Synthesis, evaluation, and radiolabeling of new potent positive allosteric modulators of the metabotropic glutamate receptor 2 as potential tracers for positron emission tomography imaging.

PubWeight™: 0.86‹?›

🔗 View Article (PMID 22992024)

Published in J Med Chem on October 11, 2012

Authors

José-Ignacio Andrés1, Jesús Alcázar, José María Cid, Meri De Angelis, Laura Iturrino, Xavier Langlois, Hilde Lavreysen, Andrés A Trabanco, Sofie Celen, Guy Bormans

Author Affiliations

1: Medicinal Chemistry, Janssen Research & Development , Janssen-Cilag S.A., C/Jarama 75, 45007 Toledo, Spain. iandres@its.jnj.com

Articles by these authors

Autologous bone marrow-derived stem-cell transfer in patients with ST-segment elevation myocardial infarction: double-blind, randomised controlled trial. Lancet (2006) 7.33

18F-flutemetamol amyloid imaging in Alzheimer disease and mild cognitive impairment: a phase 2 trial. Ann Neurol (2010) 3.49

Optimized in vivo detection of dopamine release using 18F-fallypride PET. J Nucl Med (2012) 2.18

The acyclic CB1R inverse agonist taranabant mediates weight loss by increasing energy expenditure and decreasing caloric intake. Cell Metab (2008) 1.94

[18F]MK-9470, a positron emission tomography (PET) tracer for in vivo human PET brain imaging of the cannabinoid-1 receptor. Proc Natl Acad Sci U S A (2007) 1.73

Phase 1 study of the Pittsburgh compound B derivative 18F-flutemetamol in healthy volunteers and patients with probable Alzheimer disease. J Nucl Med (2009) 1.70

Regional brain activation during proximal stomach distention in humans: A positron emission tomography study. Gastroenterology (2005) 1.58

Highly efficient multicistronic lentiviral vectors with peptide 2A sequences. Hum Gene Ther (2009) 1.54

Increased ventral striatal CB1 receptor binding is related to negative symptoms in drug-free patients with schizophrenia. Neuroimage (2013) 1.48

Brain type 1 cannabinoid receptor availability in patients with anorexia and bulimia nervosa. Biol Psychiatry (2011) 1.48

Functional impact of allosteric agonist activity of selective positive allosteric modulators of metabotropic glutamate receptor subtype 5 in regulating central nervous system function. Mol Pharmacol (2011) 1.46

Prognostic value of pretransplantation positron emission tomography using fluorine 18-fluorodeoxyglucose in patients with aggressive lymphoma treated with high-dose chemotherapy and stem cell transplantation. Blood (2003) 1.40

[(18)F]FDG PET monitoring of tumour response to chemotherapy: does [(18)F]FDG uptake correlate with the viable tumour cell fraction? Eur J Nucl Med Mol Imaging (2003) 1.35

Direct comparison of 18F-FDG and 11C-methionine PET in suspected recurrence of glioma: sensitivity, inter-observer variability and prognostic value. Eur J Nucl Med Mol Imaging (2004) 1.30

Characterization of pinhole SPECT acquisition geometry. IEEE Trans Med Imaging (2003) 1.27

A dual-targeting anticancer approach: soil and seed principle. Radiology (2011) 1.21

Characterization of an orphan G protein-coupled receptor localized in the dorsal root ganglia reveals adenine as a signaling molecule. Proc Natl Acad Sci U S A (2002) 1.18

Toward waste-free production of Heck products with a catalytic palladium system under oxygen. Angew Chem Int Ed Engl (2003) 1.17

JNJ16259685, a highly potent, selective and systemically active mGlu1 receptor antagonist. Neuropharmacology (2004) 1.16

Systemic immune activation leads to neuroinflammation and sickness behavior in mice. Mediators Inflamm (2013) 1.14

