Effect of the leaving group on the electrodic reduction mechanism of anti-Helicobacter pylori metronidazole derivatives, in aprotic and protic media

Bioelectrochemistry

Volumn 63, Issue 1-2, 2004, Pages 353-357

  Cavalcanti, J C M ^a   De Abreu, F C ^a   Oliveira, N V ^a   De Moura, M A B F ^a   Chaves, J G ^b   Alves, R J ^b   Bertinaria, M ^c   Fruttero, R ^c   Goulart, M O F ^a  

^a Cd Univ Tabuleiro Do Martins   (Brazil)

^b FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

^c UNIVERSITY OF TURIN   (Italy)

Author keywords

5 Nitroimidazole reduction; Anti Helicobacter pylori; Dissociative electron transfer; Leaving group effect; Reductive elimination; Self protonation

Indexed keywords

CYCLIC VOLTAMMETRY; DRUG PRODUCTS; ELECTROCHEMISTRY; ELECTRODES; ELECTROLYSIS; PHOSPHATES; REDOX REACTIONS;

ELECTRODIC REDUCTION; ELECTRON TRANSFER (ET);

BIOCHEMISTRY;

AMMONIA; BROMINE; BUFFER; CARBON; CHLORINE; DIMETHYL SULFOXIDE; GLASS; HALIDE; IMIDAZOLE; IODINE; METRONIDAZOLE; NITROGEN; NITROIMIDAZOLE DERIVATIVE; PHOSPHATE; TETRABUTYLAMMONIUM;

CONFERENCE PAPER; CORRELATION ANALYSIS; CYCLIC POTENTIOMETRY; DRUG ACTIVITY; ELECTRODE; ELECTROLYSIS; ELECTRON TRANSPORT; HELICOBACTER PYLORI; PROTON TRANSPORT; REDUCTION KINETICS; WAVEFORM;

ANTI-BACTERIAL AGENTS; DIMETHYL SULFOXIDE; DRUG EVALUATION, PRECLINICAL; ELECTROCHEMISTRY; ELECTRODES; HELICOBACTER PYLORI; HYDROGEN-ION CONCENTRATION; METRONIDAZOLE; OXIDATION-REDUCTION; QUATERNARY AMMONIUM COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

HELICOBACTER; HELICOBACTER PYLORI;

EID: 2042494620     PISSN: 15675394     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bioelechem.2003.10.031     Document Type: Conference Paper

References (19)

1. Tracy J.W., Webster T. Jr. Drug used in the chemotherapy of protozoal infections. Hardman J.G., Limbird L.E., Goodman L.S., Gilman A. Goodman and Gilman's: The Pharmacological Basis of Therapeutics. 10th ed. 2001;1105-1109 McGrawn-Hill, New York
2. Jenks P.J., Edwards D.I. Metronidazole resistance in Helicobacter pylori. Int. J. Antimicrob. Agents. 19:2002;1-7
3. Tocher J.H. Reductive activation of nitroheterocyclic compounds. Gen. Pharmacol. 28:1997;485-487
4. Wardman P. Electron transfer and oxidative stress as key factors in the design of drugs selectively active in hypoxia. Curr. Med. Chem. 8:2001;739-761
5. Li C.-Y., Jenq J. Kinetic study of one-electron reduction of aromatic quinones with aminoalkylamino side chains in N, N-dimethylformamide by square wave voltammetry and allied techniques. Electrochim. Acta. 36:1991;269-276
6. Livertoux M.-H., Lagrange P., Minn A. The superoxide production mediated by the redox cycling of xenobiotics in rat brain microsomes is dependent on their reduction potential. Brain Res. 725:1996;207-216
7. Roffia S., Gottardi C., Vianello E. Electrochemical behaviour of 4-nitroimidazole and 2-methyl-5-nitroimidazole. Autoprotonation of anion radical and redox-catalysed reduction of the supporting electrolyte cation. J. Electroanal. Chem. 142:1982;263-275
8. Tocher J.H., Edwards D.I. Evidence for the direct interaction of reduced metronidazole derivatives with DNA bases. Biochem. Pharmacol. 48:1994;1089-1094
9. Barety D., Resibois B., Vergoten G., Moschetto Y. Electrochemical behaviour of nitroimidazole derivatives in dimethylsulphoxide. J. Electroanal. Chem. 162:1984;335-341
10. La-Scalea M.A., Serrano S.H.P., Gutz I.G.R. Voltammetric behaviour of metronidazole at mercury electrodes. J. Braz. Chem. Soc. 10:1999;127-135
11. R.J. Alves, personal communication.
12. Bertinaria M., Galli U., Sorba G., Fruttero R., Gasco A., Brenciaglia M.I., Scaltrito M.M., Dubini F. Synthesis and anti-Helicobacter pylori properties of NO-donor metronidazole hybrids and related compounds. Drug Dev. Res. 60:2003;225-239
13. de Abreu F.C., de Paula F.S., dos Santos A.F., Sant'Ana A.E.G., de Almeida M.V., Cesar E.T., Trindade M.N., Goulart M.O.F. Synthesis, electrochemistry and molluscicidal activity of nitroaromatics. Effects of substituents and the role of redox potential. Bioorg. Med. Chem. 9:2001;659-664
14. Arguelho M.L.P.M., Silva G.M., Stradiotto N.R. Electroreduction of benznidazole in dimethylsulphoxide. J. Electrochem. Soc. 148:2001;D1-D3
15. Antonello S., Crisma M., Formaggio F., Moretto A., Taddel F., Toniolo C., Maran F. Insights into the free-energy dependence of intramolecular dissociative electron transfer. J. Am. Chem. Soc. 124:2002;11503-11513
16. Everett S.A., Naylor M.A., Patel K.B., Stratford M.R.L., Wardman P. A 2-nitroimidazole carbamate prodrug of 5-amino-1-(chloromethyl)-3-[(5, 6, 7-trimethoxyindol-2-yl)carbonyl]-1, 2-dihydro-3H-benz[E]indole(amino-seco-CBI- TMI) for use with ADEPT and GDEPT. Bioorg. Med. Chem. Lett. 9:1999;1267-1272
17. Heimbrook D.C., Shyam K., Sartorelli A.C. Novel 1-haloalkyl-2- nitroimidazole bioreductive alkylating-agents. Anti-Cancer Drug Des. 2:1988;339-350
18. Mayalarp S.P., Hargreaves R.H.J., Butler J., O'Hare C.C., Hartley J.A. Cross-linking and sequence specific alkylation of DNA by aziridinylquinones: 1. Quinone methides. J. Med. Chem. 39:1996;531-537
19. Bays J.P., Blumer S.T., Baral-Tosh S., Behar D., Neta P. Intramolecular electron transfer and dehalogenation of nitroaromatic anion radicals. J. Am. Chem. Soc. 105:1983;320-324