Two C-Methyl derivatives of [11C]WAY-100635-effects of an amido α-methyl group on metabolism and brain 5-HT1A receptor radiol igand behavior in monkey

Molecular Imaging and Biology

Volumn 7, Issue 3, 2005, Pages 209-219

  McCarron, Julie A ^a,d   Marchais Oberwinkler, Sandrine ^b   Pike, Victor W ^a   Tarkiainen, Jari ^c   Halldin, Christer ^c   Sóvagó, Judit ^c   Gulyas, Balàzs ^c   Wikström, Hakan V ^b   Farde, Lars ^c  

^a HAMMERSMITH HOSPITAL   (United Kingdom)

^b UNIVERSITY MEDICAL CENTER GRONINGEN   (Netherlands)

^c KAROLINSKA UNIVERSITY HOSPITAL   (Sweden)

^d NATIONAL INSTITUTE OF MENTAL HEALTH   (United States)

Author keywords

5 HT1A receptors; alpha; Methyl; Carbon 11; Metabolism; PET; Radioligand; WAY 100635

Indexed keywords

[N [2 [1 [4 (2 METHOXYPHENYL)PIPERAZINYL](2 METHYLETHYL)]] N PYRIDINYL]CYCLOHEXANECARBOXAMIDE C 11; N [2 [1 [4 (2 METHOXYPHENYL)PIPERAZINYL]ETHYL] N PYRIDINYL]CYCLOHEXANE 1' METHYL CARBOXAMIDE C 11; N [2 [4 (2 METHOXYPHENYL) 1 PIPERAZINYL]ETHYL] N (2 PYRIDYL)CYCLOHEXANECARBOXAMIDE; RADIOLIGAND; SEROTONIN 1A RECEPTOR; UNCLASSIFIED DRUG; CARBON; LIGAND; LIPID; PIPERAZINE DERIVATIVE; PYRIDINE DERIVATIVE; SEROTONIN 1 RECEPTOR;

ANIMAL EXPERIMENT; ARTICLE; BINDING AFFINITY; BRAIN REGION; CEREBELLUM; CONTROLLED STUDY; DRUG METABOLISM; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG UPTAKE; MALE; MONKEY; NONHUMAN; POSITRON EMISSION TOMOGRAPHY; PRIORITY JOURNAL; RADIOACTIVITY; AMINATION; ANIMAL; BLOOD; BRAIN; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; HAPLORHINI; HYDROPHOBICITY; IC 50; METABOLISM; METHYLATION; RADIOASSAY; RADIOCHEMISTRY; SYNTHESIS;

MACACA FASCICULARIS;

AMINATION; ANIMALS; BRAIN; CARBON RADIOISOTOPES; HAPLORHINI; HYDROPHOBICITY; INHIBITORY CONCENTRATION 50; LIGANDS; LIPIDS; METHYLATION; MOLECULAR STRUCTURE; PIPERAZINES; POSITRON-EMISSION TOMOGRAPHY; PYRIDINES; RADIOCHEMISTRY; RADIOLIGAND ASSAY; RECEPTORS, SEROTONIN, 5-HT1;

EID: 24744455283     PISSN: 15361632     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11307-005-4127-5     Document Type: Article

References (38)