Gender-dependent increases with healthy aging of the human cerebral cannabinoid-type 1 receptor binding using [(18)F]MK-9470 PET. Neuroimage (2007) 1.12

Noninvasive monitoring of long-term lentiviral vector-mediated gene expression in rodent brain with bioluminescence imaging. Mol Ther (2006) 1.11

Construction and evaluation of multitracer small-animal PET probabilistic atlases for voxel-based functional mapping of the rat brain. J Nucl Med (2006) 1.10

Characterization of 2-[[4-fluoro-3-(trifluoromethyl)phenyl]amino]-4-(4-pyridinyl)-5-thiazolemethanol (JNJ-1930942), a novel positive allosteric modulator of the {alpha}7 nicotinic acetylcholine receptor. J Pharmacol Exp Ther (2010) 1.09

Specific targeting highly conserved residues in the HIV-1 reverse transcriptase primer grip region. Design, synthesis, and biological evaluation of novel, potent, and broad spectrum NNRTIs with antiviral activity. J Med Chem (2005) 1.08

Non-invasive detection and quantification of acute myocardial infarction in rabbits using mono-[123I]iodohypericin microSPECT. Eur Heart J (2007) 1.07

Abeta amyloid deposition in the language system and how the brain responds. Brain (2007) 1.05

Anxiolytic- and antidepressant-like profile of a new CRF1 receptor antagonist, R278995/CRA0450. Eur J Pharmacol (2004) 1.04

Effects of mGlu1 receptor blockade on anxiety-related behaviour in the rat lick suppression test. Psychopharmacology (Berl) (2004) 1.03

Regional cerebral blood flow during gastric balloon distention in functional dyspepsia. Gastroenterology (2007) 1.02

Scaffold hopping from pyridones to imidazo[1,2-a]pyridines. New positive allosteric modulators of metabotropic glutamate 2 receptor. Bioorg Med Chem Lett (2009) 1.02

Optimization of geometrical calibration in pinhole SPECT. IEEE Trans Med Imaging (2005) 1.01

Measuring extrastriatal dopamine release during a reward learning task. Hum Brain Mapp (2011) 1.01

Necrosis avidity of (99m)Tc(CO)3-labeled pamoic acid derivatives: synthesis and preliminary biological evaluation in animal models of necrosis. Bioconjug Chem (2007) 1.01

[3H]R214127: a novel high-affinity radioligand for the mGlu1 receptor reveals a common binding site shared by multiple allosteric antagonists. Mol Pharmacol (2003) 1.01

Relationship of type 1 cannabinoid receptor availability in the human brain to novelty-seeking temperament. Arch Gen Psychiatry (2009) 1.01

Image-derived input function for [11C]flumazenil kinetic analysis in human brain. Mol Imaging Biol (2003) 0.99

Explaining Andean potato weevils in relation to local and landscape features: a facilitated ecoinformatics approach. PLoS One (2012) 0.99

Metabotropic glutamate receptor 1 blockade impairs acquisition and retention in a spatial Water maze task. Behav Brain Res (2005) 0.98

Striatal gene expression of RGS2 and RGS4 is specifically mediated by dopamine D1 and D2 receptors: clues for RGS2 and RGS4 functions. J Neurochem (2003) 0.97

Dihydrothiazolopyridone derivatives as a novel family of positive allosteric modulators of the metabotropic glutamate 5 (mGlu5) receptor. J Med Chem (2013) 0.97

Abnormal regional brain activity during rest and (anticipated) gastric distension in functional dyspepsia and the role of anxiety: a H(2)(15)O-PET study. Am J Gastroenterol (2010) 0.96

Necrosis avid contrast agents: functional similarity versus structural diversity. Invest Radiol (2005) 0.96

Discovery of 3-cyclopropylmethyl-7-(4-phenylpiperidin-1-yl)-8-trifluoromethyl[1,2,4]triazolo[4,3-a]pyridine (JNJ-42153605): a positive allosteric modulator of the metabotropic glutamate 2 receptor. J Med Chem (2012) 0.96

