Effect of sydnone SYD-1, a mesoionic compound, on energy-linked functions of rat liver mitochondria

Chem Biol Interact. 2007 Sep 20;169(3):160-70. doi: 10.1016/j.cbi.2007.06.003. Epub 2007 Jun 14.

Abstract

An important antitumour effect of SYD-1 (3-[4-chloro-3-nitrophenyl]-1,2,3-oxadiazolium-5-olate) has been shown. We now report the effects of this mesoionic compound on mitochondrial metabolism. SYD-1 (1.5 micromol mg(-1) protein) dose-dependently inhibited the respiratory rate by 65% and 40% in state 3 using sodium glutamate and succinate, respectively, as substrates. Phosphorylation efficiency was depressed by SYD-1, as evidenced by stimulation of the state 4 respiratory rate, which was more accentuated with glutamate ( approximately 180%) than with succinate ( approximately 40%), with 1.5 micromol mg(-1) protein of SYD-1. As a consequence of the effects on states 3 and 4, the RCC and ADP/O ratios were lowered by SYD-1 using both substrates, although this effect was stronger with glutamate. The formation of membrane electrical potential was inhibited by approximately 50% (1.5 micromol SYD-1mg(-1) protein). SYD-1 interfered with the permeability of the inner mitochondrial membrane, as demonstrated by assays of mitochondrial swelling in the presence of sodium acetate and valinomycin +K(+). SYD-1 (1.5 micromol mg(-1) protein) inhibited glutamate completely and succinate energized-mitochondrial swelling by 80% in preparations containing sodium acetate. The swelling of de-energized mitochondria induced by K(+) and valinomycin was inhibited by 20% at all concentrations of SYD-1. An analysis of the segments of the respiratory chain suggested that the SYD-1 inhibition site goes beyond the complex I and includes complexes III and IV. Glutamate dehydrogenase was inhibited by 20% with SYD-1 (1.5 micromol mg(-1) protein). The hydrolytic activity of complex F(1)F(o) ATPase in intact mitochondria was greatly increased ( approximately 450%) in the presence of SYD-1. Our results show that SYD-1 depresses the efficiency of electron transport and oxidative phosphorylation, suggesting that these effects may be involved in its antitumoural effect.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Adenosine Triphosphatases / metabolism
  • Animals
  • Cell Membrane / chemistry
  • Cell Membrane / metabolism
  • Cell Respiration / drug effects
  • Ions / chemistry
  • Male
  • Membrane Potentials / drug effects
  • Mitochondria, Liver / drug effects*
  • Mitochondria, Liver / enzymology
  • Mitochondrial Swelling / drug effects
  • Molecular Structure
  • Oligomycins / pharmacology
  • Oxadiazoles / chemical synthesis
  • Oxadiazoles / pharmacology*
  • Rats
  • Rats, Wistar
  • Sydnones / chemistry
  • Sydnones / pharmacology*

Substances

  • 3-(4-chloro-3-nitrolphenyl)-1,2,3-oxadiazolium-5-olate
  • Ions
  • Oligomycins
  • Oxadiazoles
  • Sydnones
  • Adenosine Triphosphatases