Synthesis and biological evaluation of novel carbon-11 labeled pyridyl ethers: candidate ligands for in vivo imaging of α4β2 nicotinic acetylcholine receptors (α4β2-nAChRs) in the brain with positron emission tomography

Bioorganic and Medicinal Chemistry

Volumn 17, Issue 13, 2009, Pages 4367-4377

  Gao, Yongjun ^a   Ravert, Hayden T ^a   Kuwabara, Hiroto ^a   Xiao, Yingxian ^b   Endres, Christopher J ^c   Hilton, John ^a   Holt, Daniel P ^a   Kumar, Anil ^a   Alexander, Mohab ^a   Wong, Dean F ^a   Dannals, Robert F ^a   Horti, Andrew G ^a  

^a PET Center   (United States)

^b GEORGETOWN UNIVERSITY   (United States)

^c JOHNS HOPKINS UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

nAChR; Nicotinic acetylcholine receptor; PET; Radioligand

Indexed keywords

2 CHLORO 3 [2 CHLORO 5 (PYRIDINYL)METHOXY] 5 [(1 METHYL 2 PYRROLIDINYL)METHOXY]PYRIDINE; 2 CHLORO 3 [2 CHLORO 5 (PYRIDINYL)METHOXY] 5 [(1 METHYL 2 PYRROLIDINYL)METHOXY]PYRIDINE C 11; 2 CHLORO 3 [2 FLUORO 4 (PYRIDINYL)METHOXY] 5 [( METHYL 2 PYRROLIDINYL)METHOXY]PYRIDINE; 2 CHLORO 3 [2 FLUORO 4 (PYRIDINYL)METHOXY] 5 [(1 METHYL 2 PYRROLIDINYL)METHOXY]PYRIDINE C 11; 3 (2 AZETIDINYLMETHOXY)PYRIDINE; 5 [(PYRROLIDIN 2 YL)METHOXY] 3 [(6 CHLOROPYRIDIN 3 YL)METHOXY] 2 CHLOROPYRIDINE; CARBON 11; EPIBATIDINE; ETHER DERIVATIVE; LIGAND; NICOTINE; NICOTINIC RECEPTOR ALPHA2BETA2; NICOTINIC RECEPTOR ALPHA2BETA4; NICOTINIC RECEPTOR ALPHA3BETA2; NICOTINIC RECEPTOR ALPHA3BETA4; NICOTINIC RECEPTOR ALPHA4BETA2; PYRIDINE DERIVATIVE; RECEPTOR SUBTYPE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ARTICLE; BABOON; BINDING COMPETITION; BRAIN FUNCTION; CEREBELLUM; CONTROLLED STUDY; DRUG RECEPTOR BINDING; DRUG SCREENING; DRUG SELECTIVITY; DRUG SYNTHESIS; IN VIVO STUDY; ISOTOPE LABELING; MALE; MOUSE; NEUROIMAGING; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIMATE; QUANTITATIVE ANALYSIS; RAT; RECEPTOR AFFINITY; STRUCTURE ACTIVITY RELATION; THALAMUS;

ANIMALS; BRAIN CHEMISTRY; CARBON RADIOISOTOPES; HUMANS; LIPIDS; MALE; MICE; PAPIO; POSITRON-EMISSION TOMOGRAPHY; PROTEIN BINDING; RADIOPHARMACEUTICALS; RATS; RATS, WISTAR; RECEPTORS, NICOTINIC; STRUCTURE-ACTIVITY RELATIONSHIP;

ANIMALIA;

EID: 66449110673     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2009.05.021     Document Type: Article

References (40)

