Radioligand development for molecular imaging of the central nervous system with positron emission tomography

Drug Discovery Today

Volumn 19, Issue 12, 2014, Pages 1936-1944

  Honer, Michael ^a   Gobbi, Luca ^a   Martarello, Laurent ^a   Comley, Robert A ^a  

^a F HOFFMANN LA ROCHE LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON 11; FLUORINE 18; ISOREMOXIPRIDE; N SEC BUTYL 1 (2 CHLOROPHENYL) N METHYL 3 ISOQUINOLINECARBOXAMIDE; NITROGEN; OXYGEN 18; RADIOLIGAND; LIGAND; RADIOISOTOPE; RADIOPHARMACEUTICAL AGENT;

BINDING SITE; BLOOD BRAIN BARRIER; CENTRAL NERVOUS SYSTEM; CHEMICAL STRUCTURE; DISSOCIATION CONSTANT; DRUG CLEARANCE; DRUG SCREENING; DRUG TARGETING; GOOD MANUFACTURING PRACTICE; HUMAN; HYDROGEN BOND; INHIBITION CONSTANT; ISOTOPE LABELING; LICENCE; LIPOPHILICITY; MEMBRANE PERMEABILITY; MOLECULAR IMAGING; MOLECULAR WEIGHT; PATIENT SAFETY; PHYSICAL CHEMISTRY; POSITRON EMISSION TOMOGRAPHY; RADIATION EXPOSURE; RADIOCHEMISTRY; REVIEW; SIGNAL NOISE RATIO; ANIMAL; BRAIN; CHEMISTRY; DIAGNOSTIC USE; DRUG DEVELOPMENT; DRUG LEGISLATION; SCINTISCANNING;

ANIMALS; BRAIN; DRUG DISCOVERY; HUMANS; LEGISLATION, DRUG; LIGANDS; MOLECULAR IMAGING; POSITRON-EMISSION TOMOGRAPHY; RADIOISOTOPES; RADIOPHARMACEUTICALS;

EID: 84919391402     PISSN: 13596446     EISSN: 18785832     Source Type: Journal    
DOI: 10.1016/j.drudis.2014.08.012     Document Type: Review

References (74)

