Diethyl 2-phenyl-2 tellurophenyl vinylphosphonate: An organotellurium compound with low toxicity

Toxicology

Volumn 224, Issue 1-2, 2006, Pages 100-107

  de Ávila, Daiana Silva ^a   Beque, Marisa C ^a   Folmer, Vanderlei ^a   Braga, Antônio L ^a   Zeni, Gilson ^a   Nogueira, Cristina Wayne ^a   Soares, Félix Alexandre Antunes ^a   Rocha, João Batista Teixeira ^a  

^a FEDERAL UNIVERSITY OF SANTA MARIA   (Brazil)

Author keywords

Delta aminolevulinate dehydratase activity; Diethyl 2 phenyl 2 tellurophenyl vinylphosphonate; Organotellurium compounds; Toxicity

Indexed keywords

DIETHYL 2 PHENYL 2 TELLUROPHENYL VINYLPHOSPHONATE; DIMETHYL SULFOXIDE; ORGANOTELLURIUM DERIVATIVE; PORPHOBILINOGEN SYNTHASE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ANTIOXIDANT ACTIVITY; ARTICLE; BIOLOGICAL ACTIVITY; BRAIN; CHRONIC TOXICITY; COMPARATIVE STUDY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG MEGADOSE; ENZYME ACTIVATION; IN VITRO STUDY; IN VIVO STUDY; KIDNEY; LIVER; LIVER TOXICITY; LONG TERM EXPOSURE; LOW DRUG DOSE; NEPHROTOXICITY; NEUROTOXICITY; NONHUMAN; PRIORITY JOURNAL; PROTEIN EXPRESSION; RAT; TISSUE DISTRIBUTION;

ANIMALIA; RODENTIA;

EID: 84984538794     PISSN: 0300483X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tox.2006.04.027     Document Type: Article

References (44)

