Growth inhibitory effects of 3'-nitro-3-phenylamino nor-beta-lapachone against HL-60: A redox-dependent mechanism

Toxicology in Vitro

Volumn 26, Issue 4, 2012, Pages 585-594

  Araujo A J ^a   de Souza, A A ^b   da Silva Junior E N ^c,d   Marinho Filho, J D B ^a   de Moura, M A B F ^b   Rocha, D D ^a   Vasconcellos, M C ^e   Costa, C O ^b   Pessoa, C ^a   de Moraes, M O ^a   Ferreira, V F ^f   de Abreu, F C ^b   Pinto, A V ^d   Montenegro, R C ^g   Costa Lotufo, L V ^a   Goulart, M O F ^b,h  

^a FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

^b FEDERAL UNIVERSITY OF ALAGOAS   (Brazil)

^c FEDERAL UNIVERSITY OF MINAS GERAIS   (Brazil)

^d FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^e FEDERAL UNIVERSITY OF AMAZONAS   (Brazil)

^f FLUMINENSE FEDERAL UNIVERSITY   (Brazil)

^g FEDERAL UNIVERSITY OF PARÁ   (Brazil)

^h UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Apoptosis; Bioelectrochemistry; Cytotoxicity; DNA sensors; Nitroquinone; Nor beta lapachone

Indexed keywords

2,2 DIMETHYL (3H) 3 (N 3' NITROPHENYLAMINO)NAPHTHO [1,2 B]FURAN 4,5 DIONE; 3' NITRO 3 PHENYLAMINO NOR BETA LAPACHONE; ACETYLCYSTEINE; ADENINE; ANTINEOPLASTIC AGENT; BETA LAPACHONE; CASPASE 3; CASPASE 7; DOUBLE STRANDED DNA; DOXORUBICIN; GUANINE; PHOSPHATIDYLSERINE; QUINONE DERIVATIVE; REACTIVE OXYGEN METABOLITE; SINGLE STRANDED DNA; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER CELL CULTURE; CELL DEATH; CELL MEMBRANE DEPOLARIZATION; CONTROLLED STUDY; CYCLIC POTENTIOMETRY; DNA FRAGMENTATION; DRUG CYTOTOXICITY; DRUG STRUCTURE; ELECTROCHEMISTRY; ENZYME ACTIVATION; FLOW CYTOMETRY; GENOTOXICITY; GROWTH INHIBITION; HUMAN; HUMAN CELL; MITOCHONDRION; NUCLEOPHILICITY; OXIDATION REDUCTION REACTION; OXIDATIVE STRESS; SENSOR;

ANTINEOPLASTIC AGENTS; APOPTOSIS; BENZOFURANS; CELL SURVIVAL; COMET ASSAY; DNA DAMAGE; HL-60 CELLS; HUMANS; NAPHTHOQUINONES; OXIDATION-REDUCTION; REACTIVE OXYGEN SPECIES;

EID: 84859771654     PISSN: 08872333     EISSN: 18793177     Source Type: Journal    
DOI: 10.1016/j.tiv.2012.02.003     Document Type: Article

References (47)

