123I-MSP and F[11C]MSP: new selective 5-HT2A receptor radiopharmaceuticals for in vivo studies of neuronal 5-HT2 serotonin receptors. Synthesis, in vitro binding study with unlabelled analogues and preliminary in vivo evaluation in mice

Life Sci. 1998;63(22):2001-13. doi: 10.1016/s0024-3205(98)00478-0.

Abstract

In vitro binding study on bovine brain membranes using [3H]SCH23390, [3H]spiperone, [3H]prazosin and [3H]RP62203 as radioligands (for D1, D2, alpha1 and 5-HT2A receptors respectively) indicate that the new butyrophenones 8-[3-(4-fluorobenzoyl)propyl]-1-methyl-1,3,8-triazaspiro[4,5]de can-4-one (FMSP) and 8-[3-(4-iodobenzoyl)propyl]-1-methyl-1,3,8-triazaspiro[4,5]deca n-4-one (IMSP) exhibit a significantly higher selectivity for the 5-HT2A over D1, D2 and alpha1 receptors. Consequently, the radiolabelled analogues F[11C]MSP and 123I-MSP were prepared in attempt to obtain potential radiopharmaceuticals for in vivo imaging of neuronal 5-HT2A receptors with positron emission tomography (PET) and single photon emission tomography (SPET). F[11C]MSP was synthesized by reaction of [11C]CH3I with 8-[3-(4-fluorobenzoyl)propyl]-1,3,8-triazaspiro[4,5]decan-4- one (DMSP) in 12 +/- 3% radiochemical yield, whereas 123I-MSP was obtained in 82 +/- 8% radiochemical yield by a no-carrier-added Cu(I)-assisted [123I]iododebromination of 8-[3-(4-bromo-benzoyl)propyl]-1-methyl-1,3,8-triazaspiro[4,5]de can-4-ene (BrMSP). In vivo pharmacokinetic and brain binding characterization of 123I-MSP assessed in mice following intravenous injection, showed a fast clearance of 123I-MSP from blood and relatively high initial uptakes in the liver, kidneys and in the lung. Significant uptake and long retention were observed in the brain (up to 1.64% i.d., 60 min p.i.), with a regional accumulation of radioactivity consistent with the reported 5-HT2A receptors distribution in the brain. Frontal cortex to cerebellum ratio of 3.5 was calculated at 60 min p.i. Furthermore, the initial brain uptake was significantly reduced after pretreatment of the animals with ritanserin, a selective 5-HT2 antagonist, and by preinjection of the non-radiolabelled analog IMSP, thus indicating the specificity of the brain uptake. These data suggest that 123I-MSP may be a promising compound for studying the serotoninergic 5-HT2 receptors with SPET. Due to the low specific activity of F[11C]MSP currently obtained by the [11C]methylation reaction, systematic in vivo investigation of F[11C]MSP are as yet not feasable.

MeSH terms

  • Animals
  • Biotransformation
  • Carbon Radioisotopes
  • Cattle
  • Chromatography, High Pressure Liquid
  • Frontal Lobe / metabolism
  • In Vitro Techniques
  • Iodine Radioisotopes
  • Ligands
  • Membranes / drug effects
  • Membranes / metabolism
  • Mice
  • Neurons / drug effects
  • Neurons / metabolism*
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / metabolism
  • Radiopharmaceuticals / pharmacokinetics
  • Receptor, Serotonin, 5-HT2A
  • Receptors, Serotonin / drug effects*
  • Spironolactone / chemical synthesis*
  • Spironolactone / metabolism
  • Spironolactone / pharmacokinetics
  • Tissue Distribution

Substances

  • 8-(3-(4-fluorobenzoyl)propyl)-1-methyl-1,3,8-triazaspiro(4,5)decan-4-one
  • 8-(3-(4-iodobenzoyl)propyl)-1-methyl-1,3,8-triazaspiro(4,5)decan-4-one
  • Carbon Radioisotopes
  • Iodine Radioisotopes
  • Ligands
  • Radiopharmaceuticals
  • Receptor, Serotonin, 5-HT2A
  • Receptors, Serotonin
  • Spironolactone