Synthesis and evaluation of candidate PET radioligands for corticotropin-releasing factor type-1 receptors

Nuclear Medicine and Biology

Volumn 41, Issue 6, 2014, Pages 524-535

  Lodge, Nicholas J ^a   Li, Yu Wen ^a   Chin, Frederick T ^b,c   Dischino, Douglas D ^a   Zoghbi, Sami S ^b   Deskus, Jeffrey A ^a   Mattson, Ronald J ^a   Imaizumi, Masao ^b   Pieschl, Rick ^a   Molski, Thaddeus F ^a   Fujita, Masahiro ^b   Dulac, Heidi ^a   Zaczek, Robert ^a   Bronson, Joanne J ^a   Macor, John E ^a   Innis, Robert B ^b   Pike, Victor W ^b  

^a BRISTOL MYERS SQUIBB   (United States)

^b NATIONAL INSTITUTE OF MENTAL HEALTH   (United States)

^c STANFORD UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

Autoradiography; Corticotropin releasing factor (CRF); Positron emission tomography (PET); Rhesus monkey

Indexed keywords

3 [PHENYLAMINO] PYRAZIN 2(1H) ONE DERIVATIVE; 8 (2,4 DICHLOROPHENYL) 4 [2 METHOXY 1 (METHOXYMETHYL)ETHYLAMINO] 2,7 DIMETHYLPYRAZOLO[1,5 A][1,3,5]TRIAZINE; BMS 606581; BMS 626493; BMS 665330; BMS 709460; BMS 709460 C 11; BMS 721313; BMS 721313 F 18; BMS 728300; BMS 728300 H 3; BMS 732098; BMS 732098 F 18; CARBON 11; CORTICOTROPIN RELEASING FACTOR ANTAGONIST; CORTICOTROPIN RELEASING FACTOR RECEPTOR 1; DMP 904; FLUORINE 18; IODINE 125; MOLECULAR SCAFFOLD; PYRAZINE DERIVATIVE; RADIOLIGAND; TRITIUM; UNCLASSIFIED DRUG; CORTICOTROPIN RELEASING FACTOR RECEPTOR; LIGAND;

ADULT; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; BRAIN MEMBRANE; BRAIN STEM; BRAIN TISSUE; CEREBELLUM; DRUG DISTRIBUTION; DRUG SCREENING; DRUG SYNTHESIS; FRONTAL CORTEX; IC 50; IN VITRO STUDY; ISOTOPE LABELING; LIMBIC CORTEX; LIPOPHILICITY; MALE; NEUROIMAGING; NONHUMAN; PET SCANNER; POSITRON EMISSION TOMOGRAPHY; RAT; RECEPTOR AFFINITY; RECEPTOR BINDING; RECEPTOR DENSITY; RHESUS MONKEY; THALAMUS; TISSUE SECTION; ANIMAL; BRAIN; CHEMISTRY; DIAGNOSTIC USE; METABOLISM; PROCEDURES; RADIOCHEMISTRY; SCINTISCANNING; SYNTHESIS; TISSUE DISTRIBUTION;

ANIMALS; BRAIN; CHEMISTRY TECHNIQUES, SYNTHETIC; LIGANDS; MACACA MULATTA; MALE; POSITRON-EMISSION TOMOGRAPHY; PYRAZINES; RADIOCHEMISTRY; RATS; RECEPTORS, CORTICOTROPIN-RELEASING HORMONE; TISSUE DISTRIBUTION;

EID: 84901280678     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2014.03.005     Document Type: Article

References (44)

