Diethyl 2-phenyl-2 tellurophenyl vinylphosphonate: an organotellurium compound with low toxicity.
It is well-known that organotellurium compounds can have antioxidant activity in vitro, but in vivo these compounds can be potentially toxic to rodents. Here we investigated the potential in vitro and ex vivo toxicity of a new beta-organochalcogenyl vinylphosphonate, the diethyl 2-phenyl-2 tellurophenyl vinylphosphonate. The in vitro antioxidant activity of this organotellurium compound was also investigated. In vitro, the rate of dithiotreitol (DTT) oxidation was increased and the activity of cerebral, renal and hepatic delta-aminolevulinate dehydratase (delta-ALA-D) was decreased by diethyl 2-phenyl-2-tellurophenyl vinylphosphonate (120-1200 microM), indicating that this compound oxidize-SH groups. The antioxidant activity was also observed in brain, liver and kidney, in very low concentrations (0.4, 1.0, 4.0, 10.0 and 40.0 microM), and this capacity was comparable to the antioxidant standard organotellurium compound, diphenyl ditelluride. In vivo, delta-ALA-D activity in liver, kidney and brain of mice treated for 12 days with dimethylsulfoxide (DMSO) as vehicle, 25, 75 or 250 micromol/kg of diethyl 2-phenyl-2-tellurophenyl vinylphosphonate was not affected. Furthermore, only one animal treated with the highest dose died, whereas all animals treated with diphenyl ditteluride died in the fourth day. These results suggest that this novel organotellurium compound interacts with the sulfhydryl groups, however only at higher doses when compared with diphenyl ditelluride. Since diethyl 2-phenyl-2 tellurophenyl vinylphosphonate had low toxicity to mice after sub-chronic exposure, it becomes important to investigate its possible pharmacological properties.
de Avila
Daiana Silva
DS
Departamento de Química, Centro de Ciências Naturais e Exatas, Universidade Federal de Santa Maria, CEP 97105-900 Santa Maria, RS, Brazil.
Beque
Marisa C
MC
Folmer
Vanderlei
V
Braga
Antônio L
AL
Zeni
Gilson
G
Nogueira
Cristina Wayne
CW
Soares
Félix Alexandre Antunes
FA
Rocha
João Batista Teixeira
JB
D000818:Animals; D015415:Biomarkers; D001835:Body Weight / Q000187:drug effects; D001921:Brain / Q000187:drug effects / Q000201:enzymology; D004229:Dithiothreitol / Q000378:metabolism; D007668:Kidney / Q000187:drug effects / Q000201:enzymology; D007700:Kinetics; D015227:Lipid Peroxidation / Q000187:drug effects; D008099:Liver / Q000187:drug effects / Q000201:enzymology; D008297:Male; D051379:Mice; D009929:Organ Size / Q000187:drug effects; D009942:Organometallic Compounds / Q000633:toxicity*; D063065:Organophosphonates / Q000633:toxicity*; D010084:Oxidation-Reduction; D000623:Porphobilinogen Synthase / Q000037:antagonists & inhibitors*; D051381:Rats; D017208:Rats, Wistar; D013438:Sulfhydryl Compounds / Q000494:pharmacology; D016019:Survival Analysis; D013691:Tellurium / Q000633:toxicity*; D017392:Thiobarbituric Acid Reactive Substances / Q000378:metabolism
D015415:Biomarkers; D009942:Organometallic Compounds; D063065:Organophosphonates; D013438:Sulfhydryl Compounds; D017392:Thiobarbituric Acid Reactive Substances; C512415:diethyl 2-phenyl-2 tellurophenyl vinylphosphonate; D000623:Porphobilinogen Synthase; D013691:Tellurium; D004229:Dithiothreitol