A new 18F-labeled fluoroacetylmorpholino derivative of vesamicol for neuroimaging of the vesicular acetylcholine transporter

Nuclear Medicine and Biology

Volumn 35, Issue 2, 2008, Pages 185-195

  Sorger, Dietlind ^a   Scheunemann, Matthias ^b   Großmann, Udo ^a   Fischer, Steffen ^b   Vercouille, Johnny ^b   Hiller, Achim ^b   Wenzel, Barbara ^b   Roghani, Ali ^c   Schliebs, Reinhard ^a   Brust, Peter ^b   Sabri, Osama ^a   Steinbach, Jörg ^b  

^a UNIVERSITY OF LEIPZIG   (Germany)

^b Institute of Interdisciplinary Isotope Research   (Germany)

^c TEXAS TECH UNIVERSITY HEALTH SCIENCES CENTER SCHOOL OF MEDICINE   (United States)

Author keywords

Affinity; Biodistribution; Cholinergic neurons; Radiosynthesis; Rat; Selectivity; VAChT; Vesamicol

Indexed keywords

2 BROMO 1 [7 HYDROXY 6 (4 PHENYLPIPERIDIN 1 YL)OCTAHYDROBENZ[1,4]OXAZIN 4 YL]ETHANONE; 2 FLUORO 1 [7 HYDROXY 6 (4 PHENYLPIPERIDIN 1 YL)OCTAHYDROBENZ[1,4]OXAZIN 4 YL]ETHANONE F18; BENZOXAZINE DERIVATIVE; BRAIN EXTRACT; BROMINE DERIVATIVE; SIGMA OPIATE RECEPTOR; TRACER; TRITIUM; UNCLASSIFIED DRUG; VESAMICOL; VESAMICOL DERIVATIVE; VESICULAR ACETYLCHOLINE TRANSPORTER; FLUORINE; MORPHOLINE DERIVATIVE; PIPERIDINE DERIVATIVE; RADIOPHARMACEUTICAL AGENT; SIGMA 1 OPIATE RECEPTOR; SIGMA 2 OPIATE RECEPTOR; SIGMA-1 RECEPTOR; SIGMA-2 RECEPTOR;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; AUTORADIOGRAPHY; BRAIN; BRAIN CORTEX; BRAIN REGION; BRAIN SLICE; BRAIN VENTRICLE; CELL STRAIN; CEREBELLUM; CHOLINERGIC SYSTEM; COMPARATIVE STUDY; COMPUTER; COMPUTER SYSTEM; CONTROLLED STUDY; CORPUS STRIATUM; DRUG ACTIVITY; DRUG BLOOD LEVEL; DRUG BRAIN LEVEL; DRUG CONFORMATION; DRUG DEGRADATION; DRUG DISTRIBUTION; DRUG METABOLISM; DRUG PROTEIN BINDING; DRUG PURITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TRANSPORT; EX VIVO STUDY; FEMALE; GENE OVEREXPRESSION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HIPPOCAMPUS; HUMAN; HYDROPHILICITY; IC 50; IN VIVO STUDY; LIPOPHILICITY; NEUROIMAGING; NONHUMAN; PHYSICAL CHEMISTRY; PLASMA PROTEIN BINDING; POSITRON EMISSION TOMOGRAPHY; RADIOACTIVITY; RADIOCHEMISTRY; RAT; ANIMAL; BINDING COMPETITION; CHEMISTRY; DRUG ANTAGONISM; ISOTOPE LABELING; METABOLIC CLEARANCE RATE; METHODOLOGY; PROTEIN BINDING; SCINTISCANNING; SPRAGUE DAWLEY RAT; SYNTHESIS;

