Antitumour activity of S-p-bromobenzylglutathione cyclopentyl diester in vitro and in vivo. Inhibition of glyoxalase I and induction of apoptosis

Biochem Pharmacol. 1996 May 17;51(10):1365-72. doi: 10.1016/0006-2952(96)00059-7.

Abstract

The glyoxalase I inhibitor diester, S-p-bromobenzyl-glutathione cyclopentyl diester (BrBzGSHCp2), inhibited the growth of human leukaemia 60 (HL60) cells in vitro. The median growth inhibitory concentration GC50 value of BrBzGSHCp2 was 4.23 +/- 0.001 microM (n = 21), and the median toxic concentration TC50 value was 8.86 +/- 0.01 microM (n = 21). BrBzGSHCp2 inhibited DNA synthesis in the third hr of incubation: the median inhibitory concentration IC50 value was 6.11 +/- 0.02 microM (n = 8). Incubation of HL60 cells with 10 microM BrBzGSHCp2 delivered the diester into cells: de-esterification of the diester there in lead to formation of the S-p-bromobenzylglutathione, inhibition of glyoxalase I activity in situ, increase in the methylglyoxal concentration after 1 hr, and induction of apoptosis after 6 hr. BrBzGSHCp2 (50-200 mg/kg) also inhibited the growth of murine adenocarcinoma 15A in vivo. Glyoxalase I inhibitor diesters may, therefore, inhibit tumour growth by inducing the accumulation of methylglyoxal in tumour cells, and induction of apoptosis.

MeSH terms

  • Adenocarcinoma / drug therapy*
  • Animals
  • Apoptosis
  • Cell Count / drug effects
  • Dose-Response Relationship, Drug
  • Esters / pharmacology*
  • Glutathione / analogs & derivatives*
  • Glutathione / pharmacology
  • Humans
  • In Vitro Techniques
  • Leukemia / drug therapy
  • Mice

Substances

  • Esters
  • S-4-bromobenzylglutathione cyclopentyl diester
  • Glutathione