5-tert-Butyl-2-(4′-[18F]fluoropropynylphenyl)-1,3-dithiane oxides: potential new GABAA receptor radioligands

Nuclear Medicine and Biology

Volumn 35, Issue 5, 2008, Pages 549-559

  Li, Xuehe ^a   Jung, Yong Woon ^a   Snyder, Scott E ^a   Blair, Joseph ^a   Sherman, Philip S ^a   Desmond, Timothy ^a   Frey, Kirk A ^a   Kilbourn, Michael R ^a  

^a UNIVERSITY OF MICHIGAN MEDICAL SCHOOL   (United States)

Author keywords

emission computed; Fluorine 18; GABA; Picrotoxin; Tomography

Indexed keywords

4 AMINOBUTYRIC ACID A RECEPTOR; 5 TERT BUTYL 2 (4' FLUOROPROPYNYLPHENYL) 1,3 DITHIANE OXIDE F 18; 5 TERT BUTYL 2 (4' FLUOROPROPYNYLPHENYL) 2 METHYL 1,1 DIOXO 1,3 DITHIANE; 5 TERT BUTYL 2 (4' FLUOROPROPYNYLPHENYL) 2 METHYL 1,1,3,3 TETROXO 1,3 DITHIANE; FLUORINE 18; RADIOLIGAND; SULFUR;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BRAIN; BRAIN CORTEX; CEREBELLUM; CONTROLLED STUDY; CORPUS STRIATUM; DRUG DISTRIBUTION; DRUG STRUCTURE; DRUG UPTAKE; FLUORINATION; ISOTOPE LABELING; MEDULLA OBLONGATA; MOUSE; NONHUMAN; OXIDATION; PONS; POSITRON EMISSION TOMOGRAPHY;

ANIMALS; BINDING, COMPETITIVE; BRAIN; CYCLIC S-OXIDES; FEMALE; FLUORINE RADIOISOTOPES; MAGNETIC RESONANCE SPECTROSCOPY; MICE; MOLECULAR CONFORMATION; POSITRON-EMISSION TOMOGRAPHY; RADIOPHARMACEUTICALS; RECEPTORS, GABA-A; STEREOISOMERISM; TISSUE DISTRIBUTION;

EID: 45449118281     PISSN: 09698051     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.nucmedbio.2007.08.003     Document Type: Article

References (45)