Kinetic analysis of the cannabinoid-1 receptor PET tracer [(18)F]MK-9470 in human brain. Eur J Nucl Med Mol Imaging (2009) 0.96

Metabotropic glutamate receptors: their therapeutic potential in anxiety. Curr Top Behav Neurosci (2010) 0.95

Preclinical evaluation of 18F-JNJ41510417 as a radioligand for PET imaging of phosphodiesterase-10A in the brain. J Nucl Med (2010) 0.95

Optimization of an ether series of mGlu5 positive allosteric modulators: molecular determinants of MPEP-site interaction crossover. Bioorg Med Chem Lett (2012) 0.94

Dopamine receptor-mediated regulation of RGS2 and RGS4 mRNA differentially depends on ascending dopamine projections and time. Eur J Neurosci (2004) 0.93

Discovery of 1,5-disubstituted pyridones: a new class of positive allosteric modulators of the metabotropic glutamate 2 receptor. ACS Chem Neurosci (2010) 0.93

Radiolabeled iodohypericin as tumor necrosis avid tracer: diagnostic and therapeutic potential. Int J Cancer (2012) 0.93

Evaluation of tumor affinity of mono-[(123)I]iodohypericin and mono-[(123)I]iodoprotohypericin in a mouse model with a RIF-1 tumor. Contrast Media Mol Imaging (2007) 0.93

Non-invasive grading of brain tumours using dynamic amino acid PET imaging: does it work for 11C-methionine? Eur J Nucl Med Mol Imaging (2007) 0.93

Tetrahydronaphthyridine and dihydronaphthyridinone ethers as positive allosteric modulators of the metabotropic glutamate receptor 5 (mGlu₅). J Med Chem (2014) 0.92

mGluR2 positive allosteric modulators: a patent review (2009 - present). Expert Opin Ther Pat (2013) 0.92

New positive allosteric modulators of the metabotropic glutamate receptor 2 (mGluR2): identification and synthesis of N-propyl-8-chloro-6-substituted isoquinolones. Bioorg Med Chem Lett (2010) 0.91

Bibenzyl- and stilbene-core compounds with non-polar linker atom substituents as selective ligands for estrogen receptor beta. Eur J Med Chem (2009) 0.91

Metabotropic glutamate 1 receptor distribution and occupancy in the rat brain: a quantitative autoradiographic study using [3H]R214127. Neuropharmacology (2004) 0.91

18F-FDG labeling of mesenchymal stem cells and multipotent adult progenitor cells for PET imaging: effects on ultrastructure and differentiation capacity. J Nucl Med (2013) 0.91

Construction and evaluation of quantitative small-animal PET probabilistic atlases for [¹⁸F]FDG and [¹⁸F]FECT functional mapping of the mouse brain. PLoS One (2013) 0.90

Imidazo[1,2-a]pyridines: orally active positive allosteric modulators of the metabotropic glutamate 2 receptor. J Med Chem (2012) 0.90

In vivo quantification of calcitonin gene-related peptide receptor occupancy by telcagepant in rhesus monkey and human brain using the positron emission tomography tracer [11C]MK-4232. J Pharmacol Exp Ther (2013) 0.90

Combined alpha2 and D2/3 receptor blockade enhances cortical glutamatergic transmission and reverses cognitive impairment in the rat. Int J Neuropsychopharmacol (2005) 0.89

Metabolic-dopaminergic mapping of the 6-hydroxydopamine rat model for Parkinson's disease. Eur J Nucl Med Mol Imaging (2007) 0.89

Templated misfolding of Tau by prion-like seeding along neuronal connections impairs neuronal network function and associated behavioral outcomes in Tau transgenic mice. Acta Neuropathol (2015) 0.88

Benzazaborinines as Novel Bioisosteric Replacements of Naphthalene: Propranolol as an Example. J Med Chem (2015) 0.88

