Isolation, purification, and biological activity of mono- and dihydroxylated paclitaxel metabolites from human feces

Cancer Chemother Pharmacol. 1995;36(4):299-304. doi: 10.1007/BF00689047.

Abstract

Three metabolites of the cytotoxic drug paclitaxel (Taxol) were isolated and purified from the feces of cancer patients receiving the agent as an intravenous infusion. The procedures involved sample homogenization in water followed by liquid-liquid extraction with diethyl ether and high-performance liquid chromatography (HPLC). Approximately 1-3.5 mg of each metabolite was obtained from 100 g of feces. As judged from the chromatographic traces of analytical HPLC with ultraviolet (UV) detection at 227 nm, the purity of each compound was > 97%. On-line photodiode-array detection demonstrated that the UV spectrum of the isolated compounds closely resembles that of the parent drug. Mass spectrometry provided evidence that these metabolites are mono- and dihydroxy-substituted derivatives, namely, 6 alpha-hydroxypaclitaxel, 3'-p-hydroxypaclitaxel, and 6 alpha, 3'-p-dihydroxypaclitaxel. The two 6 alpha-hydroxy-substituted metabolites were shown to have lost their cytotoxicity in in vitro clonogenic assays using the A2780 human ovarian carcinoma and the CC531 rat colon-carcinoma tumor cell lines. In addition, the metabolites showed reduced myelotoxic effects as compared with paclitaxel in an in vitro hemopoietic progenitor toxicity assay. Our procedure for the isolation and purification of paclitaxel metabolites in milligram quantities should be useful for testing the biological activities of these compounds and for the preparation of calibration standards essential for pharmacokinetics studies.

MeSH terms

  • Animals
  • Bone Marrow Cells
  • Chromatography, High Pressure Liquid
  • Colonic Neoplasms / pathology
  • Feces / chemistry*
  • Female
  • Hematopoietic Stem Cells / drug effects
  • Humans
  • Hydroxylation
  • Ovarian Neoplasms / pathology
  • Paclitaxel / analogs & derivatives*
  • Paclitaxel / isolation & purification
  • Paclitaxel / metabolism*
  • Paclitaxel / pharmacology
  • Rats
  • Spectrometry, Mass, Fast Atom Bombardment
  • Taxoids*
  • Tumor Cells, Cultured / drug effects
  • Tumor Stem Cell Assay

Substances

  • Taxoids
  • 6-hydroxytaxol
  • Paclitaxel