Synthesis and PET evaluation of (R)-[S-methyl-11C] thionisoxetine, a candidate radioligand for imaging brain norepinephrine transporters

Journal of Labelled Compounds and Radiopharmaceuticals

Volumn 49, Issue 11, 2006, Pages 1007-1019

  Schou, Magnus ^a,b   Pike, Victor W ^b   Varrone, Andrea ^a   Gulyás, Balázs ^a   Farde, Lars ^a   Halldin, Christer ^a  

^a KAROLINSKA INSTITUTE   (Sweden)

^b NATIONAL INSTITUTE OF MENTAL HEALTH   (United States)

Author keywords

Carbon 11; Monkey; Norepinephrine transporter; PET; Radioligand

Indexed keywords

ALKYLATION; AMINO ACIDS; BRAIN; CARBON; NOREPINEPHRINE; POSITRON EMISSION TOMOGRAPHY; PROPIONIC ACID; SULFUR COMPOUNDS;

CARBON-11; METHYL IODIDE; MONKEY; NOREPINEPHRINE TRANSPORTER; PHENYLTHIO; POTENT INHIBITOR; PROPANOATE; RADIOLIGANDS; TETRA-HYDROFURAN; TETRAHYDROFURANS;

RADIOACTIVITY;

CARBON 11; METHYL 3 (2 3 (METHYLAMINO) 1 PHENYLPROPOXY)PHENYLTHIO) PROPANOATE; METHYL IODIDE; NORADRENALIN TRANSPORTER; PROPIONIC ACID DERIVATIVE; RADIOLIGAND; TETRAHYDROFURAN; THIONISOXETINE; UNCLASSIFIED DRUG;

ARTICLE; BRAIN; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; ISOTOPE LABELING; METHYLATION; MONKEY; NEUROIMAGING; POSITRON EMISSION TOMOGRAPHY;

MACACA FASCICULARIS;

EID: 33751544030     PISSN: 03624803     EISSN: 10991344     Source Type: Journal    
DOI: 10.1002/jlcr.1128     Document Type: Article

References (44)