1. Alami M., Ferri F., and Gaslain Y. A two-step synthesis of terbinafine. Tetrahedron Lett. 37 (1996) 57-58
2. Andersson C.M., Brattsand R., and Hallberg A. Diaryl tellurides as inhibitors of lipid peroxidation in biological and chemical systems. Free Radic. Res. 20 (1994) 401-410
3. Andersson C.-M., Hallberg A., Brattsand R., Cotgrave I.A., Engman L., and Persson J. Glutathione peroxidase-like activity of diaryl tellurides. Bioorg. Med. Chem. Lett. 3 (1993) 2553-2558
4. Attebery M., and Sailer B.L. Detection of apoptosis occurring in promyelocitic (line HL-60) cell populations induced by novel organotellurium compounds. BIOS 73 (2002) 52-60
5. Barbosa N.B.V., Rocha J.B.T., Zeni G., Emanuelli T., Beque M.C., and Braga A.L. Effect of organic forms of Selenium on delta-aminolevulinate dehydratase from liver, kidney and brain of adult rats. Toxicol. Appl. Pharmacol. 149 (1998) 243-253
6. Bechara E.J.H., Medeiros M.H.G., Monteiro H.P., Hermes-Lima M., Pereira B., Demasi M., Costa C., Adballa D.S.P., Onuki J., Wendel C.M.A., and Masci P.D. A free radical hypothesis of lead poisoning and in Born porphyrias associated with 5-aminolevulinic overload. Quim. Nova 16 (1993)
7. Bellé N.V., Dalmolin G.D., Fonini G., Rubin M.A., and Rocha J.B.T. Polyamines reduced lipid peroxidation induced by different pro-oxidant agents. Brain Res. 1008 (2004) 245-251
8. Borges V.C., Nogueira C.W., Zeni G., and Rocha J.B. Organochalcogens affect neurotransmission in human platelets. Neurochem. Res. 29 (2003) 1505-1509
9. Borges V.C., Rocha J.B.T., and Nogueira C.W. Effect of diphenyl diselenide, diphenyl ditelluride and ebselen on cerebral Na+, K+ ATPase activity in rats. Toxicology 215 (2005) 191-197
10. Braga A.L., Alves E.F., Silveira C.C., and Andrade L.H. Stereoselective addition of sodium organyl chalcogenolates toalkynylphosphonates: synthesis of diethyl 2-(organyl)-2-(organochalcogenyl)vinylphosphonates. Tetrahedron Lett. 41 (2000) 161-163
11. Braga A.L., Rhodem C.R.T., Zeni G., Silveira C.C., and Andrade L.H. Stereospecific synthesis of phosphono-(1Z, 3E)-dienyl compounds and vinyl-phosphines oxides. J. Organomet. Chem. 682 (2003) 35-40
12. Braga A.L., Leandro H.L., Silveira C.C., Moro A.V., and Zeni G. Stereospecific formation of enynephosphonates via Palladium-catalyzed cross-coupling reaction of beta-organotelluro vinylphosphonates with alkynes. Tetrahedron Lett. 42 (2001) 8563-8565
13. Briviba K., Tamler R., Klotz L.-O., Engman L., Cotgreave I.A., and Sies H. Protection against organotellurium compounds against peroxynitrite-mediated oxidation and nitration reactions. Biochem. Pharmacol. 55 (1998) 817-823
14. Comasseto J.V., Ling L.W., Petragnani N., and Stefani H.A. Vinylic selenides and tellurides-preparation, reactivity an synthetic application. Synthesis 4 (1997) 373
15. Cunha L.O.R., Urano M.E., Chagas J.R., Almeida P.C., Bincoletto C., Tersariol I.L.S., and Comasseto J.V. Tellurium-based cysteine protease inhibitors: evaluation of novel organotellurium (IV) compounds as inhibitors of human Cathepsin B. Bioorg. Med. Chem. Lett. 15 (2005) 755-760
16. Emanuelli T., Pagel F.W., Alves L.B., Regner A., and Souza D.O. Inhibition of adenylate cyclase activity by 5-aminolevulinic acid in rat and human brain. Neurochem. Int. 38 (2001) 213-218
17. Engman L., Stern D., Cotgreave I., and Andersson C.M. Thiol peroxidase activity of diaryl ditellurides as determined by a 1H NMR method. J. Am. Chem. Soc. 114 (1992) 9737-9743
18. Engman L., Person J., Vessman K., Ekstrom M., Berglund M., and Andersson C.-M. Organotellurium compounds as efficient retarders of lipid peroxidation in methanol. Free Radic. Biol. Med. 19 (1995) 441-452
19. Fairhill L.T. Tellurium. Industrial Toxicology (1969), Hafner Publishing Co., New York p. 120
20. Goodrum J.F. Role of organotellurium species in tellurium neuropathy. Neurochem. Res. 10 (1998) 1313-1319
21. Grissom J.W., Gunawardena G.U., Klingberg D., and Huang D. The chemistry of enediynes, enyne allenes and related compounds. Tetrahedron 52 (1996) 6453-6518
22. Jaffe E.K. Porphobilinogen synthase, the first source of heme's asymetry. J. Bioenerg. Biomembr. 27 (1995) 169-179
