Synthesis and characterization of a 11C-labelled derivative of S12968: an attempt to image in vivo brain calcium channels

Nucl Med Biol. 1998 May;25(4):339-42. doi: 10.1016/s0969-8051(97)00211-4.

Abstract

[11C]S11568 (3-ethyl-5-methyl 2-[2-(2-aminoethoxy)ethoxymethyl]-4-(2,3-dichlorophenyl)-6-methyl- 1,4-dihydropyridine-3,5-dicarboxylate) is a powerful ligand for the visualization of the cardiac calcium channel in vivo using PET. The aim of the present study was to synthesize a lipophilic, nonionized derivative of S11568 to facilitate its penetration into the brain. To increase the lipophilicity and to remove simultaneously the ionic nature of our ligand, the N-tert-butoxycarbonyl (N-Boc) derivative of S11568 was synthesized. An IC50 value of 1.7 nM for this derivative confirmed that both the affinity and selectivity for the calcium channel was unaltered by this chemical modification (S11568 with IC50 value of 9.9 nM). The biologically more active enantiomer of S11568, the levogyre isomer S12968, was labelled with 11C using [11C]iodomethane. The lipophilicity of the N-Boc derivative was increased by a factor of three to four when compared to the parent compound (as determined by the measurement of the octanol/buffer partition coefficients). In vivo, this derivative slightly crosses the blood-brain barrier, as demonstrated by a 4-fold increase (with respect to the parent compound S12968) of the radioactivity in the brain using the 11C-labelled N-Boc S12968. This uptake remained too low to be suitable for imaging calcium channels.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Blood-Brain Barrier
  • Brain / metabolism*
  • Calcium Channel Blockers / chemical synthesis*
  • Calcium Channel Blockers / chemistry
  • Calcium Channel Blockers / pharmacokinetics*
  • Calcium Channels / metabolism*
  • Dihydropyridines / chemical synthesis*
  • Dihydropyridines / chemistry
  • Dihydropyridines / pharmacokinetics*
  • Male
  • Rats
  • Rats, Sprague-Dawley
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tissue Distribution
  • Tomography, Emission-Computed

Substances

  • Calcium Channel Blockers
  • Calcium Channels
  • Dihydropyridines
  • S 11568