ANIMALS; AUTORADIOGRAPHY; BINDING, COMPETITIVE; BRAIN; FEMALE; FLUORINE RADIOISOTOPES; ISOTOPE LABELING; METABOLIC CLEARANCE RATE; MORPHOLINES; PC12 CELLS; PIPERIDINES; POSITRON-EMISSION TOMOGRAPHY; PROTEIN BINDING; RADIOPHARMACEUTICALS; RATS; RATS, SPRAGUE-DAWLEY; RECEPTORS, SIGMA; VESICULAR ACETYLCHOLINE TRANSPORT PROTEINS;

EID: 39049096694     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2007.10.004     Document Type: Article

References (46)

1. Schliebs R., and Arendt T. The significance of the cholinergic system in the brain during aging and in Alzheimer's disease. J Neural Transm 113 (2006) 1625-1644
2. Sivaprakasam K. Towards a unifying hypothesis of Alzheimer's disease: cholinergic system linked to plaques, tangles and neuroinflammation. Curr Med Chem 13 (2006) 2179-2188
3. Whitehouse P.J., Price D.L., Struble R.G., Clark A.W., Coyle J.T., and Delon M.R. Alzheimer's disease and senile dementia: loss of neurons in the basal forebrain. Science 215 (1982) 1237-1239
4. Bowen D.M., Smith C.B., White P., Goodhardt M.J., Spillane J.A., Flack R.H., et al. Chemical pathology of organic dementias. I. Validity of biochemical measurements on human post-mortem brain specimens. Brain 100 (1977) 397-426
5. Etienne P., Robitaille Y., Wood P., Gauthier S., Nair N.P., and Quirion R. Nucleus basalis neuronal loss, neuritic plaques and choline acetyltransferase activity in advanced Alzheimer's disease. Neuroscience 19 (1986) 1279-1291
6. McGeer P.L. The 12th J. A. F. Stevenson memorial lecture. Aging, Alzheimer's disease, and the cholinergic system. Can J Physiol Pharmacol 62 (1984) 741-754
7. Eiden L.E. The cholinergic gene locus. J Neurochem 70 (1998) 2227-2240
8. Erickson J.D., Varoqui H., Schäfer M.K.H., Modi W., Diebler M.F., Weihe E., et al. Functional identification of a vesicular acetylcholine transporter and its expression from a "cholinergic" gene locus. J Biol Chem 269 (1994) 21929-21932
9. Roghani A., and Carroll P.T. Analysis of uptake and release of newly synthesized acetylcholine in PC12 cells overexpressing the rat vesicular acetylcholine transporter (VAChT). Brain Res Mol Brain Res 100 (2002) 21-30
10. Mallet J., Houhou L., Pajak F., Oda Y., Cervini R., Bejanin S., et al. The cholinergic locus: ChAT and VAChT genes. J Physiol Paris 92 (1998) 145-147
11. Sihver W., Gillberg P.G., Svensson A.L., and Nordberg A. Autoradiographic comparison of [3H](-)nicotine, [3H]cytisine and [3H]epibatidine binding in relation to vesicular acetylcholine transport sites in the temporal cortex in Alzheimer's disease. Neuroscience 94 (1999) 685-696
12. Ikeda E., Shiba K., Mori H., Ichikawa A., Sumiya H., Kuji I., et al. Reduction of vesicular acetylcholine transporter in beta-amyloid protein-infused rats with memory impairment. Nucl Med Commun 21 (2000) 933-937
13. 3H]Vesamicol binding in brain: autoradiographic distribution, pharmacology, and effects of cholinergic lesions. Synapse 2 (1988) 486-493
14. Marien M.R., Parsons S.M., and Altar C.A. Quantitative autoradiography of brain binding sites fore the vesicular acetylcholine transport blocker 2-(4-phenylpiperidino)cyclohexanol (AH5183). Proc Natl Acad Sci. U S A 84 (1987) 876-880
15. Parsons S.M., Bahr B.A., Rogers G.A., Clarkson E.D., Noremberg K., and Hicks B.W. Acetylcholine transporter - vesamicol receptor pharmacology and structure. Prog Brain Res 98 (1993) 175-181
