Enzymatic reduction studies of nitroheterocycles

Biochemical Pharmacology

Volumn 57, Issue 5, 1999, Pages 549-557

  Viodé, C écile ^a   Bettache, Nadir ^b   Cenas, Narimantas ^c   Krauth Siegel, R Luise ^d   Chauvière, G érard ^a   Bakalara, Norbert ^e   Périé, Jacques ^a  

^a Université Paul Sabatier   (France)

^b CNRS   (France)

^c LITHUANIAN ACADEMY OF SCIENCES   (Lithuania)

^d UNIVERSITY OF HEIDELBERG   (Germany)

^e UNIVERSITÉ DE BORDEAUX   (France)

Author keywords

Chagas' disease; Lipoamide dehydrogenase; Nitro anion radical; Nitroheterocycle; Oxygen metabolism; Trypanothione reductase

Indexed keywords

2 AMINO 5 (1 METHYL 5 NITRO 2 IMIDAZOLYL) 1,3,4 THIADIAZOLE; DIHYDROLIPOAMIDE DEHYDROGENASE; FERREDOXIN NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE REDUCTASE; HETEROCYCLIC NITRO COMPOUND; LACTATE CYTOCHROME C REDUCTASE; METRONIDAZOLE; NIFURTIMOX; NITROIMIDAZOLE DERIVATIVE; OXIDOREDUCTASE; OXYGEN; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE FERRIHEMOPROTEIN REDUCTASE; TRYPANOTHIONE REDUCTASE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL TISSUE; ANTIPROTOZOAL ACTIVITY; ARTICLE; CONTROLLED STUDY; ELECTRON SPIN RESONANCE; LIVER; METABOLISM; MICROSOME; NONHUMAN; PRIORITY JOURNAL; RAT; REDUCTION; TRYPANOSOMA CRUZI;

ANIMALS; BIOTRANSFORMATION; CHAGAS DISEASE; ELECTRON SPIN RESONANCE SPECTROSCOPY; FERREDOXIN-NADP REDUCTASE; L-LACTATE DEHYDROGENASE; L-LACTATE DEHYDROGENASE (CYTOCHROME); METRONIDAZOLE; MOLECULAR STRUCTURE; NADH DEHYDROGENASE; NADPH-FERRIHEMOPROTEIN REDUCTASE; NIFURTIMOX; NITROIMIDAZOLES; OXIDATION-REDUCTION; RATS; THIADIAZOLES; TRYPANOSOMA CRUZI;

EID: 0033105093     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(98)00324-4     Document Type: Article

References (60)

