49
Views
42
CrossRef citations to date
0
Altmetric
Research Article

ESR Spin Trapping Studies of Free Radicals Generated from Nitrofuran Derivative Analogues of Nifurtimox by Electrochemical and Trypanosoma cruzi Reduction

, , , , , , , , & show all
Pages 993-1001 | Published online: 07 Jul 2009

References

  • Schofield, C.J. (1985) "Control of Chagas' disease vectors", Br. Med. Bull. 41, 187, http://www.who.int/whr/2001.
  • Cerecetto, H. and Gonzalez, M. (2002) "Chemotherapy of chagas' disease: status and new developments", Curr. Topics Med. Chem. 2, 1185.
  • Docampo, R. and Stoppani, A.O.M. (1980) "Generation of oxygen-reduction derivates induced by nifurtimox and other nitrocompounds in Trypanosoma cruzi", Medicina 40(Suppl. 1>), 10.
  • Docampo, R. and Moreno, S.N.J. (1984) "Free radical intermediates in the trypanocidal action of drugs and phagocytic cells", In: Pryor, W.A., ed, Free radicals in Biology (Academic Press, New York) Vol VI, pp 243–288.
  • Docampo, R. and Moreno, S.N.J. (1984) "Free radical intermediates in the trypanocidal action of drugs and phagocytic cells", In: Bors, W., ed, Oxygen Radicals in Chemistry and Biology, pp 749–751.
  • Docampo, R., Moreno, S.N.J., Stoppani, A.O.M., Leon, W., Cruz, ES., Villalta, F. and Muniz, R.P.A. (1981) "Mechanism of nifurtimox toxicity in different forms of Trypanosoma cruzi", Biol. Biochem. Pharmacol. 30, 1947.
  • Tracy, J.M. and Webster, L.T. (2001) "Drugs used in the chemotherapy of protozoal infections: amebiasis, trichomo-niasis, trypanosomiasis, leishmaniasis, and other protozoal infections", In: Hardman, J.G.,Limbird, L.E. and Gilman, A.G., eds, Goodman and Gilman's "The Pharmacological Basis of Therapeutics" (Mc Graw-Hill, New York), pp 1097–1120.
  • Cerecetto, H., Mester, B., Onetto, S., Seoane, G., Gonzalez, M. and Zinola, Z. (1992) "Formal potential of new analogues of nifurtimox: relationship to activity", Farmaco 47(9), 1207.
  • Cerecetto, H., Di Maio, J., lbarruri, G., Seoane, G., Denicola, A., Peluffo, G., Quijano, C. and Paulino, M. (1998) "Synthesis and anti-trypanosomal activity of novel 5-nitro-2-furalde-hyde and 5-nitrothiophene-2-carboxaldehyde semicarbazone derivatives", Farmaco 53, 89.
  • Di Maio, R., Cerecetto, H., Seoane, G., Ochoa, C., Aran, V.J., Perez, E., Gómez, A., Muelas, S. and Martinez, A.R. (1999) "Synthesis and antichagasic properties of new 1,2,6-thia-diazin-3,5-dione-1,1-dioxides and related compounds", Arz-neimittel-Forsch. Drug. Res. 49, 759.
  • Cerecetto, H., Di Maio, R., Gonzalez, M., Risso, M., Sagrera, G., Seoane, G., Denicola, A., Peluffo, G., Quijano, C., Basombrio, MA., Stoppani, A.O.M., Paulino, M. and Olea-Azar, C. (2000) "Synthesis and antitrypanosomal evaluation of E-isomer of 5-nitro-2-furaldehyde and 5-nitrothiophene-2-carboxaldehyde semicarbazone derivatives. Structure-activity relationships", Fur. J. Med. Chem. 35, 343.
  • Muelas, S., Di Maio, R., Cerecetto, H., Seoane, G., Ochoa, C., Escario, J.A. and Gómez-Barrio, A. (2001) "New thiadiazine derivatives with activity against Trypanosoma cruzi amasti-gote", Folia Parasit. 48, 105.
  • Martinez-Merino, V. and Cerecetto, H. (2001) "CoMFA-SIMCA model antichagasic nitrofurazone derivatives", Bioorg. Med. Chem. 9, 1025.
  • Paulino, M., Iribarne, E, Hansz, M., Vega, M., Seoane, G., Cerecetto, H., Di Maio, R., Caracelli, I., Zukerman-Schpector, J., Olea, C., Stoppani, A.O.M. and Tapia, 0. (2002) "Computer assisted design of potentially active anti-trypanosomal compounds", J. Mol. Struct. Theochem. 584, 95.
  • Bouteille, B., Marie-Daragon, A., Chauvière, G., De Albuquerque, C., Enanga, B., Darde, ML., Vallat, M., Perie, J. and Dumas, M. (1995) "Effect of megazol in Trypanosoma brucei brucei acute and subacute infection in Swiss mice", Acta Trop. 60, 7.