Whole-body biodistribution and radiation dosimetry of the cannabinoid type 2 receptor ligand [11C]-NE40 in healthy subjects. Mol Imaging Biol (2013) 0.88

Changes in cerebral CB1 receptor availability after acute and chronic alcohol abuse and monitored abstinence. J Neurosci (2014) 0.88

Quantification of 18F-JNJ-42259152, a novel phosphodiesterase 10A PET tracer: kinetic modeling and test-retest study in human brain. J Nucl Med (2013) 0.88

Pharmacological characterization of JNJ-40068782, a new potent, selective, and systemically active positive allosteric modulator of the mGlu2 receptor and its radioligand [3H]JNJ-40068782. J Pharmacol Exp Ther (2013) 0.88

EANM guideline for the preparation of an Investigational Medicinal Product Dossier (IMPD). Eur J Nucl Med Mol Imaging (2014) 0.87

A PET brain reporter gene system based on type 2 cannabinoid receptors. J Nucl Med (2011) 0.87

Whole-body biodistribution and radiation dosimetry of the human cannabinoid type-1 receptor ligand 18F-MK-9470 in healthy subjects. J Nucl Med (2008) 0.87

Synthesis and evaluation of a (99m)Tc-MAMA-propyl-thymidine complex as a potential probe for in vivo visualization of tumor cell proliferation with SPECT. Nucl Med Biol (2007) 0.87

Discovery of a new class of potential multifunctional atypical antipsychotic agents targeting dopamine D3 and serotonin 5-HT1A and 5-HT2A receptors: design, synthesis, and effects on behavior. J Med Chem (2009) 0.87

Pharmacology of JNJ-37822681, a specific and fast-dissociating D2 antagonist for the treatment of schizophrenia. J Pharmacol Exp Ther (2012) 0.87

Synthesis and evaluation of 18F- and 11C-labeled phenyl-galactopyranosides as potential probes for in vivo visualization of LacZ gene expression using positron emission tomography. Bioconjug Chem (2008) 0.86

Regional changes in type 1 cannabinoid receptor availability in Parkinson's disease in vivo. Neurobiol Aging (2011) 0.86

Reconsideration of 5-hydroxytryptamine (5-HT)(7) receptor distribution using [(3)H]5-carboxamidotryptamine and [(3)H]8-hydroxy-2-(di-n-propylamino)tetraline: analysis in brain of 5-HT(1A) knockout and 5-HT(1A/1B) double-knockout mice. J Pharmacol Exp Ther (2002) 0.86

Widespread decrease of type 1 cannabinoid receptor availability in Huntington disease in vivo. J Nucl Med (2010) 0.86

[18F]EF3 is not superior to [18F]FMISO for PET-based hypoxia evaluation as measured in a rat rhabdomyosarcoma tumour model. Eur J Nucl Med Mol Imaging (2008) 0.86

Gene expression profiles highlight adaptive brain mechanisms in corticotropin releasing factor overexpressing mice. Brain Res Mol Brain Res (2004) 0.85

Non-invasive imaging of neuropathology in a rat model of alpha-synuclein overexpression. Neurobiol Aging (2006) 0.85

Fetal gene transfer with lentiviral vectors: long-term in vivo follow-up evaluation in a rat model. Am J Obstet Gynecol (2007) 0.85

The impact of aggregation on the biodistribution of hypericin. Int J Oncol (2006) 0.85

Regional brain activity in functional dyspepsia: a H(2)(15)O-PET study on the role of gastric sensitivity and abuse history. Gastroenterology (2010) 0.85

Optimal buffer choice of the radiosynthesis of (68)Ga-Dotatoc for clinical application. Nucl Med Commun (2010) 0.85

Pretargeting of necrotic tumors with biotinylated hypericin using 123I-labeled avidin: evaluation of a two-step strategy. Invest New Drugs (2011) 0.85