Genotoxicity of the copper antineoplastic coordination complexes casiopeinas®

Toxicology in Vitro

Volumn 25, Issue 7, 2011, Pages 1376-1384

  Serment Guerrero, J ^a   Cano Sanchez, P ^b   Reyes Perez, E ^a   Velazquez Garcia, F ^a   Bravo Gomez, M E ^b   Ruiz Azuara, L ^b  

^a INSTITUTO NACIONAL DE INVESTIGACIONES NUCLEARES   (Mexico)

^b UNIVERSIDAD NACIONAL AUTÓNOMA DE MÉXICO   (Mexico)

Author keywords

Antineoplastic; Casiopeinas; Copper chelates; ROS

Indexed keywords

(4,4' DIMETHYL 2,2' BIPYRIDINE)(ACETYLACETONATO)COPPER NITRATE; (4,7 DIMETHYL 1,10 PHENANTHROLINE)(ACETYLACETONATO)COPPER NITRATE; (4,7 DIMETHYL 1,10 PHENANTHROLINE)(GLYCINATO)COPPER NITRATE; (4,7 DIPHENYL 1,10 PHENANTHROLINE)(ACETYLACETONATO)COPPER NITRATE; 1,10 PHENANTHROLINE COPPER; ANTINEOPLASTIC METAL COMPLEX; CASIOPEINA; HYDROGEN PEROXIDE; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ARTICLE; CELL DEATH; COMET ASSAY; CONTROLLED STUDY; DENSITOMETRY; DNA DEGRADATION; DNA FRAGMENTATION; DNA STRAND BREAKAGE; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; GENOTOXICITY; HELA CELL; HUMAN; HUMAN CELL; LYMPHOCYTE; OXIDATIVE STRESS; PERIPHERAL LYMPHOCYTE;

ANIMALS; ANTINEOPLASTIC AGENTS; COMET ASSAY; COPPER; DNA FRAGMENTATION; DNA REPAIR; HELA CELLS; HUMANS; LYMPHOCYTES; MICE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; MUTAGENICITY TESTS; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PLASMIDS; STRUCTURE-ACTIVITY RELATIONSHIP;

MUS;

EID: 84860406709     PISSN: 08872333     EISSN: 18793177     Source Type: Journal    
DOI: 10.1016/j.tiv.2011.05.008     Document Type: Article

References (42)

