Medicinal Chemistry strategies for PET tracer discovery

Drug Discovery Today: Technologies - Tập 25 - Trang 11-17 - 2017
José Ignacio Andrés1, Mark Schmidt2
1Discovery Sciences, Janssen Research & Development, Janssen-Cilag S. A., C/Jarama 75A, 45007 Toledo, Spain
2Neuroscience Therapeutic Area, Janssen Research & Development, Division of Janssen Pharmaceutica, NV, Turnhoutseweg 30, Beerse 2340, Belgium

Tài liệu tham khảo

Hargreaves, 2008, The role of molecular imaging in drug discovery and development, Clin Pharmacol Ther, 83, 349, 10.1038/sj.clpt.6100467 Vallabhajosula, 2011, A broad overview of positron emission tomography radiopharmaceuticals and clinical applications: what is new, Semin Nucl Med, 41, 246, 10.1053/j.semnuclmed.2011.02.003 Salloway, 2014, Two phase III trials of bapineuzumab in mild-to-moderate Alzheimer’s disease, N Engl J Med, 370, 322, 10.1056/NEJMoa1304839 Laruelle, 2003, Relationships between radiotracer properties and image quality in molecular imaging of the brain with positron emission tomography, Mol Imaging Biol, 5, 363, 10.1016/j.mibio.2003.09.009 Pike, 2009, PET radiotracers: crossing the blood-brain barrier and surviving metabolism, Trends Pharmacol Sci, 30, 431, 10.1016/j.tips.2009.05.005 Piel, 2014, Positron emission tomography in CNS drug discovery and drug monitoring, J Med Chem, 57, 9232, 10.1021/jm5001858 Ariza, 2015, Tau positron emission tomography (PET) imaging: past, present, and future, J Med Chem, 58, 4365, 10.1021/jm5017544 Serdons, 2009, Developing new molecular imaging probes for PET, Methods, 48, 104, 10.1016/j.ymeth.2009.03.010 Roeda, 2010, Aliphatic nucleophilic radiofluorination, Curr Radiopharm, 3, 81, 10.2174/1874471011003020081 Preshlock, 2016, 18F-Labeling of arenes and heteroarenes for applications in positron emission tomography, Chem Rev, 116, 719, 10.1021/acs.chemrev.5b00493 Kealey, 2014, Transition metal mediated [11C]carbonylation reactions: recent advances and applications, J Label Compd Radiopharm, 57, 195, 10.1002/jlcr.3150 Antoni, 2015, Development of carbon-11 labelled PET tracers—radiochemical and technological challenges in a historic perspective, J Label Compd Radiopharm, 58, 65, 10.1002/jlcr.3258 Rotstein, 2016, 11CO bonds made easily for positron emission tomography radiopharmaceuticals, Chem Soc Rev, 45, 4708, 10.1039/C6CS00310A Harada, 2016, 18F-THK-5351: a novel PET radiotracer for imaging neurofibrillary pathology in Alzheimer’s disease, J Nucl Med, 57, 208, 10.2967/jnumed.115.164848 Wang, 2014, In vivo imaging of histone deacetylases (HDACs) in the central nervous system and major peripheral organs, J Med Chem, 19, 7999, 10.1021/jm500872p He, 2017, 1-(4-[18F]Fluorobenzyl)-4-[(tetrahydrofuran-2-yl)methyl]piperazine: a novel suitable radioligand with low lipophilicity for imaging σ1 receptors in the brain, J Med Chem, 60, 4161, 10.1021/acs.jmedchem.6b01723 Fujinaga, 2017, Development of a 18F-labeled radiotracer with improved brain kinetics for positron emission tomography imaging of translocator protein (18kDa) in ischemic brain and glioma, J Med Chem, 60, 4047, 10.1021/acs.jmedchem.7b00374 Prabhakaran, 2017, Radiosynthesis and in vivo evaluation of [11C]​A1070722, a high affinity GSK-​3 PET tracer in primate brain, ACS Chem Neurosci, 8, 1697, 10.1021/acschemneuro.6b00376 Schmidt, 2017, The value of PET ligand discovery to CNS drug development, Future Med Chem, 9, 351, 10.4155/fmc-2017-0018 Andrés, 2011, Synthesis, in vivo occupancy, and radiolabeling of potent phosphodiesterase subtype-10 inhibitors as candidates for positrón emission tomography imaging, J Med Chem, 54, 5820, 10.1021/jm200536d Van Laere, 2013, Quantification of 18F-JNJ-42259152, a novel phosphodiesterase 10A PET tracer: kinetic modeling and test-retest study in human brain, J Nucl Med, 54, 1285, 10.2967/jnumed.112.118679 Andrés, 2012, Synthesis, evaluation, and radiolabeling of new potent positive allosteric modulators of the metabotropic glutamate receptor 2 as potential tracers for positron emission tomography imaging, J Med Chem, 55, 8685, 10.1021/jm300912k Lipinski, 2016, Rule of five in 2015 and beyond: target and ligand structural limitations, ligand chemistry structure and drug discovery project decisions, Adv Drug Delivery Rev, 101, 34, 10.1016/j.addr.2016.04.029 Guo, 2009, A biomathematical modeling approach to central nervous system