Biodistribution studies of two 18F-labeled pyridinylphenyl amides as subtype selective radioligands for the dopamine D3 receptor

Nuclear Medicine and Biology

Volumn 41, Issue 3, 2014, Pages 223-228

  Hocke, Carsten ^a   Cumming, Paul ^a   Maschauer, Simone ^a   Kuwert, Torsten ^a   Gmeiner, Peter ^a   Prante, Olaf ^a  

^a UNIVERSITY OF ERLANGEN NUREMBERG   (Germany)

Author keywords

Autoradiography; Biodistribution studies; D3 receptor; Dopamine receptor; PET; Positron emission tomography

Indexed keywords

AMIDE; DIAGNOSTIC AGENT; DOPAMINE 3 RECEPTOR; DOPAMINE RECEPTOR; FLUORINE; LIGAND;

ANIMAL; ARTICLE; AUTORADIOGRAPHY; BIODISTRIBUTION STUDIES; BLOOD; BRAIN; D3 RECEPTOR; ENZYME SPECIFICITY; FEMALE; HUMAN; METABOLISM; PET; POSITRON EMISSION TOMOGRAPHY; RAT; SCINTISCANNING; TISSUE DISTRIBUTION;

AUTORADIOGRAPHY; BIODISTRIBUTION STUDIES; D3 RECEPTOR; DOPAMINE RECEPTOR; PET; POSITRON EMISSION TOMOGRAPHY;

AMIDES; ANIMALS; BRAIN; FEMALE; FLUORINE RADIOISOTOPES; HUMANS; LIGANDS; POSITRON-EMISSION TOMOGRAPHY; RATS; RECEPTORS, DOPAMINE D3; SUBSTRATE SPECIFICITY; TISSUE DISTRIBUTION;

EID: 84893949929     PISSN: 09698051     EISSN: 18729614     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2013.12.014     Document Type: Article

References (38)