1. Tejani-Butt SM, Yang JX, Zaffar H. Brain Res 1993; 631: 147-150.
2. Klimek V, Stockmeier C, Overholser J, Meltzer HY, Kalka S, Dilley G, Ordway GA. J Neurosci 1997; 17: 8451-8458.
3. Ressler KJ, Nemeroff CB. Biol Psychiatry 1999; 46: 1219-1233.
4. Spencer T, Heiligenstein JH, Biederman J, Faries DE, Kratochvil CJ, Conners CK, Potter WZ. J Clin Psychiatry 2002; 63: 1140-1147.
5. Brunello N, Kasper S, Leonard B, Montgomery S, Nelson JC, Paykel E, Versiani M, Racagni G. Eur Neuropsychopharmacol 2002; 12: 461-475.
6. Tejani-Butt SM, Brunswick DJ, Frazer A. Eur J Pharmacol 1990; 191: 239-243.
7. Cheetham SC, Viggers JA, Butler SA, Prow MR, Heal DJ. Neuropharmacology 1996; 35: 63-70.
8. Tejani-Butt SM. J Pharm Exp Ther 1992; 260: 427-436.
9. Ordway GA, Stockmeier CA, Cason GW, Klimek V. J Neurosci 1997; 17: 1710-1719.
10. Haka MS, Kilbourn MR. Nucl Med Biol 1989; 16: 771-774.
11. Ding YS, Lin KS, Logan J, Benveniste H, Carter P. J Neurochem 2005; 94: 337-351.
12. Schou M, Sóvagó J, Pike VW, Gulyás B, Bøgesø K, Farde L, Halldin C. Mol Imaging Biol 2005; 7: 1-8.
13. Kiyono Y, Kanegawa N, Kawashima H, Kitamura Y, Iida Y, Saji H. Nucl Med Biol 2004; 31: 147-153.
14. Kung M-P, Choi S-R, Hou C, Zhuang Z-P, Foulon C, Kung HF. Nucl Med Biol 2004; 31: 533-541.
15. McConathy J, Owens MJ, Kilts CD, Malveaux EJ, Camp VM, Votaw JR, Nemeroff CB, Goodman MM. Nucl Med Biol 2004; 31: 705-718.
16. Lin K-S, Ding Y-S, Betzel T, Quandt G. J Label Compd Radiopharm 2005; 48: S152.
17. McConathy J, Owens MJ, Kilts CD, Malveaux EJ, Votaw JR, Nemeroff CB, Goodman MM. Nucl Med Biol 2005; 32: 593-605.
18. Ding YS, Lin KS, Garza V, Carter P, Alexoff D, Logan J, Shea C, Xu YW, King P. Synapse 2003; 50: 345-352.
19. Schou M, Halldin C, Sóvágó J, Pike VW, Gulyás B, Mozley PD, Johnson DP, Hall H, Innis RB, Farde L. Nucl Med Biol 2003; 30: 707-714.
20. Wilson AA, Johnson DP, Mozley P, Hussey D, Ginovart N, Nobrega J. Garcia A, Meyer J, Houle S. Nucl Med Biol 2003; 30: 85-92.
21. Schou M, Halldin C, Sóvágó J, Pike VW, Hall H, Gulyás B, Mozley PD, Dobson D, Shchukin E, Innis RB, Farde L. Synapse 2004; 53: 57-67.
22. Andrée B, Seneca N, Schou M, Mozley PD, Potter WZ, Farde L, Gulyas B, Halldin C. Eur J Nucl Med Mol Imaging 2004; 31: S208.
23. Farde L, Eriksson L, Blomquist G, Halldin C. J Cereb Blood Flow Metab 1989; 9: 696-708.
24. Schou M, Halldin C, Pike VW, Mozley PD, Dobson D, Innis RB, Farde L, Hall H. Eur Neuropsychopharmacol 2005; 15: 517-520.
25. Gehlert DR, Hemrick-Luecke SK, Schober DA, Krushinski J, Howbert JJ, Robertson DW, Wong DT, Fuller RW. Life Sci 1995; 56: 1915-1920.
26. Wong DT, Threlkeld PG, Best KL, Bymaster FP. J Pharmacol Exp Ther 1982; 222: 61-65.
27. Marjamaki P, Zessin J, Eskola O, Gronroos T, Haaparanta M, Bergman J, Lehikoinen P, Forsback S, Brust P, Steinbach J, Solin O. Synapse 2003; 47: 45-53.
28. Zhang M-R, Ogawa M, Furutsuka K, Yoshida Y, Suzuki K. J Fluorine Chem 2004; 125: 1879-1886.
29. Zessin J, Gucker P, Ametamey SM, Steinbach J, Brust P, Vollenweider FX, Johannsen B, Schubiger PA. J Label Compd Radiopharm 1999; 42: 1301-1312.
30. McKinnon DM. Can J Chem 1980; 58: 2761-2764.
31. Nishimura O, Kitada C, Fujino M. Chem Pharm Bull 1978; 26: 1576-1585.
32. Hoffman K, Bridgewater A, Axelrod AE. J Am Chem Soc 1949; 71: 1253-1257.
33. Suehiro M, Wang TS, Yatabe T, Van Heertum RL, Mann JJ. J Label Compd Radiopharm 1998; 41: 725-730.
34. Pinchart A, Dallaire C, Bierbeek AV, Gingras M. Tetrahedron Lett 1999; 40: 5479-5482.
35. Becht J-M, Wagner A, Mioskowski C. J Org Chem 2003; 68: 5758-5761.
36. Chumpradit S, Kung MP, Panyachotipun C, Prapansiri V, Foulun C, Brooks BP, Szabo SA, Tejani-Butt S, Frazer A, Kung HF. J Med Chem 1992; 35: 4492-4497.
37. Mitsunobu O. Synthesis 1981; 1: 1-30.
38. Charnay Y, Leger L, Vallet P, Hof P, Juovet M, Bouras C. Neuroscience 1995; 69: 259-270.
39. Donnan G, Kaczmarczyk S, Paxinos G, Chilco P, Kalnins R, Woodhouse D, Mendelsohn F. J Comp Neurol 1991; 304: 419-434.
40. Smith H, Smith HR, Beveridge TJ, Porrino LJ. Neuroscience 2006; 138: 703-714.
41. Någren K, Truong P, Helin S, Amir A, Halldin C. J Label Compd Radiopharm 2003; 46: S76.
42. Wienhard K, Dahlbom M, Eriksson L, Michel C, Bruckbauer T, Pietrzyk U, Heiss W. J Comput Assist Tomogr 1994; 18: 110-118.
43. Karlsson P, Farde L, Halldin C, Swahn C-G, Sedvall G, Foged C, Hansen K, Skrumsager B. Psychopharmacology 1993; 113: 149-156.
44. Halldin C, Swahn C-G, Farde L, Sedvall G. Kluwer Academic Publishers: Dodrecht Comar D. (ed.). PET for Drug Development and Evaluation 1995; 55-65.