Literature DB >> 20694167

[carbonyl-C]Benzyl acetate: automated radiosynthesis via Pd-mediated [C]carbon monoxide chemistry and PET measurement of brain uptake in monkey.

Shuiyu Lu1, Jinsoo Hong, Tetsuji Itoh, Masahiro Fujita, Osamu Inoue, Robert B Innis, Victor W Pike.   

Abstract

[carbonyl-(11)C]Benzyl acetate ([(11)C]1) has been proposed as a potential agent for imaging glial metabolism of acetate to glutamate and glutamine with positron emission tomography (PET). [(11)C]1 was synthesized from [(11)C]carbon monoxide, iodomethane and benzyl alcohol via palladium-mediated chemistry. The radiosynthesis was automated with a modified Synthia platform controlled with in-house developed Labview software. Under production conditions, [(11)C]1 was obtained in 10% (n = 6) decay-corrected radiochemical yield from [(11)C]carbon monoxide in > 96% radiochemical purity and with an average specific radioactivity of 2,415 mCi/micromol. The total radiosynthesis time was about 45 min. Peak uptake of radioactivity in brain (SUV = 3.1) was relatively high and may be amenable to measuring uptake and metabolism of acetate in glial cells of the brain.

Entities:  

Year:  2010        PMID: 20694167      PMCID: PMC2914334          DOI: 10.1002/jlcr.1779

Source DB:  PubMed          Journal:  J Labelled Comp Radiopharm        ISSN: 0362-4803            Impact factor:   1.921


  11 in total

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Authors:  U C POZZANI; C P CARPENTER; P E PALM; C S WEIL; J H NAIR
Journal:  J Occup Med       Date:  1959-12

2.  [carbonyl-11C]Desmethyl-WAY-100635 (DWAY) is a potent and selective radioligand for central 5-HT1A receptors in vitro and in vivo.

Authors:  V W Pike; C Halldin; J A McCarron; C Lundkvist; E Hirani; H Olsson; S P Hume; P Karlsson; S Osman; C G Swahn; H Hall; H Wikström; M Mensonidas; K G Poole; L Farde
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Authors:  Osamu Inoue; Rie Hosoi; Sotaro Momosaki; Keisuke Yamamoto; Misato Amitani; Masatoshi Yamaguchi; Antony Gee
Journal:  Nucl Med Biol       Date:  2006-11       Impact factor: 2.408

4.  Synthesis and biodistribution of [(11)C]R116301, a promising PET ligand for central NK(1) receptors.

Authors:  M Van der Mey; C G M Janssen; F E Janssens; M Jurzak; X Langlois; F M Sommen; B Verreet; A D Windhorst; J E Leysen; J D M Herscheid
Journal:  Bioorg Med Chem       Date:  2005-03-01       Impact factor: 3.641

5.  [14C]Benzyl acetate is a potential radiotracer for the measurement of glial metabolism in the rat brain.

Authors:  Sotaro Momosaki; Rie Hosoi; Tomoya Sanuki; Kenichiro Todoroki; Masatoshi Yamaguchi; Antony Gee; Osamu Inoue
Journal:  Nucl Med Biol       Date:  2007-09-04       Impact factor: 2.408

6.  Evaluation of radiolabeled acetate and fluoroacetate as potential tracers of cerebral oxidative metabolism.

Authors:  J L Lear; R F Ackermann
Journal:  Metab Brain Dis       Date:  1990-03       Impact factor: 3.584

7.  Preparation of [1-11C]acetate--an agent for the study of myocardial metabolism by positron emission tomography.

Authors:  V W Pike; M N Eakins; R M Allan; A P Selwyn
Journal:  Int J Appl Radiat Isot       Date:  1982-07

8.  Effect of astrocytic energy metabolism depressant on 14C-acetate uptake in intact rat brain.

Authors:  Rie Hosoi; Maki Okada; Jun Hatazawa; Antony Gee; Osamu Inoue
Journal:  J Cereb Blood Flow Metab       Date:  2004-02       Impact factor: 6.200

9.  Acetate and fluoroacetate as possible markers for glial metabolism in vivo.

Authors:  D Muir; S Berl; D D Clarke
Journal:  Brain Res       Date:  1986-08-20       Impact factor: 3.252

10.  Radical carbonylation with [11C]carbon monoxide promoted by oxygen-centered radicals: experimental and DFT studies of the mechanism.