1. Kienast T., Heinz A. Dopamine and the diseased brain. CNS Neurol Disord Drug Targets 2006, 5:109-131.
2. Sokoloff P., Diaz J., Le Foll B., Guillin O., Leriche L., Bezard E., et al. The dopamine D-3 receptor: a therapeutic target for the treatment of neuropsychiatric disorders. CNS Neurol Disord Drug Targets 2006, 5:25-43.
3. Newman A.H., Grundt P., Nader M.A. Dopamine D3 receptor partial agonists and antagonists as potential drug abuse therapeutic agents. J Med Chem 2005, 48:3663-3679.
4. Sokoloff P., Giros B., Martres M.P., Bouthenet M.L., Schwartz J.C. Modular-cloning and characterization of a novel dopamine receptor (D3) as a target for neuroleptics. Nature 1990, 347:146-151.
5. Cumming P. Absolute abundances and affinity states of dopamine receptors in mammalian brain: a review. Synapse 2011, 65:892-909.
6. Wong D.F., Pomper M.G. Predicting the success of a radiopharmaceutical for in vivo imaging of central nervous system neuroreceptor systems. Mol Imaging Biol 2003, 5:350-362.
7. Lee C.M., Farde L. Using positron emission tomography to facilitate CNS drug development. TiPS 2006, 27:310-316.
8. Levesque D., Diaz J., Pilon C., Martres M.P., Giros B., Souil E., et al. Identification, characterization, and localization of the dopamine-D3 receptor in rat-brain using 7-[H-3]hydroxy-N, N-di-normal-propyl-2-aminotetralin. Proc Natl Acad Sci U S A 1992, 89:8155-8159.
9. Lahti R.A., Roberts R.C., Tamminga C.A. D-2-family receptor distribution in human postmortem tissue: an autoradiographic study. Neuroreport 1995, 6:2505-2512.
10. Levesque D. Aminotetralin drugs and D-3 receptor functions - What may partially selective D-3 receptor ligands tell us about dopamine D-3 receptor functions?. Biochem Pharmacol 1996, 52:511-518.
11. Stanwood G.D., Artymyshyn R.P., Kung M.P., Kung H.F., Lucki I., McGonigle P. Quantitative autoradiographic mapping of rat brain dopamine D3 binding with [I-125]7-OH-PIPAT: evidence for the presence of D3 receptors on dopaminergic and nondopaminergic cell bodies and terminals. J Pharmacol Exp Ther 2000, 295:1223-1231.
12. Prante O., Maschauer S., Banerjee A. Radioligands for the dopamine receptor subtypes. J Labelled Comp Radiopharm 2013, 56:130-148.
13. 18F]fluorophenylazocarboxylic esters. Chem Eur J 2013, 10.1002/chem.201303409.
14. Graff-Guerrero A., Willeit M., Ginovart N., Mamo D., Mizrahi R., Rusjan P., et al. Brain region binding of the D-2/3 agonist [C-11]-(+)-PHNO and the D-2/3 antagonist [C-11]raclopride in healthy humans. Hum Brain Mapp 2008, 29:400-410.
15. Rabiner E.A., Slifstein M., Nobrega J., Plisson C., Huiban M., Raymond R., et al. In vivo quantification of regional dopamine-D3 receptor binding potential of (+)-PHNO: studies in non-human primates and transgenic mice. Synapse 2009, 63:782-793.
16. Seeman P., Wilson A., Gmeiner P., Kapur S. Dopamine D2 and D3 receptors in human putamen, caudate nucleus, and globus pallidus. Synapse 2006, 60:205-211.
17. Vasdev N., Seeman P., Garcia A., Stableford W.T., Nobrega J.N., Houle S., et al. Syntheses and in vitro evaluation of fluorinated naphthoxazines as dopamine D2/D3 receptor agonists: radiosynthesis, ex vivo biodistribution and autoradiography of [F-18]F-PHNO. Nucl Med Biol 2007, 34:195-203.
18. Böckler F., Gmeiner P. The structural evolution of dopamine D-3 receptor ligands: structure-activity relationships and selected neuropharmacological aspects. Pharmacol Ther 2006, 112:281-333.
19. Saur O., Hackling A.E., Perachon S., Schwartz J.C., Sokoloff P., Stark H. N-(4-(4-(2-halogenophenyl)piperazin-1-yl)butyl) substituted cinnamoyl amide derivatives as dopamine D-2 and D-3 receptor ligands. Arch Pharm 2007, 340:178-184.
20. Newman A.H., Grundt P., Cyriac G., Deschamps J.R., Taylor M., Kumar R., et al. N-(4-(4-(2,3-dichloro- or 2-methoxyphenyl)piperazin-1-yl)butyl)heterobiarylcarboxamides with functionalized linking chains as high affinity and enantioselective D3 receptor antagonists. J Med Chem 2009, 52:2559-2570.