1. Britton D.R., Koob G.F., Rivier J., Vale W. Intraventricular corticotropin-releasing factor enhances behavioral effects of novelty. Life Sci 1982, 31:363-367.
2. Fisher L.A. Central actions of corticotropin-releasing factor on autonomic nervous activity and cardiovascular functioning. Corticotropin-releasing factor 1993, 243-257. Wiley.
3. Zorrilla E.P., Tache Y., Koob G.F. Nibbling at CRF receptor control of feeding and gastrocolonic motility. TIPS 2003, 24:421-427.
4. Stengel A., Tache Y. Corticotropin-releasing factor signaling and visceral response to stress. Exp Biol Med 2010, 235:1168-1178.
5. Nemeroff C., Vale W.W. The neurobiology of depression: in-roads in treatment and new drug discovery. J Clin Psychiatry 2005, 66:5-13.
6. Timpl P., Spanagel R., Sillaber I., Kresse A., Reul J.M.H.M., Stalla G.K., et al. Impaired stress response and reduced anxiety in mice lacking a functional corticotropin-releasing hormone receptor 1. Nat Genet 1998, 19:162-166.
7. Müller M.B., Zimmermann S., Sillaber I., Hagemeyer T.P., Deussin J.M., Timpl P., et al. Limbic corticotropin-releasing hormone receptor 1 mediates anxiety-related behavior and hormonal adaptation to stress. Nat Neurosci 2003, 6:1100-1107.
8. 1 antagonists. CNS Drug Rev 2005, 11:21-52.
9. Kehne J.H., Cain C.K. Therapeutic utility of non-peptidic CRF1 receptor antagonists in anxiety, depression, and stress-related disorders: evidence from animal models. Pharmacol Ther 2010, 128:460-487.
10. Alonzo R., Griebel G., Pavone G., Stemmelin J., Le Fur G., Soubrie P. Blockage of CRF1 or V1b receptors reverses stress-induced suppression of neurogenesis in a mouse model of depression. Mol Psychiatry 2004, 9:278-286.
11. Overstreet D.H., Griebel G. Antidepressant-like effects of CRF1 receptor antagonist SSR125543 in an animal model of depression. Eur J Pharmacol 2004, 497:49-53.
12. Coric V., Feldman H.H., Oren D.A., Shekhar A., Pultz J., Dockens R.C., et al. Multicenter, randomized, double-blind, active comparator and placebo-controlled trial of a corticotropin-releasing factor receptor-1 antagonist in generalized anxiety disorder. Depress Anxiety 2010, 27:417-425.
13. Zorrilla E.P., Heilig M., de Wit H., Shaham Y. Behavioral, biological, and chemical perspectives on targeting CRF1 receptor antagonists to treat alcoholism. Drug Alcohol Depend 2013, 128:175-186.
14. Adamec R., Fougere D., Risbrough V. CRF receptor blockade prevents initiation and consolidation of stress effects on affect in the predator stress model of PTSD. Int J Neuropsychopharmacol 2010, 13:747-757.
15. Hsin L.-W., Webster E.L., Chrousos G.P., Gold P.W., Eckelman W.C., Contoreggi C., et al. Synthesis and biological activity of fluoro-substituted pyrrolo[2,3-d]pyrimidines: the development of potential positron emission tomography imaging agents for the corticotropin-releasing hormone type 1 receptor. Bioorg Med Chem Lett 2000, 10:707-710.
16. Martarello L., Kilts C.D., Ely T., Owens M.J., Nemeroff C.B., Camp M., et al. Synthesis and characterization of fluorinated and iodinated pyrrolopyrimidines as PET/SPECT ligands for the CRF1 receptor. Nucl Med Biol 2001, 28:187-195.
17. 76Br]MJL-1-109-2. J Med Chem 2003, 46:3559-3562.
18. 76Br]BMK-152, a nonpeptide analogue, with high affinity and low nonspecific binding for the corticotropin-releasing factor type 1 receptor. Synapse 2011, 65:910-918.
19. 1 receptors. Bioorg Med Chem 2006, 14:4029-4034.
20. 11C]DMP696: is the target of sufficient density?. Nucl Med Biol 2007, 34:353-361.
21. Clark J.D., Baldwin R.L., Bayne K.A., Brown M.J., Gebhart G.F., Gonder J.C., et al. Guide for the care and use of laboratory animals 1996, National Academy Press, Washington DC.
22. 1 receptors with PET. J Label Compd Radiopharm 2006, 49:17-31.