1. Asche C. Antitumour quinones. Mini-Rev. Med. Chem. 2005, 5:449-467.
2. Ausubel F.M., Brent R., Kingston R.E., Moore D.D., Seidmann J.G., Struhl K. Current Protocols in Molecular Biology 1990, vol. 2. John Wiley & Sons, Inc., New York.
3. Bova M.P., Mattson M.N., Vasile S., Tam D., Holsinge L., Bremer M., Hui T., McMahon G., Rice A., Fukuto J.M. The oxidative mechanism of action of ortho-quinone inhibitors of protein-tyrosine phosphatase alpha is mediated by hydrogen peroxide. Arch. Biochem. Biophys. 2004, 429:30-41.
4. Brett A.M.O., Goulart M.O.F., de Abreu F.C. Reduction of lapachones and their reaction with L-cysteine and mercaptoethanol on glassy carbon electrodes. Bioelectrochemistry 2002, 56:53-55.
5. Cavalcanti J.C.M., Oliveira N.V., de Moura M.A.B.F., Chaves J.B., Alves R.J., de Abreu F.C., Goulart M.O.F. Effect of the leaving group on the electrodic reduction mechanism of anti-Helicobacter pylori metronidazole derivatives, in aprotic and protic media. Bioelectrochemistry 2004, 63:353-357.
6. Cavalcanti B.C., Barros F.W.A., Cabral I.O., Ferreira J.R.O., Magalhães H.I.F., Júnior H.V.N., da Silva Júnior E.N., de Abreu F.C., Costa C.O., Goulart M.O.F., Moraes M.O., Pessoa C. Preclinical genotoxicology of nor-β-lapachone in human cultured lymphocytes and Chinese hamster lung fibroblasts. Chem. Res. Toxicol. 2011, 24:1560-1574.
7. da Silva Júnior E.N., de Souza M.C.B.V., Pinto A.V., Pinto M.C.F.R., Goulart M.O.F., Barros F.W.A., Pessoa C., Costa-Lotufo L.V., Montenegro R.C., Moraes M.O., Ferreira V.F. Synthesis and potent antitumor activity of new arylamino derivatives of nor-β-lapachone and nor-α-lapachone. Bioorg. Med. Chem. 2007, 15:7035-7041.
8. da Silva Júnior E.N., Moura M.A.B.F., Pinto A.V., Pinto M.C.F.R., de Souza M.C.B.V., Araújo A.J., Pessoa C., Costa-Lotufo L.V., Montenegro R.C., Moraes M.O., Ferreira V.F., Goulart M.O.F. Cytotoxic, trypanocidal activities and physicochemical parameters of nor-β-lapachone-based 1,2,3-triazoles. J. Braz. Chem. Soc. 2009, 20:635-643.
9. da Silva Júnior E.N., de Deus C.F., Martins J.B.L., Lima A.B., Cavalcanti B.C., Pessoa C., Costa-Lotufo L.V., Montenegro R.C., Moraes M.O., Pinto M.C.F.R., de Simone C.A., Ferreira V.F., Goulart M.O.F., Andrade K.Z., Pinto A.V. 3-Arylamino and 3-alkoxy-nor-β-lapachone derivatives: synthesis and cytotoxicity against cancer cell lines. J. Med. Chem. 2010, 53:504-508.
10. Darzynkiewicz Z., Bruno S., Del Bino G., Gorczyca M., Hotz M.A., Lassota P., Traganos F. Features of apoptotic cells measured by flow cytometry. Cytometry 1992, 13:795-808.
11. de Abreu F.C., Ferraz P.A.M., Goulart M.O.F. Some applications of electrochemistry in biomedical chemistry. Emphasis on the correlation of electrochemical and bioactive properties. J. Braz. Chem. Soc. 2002, 13:19-35.
12. de Abreu F.C., Goulart M.O.F., Brett A.M.O. Reduction of lapachones in aqueous media at a glassy carbon electrode. Electroanalysis 2002, 14:29-34.
13. de Abreu F.C., Ferreira D.C.M., Goulart M.O.F., Buriez O., Amatore C. Electrochemical activation of beta-lapachone in beta-cyclodextrin inclusion complexes and reactivity of its reduced form towards oxygen in aqueous solutions. J. Electroanal. Chem. 2007, 608:125-132.
