Preparation and radiosynthesis of [18F]FE@CFN (2-[ 18F]fluoroethyl 4-[N-(1-oxopropyl)-N-phenylamino]-1-(2-phenylethyl)- 4-piperidinecarboxylate): A potential μ-opioid receptor imaging agent

Radiochimica Acta

Volumn 95, Issue 1, 2007, Pages 33-38

  Wadsak, W ^a,b   Key Mien, L ^a,b   Ettlinger, D E ^a   Feitscher, S ^a,b   Lanzenberger, R ^a   Marton, J ^c   Dudczak, R ^a,d   Kletter, K ^a   Mitterhauser, M ^a,b  

^a MEDICAL UNIVERSITY OF VIENNA   (Austria)

^b UNIVERSITY OF VIENNA   (Austria)

^c ABX Advanced Biochemical Compounds GmbH   (Germany)

^d LUDWIG BOLTZMANN INSTITUTE FOR LUNG VASCULAR RESEARCH   (Austria)

Author keywords

Carfentanil; Fluorine 18; Fluoroalkylation; Opioid receptor; PET

Indexed keywords

EID: 34047230216     PISSN: 00338230     EISSN: None     Source Type: Journal    
DOI: 10.1524/ract.2007.95.1.33     Document Type: Article

References (28)

1. Pert, C. B., Snyder, S. H.: Opiate receptor. Demonstration in nervous tissue. Science 179, 1011 (1973).
2. Fowler, C. J., Fraser, G. L.: Mu-, delta-, kappa-opioid receptors and their subtypes. A critical review with emphasis on radioligand binding experiments. Neurochem. Int. 24, 401 (1994).
3. Frost, J. J., Wagner Jr., H. N., Dannals, R. F., Ravert, H. T., Links, J. M., Wilson, A. A., Burns, H. D., Wong, D. F., McPherson, R. W., Rosenbaum, A. E.: Imaging opiate receptors in the human brain by positron tomography. J. Comp. Ass. Tomogr. 9, 231 (1985).
4. Heinz, A., Reimold, M., Wrase, J., Hermann, D., Croissant, B., Mundle, G., Dohmen, B. M., Braus, D. H., Schumann, G., Machulla, H. J., Bares, R., Mann, K.: Correlation of stable elevations in striatal {micro}-opioid receptor availability in detoxified alcoholic patients with alcohol craving: a positron emission tomography study using carbon 11-labeled carfentanil. Arch. Gen. Psych. 62, 57 (2005).
5. Greenwald, M. K., Johanson, C. E., Moody, D. E., Woods, J. H., Kilbourn, M. R., Koeppe, R. A., Schuster, C. R., Zubieta, J. K.: Effects of buprenorphine maintenance dose on mu-opioid receptor availability, plasma concentrations, and antagonist blockade in heroin-dependent volunteers. Neuropsychopharmacology 28, 2000 (2003).
6. Sprenger, T., Berthele, A., Platzer, S., Boecker, H., Tolle, T. R.: What to learn from in vivo opioidergic brain imaging? Eur. J. Pain 9, 117 (2005).
7. 11C]-carfentanil and positron emission tomography (PET). Pain 99, 589 (2002).
8. Madar, I., Lesser, R. P., Krauss, G., Zubieta, J. K., Lever, J. R., Kinter, C. M., Ravert, H. T., Musachio, J. L., Mathews, W. B., Dannals, R. F., Frost, J. J.: Imaging of delta- and mu-opioid receptors in temporal lobe epilepsy by positron emission tomography. Ann. Neur. 41, 358 (1997).
9. Villemagne, P. S., Dannals, R. F., Ravert, H. T., Frost, J. J.: PET imaging of human cardiac opioid receptors. Eur. J. Nucl. Med. Mol. Imaging 29, 1385 (2002).
10. Kienbaum, P., Heuter, T., Michel, M. C., Scherbaum, N., Gastpar, M., Peters, J.: Chronic mu-opioid receptor stimulation in humans decreases muscle sympathetic nerve activity. Circulation 103, 850 (2001).
11. Kienbaum, P., Heuter, T., Scherbaum, N., Gastpar, M., Peters, J.: Chronic mu-opioid receptor stimulation alters cardiovascular regulation in humans: differential effects on muscle sympathetic and heart rate responses to arterial hypotension. J. Cardiovasc. Pharm. 40, 363 (2002).
12. Jewett, D. M., Kilbourn, M. R.: in vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor. Nucl. Med. Biol. 31, 321 (2004).
13. 18F- Cyprodime [abstract]. J. Lab. Compd. Radiopharm. 46, 175 (2003).
14. 11C-carfentanil from mu-opioid receptor imaging with PET [abstract]. Eur. J. Nucl. Med. Mol. Imaging 31, 250 (2004).
15. 18F-Labeled sufentanil for PET-imaging of μ-opioid receptors. Bioorg. Med. Chem. Lett. 15, 1773 (2005).
16. 18F]FETO, a novel potential 11-beta hydroxylase inhibitor. J. Lab. Compd. Radiopharm. 46, 379 (2003).
17. 18F]FFMZ). J. Lab. Compd. Radiopharm. 46, 1229 (2003).
18. 18F]FETO with respect to the adrenocortical and GABAergic system in rats. Eur. J. Nucl. Med. Mol. Imaging 30, 1398 (2003).
19. 18F]-FFMZ), a potential GABA receptor ligand for PET. Nucl. Med. Biol. 31, 291 (2004).
20. 18F] FE@CIT, a new potential tracer for the dopamine transporter. Synapse 55, 73 (2005).
21. 18F]fluoroalkyl esters of carfentanil. J. Lab. Compd. Radiopharm. 48, 771 (2005).
22. Janssen, P. A. J., Van Daele, G. H. P.: N-(4-piperidinyl)- N-phenyl-amides and carbamates. US Patent 3,99,834 (1976).
23. Van Daele, P. H. G., De Bruyn, M. F. L., Boey, J. M., Sanczuk, S., Agten, J. T. M., Janssen. P. A. J.: Synthetic analgesics: n-(1-[2-arylethyl]-4- substituted 4-piperidinyl) N-arylalkanamides. Arzneimittel-Forschung (Drug Res.) 26, 1521 (1976).
24. 13C NMR studies of isomeric piperidine derivatives with opiate properties and related compounds. Org. Magn. Res. 15, 275 (1981).
25. Chi, D., Kilbourn, M., Katzenellenbogen, J., Welsh, M.: A rapid and efficient method for the fluoroalkylation of amines and amides. Development of a method suitable for incorporation of the shortlived positron emitting radionuclide fluorine-18. J. Org. Chem. 52, 658 (1987).
26. Janssen, P. A. J., Van Daele, G. H. P.: N-(4-piperidinyl)-N-phenyl-amides. US Patent 4, 179, 569 (1979).
27. Zubieta, J. K., Smith, Y. R., Bueller, J. A., Xu, Y., Kilbourn, M. R., Jewett, D. M., Meyer, C. R., Koeppe, R. A., Stohler, C. S.: Regional mu opioid receptor regulation of sensory and affective dimensions of pain. Science 293, 311 (2001).
28. 18F]-FETO for adrenocortical PET imaging: a pilot study in healthy volunteers. Eur. J. Nucl. Med. Mol. Imaging 33, 669 (2006).