Bis selenide alkene derivatives: A class of potential antioxidant and antinociceptive agents

Pharmacol Biochem Behav. 2006 Feb;83(2):221-9. doi: 10.1016/j.pbb.2006.02.002. Epub 2006 Mar 20.

Abstract

Bis and tris-selenide alkene derivatives, a class of organoselenium compounds, were screened for antinociceptive and antioxidant activities. In vitro, bis-selenide alkene 1c (R=2,4,6-Me(3)C(6)H(2)), 1d (R=4-ClC(6)H(4)) and 1e (R=4-MeOC(6)H(4)) protected against lipid peroxidation about 50%, whereas 1b (R=C(6)H(5)) and 1a (R=C(4)H(9)) protected only 23%. Compound 1d presented lesser IC(50) against lipid peroxidation than other bis-selenide alkene compounds (1d>1e> or =1c>1a=1b). The maximal inhibitory effect of tris-selenide alkenes on lipid peroxidation was in the following order 2c>2a=2b. Compound 1e increased the rate of GSH, but not DTT, oxidation. Tris-selenide alkene 2c (R=4-MeOC(6)H(4)) demonstrated the higher rate of thiol oxidation, while 2a (R=C(6)H(5)) did not change DTT oxidation but oxidized GSH. Conversely, compound 2b (R=4-ClC(6)H(4)) did not change the rate of GSH oxidation, but oxidized DDT. Bis-selenide alkene derivatives 1c, 1d and 1e were the most promising compounds tested in vitro. In vivo, compounds 1c and 1d (5-50mg/kg, subcutaneously) produced significant inhibition of acetic acid- and capsaicin-induced pain. Compounds 1c and 1d increased the tail-flick response latency time. The antinociception effect of 1c and 1d was not abolished by naloxone (an antagonist of opioid receptor, 1mg/kg, subcutaneously), suggesting that the antinociceptive effect is not influenced by the opioidergic mechanism.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / pharmacology*
  • Analgesics / pharmacology*
  • Animals
  • Antioxidants / pharmacology*
  • Capsaicin / administration & dosage
  • Dithiothreitol / metabolism
  • Glutathione / metabolism
  • Lipid Peroxidation / drug effects
  • Male
  • Narcotic Antagonists
  • Oxidoreductases Acting on Sulfur Group Donors / metabolism
  • Pain / chemically induced
  • Rats
  • Rats, Wistar
  • Selenium / chemistry*

Substances

  • Alkenes
  • Analgesics
  • Antioxidants
  • Narcotic Antagonists
  • Oxidoreductases Acting on Sulfur Group Donors
  • thiol oxidase, 47 kDa
  • Glutathione
  • Selenium
  • Capsaicin
  • Dithiothreitol