Redox cycling of o-naphthoquinones in trypanosomatids. Superoxide and hydrogen peroxide production

Biochemical Pharmacology

Volumn 52, Issue 12, 1996, Pages 1875-1882

  Molina Portela, Maria P ^b   Fernandez Villamil, Silvia H ^b   Perissinotti, Luis J ^b   Stoppani, Andres O M ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b NONE

Author keywords

Crithidia fasciculata; hydrogen peroxide; lapachones; Leptomonas seymouri; mansonones; o naphthoquinones; oxidative damage; superoxide

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ALPHA LAPACHONE; BETA LAPACHONE; CG 10 248; CG 8 935; CG 9 442; HYDROGEN PEROXIDE; MANSONONE; REACTIVE OXYGEN METABOLITE; SEMIQUINONE; SUPEROXIDE; SUPEROXIDE DISMUTASE; THIOL; UNCLASSIFIED DRUG;

ANIMAL CELL; ARTICLE; CELL GROWTH; CELL RESPIRATION; CONCENTRATION RESPONSE; CONTROLLED STUDY; CRITHIDIA FASCICULATA; CYTOTOXICITY; ELECTRON SPIN RESONANCE; NONHUMAN; OXIDATION REDUCTION STATE; PRIORITY JOURNAL; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; TRYPANOSOMA;

ANIMALS; CRITHIDIA FASCICULATA; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICALS; HYDROGEN PEROXIDE; NAPHTHOQUINONES; OXIDATION-REDUCTION; OXYGEN CONSUMPTION; SULFHYDRYL COMPOUNDS; SUPEROXIDES; TRYPANOSOMATINA;

EID: 0000208613     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0006-2952(96)00601-6     Document Type: Article

References (53)