1. Le Novere N., and Changeux J.P. Nucleic Acids Res. 27 (1999) 340
2. Corringer P.J., Le Novere N., and Changeux J.P. Annu. Rev. Pharmacol. Toxicol. 40 (2000) 431
3. Karlin A. Nat. Rev. Neurosci. 3 (2002) 102
4. Millar N.S. Biochem. Soc. Trans. 31 (2003) 869
5. Clementi F., Fornasari D., and Gotti C. Trends Pharmacol. Sci. 21 (2000) 35
6. Romanelli M.N., Gratteri P., Guandalini L., Martini E., Bonaccini C., and Gualtieri F. ChemMedChem 2 (2007) 746
7. Holladay M.W., Dart M.J., and Lynch J.K. J. Med. Chem. 40 (1997) 4169
8. Lloyd G.K., and Williams M. J. Pharmacol. Exp. Ther. 292 (2000) 461
9. Abreo M.A., Lin N.H., Garvey D.S., Gunn D.E., Hettinger A.M., Wasicak J.T., Pavlik P.A., Martin Y.C., Donnelly-roberts D.L., Anderson D.J., Sullivan J.P., Williams M., Arneric S.P., and Holladay M.W. J. Med. Chem. 39 (1996) 817
10. Lin N.H., Li Y., He Y., Holladay M.W., Kuntzweiler T., Anderson D.J., Campbell J.E., and Arneric S.P. Bioorg. Med. Chem. Lett. 11 (2001) 631
11. Horti A.G., and Villemagne V.L. Curr. Pharm. Des. 12 (2006) 3877
12. Paterson D., and Nordberg A. Prog. Neurobiol. 61 (2000) 75
13. Gundisch D. Curr. Pharm. Des. 6 (2000) 1143
14. Villemagne V.L., Musachio J.L., and Scheffel U. In: Arneric S.P., and Brioni J.D. (Eds). Neuronal Nicotinic Receptors, Pharmacology and Therapeutic Opportunities (1999), Johns Wiley & Sons, New York 235
15. Sihver W., Langstrom B., and Nordberg A. Acta Neurol. Scand. Suppl. 176 (2000) 27
16. Sihver W., Nordberg A., Langstrom B., Mukhin A.G., Koren A.O., Kimes A.S., and London E.D. Behav. Brain Res. 113 (2000) 143
17. Volkow N.D., Ding Y.S., Fowler J.S., and Gatley S.J. Biol. Psychiatry 49 (2001) 211
18. Ding Y.S., and Fowler J. Nucl. Med. Biol. 32 (2005) 707
19. Kimes A.S., Horti A.G., London E.D., Chefer S.I., Contoreggi C., Ernst M., Friello P., Koren A.O., Kurian V., Matochik J.A., Pavlova O., Vaupel D.B., and Mukhin A.G. FASEB J. 17 (2003) 1331
20. Bottlaender M., Valette H., Roumenov D., Dolle F., Coulon C., Ottaviani M., Hinnen F., and Ricard M. J. Nucl. Med. 44 (2003) 596
21. Ding Y.S., Fowler J.S., Logan J., Wang G.J., Telang F., Garza V., Biegon A., Pareto D., Rooney W., Shea C., Alexoff D., Volkow N.D., and Vocci F. Synapse 53 (2004) 184
22. Dollé F., Dolci L., Valette H., Hinnen F., Vaufrey F., Guenther I., Fuseau C., Coulon C., Bottlaender M., and Crouzel C. J. Med. Chem. 42 (1999) 2251
23. Mitkovski S., Villemagne V.L., Novakovic K.E., O'Keefe G., Tochon-Danguy H., Mulligan R.S., Dickinson K.L., Saunder T., Grégoire M.-C., Bottlaender M., Dollé F., and Rowe C.C. Nucl. Med. Biol. 32 (2005) 585
24. Gallezot J.-D., Bottlaender M., Grégoire M.-C., Roumenov D., Deverre J.-R., Coulon C., Ottaviani M., Dollé F., Syrota A., and Valette H. J. Nucl. Med. 46 (2005) 240
25. Horti A.G., Chefer S.I., Mukhin A.G., Koren A.O., Gundisch D., Links J.M., Kurian V., Dannals R.F., and London E.D. Life Sci. 67 (2000) 463
26. Horti, A. G.; Gao, Y.; Kuwabara, H.; Dannals, R. F. Life Sci. 2009, in press. doi:10.1016/j.lfs.2009.02.029.
27. Brown L., Chefer S., Pavlova O., Vaupel D.B., Koren A.O., Kimes A.S., Horti A.G., and Mukhin A.G. J. Neurochem. 91 (2004) 600
28. Brown L.L., Kulkarni S., Pavlova O.A., Koren A.O., Mukhin A.G., Newman A.H., and Horti A.G. J. Med. Chem. 45 (2002) 2841
29. Brown L.L., Pavlova O., Mukhin A., Kimes A.S., and Horti A.G. Bioorg. Med. Chem. 9 (2001) 3055
30. Gao Y., Ravert H.T., Holt D., Dannals R.F., and Horti A.G. Appl. Radiat. Isot. 65 (2007) 947
31. Waterhouse R.N. Mol. Imaging Biol. 5 (2003) 376
32. Xiao Y., and Kellar K.J. J. Pharmacol. Exp. Ther. 310 (2004) 98
33. Meyer E.L., Xiao Y., and Kellar K.J. Mol. Pharmacol. 60 (2001) 568
34. Lukas R.J., Changeux J.P., Le Novere N., Albuquerque E.X., Balfour D.J., Berg D.K., Bertrand D., Chiappinelli V.A., Clarke P.B., Collins A.C., Dani J.A., Grady S.R., Kellar K.J., Lindstrom J.M., Marks M.J., Quik M., Taylor P.W., and Wonnacott S. Pharmacol. Rev. 51 (1999) 397
35. Chefer S.I., London E.D., Koren A.O., Pavlova O.A., Kurian V., Kimes A.S., Horti A.G., and Mukhin A.G. Synapse 48 (2003) 25
36. Ashburner J.T., and Friston K.J. In: Friston K.J., Ashburner J.T., Kiebel S.J., and Nichols T.E. (Eds). Statistical Parametric Mapping: The Analysis of Functional Brain Images (2007), Academic Press
37. Kuwabara H., Cumming P., Reith J., Leger G., Diksic M., Evans A.C., and Gjedde A. J. Cereb. Blood Flow Metab. 13 (1993) 43
38. Mintun M.A., Raichle M.E., Kilbourn M.R., Wooten G.F., and Welch M.J. Ann. Neurol. 15 (1984) 217
39. Innis R.B., Cunningham V.J., Delforge J., Fujita M., Gjedde A., Gunn R.N., Holden J., Houle S., Huang S.C., Ichise M., Iida H., Ito H., Kimura Y., Koeppe R.A., Knudsen G.M., Knuuti J., Lammertsma A.A., Laruelle M., Logan J., Maguire R.P., Mintun M.A., Morris E.D., Parsey R., Price J.C., Slifstein M., Sossi V., Suhara T., Votaw J.R., Wong D.F., and Carson R.E. J. Cereb. Blood Flow Metab. 27 (2007) 1533
40. Hilton J., Yokoi F., Dannals R.F., Ravert H.T., Szabo Z., and Wong D.F. Nucl. Med. Biol. 27 (2000) 627