Authors:  Oleksiy Itsenko; Daniel Norberg; Torben Rasmussen; Bengt Långström; Chryssostomos Chatgilialoglu
Journal:  J Am Chem Soc       Date:  2007-07-03       Impact factor: 15.419

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  9 in total

Review 1.  (11)C[double bond, length as m-dash]O bonds made easily for positron emission tomography radiopharmaceuticals.

Authors:  Benjamin H Rotstein; Steven H Liang; Michael S Placzek; Jacob M Hooker; Antony D Gee; Frédéric Dollé; Alan A Wilson; Neil Vasdev
Journal:  Chem Soc Rev       Date:  2016-08-22       Impact factor: 54.564

2.  Synthesis and evaluation of two new candidate high-affinity full agonist PET radioligands for imaging 5-HT1B receptors.

Authors:  Anton Lindberg; Shuiyu Lu; Sangram Nag; Magnus Schou; Jeih-San Liow; Sami S Zoghbi; Michael P Frankland; Robert L Gladding; Cheryl L Morse; Akihiro Takano; Nahid Amini; Charles S Elmore; Yong Sok Lee; Robert B Innis; Christer Halldin; Victor W Pike
Journal:  Nucl Med Biol       Date:  2019-01-26       Impact factor: 2.408

Review 3.  Chemistry for Positron Emission Tomography: Recent Advances in 11 C-, 18 F-, 13 N-, and 15 O-Labeling Reactions.

Authors:  Xiaoyun Deng; Jian Rong; Lu Wang; Neil Vasdev; Lei Zhang; Lee Josephson; Steven H Liang
Journal:  Angew Chem Int Ed Engl       Date:  2019-01-14       Impact factor: 15.336

4.  Exploration of the labeling of [11C]tubastatin A at the hydroxamic acid site with [11C]carbon monoxide.

Authors:  Shuiyu Lu; Yi Zhang; Jay H Kalin; Lisheng Cai; Alan P Kozikowski; Victor W Pike
Journal:  J Labelled Comp Radiopharm       Date:  2015-12-08       Impact factor: 1.921

5.  [Carboxyl-11 C]Labelling of Four High-Affinity cPLA2α Inhibitors and Their Evaluation as Radioligands in Mice by Positron Emission Tomography.

Authors:  Martin J Fisher; Lindsay McMurray; Shuiyu Lu; Cheryl L Morse; Jeih-San Liow; Sami S Zoghbi; Aneta Kowalski; George L Tye; Robert B Innis; Franklin I Aigbirhio; Victor W Pike
Journal:  ChemMedChem       Date:  2018-01-10       Impact factor: 3.466

6.  [11C]deschloroclozapine is an improved PET radioligand for quantifying a human muscarinic DREADD expressed in monkey brain.

Authors:  Xuefeng Yan; Sanjay Telu; Rachel M Dick; Jeih-San Liow; Paolo Zanotti-Fregonara; Cheryl L Morse; Lester S Manly; Robert L Gladding; Stal Shrestha; Walter Lerchner; Yuji Nagai; Takafumi Minamimoto; Sami S Zoghbi; Robert B Innis; Victor W Pike; Barry J Richmond; Mark Ag Eldridge
Journal:  J Cereb Blood Flow Metab       Date:  2021-04-14       Impact factor: 6.200

7.  11C-Labeling of Aryl Ketones as Candidate Histamine Subtype-3 Receptor PET Radioligands through Pd(0)-Mediated 11C-Carbonylative Coupling.

Authors:  Fabrice G Siméon; William J Culligan; Shuiyu Lu; Victor W Pike
Journal:  Molecules       Date:  2017-05-12       Impact factor: 4.411

Review 8.  Small Molecule Radiopharmaceuticals - A Review of Current Approaches.

Authors:  Shubhra Chaturvedi; Anil K Mishra
Journal:  Front Med (Lausanne)       Date:  2016-02-23

9.  "In-loop" carbonylation-A simplified method for carbon-11 labelling of drugs and radioligands.

Authors:  Mélodie Ferrat; Kenneth Dahl; Christer Halldin; Magnus Schou
Journal:  J Labelled Comp Radiopharm       Date:  2020-01-21       Impact factor: 1.921

  9 in total

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