Synthesis of carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives as new potential PET tracers for imaging of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)

Mingzhang Gao, Min Wang, Qi-Huang Zheng

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11 Citations (Scopus)

Abstract

The target tracer carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives, N-(3-[11C]methoxy-4-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (3-[11C]4a) and N-(4-[11C]methoxy-3-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (4-[11C]4a); 2-((6-amino-9H-purin-8-yl)thio)-N-(3-[11C]methoxy-4-methoxyphenyl)acetamide (3-[11C]8a) and 2-((6-amino-9H-purin-8-yl)thio)-N-(4-[11C]methoxy-3-methoxyphenyl)acetamide (4-[11C]8a), were prepared by O-[11C]methylation of their corresponding precursors with [11C]CH3OTf under basic condition (2 N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 185-555 GBq/μmol.

Original languageEnglish (US)
Pages (from-to)1371-1375
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume26
Issue number5
DOIs
StatePublished - Mar 1 2016

Fingerprint

nucleotide pyrophosphatase
Thioacetamide
Phosphoric Diester Hydrolases
Carbon
Derivatives
Imaging techniques
Methylation
Solid Phase Extraction
acetamide
purine

Keywords

  • Brain cancers
  • Carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives
  • Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)
  • Positron emission tomography (PET)
  • Type 2 diabetes

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Molecular Biology
  • Molecular Medicine
  • Organic Chemistry
  • Drug Discovery
  • Pharmaceutical Science

Cite this

@article{44279b74dffb4b7bba21a79b4b2fb78a,
title = "Synthesis of carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives as new potential PET tracers for imaging of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)",
abstract = "The target tracer carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives, N-(3-[11C]methoxy-4-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (3-[11C]4a) and N-(4-[11C]methoxy-3-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (4-[11C]4a); 2-((6-amino-9H-purin-8-yl)thio)-N-(3-[11C]methoxy-4-methoxyphenyl)acetamide (3-[11C]8a) and 2-((6-amino-9H-purin-8-yl)thio)-N-(4-[11C]methoxy-3-methoxyphenyl)acetamide (4-[11C]8a), were prepared by O-[11C]methylation of their corresponding precursors with [11C]CH3OTf under basic condition (2 N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60{\%} radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99{\%}, and the specific activity at end of synthesis (EOS) was 185-555 GBq/μmol.",
keywords = "Brain cancers, Carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives, Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1), Positron emission tomography (PET), Type 2 diabetes",
author = "Mingzhang Gao and Min Wang and Qi-Huang Zheng",
year = "2016",
month = "3",
day = "1",
doi = "10.1016/j.bmcl.2016.01.081",
language = "English (US)",
volume = "26",
pages = "1371--1375",
journal = "Bioorganic and Medicinal Chemistry Letters",
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TY - JOUR

T1 - Synthesis of carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives as new potential PET tracers for imaging of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)

AU - Gao, Mingzhang

AU - Wang, Min

AU - Zheng, Qi-Huang

PY - 2016/3/1

Y1 - 2016/3/1

N2 - The target tracer carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives, N-(3-[11C]methoxy-4-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (3-[11C]4a) and N-(4-[11C]methoxy-3-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (4-[11C]4a); 2-((6-amino-9H-purin-8-yl)thio)-N-(3-[11C]methoxy-4-methoxyphenyl)acetamide (3-[11C]8a) and 2-((6-amino-9H-purin-8-yl)thio)-N-(4-[11C]methoxy-3-methoxyphenyl)acetamide (4-[11C]8a), were prepared by O-[11C]methylation of their corresponding precursors with [11C]CH3OTf under basic condition (2 N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 185-555 GBq/μmol.

AB - The target tracer carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives, N-(3-[11C]methoxy-4-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (3-[11C]4a) and N-(4-[11C]methoxy-3-methoxyphenyl)-2-((5-methoxy-3H-imidazo[4,5-b]pyridin-2-yl)thio)acetamide (4-[11C]4a); 2-((6-amino-9H-purin-8-yl)thio)-N-(3-[11C]methoxy-4-methoxyphenyl)acetamide (3-[11C]8a) and 2-((6-amino-9H-purin-8-yl)thio)-N-(4-[11C]methoxy-3-methoxyphenyl)acetamide (4-[11C]8a), were prepared by O-[11C]methylation of their corresponding precursors with [11C]CH3OTf under basic condition (2 N NaOH) and isolated by a simplified solid-phase extraction (SPE) method in 50-60% radiochemical yields based on [11C]CO2 and decay corrected to end of bombardment (EOB). The overall synthesis time from EOB was 23 min, the radiochemical purity was >99%, and the specific activity at end of synthesis (EOS) was 185-555 GBq/μmol.

KW - Brain cancers

KW - Carbon-11-labeled imidazopyridine- and purine-thioacetamide derivatives

KW - Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)

KW - Positron emission tomography (PET)

KW - Type 2 diabetes

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U2 - 10.1016/j.bmcl.2016.01.081

DO - 10.1016/j.bmcl.2016.01.081

M3 - Article

C2 - 26856922

AN - SCOPUS:84957862978

VL - 26

SP - 1371

EP - 1375

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

SN - 0960-894X

IS - 5

ER -