Nuclear Medicine and Biology
Volume 35, Issue 5 , Pages 549-559 , July 2008

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

Received 16 May 2007 ,Revised 1 August 2007 ,Accepted 16 August 2007.

References 

  1. Johnston GAR. GABAA receptor channel pharmacology. Curr Pharm Des. 2005;11:1867–1885
  2. Krogsgaard-Larsen P, Frølund B, Jørgensen FS, Schousboe A. GABAA receptor agonists, partial agonists, and antagonists. Design and therapeutic prospects. J Med Chem. 1994;37:2489–2505
  3. Burt DR. Reducing GABA receptors. Life Sci. 2003;73:1741–1758
  4. Korpi ER, Gründer G, Lüddens H. Drug interactions at GABAA receptors. Prog Neurobiol. 2002;67:113–159
  5. Katsifis A, Kassiou M. Development of radioligands for in vivo imaging of GABA(A)-benzodiazepine receptors. Mini Rev Med Chem. 2004;4:909–921
  6. Chen L, Durkin KA, Casida JE. Structural model for γ-aminobutyric acid receptor noncompetitive antagonist binding; widely diverse structures fit the same site. Proc Natl Acad Sci U S A. 2006;103:5185–5190
  7. Mulholland GK, Kilbourn MR. [18F]Fluoro-tert-butyl-bicycloorthobenzoate (FTBOB): a potential tracer for the GABAA chloride channel. J Label Compd Radiopharm. 1993;32:313
  8. Culbert PA, Chan S, Wearring AV, Chamberlain MJ, Hunter DH. Potential imaging agent for the GABAA receptor: 4-t-butyl-1-(4-[123I]iodophenyl)-2,6,7-trioxabicyclo-[2.2.2]octane. Nucl Med Biol. 1993;20:469–475
  9. Elliot M, Pullman DA, Larkin JP, Casida JE. Insecticidal 1,3-dithianes. J Agric Food Chem. 1992;40:147–151
  10. Wacher VJ, Toia RE, Casida JE. 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. 1992;40:497–505
  11. Snyder SE, Kume A, Jung Y-W, Conner SE, Sherman PS, Albin RL, et al. Synthesis of carbon-11, fluorine-18 and iodine-125 labeled GABAA-gated chloride ion channel blockers: substituted 5-t-butyl-2-phenyl-1,3-dithianes and dithiane oxides. J Med Chem. 1995;38:2663–2671
  12. Blair JB, Snyder SE, Sherman PS, Kilbourn MR. Synthesis and in vivo characterization of substituted 5-tert-butyl-2-phenyl-2-[11C]methyldithiane oxides as potential PET imaging agents for the GABAA chloride ion channel. J Label Compd Radiopharm. 1999;42(Suppl 1):S635–S637
  13. Palmer CJ, Casida JE. Insecticidal 1,3-dithianes and 1,3-dithiane 1,1-dioxides. J Agric Food Chem. 1992;40:492–496
  14. Li QX, Casida JE. Structure–activity studies leading to potent chloride channel blockers: 5e-tert-butyl-2-[4-(substituted-ethynyl)phenyl]-1,3-dithianes. Bioorg Med Chem. 1994;2:1423–1434
  15. Li QX, Casida JE. 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. 1995;3:1675–1684
  16. Eliel EL, Rao V, Smith S, Hutchins RO. Convenient and stereoselective dithiol synthesis. J Org Chem. 1975;40:524–526
  17. Scott EE, Donnelly ET, Welker ME. Preparation of substituted transition-metal (η1-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. 2003;673:67–76
  18. Huang J, Casida JE. Characterization of [3H]ethynylbicycloorthobenzoate ([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. 1996;279(3):1191–1196
  19. Huang J, Casida JE. Role of cerebellar granule cell-specific GABAA receptor subtype in the differential sensitivity of [3H]ethynylbicycloorthobenzoate binding to GABA mimetics. Neurosci Lett. 1997;225(2):85–88
  20. Nicholson RA, Lees G, Zheng J, Verdon B. Inhibition of GABA-gated chloride channels by 12,14-dichlorodehydroabietic acid in mammalian brain. Br J Pharmacol. 1999;126(5):1123–1132
  21. Kume A, Albin RL. Quantitative autoradiography of 4′-ethynyl-4-n-[2,3-3H2]propylbicycloorthobenzoate binding to the GABAA receptor complex. Eur J Pharmacol. 1994;263:163–173
  22. Wacher VJ, Casida JE. 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. 1993;41:296–302
  23. Lawrence LJ, Palmer CJ, Gee KW, Wang X, Yumamura HI, Casida JE. t-[3H]Butylbicycloorthobenzoate: new radioligand probe for the γ-aminobutyric acid-regulated chloride ionophore. J Neurochem. 1985;45:798–804
  24. Olsen RW, McCabe RT, Wamesley JK. GABAA receptor subtypes: autoradiographic comparison of GABA, benzodiazepine, and convulsant binding sites in the rat central nervous system. J Chem Neuroanat. 1990;3:59–76
