Synthesis, spectroscopy, and cytotoxicity of glycosylated acetogenin derivatives as promising molecules for cancer therapy

J Med Chem. 2000 Apr 20;43(8):1604-10. doi: 10.1021/jm990568m.

Abstract

Several glycosyl derivatives of squamocin (1) have been synthesized by glycosylation under Lewis acid catalysis with two different 1-O-acetyl sugars. Separation of these compounds has been achieved by HPLC and centrifugal partition chromatography (CPC). A detailed NMR, ESIMS, and LSIMS study allowed complete structural elucidations. The cytotoxic activity of the glycosyl derivatives was investigated and compared with that of squamocin and dihydrosquamocin against human epidermoid carcinoma cells (KB), African green monkey (Cercopithecus aethiops) kidney epithelial cells (VERO), and mouse lymphocytic leukemia cells (L1210). The antiproliferative effects of some derivatives were studied on cell cycles in mouse lymphocytic leukemia cells (L1210).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Cycle / drug effects
  • Chlorocebus aethiops
  • Drug Screening Assays, Antitumor
  • Furans / chemical synthesis*
  • Furans / chemistry
  • Furans / pharmacology
  • Glycosylation
  • Humans
  • Lactones / chemical synthesis*
  • Lactones / chemistry
  • Lactones / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mice
  • Tumor Cells, Cultured
  • Vero Cells

Substances

  • Antineoplastic Agents
  • Furans
  • Lactones
  • isomurisolenin