1. 1. Santana CF, Lima OG, D'Albuquerque IL, Lacerda AL and Martins DG, Observaçoes sôbre as propriedades anti-tumorais e toxicolögicas do extrato do líber e de alguns componentes do cerne do pau d'arco (Tabebuia avellanedae). Rev Inst Antibiot Univ Recife 8: 89-94, 1968.
2. 2. D'Albuquerque IL, Maciel MCN, Schuler AR, de Araujo M do C, Medeiros Maciel G, Cavalcanti M da SB, Gimino Martins D and Lins Lacerda A, Preparaçao e primeiras observaçoes sobre as propriedades antibióticas e antineoplásicas das naftoquinonas homólogos inferiores na série da 2-hidróxi-3-(3-metil-2-butenil)-1,4-naftoquinona (lapachol). Rev Inst Antibiot Univ Recife 12: 31-40, 1972.
3. 3. Docampo R, Cruz FS, Boveris A, Muniz RPA and Esquivel DMS, β-Lapachone enhancement of lipid peroxidation and superoxide anion and hydrogen peroxide formation by Sarcoma 180 ascites tumor cells. Biochem Pharmacol 28: 723-728, 1979.
4. 4. Schaffner-Sabba K, Schmidt-Ruppin KH, Wehrli W, Schuerch AR and Wasley JWF, β-Lapachone: Synthesis of derivatives and activities in tumor models. J Med Chem 27: 990-994, 1984.
5. 5. Boothman DA and Pardee AB, Inhibition of radiation-induced neoplastic transformation by β-lapachone. Proc Natl Acad Sci USA 86: 4963-4967, 1989.
6. 6. Li CJ, Wang C and Pardee AB, Induction of apoptosis by β-lapachone in human prostate cancer cells. Cancer Res 55: 3712-3715, 1995.
7. 7. Planchon SM, Wuerzberger S, Frydman B, Witiak DT, Hutson P, Church DR, Wilding G and Boothman DA, β-Lapachone-mediated apoptosis in human promyelocytic leukemia (HL-60) and human prostate cancer cells: A p53-independent response. Cancer Res 55: 3706-3711, 1995.
8. 8. Li CJ, Zhang LJ, Dezube BJ, Crumpacker CS and Pardee AB, Three inhibitors of type 1 human immunodeficiency virus long terminal repeat-directed gene expression and virus replication. Proc Natl Acad Sci USA 90: 1839-1842, 1993.
9. 9. Goijman SG and Stoppani AOM, Effects of β-lapachone, a peroxide-generating quinone, on macromolecule synthesis and degradation in Trypanosama cruzi. Arch Biochem Biophys 240: 273-280, 1985.
10. 10. Boveris A, Docampo R, Turrens JF and Stoppani AOM, Effect of β-lapachone on superoxide anion and hydrogen peroxide production by Trypanosoma cruzi. Biochem J 175: 431-439, 1978.
11. 11. Boveris A, Stoppani AOM, Docampo R and Cruz FS, Superoxide anion production and trypanocidal action of naphthoquinones on Trypanosoma cruzi. Comp Biochem Physiol [C] 61: 327-329, 1978.
12. 12. Cruz FS, Docampo R and de Souza W, Effect of β-lapachone on hydrogen peroxide production in Trypanosoma cruzi. Acta Trop (Basel) 35: 35-40, 1978.
13. 13. Lopez JN, Cruz FS, Docampo R, Vasconcellos ME, Sampaio MCR, Pinto AV and Gilbert B, In vitro and in vivo evaluation of the toxicity of 1,4-naphthoquinone and 1,2-naphthoquinone derivatives against Trypanosoma cruzi. Ann Trop Med Parasitol 72: 523-531, 1978.
14. 14. Docampo R, Cruz, FS, Boveris A, Muniz RPA and Esquivel DMS, Lipid peroxidation and the generation of free radicals, Superoxide anion and hydrogen peroxide in β-lapachone-treated Trypanosoma cruzi epimastigotes. Arch Biochem Biophys 186: 292-297, 1978.
15. 15. Molina Portela MP, Pahn EM de, Galeffi C and Stoppani AOM, Efecto de orto-naftoquinonas lipofílicas sobre el crecimiento y la producción de peróxidos por Leptomonas seymouri y Crithidia fasciculata. Rev Argent MicrobioJ 23: 1-14, 1991.
16. 16. Schwarcz de Tarlovsky MN, Goijman SG, Molina Portela MP and Stoppant AOM, Effect of isoxazolyl naphthoquino-neimines on growth and oxygen radical production by Trypanosoma cruzi and Crithidia fasciculata. Experientia 46: 502-505, 1990.
17. 17. Degrassi F, De Salvia R and Berghella L, The production of chromosomal alterations by β-lapachone, an activator of topoisomerase I. Mutat Res 288: 263-267, 1993.
18. 18. Li CJ, Averboukh L and Pardee AB, β-Lapachone, a novel DNA topoisomerase I inhibitor with a mode of action different from camptothecin. J Biol Chem 268: 22463-22468, 1993.
19. 19. Dubin M, Fernandez Villamil SHF and Stoppani AOM, Inhibition of microsomal lipid peroxidation and cytochrome P-450-catalyzed reactions by β-lapachone and related naphthoquinones. Biochem Pharmacol 39: 1151-1160, 1990.
20. 20. Bacchi CJ, Lambros C, Goldberg B, Hutner SH and De Carvallo GDF, Susceptibility of an insect Leptomonas and Crithidia fasciculata to several established antitrypanosomatid agents. Antimicrob Agents Chemother 6: 785-790, 1974.
21. 21. Bacchi CJ, Lambros C, Ellenbogen BB, Penkovsky LN, Sullivan W, Eyinna EE and Hutner SH, Drug-resistant Leptomonas: Cross-resistance in trypanocide-resistant clones. Antimicrob Agents Chemother 8: 688-692, 1975.
22. 22. Shapiro A, Katz LH, Hutner SH, Harracksingh C and Bacchi CJ, Crithidia media as guide to antihaemoflagellate chemotherapy aimed at porphyrin and transition-metal metabolism. In: The In Vitro Cultivation of the Pathogens of Tropical Diseases (Ed. WHO: Trop. Dis. Res. Ser.), pp. 401-415. Schwabe & Co., Basel, Switzerland, 1980.
23. 23. Coolbear KP and Midgley M, Characteristics of ethidium uptake by the trypanosomatid flagellates Crithidia fasciculata and Leptomonas seymouri. Antimicrob Agents Chemother 29: 258-262, 1986.
