Redox cycling of β-lapachone and related o-naphthoquinones in the presence of dihydrolipoamide and oxygen

Biochemical Pharmacology

Volumn 51, Issue 3, 1996, Pages 275-283

  Molina Portela, Maria P ^a,b   Stoppani, Andres O M ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b National Academy of Sciences   (Argentina)

Author keywords

dihydrolipoamide; hydroquinone auto oxidation; mansonone; o naphthoquinone; redox cycling; superoxide dismutase; lapachone

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; ALPHA LAPACHONE; AMIDE; BETA LAPACHONE; CATALASE; CG 10 248; CG 8 935; CG 9 442; DIHYDROLIPOAMIDE; MANSONONE; MENADIONE; SUPEROXIDE DISMUTASE; UNCLASSIFIED DRUG;

ABSORPTION SPECTROPHOTOMETRY; ARTICLE; AUTOOXIDATION; CATALYSIS; CONTROLLED STUDY; LIPOPHILICITY; OXIDATION; OXIDATION REDUCTION STATE; OXYGEN CONSUMPTION; PH; PRIORITY JOURNAL; REACTION ANALYSIS; REDUCTION; STOICHIOMETRY;

EID: 0030062605     PISSN: 00062952     EISSN: None     Source Type: Journal    
DOI: 10.1016/0006-2952(95)02168-X     Document Type: Article

References (29)

1. Powis G, Metabolism and reactions of quinoid anti-cancer agents. Pharmacol Ther 35: 57-162, 1987.
2. O'Brien PJ, Molecular mechanism of quinone cytotoxicity. Chem Biol Interact 80: 1-41, 1991.
3. Koster AS, Bioreductive activation of quinones: A mixed blessing. Pharm Weekbl [Sci] 13: 123-126, 1991.
4. Monks TJ, Hanzlik RP, Cohen GM, Ross D and Graham DG, Quinone chemistry and toxicity. Toxicol Appl Pharmacol 112: 2-16, 1992.
5. Anusevicius ZJ and Cénas NK, Dihydrolipoamide-mediated redox cycling of quinones. Arch Biochem Biophys 302: 420-424, 1993.
6. 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 1,4-naftoquinona (lapachol). Rev Inst Antibiot Univ Recife 12: 31-40, 1972.
7. Molina Portela MP, Pahn EM de, Galeffi C and Stoppani AOM, Efecto de orto-naftoquinonas lipofílicas sobre el crecimiento y la producción de peroxidos por Leptomonas seymouri y Crithidia fasciculata. Rev. Argent Microbiol 23: 1-14, 1991.
8. 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.
9. Boothman DA and Pardee AB, Inhibition of radiation-induced neoplastic transformation by β-lapachone. Proc Natl Acad Sci USA 86: 4963-4967, 1989.
10. Goijman SG and Stoppani AOM, Effects of β-lapachone, a peroxide-generating quinone, on macromolecule synthesis and degradation in Trypanosoma cruzi. Arch Biochem Biophys 240: 273-280, 1985.
11. 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.
12. 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.
13. Galeffi C, Casinovi CG, Delle Monache EM and Marini-Bettolo GB, Chinoni sesquiterpenici della Mansonia Altissima Chev. Nota II. Ann 1st Super Sanita 4: 305-316, 1968.
14. Reed LJ, Koike M, Levitch ME and Leach FR, Studies on the nature and reactions of protein-bound lipoic acid. J Biol Chem 232: 143-158, 1958.
15. McCord JM and Fridovich I, Superoxide dismutase. An enzymic function for erythrocuprein (hemocuprein). J Biol Chem 244: 6049-6055, 1969.
16. Molina Portela MP and Stoppani AOM, Lipoamide dehydrogenase from Trypanosoma cruzi: Some properties and cellular localization. Biochem Int 24: 147-155, 1991.
17. 2+ release by rat liver mitochondria. Arch Biochem Biophys 267: 539-550, 1988.
18. 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.
19. Winterbourn CC, Cytochrome c reduction by semiquinone radicals can be indirectly inhibited by superoxide dismutase. Arch Biochem Biophys 209: 159-167, 1981.
20. Jarabak J, Polycyclic aromatic hydrocarbon quinone-mediated oxidation reduction cycling catalyzed by a human placental NADPH-linked carbonyl reductase. Arch Biochem Biophys 291: 334-338, 1991.
21. Brunmark A and Cadenas E, Redox and addition chemistry of quinoid compounds and its biological implications. Free Radic Biol Med 7: 435-477, 1989.
22. Ishii T and Fridovich I, Dual effects of superoxide dismutase on the autoxidation of 1,4-naphthohydroquinone. Free Radic Biol Med 8: 21-24, 1990.
23. Bandy B, Moon J and Davidson AJ, Multiple actions of superoxide dismutase: Why can it both inhibit and stimulate reduction of oxygen by hydroquinones? Free Radic Biol Med 9: 143-148, 1990.
24. Dubin M, Fernandez Villamil SH and Stoppant AOM, Inhibition of microsomal lipid peroxidation and cytochrome P-450-catalyzed reactions by β-lapachone and related naphthoquinones. Biochem Pharmacol 39: 1151-1160, 1990.
25. Haenen GRMM, De Roou BM, Vermeulen NPE and Bast A, Mechanism of the reaction of ebselen with endogenous thiols; Dihydrolipoate is a better cofactor than glutathione in the peroxidase activity of ebselen. Mol Pharmacol 37: 412-422, 1990.
26. Cadenas E, Mira D, Brunmark A, Lind C, Segura-Aguilar J and Ernster L, Effect of superoxide dismutase on the autoxidation of various hydroquinones - A possible role of superoxide dismutase as a superoxide: semiquinone oxidoreductase. Free Radic Biol Med 5: 71-79, 1988.
27. - leading to loss of copper. Eur J Biochem 180: 569-575, 1989.
28. 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.
29. Suzuki YJ, Mizuno M, Tritschler HJ and Packer L, Redox regulation of NF-kB DNA binding activity by dihydrolipoate. Biochem Mol Biol Int 36: 241-246, 1995.