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

Eyup Akgün; Munawwar Sajjad; Philip S. Portoghese

doi:10.1002/jlcr.1095

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

Eyup Akgün, Munawwar Sajjad, Philip S. Portoghese

Medicinal Chemistry

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

10 Scopus citations

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 (K_i = 0.00312 nM) and antagonizes the delta opioid (DOP) agonist, DPDPE, with a K_e = 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 language	English (US)
Pages (from-to)	857-866
Number of pages	10
Journal	Journal of Labelled Compounds and Radiopharmaceuticals
Volume	49
Issue number	10
DOIs	https://doi.org/10.1002/jlcr.1095
State	Published - Sep 2006

Keywords

Delta opioid receptors
FBNTI
Fluorine-18
Positron emission tomography

Publisher link

10.1002/jlcr.1095

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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",

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

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AU - Sajjad, Munawwar

AU - Portoghese, Philip S.

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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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