1. A receptor channel pharmacology. Curr Pharm Des 11 (2005) 1867-1885
2. A receptor agonists, partial agonists, and antagonists. Design and therapeutic prospects. J Med Chem 37 (1994) 2489-2505
3. Burt D.R. Reducing GABA receptors. Life Sci 73 (2003) 1741-1758
4. A receptors. Prog Neurobiol 67 (2002) 113-159
5. Katsifis A., and Kassiou M. Development of radioligands for in vivo imaging of GABA(A)-benzodiazepine receptors. Mini Rev Med Chem 4 (2004) 909-921
6. Chen L., Durkin K.A., and Casida J.E. Structural model for γ-aminobutyric acid receptor noncompetitive antagonist binding; widely diverse structures fit the same site. Proc Natl Acad Sci U S A 103 (2006) 5185-5190
7. A chloride channel. J Label Compd Radiopharm 32 (1993) 313
8. 123I]iodophenyl)-2,6,7-trioxabicyclo-[2.2.2]octane. Nucl Med Biol 20 (1993) 469-475
9. Elliot M., Pullman D.A., Larkin J.P., and Casida J.E. Insecticidal 1,3-dithianes. J Agric Food Chem 40 (1992) 147-151
10. Wacher V.J., Toia R.E., and Casida J.E. 2-Aryl-5-tert-butyl-1,3-dithianes and their S-oxidation products: structure-activity relationships of potent insecticides acting at the GABA-gated chloride channel. J Agric Food Chem 40 (1992) 497-505
11. A-gated chloride ion channel blockers: substituted 5-t-butyl-2-phenyl-1,3-dithianes and dithiane oxides. J Med Chem 38 (1995) 2663-2671
12. A chloride ion channel. J Label Compd Radiopharm 42 Suppl 1 (1999) S635-S637
13. Palmer C.J., and Casida J.E. Insecticidal 1,3-dithianes and 1,3-dithiane 1,1-dioxides. J Agric Food Chem 40 (1992) 492-496
14. Li Q.X., and Casida J.E. Structure-activity studies leading to potent chloride channel blockers: 5e-tert-butyl-2-[4-(substituted-ethynyl)phenyl]-1,3-dithianes. Bioorg Med Chem 2 (1994) 1423-1434
15. Li Q.X., and Casida J.E. Affinity probes for the GABA-gated chloride channel: 5e-tert-butyl-2e-[4-(substituted-ethynyl)phenyl]-1,3-dithianes with photoactivatable, fluorescent, biotin, agarose and protein substituents. Bioorg Med Chem 3 (1995) 1675-1684
16. Eliel E.L., Rao V., Smith S., and Hutchins R.O. Convenient and stereoselective dithiol synthesis. J Org Chem 40 (1975) 524-526
17. 1-propargyl complexes and their [3+2] cycloaddition reactions with sulfur dioxide and disulfur monoxide. Transition-metal-carbon bond cleaving reactions of the cycloadducts which yield oxathiolene oxides and dithiolene oxides. J Org Chem 673 (2003) 67-76
18. 3H]EBOB) binding and the action of insecticides on the gamma-aminobutyric acid-gated chloride channel in cultured cerebellar granule neurons. J Pharmacol Exp Ther 279 3 (1996) 1191-1196
19. 3H]ethynylbicycloorthobenzoate binding to GABA mimetics. Neurosci Lett 225 2 (1997) 85-88
20. Nicholson R.A., Lees G., Zheng J., and Verdon B. Inhibition of GABA-gated chloride channels by 12,14-dichlorodehydroabietic acid in mammalian brain. Br J Pharmacol 126 5 (1999) 1123-1132
21. A receptor complex. Eur J Pharmacol 263 (1994) 163-173
22. Wacher V.J., and Casida J.E. Metabolism in mouse liver and photooxidation of the insecticidal cis and trans-2-(4-bromophenyl)-5-tert-butyl-1,3-dithianes. J Agric Food Chem 41 (1993) 296-302
23. 3H]Butylbicycloorthobenzoate: new radioligand probe for the γ-aminobutyric acid-regulated chloride ionophore. J Neurochem 45 (1985) 798-804
24. A receptor subtypes: autoradiographic comparison of GABA, benzodiazepine, and convulsant binding sites in the rat central nervous system. J Chem Neuroanat 3 (1990) 59-76
25. Kilbourn M.R., Pavia M.R., and Gregor V.E. Synthesis of fluorine-18 labelled GABA uptake inhibitors. Appl Radiat Isot 41 (1990) 823-828
26. 18F]GBR 13119, a dopamine uptake inhibitor, in CD-1 and C57B1/6 mice. Eur J Pharmacol 166 (1989) 331-334
27. 18F]GBR 12909, a dopamine reuptake inhibitor. J Labelled Compd Radiopharm 28 (1990) 793-800
28. 11C]nisoxetine, a norepinephrine uptake inhibitor. Nucl Med Biol 16 (1989) 771-774
29. Mulholland G.K., Otto C.A., Jewett D.M., Kilbourn M.R., Koeppe R.A., Sherman P.S., et al. Synthesis, biodistribution, dosimetry, metabolism and monkey PET studies of carbon-11 labeled (+)-2α-tropanyl benzilate, a central muscarinic receptor imaging agent. J Nucl Med 33 (1992) 423-430
30. 11C]NMPB), a muscarinic acetylcholine receptor antagonist. Nucl Med Biol 22 (1995) 13-17
31. 11C]Methyl-3-pyrrolidinyl benzilate, a high affinity reversible radioligand for PET studies of the muscarinic acetylcholine receptor. Synapse 45 (2002) 31-37
32. Skaddan M.B., Kilbourn M.R., Snyder S.E., Sherman P.S., Desmond T.J., and Frey K.A. Synthesis, radiolabeling, and biological evaluation of piperidyl and pyrolidyl benzilates as in vivo ligands for the muscarinic acetylcholine receptors. J Med Chem 43 (2000) 4552-4562
33. 11C]metanicotine) as a nicotinic receptor radioligand. Nucl Med Biol 27 (2000) 415-418
34. Mulholland G.K., Sugimoto H., Jewett D.M., and Kilbourn M.R. Simple preparation of a novel C-11 acetylcholinesterase inhibitor. J Nucl Med 30 (1989) 822
35. 11C]methoxy-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-1,2-benzisoxazole as an in vivo radioligand for acetylcholinesterase. Nucl Med Biol 26 (1999) 99-103
36. Kilbourn M.R., Jung Y.-W., Haka M.S., Gildersleeve D.L., Kuhl D.E., and Wieland D.M. Mouse brain distribution of a carbon-11 labeled vesamicol derivative: presynaptic marker of cholinergic neurons. Life Science 47 (1990) 1955-1963
37. 18F]fluoroethoxybenzovesamicol, a radiotracer for cholinergic neurons. J Labelled Compd Radiopharm 33 (1993) 583-592
38. 11C]tetrabenazine to vesicular monoamine transporters in mouse brain. Life Sci 51 (1992) 593-600
39. 11C]methoxy derivative of α-dihydrotetrabenazine: a radioligand for studying the vesicular monoamine transporter. Appl Radiat Isot 44 (1993) 1487-1489
40. Kilbourn M., and Frey K. Striatal concentrations of vesicular monoamine transporters are identical in MPTP-sensitive (C57Bl/6) and -insensitive (CD-1) mouse strains. Eur J Pharmacol 307 (1996) 227-232
41. Jewett D.M., and Kilbourn M.R. In vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor. Nucl Med Biol 31 (2004) 321-325
42. 11C]methyl labeled δ-opioid receptor radiotracers. Abstr Pap Am Chem. Soc 222 Pt 1 (2001) 213-MEDI
43. Eckelman W.C., Kilbourn M.R., and Mathis C.A. Discussion of targeting protein in vivo: in vitro guidelines. Nucl Med Biol 33 (2006) 449-451
44. 3H]Methoxytetrabenazine: a high specific activity ligand for estimating monoaminergic neuronal integrity. Neuroscience 68 (1995) 955-962
45. Kilbourn M.R. Long-term reproducibility of in vivo measures of specific binding of radioligands in rat brain. Nucl Med Biol 31 (2004) 591-595