Literature DB >> 25313330

Radiosynthesis of (11)C-Levetiracetam: A Potential Marker for PET Imaging of SV2A Expression.

Hancheng Cai1, Thomas J Mangner2, Otto Muzik3, Ming-Wei Wang4, Diane C Chugani2, Harry T Chugani3.   

Abstract

The multistep preparation of (11)C-levetiracetam ((11)C-LEV) was carried out by a one-pot radiosynthesis with 8.3 ± 1.6% (n = 8) radiochemical yield in 50 ± 5.0 min. Briefly, the propionaldehyde was converted to propan-1-imine in situ as labeling precursor by incubation with ammonia. Without further separation, the imine was reacted with (11)C-HCN to form (11)C-aminonitrile. This crude was then reacted with 4-chlorobutyryl chloride and followed by hydrolysis to yield (11)C-LEV after purification by chiral high-performance liquid chromatography (HPLC). Both the radiochemical and enantiomeric purities of (11)C-LEV were >98%.

Entities:  

Keywords:  Levetiracetam; carbon-11; positron emission tomography; synaptic vesicle protein 2A

Year:  2014        PMID： 25313330      PMCID： PMC4190623          DOI： 10.1021/ml500285t

Source DB:  PubMed          Journal:  ACS Med Chem Lett        ISSN： 1948-5875            Impact factor:   4.345


  19 in total

1.  Is levetiracetam different from other antiepileptic drugs? Levetiracetam and its cellular mechanism of action in epilepsy revisited.

Authors:  Rainer Surges; Kirill E Volynski; Matthew C Walker
Journal:  Ther Adv Neurol Disord       Date:  2008-07       Impact factor: 6.570

2.  Levetiracetam in the management of bipolar depression: a randomized, double-blind, placebo-controlled trial.

Authors:  Aybala Saricicek; Kathleen Maloney; Anjana Muralidharan; Barbara Ruf; Hilary P Blumberg; Gerard Sanacora; Boris Lorberg; Brian Pittman; Zubin Bhagwagar
Journal:  J Clin Psychiatry       Date:  2010-10-19       Impact factor: 4.384

Review 3.  Synaptic vesicle protein 2A: basic facts and role in synaptic function.

Authors:  Julieta Griselda Mendoza-Torreblanca; América Vanoye-Carlo; Bryan Víctor Phillips-Farfán; Liliana Carmona-Aparicio; Gisela Gómez-Lira
Journal:  Eur J Neurosci       Date:  2013-09-16       Impact factor: 3.386

4.  Barriers to clinical translation with diagnostic drugs.

Authors:  Lee Josephson; Markus Rudin
Journal:  J Nucl Med       Date:  2013-01-28       Impact factor: 10.057

5.  Discovery of heterocyclic nonacetamide synaptic vesicle protein 2A (SV2A) ligands with single-digit nanomolar potency: opening avenues towards the first SV2A positron emission tomography (PET) ligands.

Authors:  Joël Mercier; Laurence Archen; Véronique Bollu; Stéphane Carré; Yves Evrard; Eric Jnoff; Benoît Kenda; Bénédicte Lallemand; Philippe Michel; Florian Montel; Florence Moureau; Nathalie Price; Yannick Quesnel; Xavier Sauvage; Anne Valade; Laurent Provins
Journal:  ChemMedChem       Date:  2014-01-20       Impact factor: 3.466

6.  Automated no-carrier-added synthesis of [1-11C]-labeled D- and L-enantiomers of lactic acid.

Authors:  Konstantin Drandarov; P August Schubiger; Gerrit Westera
Journal:  Appl Radiat Isot       Date:  2006-07-18       Impact factor: 1.513

Review 7.  Levetiracetam: a review of its use in epilepsy.

Authors:  Katherine A Lyseng-Williamson
Journal:  Drugs       Date:  2011-03-05       Impact factor: 9.546

Review 8.  11CO2 fixation: a renaissance in PET radiochemistry.

Authors:  Benjamin H Rotstein; Steven H Liang; Jason P Holland; Thomas Lee Collier; Jacob M Hooker; Alan A Wilson; Neil Vasdev
Journal:  Chem Commun (Camb)       Date:  2013-05-14       Impact factor: 6.222

9.  Steroid synthesis. The modified Hunsdiecker degradation of bile acids and related compounds.

Authors:  F F Knapp
Journal:  Steroids       Date:  1979-03       Impact factor: 2.668

10.  Levetiracetam suppresses neuronal network dysfunction and reverses synaptic and cognitive deficits in an Alzheimer's disease model.