1. Edwards D.I. Nitro-imidazole drugs, action and resistance mechanism. J Antimicrobiol Chemother. 31:1993;9-20.
2. Rodriguez J.B., Gros E.G. Recent development in the control of T. cruzi, the causative agent for Chagas' disease. Curr Med Chem. 2:1995;723-742.
3. Rauth A.M. Pharmacology and toxicology of sensitizers; Mechanism studies. Int J Radiat Oncol Biol Phys. 10:1984;1293-1300.
4. Ings R.M.J., Mc Fadzean J.A., Ormerod W.E. The mode of action of Metronidazole in micro-organisms. Biochem Pharmacol. 23:1974;1421-1429.
5. Declerq P.J., Deranter C.J. In vitro reductive activation of nitro-imidazoles. Biochem Pharmacol. 35:1986;59-61.
6. Bouteille B., Marie-Daragon A., Chauviere G., De Albuquerque C., Enanga B., Darde M.L., Vallat M., Perie J., Dumas M. Effect of Megazol in Trypanosoma Brucei Brucei acute and subacute infection in Swiss mice . Acta Trop. 60:1995;73-80.
7. Jennings F.W., Chauviere G., Viode C., Murray M. Topical chemotherapy for experimental African trypanosomiasis with cerebral involvment the use of melarsoprol combined with the 5-nitroimidazole, megazol . Trop Med Int Health. 1:1996;363-366.
8. Voogd C.E., van der Stel J.J., Jacobs J.J. The mutagenic action of nitroimidazoles. IV. A comparison of the mutagenic action of several nitroimidazoles and some imidazoles. Mutat Res. 66:1979;207-221.
9. Boveris A., Sies H., Martino E.E., Docampo R., Turrens J.F., Stoppani A.O.M. Deficient metabolic utilization of hydrogen peroxide in Trypanosoma cruzi. Biochem J. 188:1980;643-648.
10. Henderson G.B., Fairlamb A.H. Trypanothione metabolism a chemotherapeutic target in Trypanosomatids . Parasitol Today. 3:1987;312-315.
11. Fairlamb A.H., Cerami A. Metabolism and functions of trypanothione in the kinetoplastida. Annu Rev Microbiol. 46:1992;695-729.
12. Krauth-Siegel R.L., Schöneck R. Trypanothione reductase and lipoamide dehydrogenase as targets for structure-based drug design. FASEB J. 9:1995;1138-1146.
13. Docampo R., Moreno S.N.J. Free radical metabolites in the mode of action of chemotherapeutic agents and phagocytic cells on T. cruzi. Rev Infect Dis. 6:1984;223-238.
14. Sreider C.M., Grinblat L., Stoppani A.O.M. Catalysis of nitrofuran redox-cycling and superoxide anion production by heart lipoamide dehydrogenase. Biochem Pharmacol. 40:1990;1849-1857.
15. Berube L.R., Farah S., Mc Clelland R.A., Rauth A.M. Effect of 1-methyl-2-nitrosoimidazole on intracellular thiol and calcium levels in Chinese hamster ovary cells. Biochem Pharmacol. 42:1991;2153-2161.
16. Cadenas E. Biochemistry of oxygen toxicity. Annu Rev Biochem. 110:1989;58-79.
17. Moreno S.N.J., Mason R.P., Docampo R. Reduction of Nifurtimox and Nitrofurantoin to free radical metabolites by rat liver mitochondria - Evidence of an outer membrane-located nitroreductase. J Biol Chem. 259:1984;6298-6305.
18. Docampo R., Stoppani A.O.M. Generation of superoxide anion and hydrogen peroxide induced by Nifurtimox in Trypanosoma cruzi. Arch Biochem Biophys. 197:1979;317-321.
19. Perez-Reyes E., Kalyanaraman B., Mason R.P. The reductive metabolism of Metronidazole and Ronidazole by aerobic liver microsomes. Mol Pharmacol. 17:1980;239-244.
20. Tsuhako M.H., Alves M.J.M., Colli W., Brener Z., Augusto O. Restricted bioreductive metabolism of a nitroimidazole-thiadiazol derivative with curative action in experimental Trypanosoma cruzi infections. Biochem Pharmacol. 38:1989;4491-4496.
21. Viode C., Chauviere G., Houee-Levin C., Perie J. Comparative study by pulse radiolysis of the radical anion derived from compounds used in Chagas' disease therapy. New J Chem. 21:1997;1331-1338.