23. Laden B.P., and Porter T.D. Inhibition oh human squalene monooxigenase by tellurium compounds: evidence of interaction with vicinal sulfhydryls. J. Lipid Res. 42 (2001) 235-240
24. Larner A.J. Biological effects of tellurium: a review. Trace Elem. Elect. 12 (1995) 26-31
25. Maciel E.N., Bolzan R.C., Braga A.L., and Rocha J.B.T. Diphenyl diselenide and diphenyl ditelluride affect delta-aminolevulinate dehydratase from liver, kidney and brain of mice. J. Biochem. Mol. Toxicol. 14 (2000) 310-319
26. Meotti F.C., Borges V.C., Zeni J.B.T., and Nogueira C.W. Potential renal and hepatic toxicity of diphenyl diselenide, diphenyl ditelluride and Ebselen for rats and mice. Toxicol. Lett. 143 (2003) 9-16
27. Nogueira C.W., Borges V.C., Zeni G., and Rocha J.B.T. Organochalcogens effects on δ- aminolevilinate dehydratase activity from human erythrocytic cells in vitro. Toxicology 191 (2003) 169-178
28. Nogueira C.W., Rotta L.N., Perry M.L., Souza D.O., and Rocha J.B.T. Diphenyl diselenide and diphenyl diteluride affect the rat glutamatergic system in vitro and in vivo. Brain Res. 906 (2001) 157-163
29. Nogueira C.W., Zeni G., and Rocha J.B.T. Organoselenium and organotellurium compounds: toxicology and pharmacology. Chem. Rev. 104 (2004) 6255-6285
30. Ohkawa H., Ohishi N., and Yagi K. Assay for lipid peroxides in animal tissues bu thiobarbituric acid reaction. Anal. Biochem. 95 (1979) 351-358
31. Petragnani N. In: Katrizky A.R., Meth-Cohn O., and Ress C.W. (Eds). Tellurium in Organic Synthesis (1994), Academic Press, San Diego, CA 89-242
32. Rao A.S., Freemerman A.J., Jarvis W.D., Chelliah J., Bear H.D., Mikkelsen R., and Grant S. Effect of AS101 on bryostatin 1-mediated differentiation induction, cell arrest, and modulation of drug-induced apoptosis in human myeloid leukemia in cells. Leukemia 10 (1996) 1150-1158
33. Ren X., Xue Y., Zhang K., Liu J., Luo G., Zheng J., Mu Y., and Shen J. A novel dicyclodextrinyl ditelluride compound with antioxidant activity. FEBS Lett. 507 (2001) 377-380
34. Rossato J.I., Ketzer L.A., Centurião F.B., Silva S.J.N., Zeni G., Braga A.L., Rubin M.A., and Rocha J.B.T. Antioxidant properties of new chalcogenides against lipid peroxidation in rat brain. Neurochem. Res. 3 (2002)
35. Sailer B.L., Liles N., Dickerson S., Sumners S., and Chasteen T.G. Organotellurium compound toxicity in a promyelocytic cell line compared to non-tellurium-containing organic analog. Toxicol. In Vitro 18 (2004) 475-482
36. Sailer B.L., Liles N., Dickerson S., and Chasteen T.G. Cytometric determination of novel organotellurium compound toxicity in a promyelocitic (HL-60) cell line. Arch. Toxicol. 77 (2003) 30-36
37. Santos F.W., Zeni G., Rocha J.B.T., Weiss S.N., Fachinetto J., Favero A.F., and Nogueira C.W. Diphenyl diselenide reverses cadmium-induced oxidative damage of mice tissues. Chem. Biol. Interact. 151 (2005) 159-165
38. Sassa S. Delta aminolevulinic acid dehydratase assay. Enzyme 28 (1982) 133-145
39. Soares F.A., Farina, Boettcher A.C., Braga A.L., and Rocha J.B.T. Organic and inorganic forma of selenium inhibited differently fish (Rhamdia quelem) and rats (Ratus novergicus) delta-aminolevulinate dhydratase. Environ. Res. 98 (2005) 46-54
40. Sredni B., Caspi R.R., Klein A., Kalechman Y., Danziger Y., Bem Ya'akov M., Tamari T., Shalit F., and Albeck M. A new immunomodulating compound (AS-101) with potential therapeutic industrial application. Nature 330 (1987) 173-176
41. Toews A.D., Eckermann M.D., Roberson S.Y., Lee S.Y., and Morell P. Primary demyelination induced by exposure to tellurium alters mRNA levels for nerve growth factor receptor, SCIP, 2′3′-cyclic nucleotide 3′phosphodiesterase, and myelin proteolipid in rat sciatic nerve. Mol. Brain Res. 11 (1991) 321-325
42. Wieslander E., Engman L., Svensjo E., Erlansson M., Johansson U., Linden M., Andersson C.-M., and Brattsand R. Antioxidative properties of organ.otellurium compounds in cell system. Biochem. Pharmacol. 55 (1998) 573-584
43. Wöhler F. Ann. Chem. 35 (1840) 111
44. 2-hybrized tellurides. Acc. Chem. Res. 36 (2003) 731-738