Authors:  Pascal E Sanchez; Lei Zhu; Laure Verret; Keith A Vossel; Anna G Orr; John R Cirrito; Nino Devidze; Kaitlyn Ho; Gui-Qiu Yu; Jorge J Palop; Lennart Mucke
Journal:  Proc Natl Acad Sci U S A       Date:  2012-08-06       Impact factor: 11.205
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  15 in total

1.  High-Yielding Automated Convergent Synthesis of No-Carrier-Added [11C-Carbonyl]-Labeled Amino Acids Using the Strecker Reaction.

Authors:  Junhao Xing; Allen F Brooks; Dylan Fink; Huibin Zhang; Morand R Piert; Peter J H Scott; Xia Shao
Journal:  Synlett       Date:  2016-11-07       Impact factor: 2.454

Review 2.  Synaptic vesicle protein 2: A multi-faceted regulator of secretion.

Authors:  Kristine Ciruelas; Daniele Marcotulli; Sandra M Bajjalieh
Journal:  Semin Cell Dev Biol       Date:  2019-03-21       Impact factor: 7.727

3.  Biodistribution and Radiation Dosimetry for the Novel SV2A Radiotracer [(18)F]UCB-H: First-in-Human Study.

Authors:  F Bretin; M A Bahri; C Bernard; G Warnock; J Aerts; N Mestdagh; T Buchanan; C Otoul; F Koestler; F Mievis; F Giacomelli; C Degueldre; R Hustinx; A Luxen; A Seret; A Plenevaux; E Salmon
Journal:  Mol Imaging Biol       Date:  2015-08       Impact factor: 3.488

4.  Kinetic evaluation and test-retest reproducibility of [11C]UCB-J, a novel radioligand for positron emission tomography imaging of synaptic vesicle glycoprotein 2A in humans.

Authors:  Sjoerd J Finnema; Nabeel B Nabulsi; Joël Mercier; Shu-Fei Lin; Ming-Kai Chen; David Matuskey; Jean-Dominique Gallezot; Shannan Henry; Jonas Hannestad; Yiyun Huang; Richard E Carson
Journal:  J Cereb Blood Flow Metab       Date:  2017-08-09       Impact factor: 6.200

Review 5.  Radiolabeling with [11C]HCN for Positron emission tomography.

Authors:  Yu-Peng Zhou; Katarina J Makaravage; Pedro Brugarolas
Journal:  Nucl Med Biol       Date:  2021-09-25       Impact factor: 2.408

6.  [18F]BIBD-181: A Novel Positron Emission Tomography Tracer Specific for Synaptic Vesicle Glycoprotein 2A.

Authors:  Zeng Jiang; Xuebo Cheng; Hualong Chen; Wei Zheng; Yuli Sun; Ziyue Yu; Tingyu Yang; Lu Zhang; Di Fan; Zhihao Yang; Yajing Liu; Lin Ai; Zehui Wu
Journal:  ACS Med Chem Lett       Date:  2022-03-30       Impact factor: 4.632

Review 7.  PET imaging of synaptic density: A new tool for investigation of neuropsychiatric diseases.

Authors:  Zhengxin Cai; Songye Li; David Matuskey; Nabeel Nabulsi; Yiyun Huang
Journal:  Neurosci Lett       Date:  2018-07-31       Impact factor: 3.046

8.  Recent progress in [11 C]carbon dioxide ([11 C]CO2 ) and [11 C]carbon monoxide ([11 C]CO) chemistry.

Authors:  Carlotta Taddei; Antony D Gee
Journal:  J Labelled Comp Radiopharm       Date:  2018-02-05       Impact factor: 1.921

Review 9.  Synaptic Vesicle Glycoprotein 2A Ligands in the Treatment of Epilepsy and Beyond.

Authors:  Wolfgang Löscher; Michel Gillard; Zara A Sands; Rafal M Kaminski; Henrik Klitgaard
Journal:  CNS Drugs       Date:  2016-11       Impact factor: 5.749

10.  Evaluating the In Vivo Specificity of [18F]UCB-H for the SV2A Protein, Compared with SV2B and SV2C in Rats Using microPET.

Authors:  Maria Elisa Serrano; Guillaume Becker; Mohamed Ali Bahri; Alain Seret; Nathalie Mestdagh; Joël Mercier; Frédéric Mievis; Fabrice Giacomelli; Christian Lemaire; Eric Salmon; André Luxen; Alain Plenevaux
Journal:  Molecules       Date:  2019-05-01       Impact factor: 4.411
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