1. Alemon-Medina R., Breña-Valle M., Muñoz-Sanchez J.L., Gracia-Mora I., Ruiz-Azuara L. Induction of oxidative damage by copper-based antineoplastic drugs (Casiopei{dotless}nas). Cancer Chemother. Pharmacol. 2007, 60:219-228.
2. Alemón-Medina R., Bravo-Gómez M.E., Gracia-Mora I., Ruiz-Azuara L. Comparison between the antiproliferative effect and intracellular glutathione depletion induced by Casiopeína IIgly and cisplatin in murine melanoma B16 cells. Toxicol. In Vitro 2011, 25:868-873.
3. Bravo-Gómez M.E., García-Ramos J.C., Gracia-Mora I., Ruiz-Azuara L. Antiproliferative activity and QSAR study of copper (II) mixed chelate [Cu(N-N)(acetylacetonato)]NO3 and [Cu(N-N)(glycinato)]NO3 complexes, (Casiopeinas®). J. Inorg. Biochem. 2009, 103:299-309.
4. Carvallo-Chaigneau F., Trejo-Solís C., Gómez-Ruiz C., Rodríguez-Aguilera E., Macías-Rosales L., Cortés-Barberena E., Cedillo-Peláez C., Gracia-Mora I., Ruiz-Azuara L., Madrid-Marina V., Constantino-Casas F. Casiopeina III-ia induces apoptosis in HCT-15 cells in vitro through caspase-dependent mechanisms and has antitumor effect in vivo. BioMetals 2008, 21:17-28.
5. Chikira M., Tomizawa Y., Fukita D., Sugizaki T., Sugawara N., Yamazaki T., Sasano A., Shindo H., Palaniandavar M., Antholine W.E. DNA-fiber EPR study of the orientation of Cu(II) complexes of 1, 10-phenanthroline and its derivatives bound to DNA: mono(phenanthroline)-copper(II) and its ternary complexes with amino acids. J Inorg Biochem. 2002, 89:163-173.
6. Collins A.R. The comet assay for DNA damage and repair. Mol. Biotechnol. 2004, 26:249-261.
7. Collins A.R., Duthie S.J., Dobson V.L. Direct enzymic detection of endogenous oxidative base damage in human lymphocyte DNA. Carcinogenesis 1993, 14:1733-1735.
8. Czene S., Testa E., Nygren J., Belyaev I., Harms-Ringdahl M. DNA fragmentation and morphological changes in apoptotic human lymphocytes. Biochem. Biophys. Res. Commun. 2002, 294:872-878.
9. De Vizcaya-Ruiz A., Rivero-Müller A., Ruiz-Ramirez L., Kass G.E., Kelland L.R., Orr R.M., Dobrota M. Induction of apoptosis by a novel copper-based anticancer compound, casiopeina II, in L1210 murine leukaemia and CH1 human ovarian carcinoma cells. Toxicol. In Vitro 2000, 14:1-5.
10. Dusinski M., Collins A. Detection of oxidised purines and UV-induced photoproducts in DNA of single cells, by inclusion of lesion-specific enzymes in the comet assay. ATLA 1996, 24:323-438.
11. Goossens V., Grooten J., De Vos K., Fiers W. Direct evidence for tumor necrosis factor-induced mitochondrial reactive oxygen intermediates and their involvement in cytotoxicity. Proc. Natl. Acad. Sci. USA 1995, 92:8115-8119.
12. Gracia-Mora I., Ruiz-Ramirez L., Gomez-Ruiz C., Tinoco-Mendez M., Marquez-Quiñones A., Romero-De Lira L., Marin-Hernandez A., Madas-Rosales L., Bravo-Gomez M.E. Knigth's move in the periodic table, from copper to Platinum, novel antitumor mixed chelate copper compounds, casiopeinas, evaluated by an in vitro human and murine cancer cell line panel. Metal Based Drugs 2001, 8:19-28.
13. Henderson L.M., Chappell J.B. Dihydrorhodamine 123: a fluorescent probe for superoxide generation?. Eur. J. Biochem. 1993, 217:973-980.
14. Henkels K.M., Turchi J.J. Cisplatin-induced apoptosis proceeds by caspase- 3-dependent and -independent pathways in cisplatin-resistant and -sensitive human ovarian cancer cell lines. Cancer Res. 1999, 59:3077-3083.
15. Huang H.L., Fang L.W., Lu S.P., Chu C.K., Luh T.Y., Lai M.Z. DNA-damaging reagents induce apoptosis through reactive oxygen species-dependent Fas aggregation. Oncogene 2003, 22:8168-8177.
16. Kachadourian R., Brechbuhl H.M., Ruiz-Azuara L., Gracia-Mora I., Day B.J. Casiopeina IIgly-induced oxidative stress and mitochondrial dysfunction in human lung cancer A549 and H157 cells. Toxicology 2010, 268:176-183.
17. Leitner H.M., Kachadourian R., Day B.J. Harnessing drug resistance. Using ABC transporter proteins to target cancer cells. Biochem. Pharmacol. 2007, 74:1677-1685.
18. Leuthauser W.C.S., Oberley W.L., Oberley D.T., Sorenson J.R.J., Ramakrishna K. Antitumor effect of a copper coordination compound with superoxide dismutase-like activity. J. Natl. Cancer Inst. 1981, 66:1077-1081.
19. Marin H.A., Gracia M.I., Ruiz-Ramírez L., Moreno S.R. Toxic effects of copper based antineoplastic drugs (Casiopeinas) on mitochondrial functions. Biochem. Pharmacol. 2003, 65:1979-1989.
20. Marzano C., Pellei M., Tisato F., Santini C. Copper complexes as anticancer agents. Anticancer Agents Med. Chem. 2009, 9:185-211.