1. P.M. Matthews Positron emission tomography molecular imaging for drug development Br. J. Clin. Pharmacol. 73 2012 175 186
2. J. Tauscher Significant dissociation of brain and plasma kinetics with antipsychotics Mol. Psychiatry 7 2002 317 321
3. S. Ostrowitzki Mechanism of amyloid removal in patients with Alzheimer disease treated with Gantenerumab Arch. Neurol. 69 2012 198 207
4. R.N. Gunn Combining PET biodistribution and equilibrium dialysis assays to assess the free brain concentration and BBB transport of CNS drugs J. Cereb. Blood Flow Metab. 32 2012 874 883
5. W. Eckelman Changes: choosing a target? Nucl. Med. Biol. 38 2011 765 769
6. G.B. Saha Basics of PET Imaging: Physics, Chemistry, and Regulations 2010 Springer
7. W.E. Klunk Imaging brain amyloid in Alzheimer's disease with Pittsburgh Compound-B Ann. Neurol. 55 2004 306 319
8. 11C]RO 15-1788, a benzodiazepine antagonist, studied in human brain in vivo by positron tomography Eur. J. Pharmacol. 110 1985 247 251
9. H.N. Wagner Jr. Imaging dopamine receptors in the human brain by positron tomography Science 221 1983 1264 1266
10. K. Herholz Use of FDG PET as an imaging biomarker in clinical trials of Alzheimer's disease Biomark. Med. 6 2012 431 439
11. G.M. Knudsen Testing for radioligand sensitivity to endogenous neurotransmitter release Eur. J. Nucl. Med. Mol. Imaging 36 2009 472 474
12. T. Jones, and E.A. Rabiner The development, past achievements, and future directions of brain PET J. Cereb. Blood Flow Metab. 32 2012 1426 1454
13. L. Zhang 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 2013 4568 4579
14. V.W. Pike PET radiotracers: crossing the blood-brain barrier and surviving metabolism Trends Pharmacol. Sci. 30 2009 431 440
15. D.F. Wong, and M.G. Pomper Predicting the success of a radiopharmaceutical for in vivo imaging of central nervous system neuroreceptor systems Mol. Imaging Biol. 5 2003 350 362
16. M. Laruelle Relationships between radiotracer properties and image quality in molecular imaging of the brain with positron emission tomography Mol. Imaging Biol. 5 2003 363 375
17. D.J. McCarthy Discovery of novel positron emission tomography tracers Annu. Rep. Med. Chem. 44 2009 501 513
18. S.M. Ametamey Molecular imaging with PET Chem. Rev. 108 2008 1501 1516
19. J.P. Holland PET radiopharmaceuticals for probing enzymes in the brain Am. J. Nucl. Med. Mol. Imaging 3 2013 194 216
20. P.H. Elsinga PET studies on P-glycoprotein function in the blood-brain barrier: how it affects uptake and binding of drugs within the CNS Curr. Pharm. Des. 10 2004 1493 1503
21. P. Kannan Factors that limit positron emission tomography imaging of p-glycoprotein density at the blood-brain barrier Mol. Pharm. 10 2013 2222 2229
22. T.T. Wager 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 2010 435 449
23. B.C. Passeleu-Le Methodologies to assess drug permeation through the blood-brain barrier for pharmaceutical research Pharm. Res. 30 2013 2729 2756
24. M. Kansy Physicochemical high throughput screening: parallel artificial membrane permeation assay in the description of passive absorption processes J. Med. Chem. 41 1998 1007 1010
25. A. Avdeef The rise of PAMPA Expert Opin. Drug Metab. Toxicol. 1 2005 325 342
26. K.M. Giacomini Membrane transporters in drug development Nat. Rev. Drug Discov. 9 2010 215 236
27. D.D. Dishino Relationship between lipophilicity and brain extraction of C-11-labeled radiopharmaceuticals J. Nucl. Med. 24 1983 1030 1038
28. R.N. Waterhouse Determination of lipophilicity and its use as a predictor of blood-brain barrier penetration of molecular imaging agents Mol. Imaging Biol. 5 2003 376 389
29. R.B. Innis Consensus nomenclature for in vivo imaging of reversibly binding radioligands J. Cereb. Blood Flow Metab. 27 2007 1533 1539
30. H. Olsson Differentiation of extrastriatal dopamine D2 receptor density and affinity in the human brain using PET Neuroimage 22 2004 794 803
31. H. Olsson, and L. Farde Potentials and pitfalls using high affinity radioligands in PET and SPET determinations on regional drug induced D2 receptor occupancy - a simulation study based on experimental data Neuroimage 14 2001 936 945
32. 6 receptor J. Nucl. Med. 53 2012 295 303
33. A.C. Tziortzi Imaging dopamine receptors in humans with (C-11)-(+)-PHNO: dissection of D3 signal and anatomy Neuroimage 54 2011 264 277
34. Z. Jiang A rapid vesicle electrokinetic chromatography method for the in vitro prediction of non-specific binding for potential PET ligands J. Pharm. Biomed. Anal. 54 2011 722 729
35. C.J. Dickson Further evaluation of quantum chemical methods for the prediction of non-specific binding of positron emission tomography tracers Phys. Chem. Chem. Phys. 13 2011 21552 21557
36. Q. Guo A biomathematical modeling approach to central nervous system radioligand discovery and development J. Nucl. Med. 50 2009 1715 1723
37. F. Dollé Special issue: carbon-11 and fluorine-18 chemistry devoted to molecular probes for imaging the brain with PET J. Labelled Compd. Radiopharm. 56 2013 65 67
38. E.O. Lawrence, and N.E. Edlefsen On the production of high speed protons Science 72 1930 376 377
