5-[18F]Fluoroalkyl pyrimidine nucleosides: probes for positron emission tomography imaging of herpes simplex virus type 1 thymidine kinase gene expression

Nucl Med Biol. 2009 Jan;36(1):29-38. doi: 10.1016/j.nucmedbio.2008.10.009.

Abstract

Introduction: The preliminary in vivo evaluation of novel 5-[(18)F]fluoroalkyl-2'-deoxyuridines ([(18)F]FPrDU, [(18)F]FBuDU, [(18)F]FPeDU; [(18)F]1a-c, respectively) and 2'-fluoro-2'-deoxy-5-[(18)F]fluoroalkyl-1-beta-d-arabinofuranosyl uracils ([(18)F]FFPrAU, [(18)F]FFBuAU, [(18)F]FFPeAU; [(18)F]1d-f, respectively) as probes for imaging herpes simplex virus type 1 thymidine kinase (HSV1-tk) gene expression is described.

Methods: [(18)F]1a-f were successfully synthesized by a rapid and efficient two-step one-pot nucleophilic fluorination reaction using 5-O-mesylate precursors and [(18)F]F(-). For in vivo studies, tumor xenografts were grown in nude mice by implanting RG2 cells stably expressing HSV1-tk (RG2TK+) and wild-type cells (RG2).

Results: Biodistribution studies at 2 h pi revealed that the uptake of [(18)F]1a-b and [(18)F]1d-e in RG2TK+ tumors was not significantly different from control tumors. However, [(18)F]1c and [(18)F]1f had an average 1.6- and 1.7-fold higher uptake in RG2TK+ tumors than control RG2 tumors. Blood activity curves for [(18)F]1c and [(18)F]1f highlight rapid clearance of radioactivity in the blood. Dynamic small animal PET (A-PET) imaging studies of tumor-bearing mice with [(18)F]1c and [(18)F]1f showed higher initial uptake (3.5- and 1.4-fold, respectively) in RG2TK+ tumors than in control tumors, with continued washout of activity from both tumors over time.

Conclusions: Biological evaluations suggest that [(18)F]1c and [(18)F]1f may have limited potential for imaging HSV1-tk gene expression due to fast washout of activity from the blood, thus significantly decreasing sensitivity and specificity of tracer accumulation in HSV1-tk-expressing tumors.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Arabinofuranosyluracil / analogs & derivatives
  • Arabinofuranosyluracil / blood
  • Arabinofuranosyluracil / metabolism
  • Arabinofuranosyluracil / pharmacokinetics
  • Cell Line, Tumor
  • Fluorine Radioisotopes
  • Gene Expression*
  • Genes, Reporter / genetics*
  • Glioma / blood
  • Glioma / genetics
  • Glioma / metabolism
  • Herpesvirus 1, Human / enzymology*
  • Herpesvirus 1, Human / genetics
  • Male
  • Mice
  • Mice, Nude
  • Positron-Emission Tomography*
  • Pyrimidine Nucleosides / blood
  • Pyrimidine Nucleosides / metabolism*
  • Pyrimidine Nucleosides / pharmacokinetics
  • Rats
  • Reproducibility of Results
  • Sensitivity and Specificity
  • Thymidine Kinase / analysis*
  • Thymidine Kinase / biosynthesis
  • Thymidine Kinase / genetics*
  • Time Factors
  • Tissue Distribution
  • Transplantation, Heterologous

Substances

  • Fluorine Radioisotopes
  • Pyrimidine Nucleosides
  • Arabinofuranosyluracil
  • fialuridine
  • Thymidine Kinase