21. Mejia C., Ruiz-Azuara L. Casiopeinas IIgly and IIIia induce apoptosis in medulloblastoma cells. Pathol. Oncol. Res. 2008, 14:467-472.
22. Mueller T., Voigt W., Simon H., Fruehauf A., Bulankin A., Grothey A., Schmoll H.J. Failure of activation of caspase-9 induces a higher threshold for apoptosis and cisplatin resistance in testicular cancer. Cancer Res. 2003, 63:513-521.
23. Nicco C., Laurent A., Chereau C., Weill B., Batteux F. Differential modulation of normal and tumor cell proliferation by reactive oxygen species. Biomed. Pharmacother. 2005, 59:169-174.
24. Rivero-Müller A., De Vizcaya-Ruiz A., Planc N., Ruiz L., Dobrota M. Mixed chelate copper complex, Casiopeina IIgly®, binds and degrades nucleic acids: a mechanism of cytotoxicity. Chem. Biol. Interact. 2007, 165:189-199.
25. Rodriguez-Enriquez S., Vital-Gonzalez P.A., Flores-Rodriguez F.L., Marin-Hernandez A., Ruiz-Azuara L., Moreno-Sanchez R. Control of cellular proliferation by modulation of oxidative phosphorylation in human and rodent fast-growing tumor cells. Toxicol. Appl. Pharmacol. 2006, 215:208-217.
26. Rodríguez-Enríquez S., Vital-González P.A., Flores-Rodríguez F.L., Marín-Hernández A., Ruiz-Azuara L., Moreno-Sánchez R. Control of cellular proliferation by modulation of oxidative phosphorylation in human and rodent fast-growing tumor cells. Toxicol. Appl. Pharmacol. 2006, 215:208-217.
27. Rodríguez-Enríquez S., Gallardo-Pérez J.C., Avilés-Salas A., Marín-Hernández A., Carreño-Fuentes L., Maldonado-Lagunas V., Moreno-Sánchez R. Energy metabolism transition in multi-cellular human tumor spheroids. J. Cell. Physiol. 2008, 216:189-197.
28. Ruiz-Azuara L., 1993. US Patent, Ap. 21 (1992), No. 5107,005; US Patent, Re 35,458, February 18 (1997); US, Patent November 19 (1996), No. 5576,326, 407543 SECOFI.
29. Ruiz-Azuara L., Bravo-Gomez M.E. Copper compounds in cancer chemotherapy. Curr Med Chem. 2010, 17:3606-3615.
30. Ruiz-Ramírez L., Gracia M.I., Moreno E.R., Gasque L., Huerta L., Mayet L., Ortiz V., Lomeli C. The antitumor activity of several transition metal complexes. J. Inorg. Biochem. 1991, 43:615.
31. Rundell M.S., Wagner E.D., Plewa M.J. The comet assay: genotoxic damage or nuclear fragmentation?. Environ. Mol. Mutagen 2003, 42:61-67.
32. Sambrook J., Fritsch E.F., Maniatis T. Molecular Cloning. A Laboratory Manual, vol. 2 1989, Cold Spring Harbor, New York. second ed.
33. Samuni A., Aronovitch J., Godinger D., Chevion M., Czapski G. On the cytotoxicity of vitamin C and metal ions. A site specific Fenton mechanism. Eur. J. Biochem. 1983, 137:119-124.
34. Schumacker P.T. Reactive oxygen species in cancer cells: live by the sword, die by the sword. Cancer cell 2006, 10:175-176.
35. Schweyer S., Soruri A., Heintze A., Radzun H.J., Fayyazi A. The role of reactive oxygen species in cisplatin-induced apoptosis in human malignant testicular germ cell lines. Int. J. Oncol. 2004, 25:1671-1676.
36. Simons A.L., Ahmad I.M., Mattson D.M., Dornfeld K.J., Spitz D.R. 2-Deoxy-d-glucose combined with cisplatin enhances cytotoxicity via metabolic oxidative stress in human head and neck cancer cells. Cancer Res. 2007, 67:3364-3370.
37. Solans X., Ruíz-Ramírez L., Martínez A., Gasque L., Moreno-Esparza R. Mixed chelate complexes. II. Structures of l-alaninato(aqua)(4,7-diphenyl-1,10-phenanthroline)copper(II) nitrite monohydrate and aqua(4,7-dimethyl-1,10-phenanthroline)(glycinato)(nitrato)copper(II) monohydrate. Acta Cryst. 1993, C49:890-893.
38. Strauss G.H.S. Non-random cell killing in cryopreservation: implications for performance of the battery of leukocyte test (BLT). I. Toxic and immunotoxic effects. Mutat. Res. 1991, 252:1-15.
39. Szatrowski T.P., Nathan C.F. Production of large amounts of hydrogen peroxide by human tumor cells. Cancer Res. 1991, 51:794-798.
40. Tardito S., Marchio L. Copper compounds in anticancer strategies. Curr. Med. Chem. 2009, 16:1325-1348.
41. Tice R.R., Agurell E., Anderson D., Burlinson B., Hartmann A., Kabayashi H., Miyamae Y., Rojas E., Ryu J.C., Sasaki Y.F. Single cell gel/comet assay: guidelines for in vitro and in vivo genetic toxicology testing. Environ. Mol. Mutagen. 2000, 35:206-221.
42. Trejo-Soli{dotless}s C., Palencia G., Zuñiga S., Rodri{dotless}guez-Ropony A., Osorio-Rico L., Sanchez-Torres L., Gracia-Mora I., Marquez-Rosado L., Sanchez A., Moreno-Garci{dotless}a M.E., Cruz A., Bravo-Gomez M.E., Ruiz-Rami{dotless}rez L., Rodri{dotless}guez-Enriquez S., Sotelo J. Cas IIgly induces apoptosis in glioma C6 cells in vitro and in vivo through caspase-dependent and caspase-independent mechanisms. Neoplasia 2005, 7:563-574.