14. de Abreu F.C., de Paula F.S., Ferreira D.C.M., Nascimento V.B., Santos A.M.C., Santoro M., Salas C.E., Lopes J.C.D., Goulart M.O.F. The application of DNA-biosensors and differential scanning calorimetry to the study of the DNA-binding agent berenil. Sensors 2008, 8:1519-1538.
15. de Souza A.A., de Moura M.A.B.F., de Abreu F.C., Goulart M.O.F., da Silva Júnior E.N., Pinto A.V., Ferreira V.F., Moscoso R., Núñez-Vergara L.J., Squella J.A. Electrochemical study, on mercury, of a meta-nitroarylamine derivative of nor-β-lapachone, an antitumor and trypanocidal compound. Quim. Nova 2010, 33:2075-2079.
16. Diculescu V.C., Paquim A.M.C., Brett A.M.O. Electrochemical DNA sensors for detection of DNA damage. Sensors 2005, 5:377-393.
17. Enari M., Sakahira H., Yokoyama H., Okawa K., Iwamatsu A., Nagata S. A caspase-activated DNase that degrades DNA during apoptosis, and its inhibitor ICAD. Nature 1998, 391:43-50.
18. Eskes R., Desagher S., Antonsson B., Martinou J.C. Bid induces the oligomerization and insertion of Bax into the outer mitochondrial membrane. Mol. Cell Biol. 2000, 20:929-935.
19. Ferreira D.C.M., Tapsoba I., Arbault S., Bouret Y., Alexandre Moreira M.S., Pinto A.V., Goulart M.O.F., Amatore C. Ex vivo activities of β-lapachone and α-lapachone on macrophages: a quantitative pharmacological analysis based on amperometric monitoring of oxidative bursts by single cells. ChemBioChem 2009, 10:528-538.
20. Foye W.O. Cancer Chemotherapeutic Agents 1995, American Chemical Society, Washington, D.C.
21. Goulart M.O.F., Ossowski T., Pipka P., Liwo A. Electrochemical study of oxygen interaction with lapachol and its radical anions. Bioelectrochemistry 2003, 59:85-87.
22. Goulart M.O.F., Lima N.M.F., Santana A.E.G., Ferraz P.A.L., Cavalcanti J.C.M., Liwo A., Falkowsky P., Ossowsky T. Electrochemical studies of isolapachol with emphasis on oxygen interaction with its radical anions. J. Electroanal. Chem. 2004, 566:25-29.
23. Goulart M.O.F., de Souza A.A., de Abreu F.C., de Paula F.S., Sales E.M., Almeida W.P., Buriez O., Amatore C. Electrochemical study of methyl 2-[p-nitrophenyl(hydroxy)methyl]acrylate. J. Electrochem. Soc. 2007, 154:121-129.
24. Gupta D., Podar K., Tai Y.T., Lin B., Hideshima T., Akiyama M., LeBlanc R., Catley L., Mitsiades N., Mitsiades C., Chauhan D., Munshi N.C., Anderson K.C. Beta-lapachone, a novel plant product, overcomes drug resistance in human multiple myeloma cells. Exp. Hematol. 2002, 30:711-720.
25. Hanahan D., Weinberg R.A. The hallmarks of cancer. Cell 2000, 100:57-70.
26. Hernández D.M., de Moura M.A.B.F., Valencia D.P., González F.J., González I., de Abreu F.C., da Silva Júnior E.N., Ferreira V.F., Pinto A.V., Goulart M.O.F., Frontana C. Inner reorganization during the radical-biradical transition in a nor-beta-lapachone derivative possessing two redox centers. Org. Biomol. Chem. 2008, 6:3414-3420.
27. Hileman E.O., Liu J., Albitar M., Keateng M.J., Huang P. Intrinsic oxidative stress in cancer cells: a biochemical basis for therapeutic selectivity. Cancer Chemother. Pharmacol. 2004, 53:209-219.
28. Hillard E.A., de Abreu F.C., Ferreira D.C.M., Jaouen G., Goulart M.O.F., Amatore C. Electrochemical parameters and techniques in drug development, with an emphasis on quinones and related compounds. Chem. Commun. 2008, 2612-2628.
29. Kerr J.F.R., Wyllie A.H., Currie A.R. Apoptosis-Basic biological phenomenon with wide-ranging implications in tissue kinetics. Brit. J. Cancer 1972, 26:239-257.
