Literature DB >> 25305528

Preparation of the metabotropic glutamate receptor 5 (mGluR5) PET tracer [(18)F]FPEB for human use: An automated radiosynthesis and a novel one-pot synthesis of its radiolabeling precursor.

Keunpoong Lim1, David Labaree2, Songye Li2, Yiyun Huang2.   

Abstract

The radiotracer 3-[(18)F]fluoro-5-(2-pyridinylethynyl)benzonitrile, or [(18)F]FPEB, is a promising PET imaging agent for the metabotropic glutamate subtype 5 receptor (mGluR5). In an effort to develop a routine production method of this radiotracer for use in clinical research we adapted its radiosynthesis to an automated chemistry module. In the meanwhile, we also developed a simplified "one-pot" method for the preparation of the nitrobenzonitrile radiolabeling precursor for [(18)F]FPEB and its reference standard to replace the existing multi-step synthetic approach.
Copyright © 2014 Elsevier Ltd. All rights reserved.

Entities:  

Keywords:  PET; Radiotracer synthesis; Suzuki coupling; [(18)F]FPEB; mGluR5

Mesh:

Substances:

Year:  2014        PMID: 25305528      PMCID: PMC4253068          DOI: 10.1016/j.apradiso.2014.09.006

Source DB:  PubMed          Journal:  Appl Radiat Isot        ISSN: 0969-8043            Impact factor:   1.513


  10 in total

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Authors:  F Ivy Carroll
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Review 2.  Metabotropic glutamate receptors: their therapeutic potential in anxiety.

Authors:  Will Spooren; Anne Lesage; Hilde Lavreysen; Fabrizio Gasparini; Thomas Steckler
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Review 4.  Metabotropic glutamate receptors in the control of mood disorders.

Authors:  Jeffrey M Witkin; Gerard J Marek; Bryan G Johnson; Darryle D Schoepp
Journal:  CNS Neurol Disord Drug Targets       Date:  2007-04       Impact factor: 4.388

5.  Suzuki-miyaura coupling of alkynylboronic esters generated in situ from acetylenic derivatives

Authors: 
Journal:  Org Lett       Date:  2000-11-16       Impact factor: 6.005

6.  Potent mGluR5 antagonists: pyridyl and thiazolyl-ethynyl-3,5-disubstituted-phenyl series.

Authors:  David Alagille; Herve DaCosta; Yelin Chen; Kamondanai Hemstapat; Alice Rodriguez; Ronald M Baldwin; P Jeffrey Conn; Jeffrey P Conn; Gilles D Tamagnan
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7.  Kinetic analysis of the metabotropic glutamate subtype 5 tracer [(18)F]FPEB in bolus and bolus-plus-constant-infusion studies in humans.

Authors:  Jenna M Sullivan; Keunpoong Lim; David Labaree; Shu-Fei Lin; Timothy J McCarthy; John P Seibyl; Gilles Tamagnan; Yiyun Huang; Richard E Carson; Yu-Shin Ding; Evan D Morris
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Review 8.  Targeting metabotropic glutamate receptors for treatment of the cognitive symptoms of schizophrenia.

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Journal:  Psychopharmacology (Berl)       Date:  2004-02-19       Impact factor: 4.530

9.  18F-FPEB, a PET radiopharmaceutical for quantifying metabotropic glutamate 5 receptors: a first-in-human study of radiochemical safety, biokinetics, and radiation dosimetry.

Authors:  Dean F Wong; Rikki Waterhouse; Hiroto Kuwabara; Jongho Kim; James R Brašić; Wichana Chamroonrat; Michael Stabins; Daniel P Holt; Robert F Dannals; Terence G Hamill; P David Mozley
Journal:  J Nucl Med       Date:  2013-02-12       Impact factor: 10.057

10.  Synthesis and preliminary biological evaluation of 3-[(18)F]fluoro-5-(2-pyridinylethynyl)benzonitrile as a PET radiotracer for imaging metabotropic glutamate receptor subtype 5.

Authors:  Ji-Quan Wang; Werner Tueckmantel; Aijun Zhu; Daniela Pellegrino; Anna-Liisa Brownell
Journal:  Synapse       Date:  2007-12       Impact factor: 2.562

  10 in total
  13 in total

1.  Test-retest reproducibility of the metabotropic glutamate receptor 5 ligand [¹⁸F]FPEB with bolus plus constant infusion in humans.

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2.  Preclinical Evaluation of 18F-PF-05270430, a Novel PET Radioligand for the Phosphodiesterase 2A Enzyme.

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3.  Production of diverse PET probes with limited resources: 24 18F-labeled compounds prepared with a single radiosynthesizer.

Authors:  Jeffrey Collins; Christopher M Waldmann; Christopher Drake; Roger Slavik; Noel S Ha; Maxim Sergeev; Mark Lazari; Bin Shen; Frederick T Chin; Melissa Moore; Saman Sadeghi; Michael E Phelps; Jennifer M Murphy; R Michael van Dam
Journal:  Proc Natl Acad Sci U S A       Date:  2017-10-10       Impact factor: 11.205

4.  Measuring the effects of ketamine on mGluR5 using [18F]FPEB and PET.

Authors:  Sophie E Holmes; Jean-Dominique Gallezot; Margaret T Davis; Nicole DellaGioia; David Matuskey; Nabeel Nabulsi; John H Krystal; Jonathan A Javitch; Christine DeLorenzo; Richard E Carson; Irina Esterlis
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5.  Iodonium ylide-mediated radiofluorination of 18F-FPEB and validation for human use.

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7.  Synthesis of 18F-Arenes from Spirocyclic Iodonium(III) Ylides via Continuous-Flow Microfluidics.

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8.  Effect of age on brain metabotropic glutamate receptor subtype 5 measured with [18F]FPEB PET.

Authors:  Adam P Mecca; Kelly Rogers; Zachary Jacobs; Julia W McDonald; Hannah R Michalak; Nicole DellaGioia; Wenzhen Zhao; Ansel T Hillmer; Nabeel Nabulsi; Keunpoong Lim; Jim Ropchan; Yiyun Huang; David Matuskey; Irina Esterlis; Richard E Carson; Christopher H van Dyck
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9.  Evaluation of the Effects of Developmental Trauma on Neurotransmitter Systems Using Functional Molecular Imaging.

Authors:  Namhun Lee; Se-Jong Oh; Jang-Woo Park; Kyung-Rok Nam; Kyung-Jun Kang; Kyo-Chul Lee; Yong-Jin Lee; June-Seek Choi; Jeong-Ho Seok; Jae-Yong Choi
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10.  Synthesis of [18F]Arenes via the Copper-Mediated [18F]Fluorination of Boronic Acids.

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