Fluoro-, bromo-, and iodopaclitaxel derivatives: synthesis and biological evaluation

Nucl Med Biol. 2003 Jan;30(1):11-24. doi: 10.1016/s0969-8051(02)00351-7.

Abstract

Paclitaxel (Taxol) is a clinically important chemotherapeutic agent. We describe the synthesis of fluoro-, bromo-, and iodopaclitaxel and their [(18)F]fluoro-, [(76)Br]bromo-, and [(124)I]iodo- analogues. [(18)F]Fluoropaclitaxel shows high uptake and rapid clearance from tissues in rats. Preadministration of paclitaxel in normal rats significantly increases (p < 0.005) retention of [(18)F]fluoropaclitaxel and [(76)Br]bromopaclitaxel in blood (33.0%), heart (32.0%), lung (37.6%) kidney (142.4%); and blood (33.4%), lung (42.3%), kidney (62.4%), respectively. [(18)F]Fluoropaclitaxel uptake in the brain of mdr1a/1b(-/-) mice is increased 1400% (p < 1.3e-07) relative to wild-type controls. Preadministration of paclitaxel or XR9576, a modulator, had little effect on the biodistribution in these mdr1a/1b(-/-) mice. As a result, [(18)F]fluoropaclitaxel will be a useful radiopharmaceutical for the study of multidrug resistant tumors.

Publication types

  • Comparative Study
  • Evaluation Study

MeSH terms

  • Animals
  • Bromine Radioisotopes / chemistry
  • Bromine Radioisotopes / pharmacokinetics
  • Cells, Cultured
  • Drug Resistance, Multiple
  • Fluorine Radioisotopes / chemistry
  • Fluorine Radioisotopes / pharmacokinetics
  • Hepatocytes / diagnostic imaging
  • Hepatocytes / metabolism*
  • Humans
  • Iodine Radioisotopes / chemistry
  • Iodine Radioisotopes / pharmacokinetics
  • Isotope Labeling / methods
  • Male
  • Mice
  • Mice, Mutant Strains
  • Organ Specificity
  • Paclitaxel / analogs & derivatives
  • Paclitaxel / chemical synthesis*
  • Paclitaxel / pharmacokinetics*
  • Radionuclide Imaging
  • Radiopharmaceuticals / chemical synthesis*
  • Radiopharmaceuticals / pharmacokinetics*
  • Rats
  • Reference Values
  • Species Specificity

Substances

  • Bromine Radioisotopes
  • Fluorine Radioisotopes
  • Iodine Radioisotopes
  • Radiopharmaceuticals
  • Paclitaxel