was undertaken. The final yield was 4% and the specific activity varied in a range of 250-400 mCi/μmol.

KW - Delta opioid receptors

KW - FBNTI

KW - Fluorine-18

KW - Positron emission tomography

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