22. Sreider C.M., Grinblat L., Stoppani A.O.M. Reduction of nitrofuran compounds by heart lipoamide dehydrogenase Role of flavin and the reactive disulfide groups . Biochem Intern. 28:1992;323-334.
23. Lohrer H., Krauth-Siegel R.L. Purification and characterization of lipoamide dehydrogenase from Trypanosoma cruzi. Eur J Biochem. 194:1990;863-869.
24. Schöneck R., Billaut-Mulot O., Numrich P., Ouaissi M.A., Krauth-Siegel R.L. Cloning, sequencing and functional expression of dihydrolipoamide dehydrogenase from the human pathogen Trypanosoma cruzi. Eur J Biochem. 243:1997;739-747.
25. Bradford M.M. A rapid and sensitive method for the quantitation of microgram quantities of protein utilising the principle of protein-dye binding. Anal Biochem. 72:1976;248-254.
26. Krauth-Siegel R.L., Sticherling C., Jöst I., Walsh C.T., Pai E.F., Kabsch W., Lantwin C.B. Crystallisation and preliminary crystallographic analysis of trypanothione reductase from Trypanosoma cruzi, the causative agent of Chagas' disease. FEBS Lett. 317:1983;105-108.
27. Nordhoff A., Bücheler U.S., Werner D., Schirmer R.H. Folding of the four domains and dimerization are impaired by the gly → glu exchange in human glutathione reductase. Implication for the design of antiparasitic drugs. Biochemistry. 32:1993;4060-4066.
28. Reed L.J., Koike M., Levitch M.E., Leach F.R. Studies on the nature and reactions of protein-bound lipoic acid J Biol Chem. 232:1958;143-158.
29. 2-cytochrome-c assembly. Biochim Biophys Acta. 1016:1990;165-176.
30. Berkelhammer G and Asato G, (American Cyanamid Co.), 2-Amino-5-(5-nitro-1-substituted-2-imidazoyl)-1,3,4-thiadiazoles and oxadiazoles. US Patent 3, 452,035, 1969.
31. Chauviere G., Rousseau B., Pillon F., Perie J. Synthesis of 2-amino-5-(1-methyl-5-nitro-[4-3H]-2-imidazolyl)-1,3,4-thiadiazole. J Labelled Compd Rad. 41:1997;47-51.
32. Boveris A., Docampo R., Turrens J.F., Stoppani A.O.M. Effect of β-Lapachone on superoxide anion and hydrogen peroxide production in Trypanosoma cruzi. Biochem J. 175:1978;431-439.
33. Jockers-Scherübl M.C., Schirmer R.H., Krauth-Siegel R.L. Trypanothione reductase from T. cruzi; catalytic properties of the enzyme and inhibition studies with trypanocidal compounds. Eur J Biochem. 180:1989;267-272.
34. Krauth-Siegel R.L., Enders B., Henderson G.B., Fairlamb A.H., Schirmer R.H. Trypanothione reductase from Trypanosoma cruzi purification and characterization of the crystalline enzyme . Eur J Biochem. 164:1987;123-128.
35. Marcinkeviciene J., Cenas N., Kullys J., Usanov S.A., Sukhova N.M., Selezneva I.S., Gryazev V.F. Nitroreductase reactions of the NADPH-adrenodoxine reductase and the adrenodoxine complex. Biomed Biochim Acta. 49:1990;167-172.
36. Tatsumi K., Kitamura S., Yoshimura H. Reduction of nitrofuran by xanthine oxidase and microsomes. Arch Biochem Biophys. 175:1976;131-137.
37. Docampo R., Moreno S.N.J., Mason R.P. Generation of superoxide anion and hydrogen peroxide during redox cycling of 5-(4-nitrophenyl)-penta-2,4-dienal by mammalian microsomes and enzymes. Chem-Biol Interact. 65:1988;123-131.
38. Filardi L.S., Brener Z. A nitroimidazole-thiadiazole derivative with curative action in experimental Trypanosoma cruzi infection. Ann Trop Med Parasitol. 76:1982;293-297.
39. Filardi LS and Brener Z, Efeito curativo do 2-amino-5-(1-metil-5-nitro-2-imidazollil)-1,3,4-tiadiazol (Megazol) em animasis inoculados com cepas de Trypanosoma cruzi resistentes ao Nifurtimox e Benznidazol. XXII Reun Pesq Bas Doença de Chagas, Fundaco Oswaldo Cruz, Brazil. p. 135, 1985.
40. Holtzman J.L., Crankshaw D.L., Peterson F.J., Polnaszek C.F. The kinetics of the aerobic reduction of nitrofurantoin by NADPH-cyt P450 (cyt c) reductase. Mol Pharmacol. 20:1981;669-673.
