Literature DB >> 21174090

Radiosynthesis and in vivo evaluation of a series of substituted 11C-phenethylamines as 5-HT (2A) agonist PET tracers.

Anders Ettrup1, Martin Hansen, Martin A Santini, James Paine, Nic Gillings, Mikael Palner, Szabolcs Lehel, Matthias M Herth, Jacob Madsen, Jesper Kristensen, Mikael Begtrup, Gitte M Knudsen.   

Abstract

PURPOSE: Positron emission tomography (PET) imaging of serotonin 2A (5-HT(2A)) receptors with agonist tracers holds promise for the selective labelling of 5-HT(2A) receptors in their high-affinity state. We have previously validated [(11)C]Cimbi-5 and found that it is a 5-HT(2A) receptor agonist PET tracer. In an attempt to further optimize the target-to-background binding ratio, we modified the chemical structure of the phenethylamine backbone and carbon-11 labelling site of [(11)C]Cimbi-5 in different ways. Here, we present the in vivo validation of nine novel 5-HT(2A) receptor agonist PET tracers in the pig brain.
METHODS: Each radiotracer was injected intravenously into anaesthetized Danish Landrace pigs, and the pigs were subsequently scanned for 90 min in a high-resolution research tomography scanner. To evaluate 5-HT(2A) receptor binding, cortical nondisplaceable binding potentials (BP(ND)) were calculated using the simplified reference tissue model with the cerebellum as a reference region.
RESULTS: After intravenous injection, all compounds entered the brain and distributed preferentially into the cortical areas, in accordance with the known 5-HT(2A) receptor distribution. The largest target-to-background binding ratio was found for [(11)C]Cimbi-36 which also had a high brain uptake compared to its analogues. The cortical binding of [(11)C]Cimbi-36 was decreased by pretreatment with ketanserin, supporting 5-HT(2A) receptor selectivity in vivo. [(11)C]Cimbi-82 and [(11)C]Cimbi-21 showed lower cortical BP(ND), while [(11)C]Cimbi-27, [(11)C]Cimbi-29, [(11)C]Cimbi-31 and [(11)C]Cimbi-88 gave rise to cortical BP(ND) similar to that of [(11)C]Cimbi-5.
CONCLUSION: [(11)C]Cimbi-36 is currently the most promising candidate for investigation of 5-HT(2A) receptor agonist binding in the living human brain with PET.

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Year:  2010        PMID: 21174090     DOI: 10.1007/s00259-010-1686-8

Source DB:  PubMed          Journal:  Eur J Nucl Med Mol Imaging        ISSN: 1619-7070            Impact factor:   9.236


  30 in total

1.  MR-based statistical atlas of the Göttingen minipig brain.

Authors:  H Watanabe; F Andersen; C Z Simonsen; S M Evans; A Gjedde; P Cumming
Journal:  Neuroimage       Date:  2001-11       Impact factor: 6.556

2.  Similar ultrastructural distribution of the 5-HT(2A) serotonin receptor and microtubule-associated protein MAP1A in cortical dendrites of adult rat.

Authors:  V Cornea-Hébert; K C Watkins; B L Roth; W K Kroeze; P Gaudreau; N Leclerc; L Descarries
Journal:  Neuroscience       Date:  2002       Impact factor: 3.590

3.  Molecular interaction of serotonin 5-HT2A receptor residues Phe339(6.51) and Phe340(6.52) with superpotent N-benzyl phenethylamine agonists.

Authors:  Michael R Braden; Jason C Parrish; John C Naylor; David E Nichols
Journal:  Mol Pharmacol       Date:  2006-09-25       Impact factor: 4.436

4.  Development of homogeneous high-affinity agonist binding assays for 5-HT2 receptor subtypes.

Authors:  J Song; D Hanniford; C Doucette; E Graham; M F Poole; A Ting; B Sherf; J Harrington; K Brunden; A Stricker-Krongrad
Journal:  Assay Drug Dev Technol       Date:  2005-12       Impact factor: 1.738

Review 5.  Consensus nomenclature for in vivo imaging of reversibly binding radioligands.

Authors:  Robert B Innis; Vincent J Cunningham; Jacques Delforge; Masahiro Fujita; Albert Gjedde; Roger N Gunn; James Holden; Sylvain Houle; Sung-Cheng Huang; Masanori Ichise; Hidehiro Iida; Hiroshi Ito; Yuichi Kimura; Robert A Koeppe; Gitte M Knudsen; Juhani Knuuti; Adriaan A Lammertsma; Marc Laruelle; Jean Logan; Ralph Paul Maguire; Mark A Mintun; Evan D Morris; Ramin Parsey; Julie C Price; Mark Slifstein; Vesna Sossi; Tetsuya Suhara; John R Votaw; Dean F Wong; Richard E Carson
Journal:  J Cereb Blood Flow Metab       Date:  2007-05-09       Impact factor: 6.200

6.  Simplified quantification of 5-HT2A receptors in the human brain with [11C]MDL 100,907 PET and non-invasive kinetic analyses.

Authors:  Philipp T Meyer; Zubin Bhagwagar; Philip J Cowen; Vincent J Cunningham; Paul M Grasby; Rainer Hinz
Journal:  Neuroimage       Date:  2010-01-18       Impact factor: 6.556

7.  High specific activity tritium-labeled N-(2-methoxybenzyl)-2,5-dimethoxy-4-iodophenethylamine (INBMeO): a high-affinity 5-HT2A receptor-selective agonist radioligand.