16. Rogers G.A., Parsons S.M., Anderson D.C., Nilsson L.M., Bahr B.A., Kornreich W.D., et al. Synthesis, in vitro acetylcholine-storage-blocking activities, and biological properties of derivatives and analogues of trans-2-(4-phenylpiperidino)cyclohexanol (Vesamicol). J Med Chem 32 (1989) 1217-1230
17. Browne S.E., Lin L., Mattsson A., Georgievska B., and Isacson O. Selective antibody-induced cholinergic cell and synapse loss produce sustained hippocampal and cortical hypometabolism with correlated cognitive deficits. Exp Neurol 170 (2001) 36-47
18. Sorger D., Schliebs R., Kampfer I., Rossner S., Heinicke J., Dannenberg C., et al. In vivo [125I]-iodobenzovesamicol binding reflects cortical cholinergic deficiency induced by specific immunolesion of rat basal forebrain cholinergic system. Nucl Med Biol 27 (2000) 23-31
19. Quinlivan M., Chalon S., Vergote J., Henderson J., Katsifis A., Kassiou M., et al. Decreased vesicular acetylcholine transporter and alpha(4)beta(2) nicotinic receptor density in the rat brain following 192 IgG-saporin immunolesioning. Neurosci Lett 415 (2007) 97-101
20. 3H]Vesamicol binding in human brain cholinergic deficiency disorders. Neurosci Lett 117 (1990) 347-352
21. 3H]Vesamicol binding in the temporal cortex of patients with Alzheimer's disease, Parkinson's disease, and rats with basal forebrain lesions. Neuroscience 35 (1990) 327-333
22. Efange S.M.N., Garland E.M., Staley J.K., Khare A.B., and Mash D.C. Vesicular acetylcholine transporter density and Alzheimer's disease. Neurobiol Aging 18 (1997) 407-413
23. Kuhl D.E., Koeppe R.A., Fessler J.A., Minoshima S., Ackermann R.J., Carey J.E., et al. In vivo mapping of cholinergic neurons in the human brain using SPECT and IBVM. J Nucl Med 35 (1993) 405-410
24. Kuhl D.E., Minoshima S., Fessler J.A., Frey K.A., Foster N.L., Ficaro E.P., et al. In vivo mapping of cholinergic terminals in normal aging. Alzheimer's disease and Parkinson's disease. Ann Neurol 40 (1996) 399-410
25. Cohen R.M. The application of positron-emitting molecular imaging tracers in Alzheimer's disease. Mol Imaging Biol 9 (2007) 204-216
26. Custers F.G., Leysen J.E., Stoof J.C., and Herscheid J.D. Vesamicol and some of its derivatives: questionable ligands for selectively labelling acetylcholine transporters in rat brain. Eur J Pharmacol 338 (1997) 177-183
27. Efange S.M., Mach R.H., Smith C.R., Khare A.B., Foulon C., Akella S.K., et al. Vesamicol analogues as sigma ligands. Molecular determinants of selectivity at the vesamicol receptor. Biochem Pharmacol 49 (1995) 791-797
28. Bando K., Naganuma T., Taguchi K., Ginoza Y., Tanaka Y., Koike K., et al. Piperazine analog of vesamicol: in vitro and in vivo characterization for vesicular acetylcholine transporter. Synapse 38 (2000) 27-37
29. Bando K., Taguchi K., Ginoza Y., Naganuma T., Tanaka Y., Koike K., et al. Synthesis and evaluation of radiolabeled piperazine derivatives of vesamicol as SPECT agents for cholinergic neurons. Nucl Med Biol 28 (2001) 251-260
30. Efange S.M., von Hohenberg K., Khare A.B., Tu Z., Mach R.H., and Parsons S.M. Synthesis and biological characterization of stable and radioiodinated (+/-)-trans-2-hydroxy-3-P[4-(3-iodophenyl)piperidyl]-1,2,3,4-tetrahydronaphthalene (3'-IBVM). Nucl Med Biol 27 (2000) 749-755