  25. Kilbourn MR, Pavia MR, Gregor VE. Synthesis of fluorine-18 labelled GABA uptake inhibitors. Appl Radiat Isot. 1990;41:823–828
  26. Kilbourn MR, Haka MS, Mulholland GK, Sherman PS, Pisani T. Regional brain distribution of [18F]GBR 13119, a dopamine uptake inhibitor, in CD-1 and C57B1/6 mice. Eur J Pharmacol. 1989;166:331–334
  27. Haka MS, Kilbourn MR. Synthesis of [18F]GBR 12909, a dopamine reuptake inhibitor. J Labelled Compd Radiopharm. 1990;28:793–800
  28. Haka MS, Kilbourn MR. Synthesis and regional brain distribution of [11C]nisoxetine, a norepinephrine uptake inhibitor. Nucl Med Biol. 1989;16:771–774
  29. Mulholland GK, Otto CA, Jewett DM, Kilbourn MR, Koeppe RA, Sherman PS, 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. 1992;33:423–430
  30. Mulholland GK, Kilbourn MR, Sherman P, Carey JE, Frey KA, Koeppe RA, et al. Synthesis, in vivo biodistribution and dosimetry of [11C]N-methylpiperidyl benzilate ([11C]NMPB), a muscarinic acetylcholine receptor antagonist. Nucl Med Biol. 1995;22:13–17
  31. Skaddan MB, Jewett DM, Sherman PS, Kilbourn MR. (R)-N-[11C]Methyl-3-pyrrolidinyl benzilate, a high affinity reversible radioligand for PET studies of the muscarinic acetylcholine receptor. Synapse. 2002;45:31–37
  32. Skaddan MB, Kilbourn MR, Snyder SE, Sherman PS, Desmond TJ, Frey KA. Synthesis, radiolabeling, and biological evaluation of piperidyl and pyrolidyl benzilates as in vivo ligands for the muscarinic acetylcholine receptors. J Med Chem. 2000;43:4552–4562
  33. Brown-Proctor C, Snyder SE, Sherman PS, Kilbourn MR. Synthesis and in vivo evaluation of (E)-N-[11C]methyl-4-(3-pyridinyl)-3-butene-1-amine ([11C]metanicotine) as a nicotinic receptor radioligand. Nucl Med Biol. 2000;27:415–418
  34. Mulholland GK, Sugimoto H, Jewett DM, Kilbourn MR. Simple preparation of a novel C-11 acetylcholinesterase inhibitor. J Nucl Med. 1989;30:822
  35. Brown-Proctor C, Snyder SE, Sherman PS, Kilbourn MR. Synthesis and evaluation of 6-[11C]methoxy-3-[2-[1-(phenylmethyl)-4-piperidinyl]ethyl]-1,2-benzisoxazole as an in vivo radioligand for acetylcholinesterase. Nucl Med Biol. 1999;26:99–103
  36. Kilbourn MR, Jung Y-W, Haka MS, Gildersleeve DL, Kuhl DE, Wieland DM. Mouse brain distribution of a carbon-11 labeled vesamicol derivative: presynaptic marker of cholinergic neurons. Life Science. 1990;47:1955–1963
  37. Mulholland GK, Jung Y-W, Wieland DM, Kilbourn MR, Kuhl DE. Synthesis of [18F]fluoroethoxybenzovesamicol, a radiotracer for cholinergic neurons. J Labelled Compd Radiopharm. 1993;33:583–592
  38. DaSilva JN, Kilbourn MR. In vivo binding of [11C]tetrabenazine to vesicular monoamine transporters in mouse brain. Life Sci. 1992;51:593–600
  39. DaSilva JN, Kilbourn MR, Mangner TJ. Synthesis of a [11C]methoxy derivative of α-dihydrotetrabenazine: a radioligand for studying the vesicular monoamine transporter. Appl Radiat Isot. 1993;44:1487–1489
  40. Kilbourn M, Frey K. Striatal concentrations of vesicular monoamine transporters are identical in MPTP-sensitive (C57Bl/6) and -insensitive (CD-1) mouse strains. Eur J Pharmacol. 1996;307:227–232
  41. Jewett DM, Kilbourn MR. In vivo evaluation of new carfentanil-based radioligands for the mu opiate receptor. Nucl Med Biol. 2004;31:321–325
  42. Kilbourn M, Pichika R, Jewett D, Sherman P, Traynor J, Husbands S, et al. Synthesis and biodistribution of novel [11C]methyl labeled δ-opioid receptor radiotracers. Abstr Pap Am Chem. Soc. 2001;222(Pt 1):213-MEDI
  43. Eckelman WC, Kilbourn MR, Mathis CA. Discussion of targeting protein in vivo: in vitro guidelines. Nucl Med Biol. 2006;33:449–451
  44. Vander Borght TM, Sima AAF, Kilbourn MR, Desmond TJ, Frey KA. [3H]Methoxytetrabenazine: a high specific activity ligand for estimating monoaminergic neuronal integrity. Neuroscience. 1995;68:955–962
  45. Kilbourn MR. Long-term reproducibility of in vivo measures of specific binding of radioligands in rat brain. Nucl Med Biol. 2004;31:591–595

PII: S0969-8051(07)00220-X

doi: 10.1016/j.nucmedbio.2007.08.003

Nuclear Medicine and Biology
Volume 35, Issue 5 , Pages 549-559 , July 2008