radioligand discovery and development, J Nucl Med, 50, 1715, 10.2967/jnumed.109.063800 Wager, 2010, Moving beyond rules: the development of a central nervous system multiparameter optimization (CNS-MPO) approach to enable alignment of druglike properties, ACS Chem Neurosci, 1, 435, 10.1021/cn100008c Zhang, 2013, Design and selection parameters to accelerate the discovery of novel central nervous system positron emission tomography (PET) ligands and their application in the development of a novel phosphodiesterase 2A PET ligand, J Med Chem, 56, 4568, 10.1021/jm400312y Naganawa, 2016, First in human assessment of the novel PDE2A PET radiotracer 18F-PF-05270430, J Nucl Med, 57, 1388, 10.2967/jnumed.115.166850 Assmus, 2015, Label-free assay for the assessment of nonspecific binding of positron emission tomography tracer candidates, Eur J Pharm Sci, 79, 27, 10.1016/j.ejps.2015.08.014 Auberson, 2016, Ligand specific efficiency (LSE) index for PET tracer optimization, ChemMedChem, 11, 1415, 10.1002/cmdc.201600112 Chernet, 2005, Use of LC/MS to assess brain tracer distribution in preclinical, in vivo receptor occupancy studies: dopamine D2, serotonin 2A and NK-1 receptors as examples, Life Sci, 78, 340, 10.1016/j.lfs.2005.04.075 Barth, 2014, Identifying novel radiotracers for PET imaging of the brain: application of LC–MS/MS to tracer identification, ACS Chem Neurosci, 5, 1148, 10.1021/cn500072r Mitch, 2011, Discovery of aminobenzyloxyarylamides as κ opioid receptor selective antagonists: application to preclinical development of a κ opioid receptor antagonist receptor occupancy tracer, J Med Chem, 54, 800, 10.1021/jm200789r Zheng, 2013, Synthesis and evaluation of 11C-LY2795050 as a κ-opioid receptor antagonist radiotracer for PET imaging, J Nucl Med, 54, 455, 10.2967/jnumed.112.109512 Donohue, 2008, Synthesis, ex vivo evaluation, and radiolabeling of potent 1,5-diphenylpirrolidin-2-one cannabinoid subtype-1 receptor ligands as candidates for in vivo imaging, J Med Chem, 51, 5833, 10.1021/jm800416m Pedregal, 2012, Development of LC–MS/MS-based receptor occupancy tracers and positron emission tomography radioligands for the nociceptin/orphanin FQ (NOP) receptor, J Med Chem, 55, 4955, 10.1021/jm201629q Andrés, 2013, Discovery of a new series of [1,2,4]triazolo[4,3-a]quinoxalines as dual phosphodiesterase 2/phosphodiesterase 10 (PDE2/PDE10) inhibitors, Bioorg & Med Chem Lett, 23, 785, 10.1016/j.bmcl.2012.11.077 Buijnsters, 2014, Structure-based design of a potent, selective and brain penetrating PDE2 inhibitor with demonstrated target engagement, ACS Med Chem Lett, 5, 1049, 10.1021/ml500262u Andrés-Gil, 2013, Janssen Pharmaceutica NV. 1-Aryl-4-methyl-[1,2,4]triazolo [4,3-a]quinoxaline derivatives as PDE2 inhibitors, PCT Int Appl Jack, 2013, Biomarker modeling of Alzheimer’s disease, Neuron, 80, 1347, 10.1016/j.neuron.2013.12.003 Sperling, 2011, Toward defining the preclinical stages of Alzheimer’s disease: recommendations from the National Institute on aging-Alzheimer’s association workgroups on diagnostic guidelines for Alzheimer’s disease, Alzheimers Dement, 7, 280, 10.1016/j.jalz.2011.03.003 Maccioni, 2010, The revitalized tau hypothesis on Alzheimer’s disease, Arch Med Res, 41, 226, 10.1016/j.arcmed.2010.03.007 Villemagne, 2015, Tau imaging: early progress and future directions, Lancet Neurol, 14, 114, 10.1016/S1474-4422(14)70252-2 Walji, 2016, Discovery of 6-(fluoro-18F)-3-(1H-pyrrolo[2,3-c]pyridine-1-yl)isoquinolin-5-amine ([18F]-MK-6240): a positron emission tomography (PET) imaging agent for quantification of neurofibrillary tangles (NFTs), J Med Chem, 59, 4778, 10.1021/acs.jmedchem.6b00166 Rombouts, 2017, Discovery of N-(pyridin-4-yl)-1,5-naphthyridin-2-amines as potential tau pathology PET tracers for Alzheimer’s disease, J Med Chem, 60, 1272, 10.1021/acs.jmedchem.6b01173 Gobbi, 2017, Identification of three novel radiotracers for imaging aggregated tau in Alzheimer’s disease with positron emission tomography, J Med Chem, 60, 7350, 10.1021/acs.jmedchem.7b00632 Hostetler, 2016, Preclinical characterization of 18F-MK-6240, a promising PET tracer for in vivo quantification of human neurofibrillary tangles, J Nucl Med, 57, 1599, 10.2967/jnumed.115.171678 Declercq, 2017, Preclinical evaluation of 18F-JNJ64349311, a novel PET tracer for tau imaging, J Nucl Med, 58, 975, 10.2967/jnumed.116.185199