Authors:  David E Nichols; Stewart P Frescas; Benjamin R Chemel; Kenneth S Rehder; Desong Zhong; Anita H Lewin
Journal:  Bioorg Med Chem       Date:  2008-04-25       Impact factor: 3.641

8.  Specific binding of [(11)C]raclopride and N-[(3)H]propyl-norapomorphine to dopamine receptors in living mouse striatum: occupancy by endogenous dopamine and guanosine triphosphate-free G protein.

Authors:  Paul Cumming; Dean F Wong; Nicholas Gillings; John Hilton; Ursula Scheffel; Albert Gjedde
Journal:  J Cereb Blood Flow Metab       Date:  2002-05       Impact factor: 6.200

9.  Synthesis and in vitro affinities of various MDL 100907 derivatives as potential 18F-radioligands for 5-HT2A receptor imaging with PET.

Authors:  Matthias M Herth; Vasko Kramer; Markus Piel; Mikael Palner; Patrick J Riss; Gitte M Knudsen; Frank Rösch
Journal:  Bioorg Med Chem       Date:  2009-03-14       Impact factor: 3.641

10.  Colocalisation of serotonin2A receptors with the glutamate receptor subunits NR1 and GluR2 in the dentate gyrus: an ultrastructural study of a modulatory role.

Authors:  C J Peddie; H A Davies; F M Colyer; M G Stewart; J J Rodríguez
Journal:  Exp Neurol       Date:  2008-03-19       Impact factor: 5.330

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  36 in total

Review 1.  PET tracers for serotonin receptors and their applications.

Authors:  J S Dileep Kumar; J John Mann
Journal:  Cent Nerv Syst Agents Med Chem       Date:  2014

Review 2.  Toxicities associated with NBOMe ingestion-a novel class of potent hallucinogens: a review of the literature.

Authors:  Joji Suzuki; Michael A Dekker; Erin S Valenti; Fabiola A Arbelo Cruz; Ady M Correa; Justin L Poklis; Alphonse Poklis
Journal:  Psychosomatics       Date:  2014-11-06       Impact factor: 2.386

3.  Effects of the hallucinogen 2,5-dimethoxy-4-iodophenethylamine (2C-I) and superpotent N-benzyl derivatives on the head twitch response.

Authors:  Adam L Halberstadt; Mark A Geyer
Journal:  Neuropharmacology       Date:  2013-09-04       Impact factor: 5.250

4.  Cerebral 5-HT2A receptor binding, but not mGluR2, is increased in tryptophan hydroxylase 2 decrease-of-function mice.

Authors:  Christinna V Jørgensen; Jacob P Jacobsen; Marc G Caron; Anders B Klein; Gitte M Knudsen; Jens D Mikkelsen
Journal:  Neurosci Lett       Date:  2013-09-17       Impact factor: 3.046

5.  The importance of small polar radiometabolites in molecular neuroimaging: A PET study with [11C]Cimbi-36 labeled in two positions.

Authors:  Annette Johansen; Hanne D Hansen; Claus Svarer; Szabolcs Lehel; Sebastian Leth-Petersen; Jesper L Kristensen; Nic Gillings; Gitte M Knudsen
Journal:  J Cereb Blood Flow Metab       Date:  2017-12-07       Impact factor: 6.200

6.  In vivo evaluation of [18F]FECIMBI-36, an agonist 5-HT2A/2C receptor PET radioligand in nonhuman primate.

Authors:  Jaya Prabhakaran; Kiran Kumar Solingapuram Sai; Francesca Zanderigo; Harry Rubin-Falcone; Matthew J Jorgensen; Jay R Kaplan; Katharine I Tooke; Akiva Mintz; J John Mann; J S Dileep Kumar
Journal:  Bioorg Med Chem Lett       Date:  2016-11-16       Impact factor: 2.823

7.  Determination of 4-bromo-2,5-dimethoxy-N-[(2-methoxyphenyl)methyl]-benzeneethanamine (25B-NBOMe) in serum and urine by high performance liquid chromatography with tandem mass spectrometry in a case of severe intoxication.

Authors:  Justin L Poklis; Carol R Nanco; Michelle M Troendle; Carl E Wolf; Alphonse Poklis
Journal:  Drug Test Anal       Date:  2013-09-02       Impact factor: 3.345

8.  [Near fatal intoxication with the novel psychoactive substance 25C-NBOMe].

Authors:  S Grautoff; J Kähler
Journal:  Med Klin Intensivmed Notfmed       Date:  2014-04-27       Impact factor: 0.840

9.  Postmortem detection of 25I-NBOMe [2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-methoxyphenyl)methyl]ethanamine] in fluids and tissues determined by high performance liquid chromatography with tandem mass spectrometry from a traumatic death.

Authors:  Justin L Poklis; Kelly G Devers; Elise F Arbefeville; Julia M Pearson; Eric Houston; Alphonse Poklis
Journal:  Forensic Sci Int       Date:  2013-10-18       Impact factor: 2.395

10.  Synthesis and in vitro evaluation of [18F]FECIMBI-36: A potential agonist PET ligand for 5-HT2A/2C receptors.

Authors:  Jaya Prabhakaran; Mark D Underwood; J S Dileep Kumar; Norman R Simpson; Suham A Kassir; Mihran J Bakalian; J John Mann; Victoria Arango
Journal:  Bioorg Med Chem Lett       Date:  2015-07-20       Impact factor: 2.823

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