Literature DB >> 24002613

Synthesis, radiolabeling, and in vivo pharmacokinetic evaluation of the amyloid beta radioligand [11C]AZD4694 in nonhuman primates.

Magnus Schou1, Katarina Varnäs, Johan Sandell, Peter Johnström, Zsolt Cselenyi, Samuel Svensson, Ryuji Nakao, Nahid Amini, Linda Bergman, Anna Sumic, Balazs Gulyas, Eva Lindström-Böö, Christer Halldin, Lars Farde.   

Abstract

PURPOSE: [(18)F]AZD4694 (2-(2-(18)F-fluoro-6-(methylamino)-3-pyridyl)benzofuran-5-ol) is a radioligand suitable for imaging of amyloid beta deposits in the living human brain using positron emission tomography (PET). Here, we report the preparation and pharmacokinetic profile of its carbon-11 (t1/2 = 20.4 min) labeled isotopolog [(11)C]AZD4694 and compare [(11)C]AZD4694 with the hitherto most widely applied amyloid PET radioligand [(11)C]Pittsburgh Compound B (PiB). PROCEDURES: The immediate unlabeled precursor to [(11)C]AZD4694 was prepared in a four-step convergent synthesis. Subsequent N-(11)C-methylation of this precursor with [(11)C]methyl iodide yielded [(11)C]AZD4694, which after isolation and formulation was injected into cynomolgus monkeys. The radioactivity in nonhuman primate brain following injection of [(11)C]AZD4694 and [(11)C]PiB was measured using PET.
RESULTS: [(11)C]AZD4694 was prepared in a 60 % incorporation yield. In a head to head comparison with [(11)C]PiB, it appeared that [(11)C]AZD4694 displayed slightly lower nonspecific binding in white matter than [(11)C]PiB as well as more rapid pharmacokinetics in the brain.
CONCLUSIONS: The advantageous pharmacokinetic profile and low nonspecific binding render [(11)C]AZD4694 a promising PET radioligand for imaging of amyloid beta in the human brain with PET.

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Year:  2014        PMID: 24002613     DOI: 10.1007/s11307-013-0666-3

Source DB:  PubMed          Journal:  Mol Imaging Biol        ISSN: 1536-1632            Impact factor:   3.488


  22 in total

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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

2.  Characterization of the radioactive metabolites of the 5-HT1A receptor radioligand, [O-methyl-11C]WAY-100635, in monkey and human plasma by HPLC: comparison of the behaviour of an identified radioactive metabolite with parent radioligand in monkey using PET.

Authors:  S Osman; C Lundkvist; V W Pike; C Halldin; J A McCarron; C G Swahn; N Ginovart; S K Luthra; C J Bench; P M Grasby; H Wikström; T Barf; I A Cliffe; A Fletcher; L Farde
Journal:  Nucl Med Biol       Date:  1996-07       Impact factor: 2.408

3.  A novel 18F-labeled pyridyl benzofuran derivative for imaging of β-amyloid plaques in Alzheimer's brains.

Authors:  Yan Cheng; Masahiro Ono; Hiroyuki Kimura; Shinya Kagawa; Ryuichi Nishii; Hideo Saji
Journal:  Bioorg Med Chem Lett       Date:  2010-08-08       Impact factor: 2.823

4.  Localization of neurofibrillary tangles and beta-amyloid plaques in the brains of living patients with Alzheimer disease.

Authors:  Kooresh Shoghi-Jadid; Gary W Small; Eric D Agdeppa; Vladimir Kepe; Linda M Ercoli; Prabha Siddarth; Stephen Read; Nagichettiar Satyamurthy; Andrej Petric; Sung-Cheng Huang; Jorge R Barrio
Journal:  Am J Geriatr Psychiatry       Date:  2002 Jan-Feb       Impact factor: 4.105

5.  Benzofuran derivatives as Abeta-aggregate-specific imaging agents for Alzheimer's disease.

Authors:  Masahiro Ono; Mei-Ping Kung; Catherine Hou; Hank F Kung
Journal:  Nucl Med Biol       Date:  2002-08       Impact factor: 2.408

6.  AZD2184: a radioligand for sensitive detection of beta-amyloid deposits.

Authors:  Allan E Johnson; Fredrik Jeppsson; Johan Sandell; David Wensbo; Jan A M Neelissen; Anders Juréus; Peter Ström; Henrietta Norman; Lars Farde; Samuel P S Svensson
Journal:  J Neurochem       Date:  2009-01-24       Impact factor: 5.372

7.  Characterisation of the appearance of radioactive metabolites in monkey and human plasma from the 5-HT1A receptor radioligand, [carbonyl-11C]WAY-100635--explanation of high signal contrast in PET and an aid to biomathematical modelling.

Authors:  S Osman; C Lundkvist; V W Pike; C Halldin; J A McCarron; C G Swahn; L Farde; N Ginovart; S K Luthra; R N Gunn; C J Bench; P A Sargent; P M Grasby
Journal:  Nucl Med Biol       Date:  1998-04       Impact factor: 2.408

8.  Preclinical properties of 18F-AV-45: a PET agent for Abeta plaques in the brain.

Authors:  Seok Rye Choi; Geoff Golding; Zhiping Zhuang; Wei Zhang; Nathaniel Lim; Franz Hefti; Tyler E Benedum; Michael R Kilbourn; Daniel Skovronsky; Hank F Kung
Journal:  J Nucl Med       Date:  2009-10-16       Impact factor: 10.057

9.  Phase 1 study of the Pittsburgh compound B derivative 18F-flutemetamol in healthy volunteers and patients with probable Alzheimer disease.

Authors:  Natalie Nelissen; Koen Van Laere; Lennart Thurfjell; Rikard Owenius; Mathieu Vandenbulcke; Michel Koole; Guy Bormans; David J Brooks; Rik Vandenberghe
Journal:  J Nucl Med       Date:  2009-07-17       Impact factor: 10.057

10.  Synthesis and evaluation of 11C-labeled 6-substituted 2-arylbenzothiazoles as amyloid imaging agents.

Authors:  Chester A Mathis; Yanming Wang; Daniel P Holt; Guo-Feng Huang; Manik L Debnath; William E Klunk
Journal:  J Med Chem       Date:  2003-06-19       Impact factor: 7.446

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  1 in total

Review 1.  Translocator Protein-18 kDa (TSPO) Positron Emission Tomography (PET) Imaging and Its Clinical Impact in Neurodegenerative Diseases.

Authors:  Anne-Claire Dupont; Bérenger Largeau; Maria Joao Santiago Ribeiro; Denis Guilloteau; Claire Tronel; Nicolas Arlicot
Journal:  Int J Mol Sci       Date:  2017-04-07       Impact factor: 5.923

  1 in total

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