31. Scheunemann M., Sorger D., Wenzel B., Heinitz K., Schliebs R., Klingner M., et al. Synthesis of novel 4- and 5-substituted benzyl ether derivatives of vesamicol and in vitro evaluation of their binding properties to the vesicular acetylcholine transporter site. Bioorg Med Chem 12 (2004) 1459-1465
32. Shiba K., Ogawa K., Ishiwata K., Yajima K., and Mori H. Synthesis and binding affinities of methylvesamicol analogs for the acetylcholine transporter and sigma receptor. Bioorg Med Chem 14 (2006) 2620-2626
33. Wenzel B., Sorger D., Heinitz K., Scheunemann M., Schliebs R., Steinbach J., et al. Structural changes of benzylether derivatives of vesamicol and their influence on the binding selectivity to the vesicular acetylcholine transporter. Eur J Med Chem 40 (2005) 1197-1205
34. Zea-Ponce Y., Mavel S., Assaad T., Kruse S.E., Parsons S.M., Emond P., et al. Synthesis and in vitro evaluation of new benzovesamicol analogues as potential imaging probes for the vesicular acetylcholine transporter. Bioorg Med Chem 13 (2005) 745-753
35. Scheunemann M., Sorger D., Kouznetsova E., Sabri O., Schliebs R., Wenzel B., et al. Sequential ring-opening of trans-1,4-cyclohaxadiene dioxide for an expedient modular approach to 6,7-disubstituted (±) hexahydro-benzo [1,4]oxazin-3-ones. Tetrahedron Lett 48 (2007) 5497-5501
36. Efange S.M., Khare A.B., Mach R.H., and Parsons S.M. Hydroxylated decahydroquinolines as ligands for the vesicular acetylcholine transporter: synthesis and biological evaluation. J Med Chem 42 (1999) 2862-2869
37. 18F-labelled vesamicol derivatives: Syntheses and preliminary in vivo small animal Positron Emission Tomography evaluation. Nucl Med Biol 21 (1994) 219-230
38. i) and the concentration of inhibitor which causes 50% inhibition (IC50) of an enzymatic reaction. Biochem Pharmacol 22 (1973) 3099-3108
39. Roghani A., Feldman J., Kohan S.A., Shirzadi A., Gundersen C.B., Brecha N., et al. Molecular cloning of a putative vesicular transporter for acetylcholine. Proc Natl Acad Sci U S A 91 (1994) 10620-10624
40. Huang Y., Hammond P.S., Wu L., and Mach R.H. Synthesis and structure-activity relationships of N-(1-benzylpiperidin-4-yl)arylacetamide analogues as potent sigma1 receptor ligands. J Med Chem 44 (2001) 4404-4415
41. Arvidsson U., Riedl M., Elde R., and Meister B. Vesicular acetylcholine transporter (VAChT) protein: a novel and unique marker for cholinergic neurons in the central and peripheral nervous systems. J Comp Neurol 378 (1997) 454-467
42. Marshall I.G. Studies on the blocking action of 2-(4-phenyl piperidino) cyclohexanol (AH5183). Br J Pharmacol 38 (1970) 503-516
43. Halldin C., Gulyas B., Langer O., and Farde L. Brain radioligands - state of the art and new trends. Q J Nucl Med 45 (2001) 139-152
44. 18F]fluoroethoxy-benzovesamicol, a PET radiotracer for the vesicular acetylcholine transporter and cholinergic synapses. Synapse 30 (1998) 263-274
45. Tu L.Q., Wright P.F., Rix C.J., and Ahokas J.T. Is fluoroacetate-specific defluorinase a glutathione S-transferase?. Comp Biochem Physiol C Toxicol Pharmacol 143 (2006) 59-66
46. Johnson J.A., el Barbary A., Kornguth S.E., Brugge J.F., and Siegel F.L. Glutathione S-transferase isoenzymes in rat brain neurons and glia. J Neurosci 13 (1993) 2013-2023