24. 24-Gutteridge WE, Ross J, Hargadon MRJ and Hudson JE, Crithidia fasciculata: A catalase-containing trypanosomatid sensitive to nitroheterocyclic drugs. Trans R Soc Trop Med Hyg 76: 493-496, 1982.
25. 25. Galeffi C, Casinovi CG, Miranda Delle Monache E and Marini-Bettolo GB, Chinoni sesquiterpenici della Mansonia Altissima Chev. - Nota II. Ann 1st Super Sanita 4: 305-316, 1968.
26. 26. Misra HP and Fridovich I, The univalent reduction of oxygen by reduced flavins and quinones. J Biol Chem 247: 188-192, 1972.
27. 27. McCord JM and Fridovich I, Superoxide dismutase. An enzymic function for erythrocuprein (hemocuprein). J Biol Chem 244: 6049-6055, 1969.
28. 28. Paget TA, Fry M and Lloyd D, Effect of inhibitors on the oxygen kinetics of Nippostrongylus brasiliensis. Mol Biochem Parasitol 22: 125-133, 1987.
29. 29. Hissin PJ and Hilf R, A fluorometric method for determination of oxidized and reduced glutathione in tissues. Anal Biochem 74: 214-226, 1976.
30. 30. Aebi H, Catalase. In: Methods of Enzymatic Analysis (Ed. Bergmeyer HU), 2nd Ed., pp. 673-684. Verlag Chemie International, Deerfield Beach, FL, 1981.
31. 31. Misra HP and Fridovich I, The role of superoxide anion in the autoxidation of epinephrine and a simple assay for superoxide dismutase. J Biol Chem 247: 3170-3175, 1972.
32. 32. Gornall AG, Bardawill CJ and David MM, Determination of serum proteins by means of the biuret reaction. J Biol Chem 177: 751-766, 1949.
33. 33. Cadenas E, Boveris A, Ragan CI and Stoppani AOM, Production of superoxide radicals and hydrogen peroxide by NADH-ubiquinone reductase and ubiquinol-cytochrome c from beef heart mitochondria. Arch Biochem Biophys 180: 248-257, 1977.
34. 34. Toner JJ and Weber MM, Respiratory control in mitochondria from Crithidia fasciculata. Biochem Biophys Res Commun 46: 652-660, 1972.
35. 35. Fairlamb AH and Cerami A, Metabolism and functions of trypanothione in the kinetoplastida. Annu Rev Microbiol 46: 695-729, 1992.
36. 36. Steenkamp DJ and Spies HSC, Identification of a major low-molecular-mass thiol of the trypanosomatid Crithidia fasciculata as ovothiol A. Facile isolation and structural analysis of the bimane derivative. Eur J Biochem 223: 43-50, 1994.
37. 2 Arch Biochem Biophys 212: 411-416, 1981.
38. 38. Le Trant N, Meshnick SR, Kitchener K, Eaton JW and Cerami A, Iron-containing superoxide dismutase from Crithidia fasciculata. J Biol Chem 258: 125-130, 1983.
39. 39. Yamakura F and Suzuki K, Inactivation of Pseudomonas iron-superoxide dismutase by hydrogen peroxide. Biochim Biophys Acta 874: 23-29, 1986.
40. 40. Beyer WF and Fridovich I, Effect of hydrogen peroxide on the iron-containing superoxide dismutase of Escherichia coli. Biochemistry 26: 1251-1257, 1987.
41. 41. Molina Portela MP and Stoppani AOM, Redox cycling of β-lapachone and related o-naphthoquinones in the presence of dihydrolipoamide and oxygen. Biochem Pharmacol 51: 275-283, 1996.
42. 42. Paulino M, Hansz M, Hikichi N, Tabares G, Molina Portela MP, Fernandez Villamil SH, Sreider CM and Stoppani AOM, Propiedades electronicas y actividad redox de naftoquinonas. An Asoc Quim Argent 82: 371-389, 1994.
43. 43. Penketh PG and Klein RA, Hydrogen peroxide metabolism in Trypanosoma brucei. Mol Biochem Parasitol 20: 111-121, 1986.
44. 44. Penketh PG, Kennedy WPK, Patton CL and Sartorelli AC, Trypanosomatid hydrogen peroxide metabolism. FEBS Lett 221: 427-431, 1987.
45. 45. Penketh PG, Kennedy WPK, Patton Cl and Sartorelli AC, Competent metabolic utilization of hydrogen peroxide by trypanosomes. Acta Trop (Basel) 44: 461-462, 1987.
46. 46. Carnieri EGS, Moreno SNJ and Docampo R, Trypanothione-dependent peroxide metabolism in Trypanosoma cruzi different stages. Mol Biochem Parasitol 61: 79-86, 1993.
47. 47. Ross D, Glutathione, free radicals and chemotherapeutic agents. Pharmacol Ther 37: 231-249, 1988.
48. 48. Biaglow JE, Varnes ME, Epp ER, Clark EP, Tuttle SW and Held KD, Role of glutathione and other thiols in cellular response to radiation and drugs. Drug Metab Rev 20: 1-12, 1989.
49. 49. Wardman P, Bioreductive activation of quinones: Redox properties and thiol reactivity. Free Radic Res Commun 8: 219-229, 1990.
50. 50. Miura T, Muraoka S and Ogiso T, Generation of semiquinone and oxygen radicals by the reaction of menadione with reduced glutathione at various pH. Chem Pharm Bull (Tokyo) 40: 709-712, 1992.
51. 51. Averill-Bates DA and Przybytkowski E, The role of glucose in cellular defences against cytotoxicity of hydrogen peroxide in Chinese hamster ovary cells. Arch Biochem Biophys 312: 52-58, 1994.
52. 52. Toxopeus C, van Holsteijn I, De Winther MPJ, van den Dobbelsteen D, Horbach GJMJ, Blaauboer BJ and Noordhoek J, Role of thiol homeostasis and adenine nucleotide metabolism in the protective effects of fructose in quinone-induced cytotoxicity in rat hepatocytes. Biochem Pharmacol 48: 1683-1692, 1994.
53. 53. Morgan WA, DNA single-strand breakage in mammalian cells induced by redox cycling quinones in the absence of oxidative stress. J Biochem Toxicol 10: 227-232, 1995.