5-Hydroxy-4-oxo-L-norvaline depletes intracellular glutathione: a new modulator of drug resistance

Biosci Biotechnol Biochem. 1999 Nov;63(11):1953-8. doi: 10.1271/bbb.63.1953.

Abstract

To search for compounds that reverse the drug resistance induced by glutathione (GSH), an original screening system to detect intracellular GSH depleters was established. Among 8843 microbes derived from the soil samples tested, the extracts of two Streptomyces species named KS6701 and KS8846, lowered the intracellular GSH level of Saccharomyces cerevisiae 5 x 47. From both the microbes, 5-hydroxy-4-oxo-L-norvaline (HON) was isolated as the active compound. At a concentration of 50-100 micrograms/ml, HON also decreased the GSH/protein level of the human ovarian tumor cell line, 2008/C13*5.25 and reversed its resistance to cisplatin. We also investigated the mechanism of the depletion. HON had little effect on gamma-glutamylcysteine synthetase (gamma-GCS) or glutathione synthetase, but HON decreased the quantity of thiol substances when it was spontaneously reacted with them. This suggested that the GSH depletion by HON occurred through a mechanism different from that of buthionine sulfoximine, a selective gamma-GCS inhibitor.

MeSH terms

  • Aminolevulinic Acid / analogs & derivatives
  • Aminolevulinic Acid / isolation & purification
  • Aminolevulinic Acid / pharmacology
  • Buthionine Sulfoximine / pharmacology
  • Drug Resistance, Multiple*
  • Female
  • Glutamate-Cysteine Ligase / metabolism
  • Glutathione / metabolism*
  • Glutathione Synthase / metabolism
  • Humans
  • Ovarian Neoplasms
  • Saccharomyces cerevisiae / drug effects
  • Saccharomyces cerevisiae / metabolism*
  • Soil Microbiology
  • Streptomyces / chemistry
  • Tumor Cells, Cultured

Substances

  • Buthionine Sulfoximine
  • 2-amino-5-hydroxy-4-oxopentanoic acid
  • Aminolevulinic Acid
  • Glutamate-Cysteine Ligase
  • Glutathione Synthase
  • Glutathione