30. Lebel C.P., Ischiropoulos H., Bondy S.C. Evaluation of the probe 2',7'-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress. Chem. Res. Toxicol. 1992, 5:227-231.
31. Li P., Nijhawan D., Budihardjo I., Srinivasula S.M., Ahmad M., Alnemri E.S., Wang X. Cytochrome C and dATP-dependent formation of Apaf-1/caspase-9 complex initiates an apoptotic protease cascade. Cell 1997, 91:479-489.
32. Melino G. The Sirens' song. Nature 2001, 412:23.
33. Mizutani H., Tada-Oikawa S., Hiraku Y., Oikawa S., Kojima M., Kawanishi S. Mechanism of apoptosis induced by a new topoisomerase inhibitor through the generation of hydrogen peroxide. J. Biol. Chem. 2002, 277:30684-30689.
34. Montenegro R.C., Araújo A.J., Molina M.T., Marinho-Filho J.D.B., Rocha D.D., Lopez-Montero E., Goulart M.O.F., Bento E.S., Alves A.P.N.N., Pessoa C., Moraes M.O., Costa-Lotufo L.V. Cytotoxic activity of naphthoquinones with special emphasis on juglone and its 5-O-methyl derivative. Chem. Biol. Interact. 2010, 184:439-448.
35. Mosmann T. Rapid colorimetric assay for cellular growth and survival application to proliferation and cyto-toxicity assays. J. Immunol. Methods 1983, 65:55-63.
36. Okada H., Mak T.W. Pathways of apoptotic and non-apoptotic death in tumour cells. Nat. Rev. Cancer 2004, 4:592-603.
37. Oliveira-Brett A.M., Vivan M., Fernandes I.R., Piedade J.A.P. Electrochemical detection of in situ adriamycin oxidative damage to DNA. Talanta 2002, 56:959-970.
38. Ossowski T., Pipka P., Liwo A., Jeziorek D. Electrochemical and UV-spectrophotometric study of oxygen and superoxide anion radical interaction with anthraquinone derivatives and their radical anions. Electrochim. Acta 2000, 45:3581-3587.
39. Ozben T. Oxidative stress and apoptosis: impact on cancer therapy. J. Pharm. Sci. 2007, 96:2181-2196.
40. Piedade J.A.P., Fernandez I.R., Brett A.M.O. Electrochemical sensing of DNA-adriamycin interactions. Bioelectrochemistry 2002, 56:81-83.
41. Planchon S.M., Wuerzberger S., Frydman B., Witiak D.T., Hutson P., Church D.R., Wilding G., Boothman D.A. β-Lapachone-mediated apoptosis in human promyelocytic leukemia (HL-60) and human prostate cancer cells: a p53-independent response. Cancer Res. 1995, 55:3706-3711.
42. Planchon S.M., Wuerzberger-Davis S.M., Pink J.J., Robertson K.A., Bornmann W.G., Boothman D.A. Bcl-2 protects against beta-lapachone-mediated caspase 3 activation and apoptosis in human myeloid leukemia (HL-60) cells. Oncol Rep. 1999, 6:485-492.
43. Rauf S., Gooding J.J., Akhtar K., Ghauri M.A., Rahman M., Anwar M.A., Khalid A.M. Electrochemical approach of anticancer drugs - DNA interaction. J. Pharm. Biomed. Anal. 2005, 37:205-217.
44. Singh N.P., McCoy M.T., Tice R.R., Schneider E.L. A simple technique for quantitation of low-levels of DNA damage in individual cells. Exp. Cell Res. 1988, 175:184-191.
45. Wang J., Ozsoz M., Cai X.H., Rivas G., Shiraishi H., Grant D.H., Chicharro M., Fernandes J., Palecek E. Interactions of antitumor drug daunomycin with DNA in solution and at the surface. Bioelectrochem. Bioenerg. 1998, 45(1998):33-40.
46. Zafarullaha M., Lia W.Q., Sylvestera J., Ahmad M. Molecular mechanisms of N-acetylcysteine actions. Cell. Mol. Life Sci. 2003, 60:6-20.
47. Ziegler U., Groscurth P. Morphological features of cell death. News Physiol. Sci. 2004, 19:124-128.