23. Christman D.R., Finn R.D., Karlström K., Wolf A.P. The production of ultra high specific activity 11C-labeled hydrogen cyanide, carbon dioxide, carbon monoxide and methane via the 14N(p, α)11C reaction. Int J Appl Radiat Isot 1975, 26:435-442.
24. 11C]methane. Appl Radiat Isot 1997, 48:153-157.
25. Bjurling P., Reineck R., Westerburg G., Gee A.D., Sutcliffe J., Långström B. Proc. sixth workshop on targetry and target chem 1995, 282-284. TRIUMF, Vancouver. J.M. Link, T.J. Ruth (Eds.).
26. Lodge N.J., Lelas S., Li Y.-W., Molski T., Grace J., Sivarao D.V., et al. Pharmacological and behavioral characterization of the novel CRF1 antagonist BMS-763534. Neuropharmacology 2013, 67:284-293.
27. 3-phenylpyrazinones as potential CRF-R1 PET imaging agents. Bioorg Med Chem Lett 2012, 22:6651-6655.
28. 18F]FECNT: a polar radiometabolite confounds brain radioligand measurements. J Nucl Med 2006, 47:520-527.
29. Li Y.-W., Hill G.R., Wong H., Kelly N., Ward K., Pierdomenico M., et al. Receptor occupancy of non-peptide CRF1 antagonist DMP696: correlation with drug exposure and anxiolytic efficacy. J Pharmacol Exp Ther 2003, 305:86-96.
30. Hoare S.R.J., Sullivan S.K., Ling N., Crowe P.D., Grigoriadis D.E. Mechanism of corticotropin-releasing factor type 1 receptor regulation by nonpeptide antagonists. Mol Pharmacol 2003, 63:751-765.
31. 2 binding sites in adult rat brain. Neuropsychopharmacology 1997, 17:308-316.
32. Sánchez M.M., Young L.Y., Plotsky P.M., Insel T.R. Autoradiographic and in situ hybridization localization of corticotropin-releasing factor 1 and 2 receptors in nonhuman primate brain. J Comp Neurol 1999, 408:365-377.
33. Kenakin T. Allosteric modulators: the new generation of receptor antagonist. Mol Interv 2004, 4:222-229.
34. Ramsey S.J., Attkins N.J., Fish R., van der Graaf P.H. Quantitative pharmacological analysis of antagonist binding kinetics at CRF1 receptors in vitro and in vivo. Br J Pharmacol 2011, 164:992-1007.
35. Fleck B.A., Hoare S.R.J., Pick R.R., Bradbury M.J., Grigoriadis D.E. Binding kinetics redefine the antagonist pharmacology of the corticotropin-releasing factor type 1 receptor. J Pharmacol Exp Ther 2012, 341:518-531.
36. 1 receptor antagonists. CNS Drug Rev 2005, 11:21-52.
37. 3H]SN003 for corticotropin-releasing factor(1) receptors. J Pharmacol Exp Ther 2003, 305:57-69.
38. Pike V.W. PET radiotracers: crossing the blood-brain barrier and surviving metabolism. TiPs 2009, 30:431-440.
39. Patel S., Gibson R. In vivo-site-directed radiotracers: a mini-review. Nucl Med Biol 2008, 35:805-815.
40. Eckelman W.C., Kilbourn M.R., Mathis C.A. Discussion targeting proteins in vivo: in vitro guidelines. Nucl Med Biol 2006, 33:449-451.
41. Grigoriadis D.E., Dent G.W., Turner J.G., Uno H., Shelton S.E., De Souza E.B., et al. Corticotropin-releasing factor (CRF) receptors in infant rhesus monkey brain and pituitary gland: biochemical characterization and autoradiographic localization. Dev Neurosci 1995, 17:357-367.
42. Lelas S., Wong H., Li Y.W., Heman K.L., Ward K.A., Zeller K.L., et al. Anxiolytic-like effects of the corticotropin-releasing factor1 (CRF1) antagonist DMP904 [4-(3-pentylamino)-2,7-dimethyl-8-(2-methyl-4-methoxyphenyl)-pyrazolo-[1,5-a]-pyrimidine] administered acutely or chronically at doses occupying central CRF1 receptors in rats. J Pharmacol Exp Ther 2004, 309:293-302.
43. Nemeroff C.B., Owens M.J., Bissette G., Andorn A.C., Stanley M. Reduced corticotropin releasing factor binding sites in the frontal cortex of suicide victims. Arch Gen Psychiatry 1988, 45:577-579.
44. Hucks D., Lowther S., Crompton M.R., Katona C.L.E., Horton R.W. Corticotropin-releasing factor binding sites in cortex of depressed suicides. Psychopharmacology 1997, 134:174-178.