1. 11C]WAY 100635 Eur J Pharmacol 301 R5-R7 10.1016/0014-2999(96)00079-9 1:CAS:528:DyaK28XjtFaqtLY%3D 8773468
2. 1A receptors in vivo Prog Med Chem 38 189-247 1:CAS:528:DC%2BD3MXivVGntbs%3D 11774795
3. 1A) receptors in the central nervous system Eur J Nucl Med 28 113-129 10.1007/s002590000394 1:CAS:528:DC%2BD3cXovFyjt7g%3D 11202445
4. L Farde H Ito C-G Swahn VW Pike C Halldin 1998 Quantitative analyses of carbonyl-carbon-11-WAY-100635 binding to central 5-hydroxtryptamine-1A receptors in man J Nucl Med 39 1965-1971 1:CAS:528:DyaK1cXnsFWjsbg%3D 9829590
5. 11C]WAY-100635 for PET NeuroImage 8 426-440 10.1006/nimg.1998.0379 1:STN:280:DyaK1M%2FjtVOmsg%3D%3D 9811559
6. 11C]WAY-100635 PET studies Nucl Med Biol 27 477-482 10.1016/S0969-8051(00)00115-3 1:CAS:528:DC%2BD3cXmtVGjtL0%3D 10962254
7. 11 C]WAY-100635 - Explanation of high signal contrast in PET and an aid to biomathematical modeling Nucl Med Biol 25 215-223 10.1016/ S0969-8051(97)00206-0 1:CAS:528:DyaK1cXisV2js7c%3D 9620626
8. 11C]WAY-100635 in humans: Comparison of arterial and reference tissue inputs J Cereb Blood Flow Metab 20 1111-1133 1:CAS:528:DC%2BD3cXltFOmu74%3D 10908045
9. 11C]WAY-100635 binding; considerations on the cerebellum Nucl Med Biol 27 483-486 10.1016/S0969-8051(00)00116-5 1:CAS:528:DC%2BD3cXmtVGjtLo%3D 10962255
10. 11C] WAY-100635 binding parameters with reference tissue models; effect of violations of model assumptions Nucl Med Biol 27 487-492 10.1016/ S0969-8051(00)00117-7 1:CAS:528:DC%2BD3cXmtVGjtLs%3D 10962256
11. 1A receptors: Syntheses, radiosyntheses, and in vitro and in vivo evaluation Nucl Med Biol 25 769-776 10.1016/S0969-8051(98)00020-1 1:CAS:528:DyaK1cXnsVChu7Y%3D 9863565
12. 1A receptors with PET: WAY-100635 and analogues Nucl Med Biol 27 463-466 10.1016/S0969-8051(00)00112-8 1:CAS:528:DC%2BD3cXmtVGjtL4%3D 10962251
13. 11C]CPC-222 Nucl Med Commun 18 1130-1134 1:CAS:528:DyaK1cXmsFSksg%3D%3D 9481759
14. 1A receptor antagonist, WAY-100635 Eur J Pharmacol 281 81-88 10.1016/0014-2999(95)00234-C 1:CAS:528:DyaK2MXntFCktbg%3D 8566121
15. 11C] WAY-100635 Eur J Pharmacol 283 R1-R3 10.1016/0014-2999(95)00438-Q 1:CAS:528:DyaK2MXnvFWiu7w%3D 7498295
16. 11C]WAY-100635 Med Chem Res 5 208-227
17. 1A receptor antagonists Bioorg Med Chem 9 695-702 10.1016/ S0968-0896(00)00287-X 1:CAS:528:DC%2BD3MXjt1ahtbw%3D 11310604
18. 11C]FLB 457 by use of the GE medical systems PETtrace MeI module J Label Compd Radiopharm 43 331-338 10.1002/(SICI)1099-1344(20000330)43:4<331::AID-JLCR320>3.0.CO;2-H 1:CAS:528:DC%2BD3cXitlajtLk%3D
19. 11C]WAY-100635 Brain Res 745 96-108 10.1016/S0006-8993(96)01131-6 1:CAS:528:DyaK2sXhs1ymsg%3D%3D 9037397
20. K Wienhard M Dahlbom L Eriksson et al. 1994 The ECAT EXACT HR: Performance of a new high resolution positron scanner J Comput Assist Tomogr 18 110-118 1:STN:280:ByuC3M%2FktVI%3D 8282858
21. 11C]NNC 756 as new radioligands for the D-1 dopamine receptor Psychopharmacology 113 149-156 1:CAS:528:DyaK2cXktVCis7c%3D 7855175
22. 11C]SCH 23390. Identification of two metabolites with HPLC Hum Psychopharmacol 9 25-31 10.1002/hup.470090103 1:CAS:528:DyaK2cXltVehsrY%3D
23. C Halldin C-G Swahn L Farde G Sedvall 1995 Radioligand disposition and metabolism. Key information in early drug development. In: D. Comar (ed) PET for drug development and evaluation Kluwer Academic Publishers Dordrecht, The Netherlands pp. 55-65
24. 1A antagonists. Int Pat WO 95/33743
25. 1A antagonists. Int Pat WO 97/03982
26. Cliffe IA, Mansell HL (1992) Piperazine derivatives. Eur Pat 0 512 755 A2
27. Brightwell CI, Shephard RG (1995) Novel processes and intermediates for the preparation of piperazine derivatives. Int Pat WO 95/33725
28. 1A receptors in the primate brain Psychopharmacology 133 196-202 10.1007/s002130050391 1:CAS:528:DyaK2sXmtl2qurw%3D 9342787
29. 1A receptors in vitro and in vivo Eur J Nucl Med 25 338-346 10.1007/s002590050230 1:CAS:528:DyaK1cXit1aktrY%3D 9553162
30. 18F]MPPF in rats Eur J Pharmacol 407 273-280 10.1016/S0014-2999(00)00752-4 1:CAS:528:DC%2BD3cXnvVals78%3D 11068023
31. 1A receptors in the living brain with PET. PhD thesis, University of Groningen, Netherlands
32. 1A receptors in living monkey Nucl Med Biol 28 177-185 10.1016/S0969-8051(00)00181-5 1:CAS:528:DC%2BD3MXisVWntL4%3D 11295428
33. 11C]WAY-100635, in monkey and human plasma by HPLC - Comparison of the behaviour of an identified metabolite with parent radioligand in monkey using PET Nucl Med Biol 23 627-634 10.1016/ 0969-8051(96)00061-3 1:CAS:528:DyaK28XlsVamur0%3D 8905828
34. P Denton C Horwell CD Johnson D Williamson 1992 Tertiary amide hydrolysis - the putative alpha methyl effect J Chem Res S12 410-411
35. TH Fife 1993 Kinetic and mechanistic effects of ease of C-N bond breaking in amide hydrolysis. The mechanisms of hydrolysis of N-acylimidazoles and N-acylbenzimidazoles Acc Chem Res 26 325-331 10.1021/ar00030a005 1:CAS:528:DyaK3sXktVyitrY%3D
36. CG Baker S-CJ Fu SM Birnbaum et al. 1952 Optical enantiomorphs of isovaline J Am Chem Soc 74 4701-4702 10.1021/ja01138a502 1:CAS:528:DyaG2cXjt1Cltw%3D%3D
37. S-JJ Fu SM Birnbaum 1953 The hydrolytic action of acylase I on N-acylamino acids J Am Chem Soc 75 918-920 10.1021/ja01100a042 1:CAS:528:DyaG3sXms1erug%3D%3D
38. HR Almond Jr. DT Manning X Niemann 1961 Interaction of α-chymotyrypsin with several α-methyl-α-acylamino acid methyl esters Biochemistry 1 243-249 10.1021/bi00908a008