Synthesis and biodistribution of R- and S-isomers of [18F]-fluoropropranolol, a lipophilic ligand for the beta-adrenergic receptor

Nucl Med Biol. 1999 Nov;26(8):891-6. doi: 10.1016/s0969-8051(99)00068-2.

Abstract

The S and R isomers of [18F]-fluoropropranolol (1-[1-fluoro-2-isopropylamino]-3-naphthalen-1-yloxy-propan-2 -ol) have been prepared by reductive alkylation of the appropriate aminoalcohols. The radiosynthesis provides a reasonable yield (approximately 25%) to give products of 99% enantiomeric excess and specific activities of 1-3 Ci/micromol. The dissociation constants for the beta2 adrenergic receptor are 0.5 and 2.5 nM for the S and the R isomers, respectively. The biodistribution data in rats show that uptake and egress of the tracer is rapid but that the result of blocking studies and the difference between the R and the S isomers suggest receptor-mediated uptake in receptor-rich tissue.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Algorithms
  • Animals
  • Fluorine Radioisotopes
  • Indicators and Reagents
  • Isotope Labeling
  • Ligands
  • Lipids / chemistry
  • Male
  • Propranolol / analogs & derivatives*
  • Propranolol / chemical synthesis
  • Propranolol / chemistry
  • Propranolol / pharmacokinetics
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / chemistry
  • Radiopharmaceuticals / pharmacokinetics
  • Rats
  • Rats, Sprague-Dawley
  • Receptors, Adrenergic, beta / chemistry
  • Receptors, Adrenergic, beta / drug effects*
  • Solubility
  • Solvents
  • Stereoisomerism
  • Tissue Distribution

Substances

  • Fluorine Radioisotopes
  • Indicators and Reagents
  • Ligands
  • Lipids
  • Radiopharmaceuticals
  • Receptors, Adrenergic, beta
  • Solvents
  • fluoropropranolol
  • Propranolol