  • Enanga, B., Keita, M., Chauvière, G., Dumas, M. and Bouteille, B. (1998) "Megazol combined with suramin: a chemotherapy regimen which reversed the CNS pathology in a model of human African trypanosomiasis in mice", Trop. Med. Int. Health 3, 736.
  • Viode, C., Bettache, N., Narimantas, C., Krauth-Siegel, R.L., Chauvière, G., Bakalara, N. and Périé, J. (1999) "Enzymatic reduction studies of nitroheterocycles", Biochem. Pharmacol. 57, 549.
  • Goijman, S.G. and Stoppani, A.O.M. (1984) "Oxygen radical and macromolecule turnover in Trypanosoma Cruzi", In: Rotilio, G. and Bannister, J.V., eds, Oxidative Damage and Related Enzymes (Harwood Academic Publishers, London, New York), pp 216–221.
  • Olea-Azar, C., Atria, AM., Mendizabal, E, Di Maio, R., Seoane, G. and Cerecetto, H. (1998) "Cyclic voltammetry and electron spin resonance studies of some analogues of Nifurtimox", Spectrosc. Lett. 31, 99.
  • Olea-Azar, C., Atria, A.M., Di Maio, R., Seoane, G. and Cerecetto, H. (1998) "Electron spin resonance and cyclic voltammetry studies of nitrofurane and nitrothiophene analogues of Nifurtimox", Spectrosc. Lett. 31, 849.
  • Rajagoplan, S. and Raman, P. (1955), Org. Synth. Collect. Vol. 3, John Wiley and Sons, 425–427.
  • Maya, J.D., Repetto, Y, Agosin, M., Ojeda, J.M., Tellez, R., Gaule, C. and Morello, A. (1997) "Effects of nifurtimox and benznidazole upon glutathione and trypanothione in epi-mastigote, trypomastigote, and amastigote forms of Trypa-nosoma cruzi", Mol. Biochem. Parasitol. 86, 101.
  • Maya, J.D., Morello, A., Repetto, Y., Rodriguez, A., Puebla, P., Caballero, E., Medarde, Notiez-Vergara, L.J., Squella, J.A., Ortiz, ME., Fuentealba, J. and San Feliciano, A. (2001) "Novel antichagasic agents of the oxazolo(thiazolo)pyridine type. Relation between redox potential, lipophilicity, parasite culture growth and respiration inhibition", Exp. Parasitol. 99, 1.
  • Letelier, M.E., Rodriguez, E., Wallace, A., Lorca, M., Repetto, Y., Morello, A. and Aldunate, J. (1990) "Trypanosoma cruzi: a possible control of transfusion induced Chagas disease by phenolic antioxidants", J. Exp. Parasitol. 71, 357.
  • Maya, J.D., Bollo, S., Nunez-Vergara, L.J., Squella, J.A., Repetto, Y., Morello, A., Perie, J. and Chauviere, G. (2003) "Trypanosoma cruzi: effect and mode of action of nitroimida-zole and nitrofuran derivatives", Biochem. Pharmacol. 65, 999.
  • Risch, M.J., Trucks, G.W., Schegel, H.B., Gill, P.N.W. Johnson, B.G., Robb, M.A., Cheeseman, J.R., Keith, K.T., Petersson, G.A., Montgomery, J.A., Raghavachari, K., Al-Laham, MA., Zakrzewski, V.G., Ortiz, J.V., Foresman, J.B., Cioslowski, J., Stefanov, B.B., Nanayakkara, A., Challacombe, M., Peng, C.Y., Ayala, P.Y., Chen, W., Wong, MN., Andres, J.L., Reploge, ES., Gomperts, R., Martin, R.L., Fox, D.J., Binkley, J.S., Defrees, D.J., Baker, J., Stewart, J.P., Head-Gordon, M., Gonzalez, C. and People, J.A. (1998) Gaussian '98, Rev. A.7, Inc, Pittsburgh, PA.
  • Baerendes, E.J., Allis, D.E. and Ros, P. (1990) "Self consistent molecular Hartree-Fock-Slater calculations. The compu-tational procedure", Chem. Phys. 2, 41.
  • Vosko, S.H. and Wilk, L. (1983) "Accurate spin-dependent electron liquid correlation enrgies for local spin density calculations a critical analysis", J. Phys. B16, 3687.
  • Stoyanovsky, D.A., Goldman, R., Jonnalagadda, S.S., Day, B.W., Claycamp, H.G. and Kagan, V.E. (1996) "Detection and characterization of the electron paramagnetic resonance-silent glutathiony1-5,5-dimethy1-1-pyrroline N-oxide adduct derived from redox cycling of phenoxyl radicals in model system and HL-60 cells", Arch. Biochem. Biophys. 330, 3.
  • Lai, C., Grover, TA. and Piette, L.H. (1979) "Hydroxyl radical production in a purified NADPH-cytochrome C (P450) reductase system", Arch. Biochem. Biophys. 193, 373.
  • Moreno, S.N.J., Schreiber, J. and Mason, R.P. (1986) "Nitrobenzyl radical metabolites from microsomal reduction of nitrobenzyl chlorides", J. Biol. Chem. 261, 7811.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.