39. A.A. Wilson Radiosynthesis and evaluation of [11C]-(+)-4-propyl-3,4,4a, 5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazin-9-ol as a potential radiotracer for in vivo imaging of the dopamine D2 high-affinity state with positron emission tomography J. Med. Chem. 48 2005 4153 4160
40. V.W. Pike Pre-clinical development of a radioligand for studies of central 5-HT1A receptors in vivo [11C]WAY-100635 Med. Chem. Res. 1995 1995 208 227
41. 2 fixation: a renaissance in PET radiochemistry Chem. Commun. (Camb.) 49 2013 5621 5629
42. T. Kihlberg, and B. Långström Biologically active 11C-labeled amides using palladium-mediated reactions with aryl halides and [11C]carbon monoxide J. Org. Chem. 64 1999 9201 9205
43. S. Kealey Copper(I) scorpionate complexes and their application in palladium-mediated [(11)C]carbonylation reactions Chem. Commun. (Camb.) 25 2009 3696 3698
44. K. Dahl Palladium-mediated [11C]carbonylation at atmospheric pressure: a general method using xantphos as supporting ligand Eur. J. Org. Chem. 2013 2013 1228 1231
45. P.W. Miller Rapid multiphase carbonylation reactions by using a microtube reactor: applications in positron emission tomography 11C-radiolabeling Angew. Chem. Int. Ed. Engl. 46 2007 2875 2878
46. 11C]carbon monoxide solutions for the synthesis of a positron emission tomography radiotracer Org. Biomol. Chem. 9 2011 3313 3319
47. P.P. Watts Positron emission tomography radiosynthesis in microreactors J. Flow Chem. 2 2012 37 42
48. P. Larsen Synthesis of [11C]iodomethane by iodination of [11C]methane Appl. Radiat. Isot. 48 1997 153 157
49. 11C PETtrace target Proceedings of the 10th International Workshop on Targetry and Target Chemistry 2004 pp. 12
50. R. Littich, and P.J. Scott Novel strategies for fluorine-18 radiochemistry Angew. Chem. Int. Ed. Engl. 51 2012 1106 1109
51. F. Dollé Fluorine-18 chemistry for molecular imaging with positron emission tomography A. Tressaud, G. Haufe, Fluorine and Health: Molecular Imaging, Biomedical Materials and Pharmaceuticals 2008 Elsevier 3 66
52. E. Lee A fluoride-derived electrophilic late-stage fluorination reagent for PET imaging Science 334 2011 639 642
53. B.M. Zeglis A pretargeted PET imaging strategy based on bioorthogonal Diels-Alder click chemistry J. Nucl. Med. 54 2013 1389 1396
54. I.N. Fleming Positron emission tomography radiopharmaceutical studies in humans: a guide to regulations for academic researchers Nucl. Med. Commun. 33 2012 899 906
55. A. Verbruggen Guideline to regulations for radiopharmaceuticals in early phase clinical trials in the EU Eur. J. Nucl. Med. Mol. Imaging 35 2008 2144 2151
56. S. Mosessian INDs for PET molecular imaging probes-approach by an academic institution Mol. Imaging Biol. 16 2014 441 448
57. World Medical Association World Medical Association Declaration of Helsinki: ethical principles for medical research involving human subjects JAMA 310 20 2013 2191 2194
58. ICH ICH M3 (R2) - Guideline on Nonclinical Safety Studies for the Conduct of Human Clinical Trials and Marketing Authorization for Pharmaceuticals In The International Conference on Harmonisation of Technical Requirements for Registration of Pharmaceuticals for Human Use (ICH) 2009
59. ICRP Radiological protection in biomedical research Ann. ICRP 22 1992 3
60. FDA Sec. 361.1 Radioactive drugs for certain research uses Code of Federal Regulations 5 2013 21
61. G.B. Saha Fundamentals of Nuclear Pharmacy 2010 Springer
62. J. van der Aart Radiation dose estimates for carbon-11-labelled PET tracers Nucl. Med. Biol. 39 2012 305 314
63. 18F-labeled PET tracers for first-in-human studies Eur. J. Nucl. Med. Mol. Imaging 40 2013 1781 1783
64. P.E. Molina Fluoro-norchloroepibatidine: preclinical assessment of acute toxicity Nucl. Med. Biol. 24 1997 743 747
65. 18F]N-methyl-NFEP: kinetics, nicotine effect, and toxicity Nucl. Med. Biol. 26 1998 139 148
66. B. Langstrom, and P. Hartvig GMP - three letters with many interpretations. Protection of patients or killing the clinical and research applications of PET? Eur. J. Nucl. Med. Mol. Imaging 35 2008 693 694
67. FDA Part 212: current good manufacturing practice for positron emission tomography drugs Code of Federal Regulations 4 2013 21
68. USP Chapter 823 Positron Emission Tomography Drugs for Compounding, Investigational and Research Uses 2014
69. P. Elsinga Guidance on current good radiopharmacy practice (cGRPP) for the small-scale preparation of radiopharmaceuticals Eur. J. Nucl. Med. Mol. Imaging 37 2010 1049 1062
70. EUROPA Regulation (EU) No 536/2014 of the European Parliament and of the Council of 16 April 2014 on clinical trials on medicinal products for human use, and repealing Directive 2001/20/EC Off. J. Eur. Union. L 2014 1 76
71. European Commission EU guidelines to good manufacturing practice medicinal products for human and veterinary use; part II basic requirements for active substances used as starting materials EudraLex: The Rules Governing Medicinal Products in the European Union 4 2005
72. MHRA Notes from MHRA MRC NCRI Workshop on Regulatory Issues in PET imaging. 2010
73. V.J. Cunningham Quantification in positron emission tomography for research in pharmacology and drug development Nucl. Med. Commun. 25 2004 643 646
74. A.A. Lammertsma, and S.P. Hume Simplified reference tissue model for PET receptor studies Neuroimage 4 1996 153 158