41. 2 radicals with nitrones in the ultraviolet photolysis of aqueous hydrogen peroxide solutions. Can J Chem. 52:1974;3547-3553.
42. Buettner G.R., Oberley L.W. Considerations in the spin trapping of superoxide and hydroxyl radical in aqueous systems using 5,5′-dimethyl-1-pyrroline-1-oxide. Biochem Biophys Res Commun. 83:1978;69-74.
43. Augusto O., Alves M.J.M., Colli W., Filardi L.S., Brener Z. Primaquine can mediate hydroxyl radical generation by Trypanosoma cruzi. Comp Biochem Physiol. 91c:1988;321-325.
44. Finkelstein E., Rosen G., Rauckman E.J., Paxton J. Spin trapping of superoxide. Mol Pharmacol. 16:1979;676-685.
45. Cenas N.K., Bironaite D.A., Kulys J.J., Sukova N.M. Interaction of nitrofurans with glutathione reductase. Biochim Biophys Acta. 1073:1991;195-199.
46. Grinblat L., Sreider C.M., Stoppani A.O.M. Nitrofuran inhibition of yeast and rat tissue glutathione reductases. Structure-activity relationships. Biochem Pharmacol. 38:1989;767-772.
47. Schirmer R.H., Müller J.G., Krauth-Siegel R.L. Disulfide reductase inhibitors as chemotherapeutic agents the design of drugs for trypanosomiasis and malaria . Angew Chem Int Ed Engl. 34:1995;141-154.
48. Henderson G.B., Ulrich P., Fairlamb A.H., Rosenberg I., Pereira M., Sela M., Cerami A. "Subversive" substrates for the enzyme trypanothione disulfide reductase alternative approach to chemotherapy of Chagas' disease . Proc Natl Acad Sci USA. 85:1988;5374-5378.
49. Cenas N., Bironaite D., Dickancaite E., Anusevicius Z., Sarlauskas J., Blanchard J.S. Chinifur, a selective inhibitor and "subversive substrate" for Trypanosoma congolense trypanothione reductase. Biochem Biophys Res Commun. 204:1994;224-229.
50. Karplus P.A., Pai E.F., Schulz G.E. A crystallographic study of the glutathione binding site of glutathione reductase at 0.3-nm resolution. Eur J Biochem. 178:1989;693-703.
51. Schönleben-Janas A., Kirsch P., Mittl P., Schirmer R.H., Krauth-Siegel R.L. Inhibition of human glutathione reductase by 10-arylisoalloxazines crystallographic, kinetic, and electrochemical studies . J Med Chem. 39:1996;1549-1554.
52. Rameau J.-P., Devillers J., Declercq J.-P., Chauviere G., Perie J. Molecular structure of 2-amino-5-(1-methyl-5-nitro-2-imidazolyl)-1,3,4-thiadiazol (Megazol) and related compounds a concerted study using X-ray crystallography, molecular mechanics, and semiempirical methods . Struct Chem. 7:1996;187-203.
53. Zollner H, in Handbook of enzyme inhibitors, (VCH Ed.), p. 102. Weinheim, 1990.
54. Kuwahara T., White R.A., Agosin M. NADPH-cytochrome c reductase of Trypanosoma cruzi. Biochem Biophys Res Commun. 124:1984;121-124.
55. Paveto J. The nitric oxide transduction pathway in Trypanosoma cruzi. J Biol Chem. 270:1985;16576-16579.
56. Denicola A., Rubbo H., Rodriguez D., Radi P. Peroxynitrite mediated cytotoxicity to Trypanosoma cruzi. Arch Biochem Biophys. 304:1993;279-286.
57. Turrens J.F., Watts B.P., Zhong L., Docampo R. Effect of Trypanosoma cruzi and T. brucei NADPH fumarate reductase by Benznidazole, and anthelmintic imidazole derivatives. Mol Biochem Parasitol. 82:1996;125-129.
58. Hofer A., Schmidt P.P., Gräslund A., Thelander L. Cloning and characterization of the R1 and R2 subunits of ribonucleotide reductase from Trypanosoma brucei. Proc Natl Acad Sci USA. 94:1997;6959-6964.
59. Dormeyer M., Schöneck R., Dittmar G.A.G., Krauth-Siegel R.L. Cloning, sequencing and expression of ribonucleotide reductase R2 from Trypanosoma brucei. FEBS Lett. 414:1997;449-453.
60. De Castro S.L., Meirelles M.L. Mechanism of action of a nitroimidazole-thiadiazole derivative upon T. cruzi tissue culture amastigotes. Mem Inst Oswaldo Cruz, Rio de Janeiro. 85:1990;95-99.