21. Leopoldo M., Lacivita E., Colabufo N.A., Berardi F., Perrone R. Synthesis and binding profile of constrained analogues of N-[4-(4-arylpiperazin-1-yl)butyl]-3-methoxybenzamides, a class of potent dopamine D-3 receptor ligands. J Pharm Pharmacol 2006, 58:209-218.
22. Schlotter K., Boeckler F., Hübner H., Gmeiner P. Fancy bioisosteres: metallocene-derived G-protein-coupled receptor ligands with subnanomolar binding affinity and novel selectivity profiles. J Med Chem 2005, 48:3696-3699.
23. Hackling A., Ghosh R., Perachon S., Mann A., Holtje H.D., Wermuth C.G., et al. N-(omega-(4-(2-methoxyphenyl)piperazin-1-yl)alkyl)carboxamides as dopamine D-2 and D-3 receptor ligands. J Med Chem 2003, 46:3883-3899.
24. Hocke C., Maschauer S., Hübner H., Löber S., Utz W., Kuwert T., et al. A series of F-18-labelled pyridinylphenyl amides as subtype-selective radioligands for the dopamine D3 receptor. ChemMedChem 2010, 5:941-948.
25. Hocke C., Prante O., Löber S., Hübner H., Gmeiner P., Kuwert T. Synthesis and evaluation of F-18-labeled dopamine D3 receptor ligands as potential PET imaging agents. Bioorg Med Chem Lett 2005, 15:4819-4823.
26. Hocke C., Prante O., Löber S., Hübner H., Gmeiner P., Kuwert T. Synthesis and radioiodination of selective ligands for the dopamine D3 receptor subtype. Bioorg Med Chem Lett 2004, 14:3963-3966.
27. Hocke C., Prante O., Salama I., Hübner H., Löber S., Kuwert T., et al. F-18-labeled FAUC 346 and BP 897 derivatives as subtype-selective potential PET radioligands for the dopamine D3 receptor. ChemMedChem 2008, 3:788-793.
28. Gillings N.M., Bender D., Falborg L., Marthi K., Munk O.L., Cumming P. Kinetics of the metabolism of four PET radioligands in living minipigs. Nucl Med Biol 2001, 28:97-104.
29. Rubins D.J., Melega W.P., Lacan G., Way B., Plenevaux A., Luxen A., et al. Development and evaluation of an automated atlas-based image analysis method for microPET studies of the rat brain. Neuroimage 2003, 20:2100-2118.
30. Pedersen K., Simonsen M., Ostergaard S.D., Munk O.L., Rosa-Neto P., Olsen A.K., et al. Mapping the amphetamine-evoked changes in [C-11]raclopride binding in living rat using small animal PET: modulation by MAO-inhibition. Neuroimage 2007, 35:38-46.
31. Logan J., Fowler J.S., Volkow N.D., Wang G.J., Ding Y.S., Alexoff D.L. Distribution volume ratios without blood sampling from graphical analysis of PET data. J Cereb Blood Flow Metab 1996, 16:834-840.
32. Zhou Y., Endres C.J., Brasic J.R., Huang S.C., Wong D.F. Linear regression with spatial constraint to generate parametric images of ligand-receptor dynamic PET studies with a simplified reference tissue model. Neuroimage 2003, 18:975-989.
33. Polakowski J.S., Segreti J.A., Cox B.F., Hsieh G.C., Kolasa T., Moreland R.B., et al. Effects of selective dopamine receptor subtype agonists on cardiac contractility and regional haemodynamics in rats. Clin Exp Pharmacol Physiol 2004, 31:837-841.
34. Schotte A., Janssen P.F.M., Bonaventure P., Leysen J.E. Endogenous dopamine limits the binding of antipsychotic drugs to D-3 receptors in the rat brain: a quantitative autoradiographic study. Histochem J 1996, 28:791-799.
35. Höfling S.B., Maschauer S., Hübner H., Gmeiner P., Wester H.J., Prante O., et al. Synthesis, biological evaluation and radiolabelling by F-18-fluoroarylation of a dopamine D-3-selective ligand as prospective imaging probe for PET. Bioorg Med Chem Lett 2010, 20:6933-6937.
36. Tome M., Moreira E., Perez-Figares J.M., Jimenez A.J. Presence of D-1- and D-2-like dopamine receptors in the rat, mouse and bovine multiciliated ependyma. J Neural Transm 2007, 114:983-994.
37. Dean B., Pavey G., Scarr E., Goeringer K., Copolov D.L. Measurement of dopamine D-2-like receptors in postmortem CNS and pituitary: differential regional changes in schizophrenia. Life Sci 2004, 74:3115-3131.
38. Herroelen L., Debacker J.P., Wilczak N., Flamez A., Vauquelin G., Dekeyser J. Autoradiographic distribution of D-3-type dopamine-receptors in human brain using [H-3] 7-hydroxy-N, N-di-N-propyl-2-aminotetralin. Brain Res 1994, 648:222-228.