Gold(III) dithiocarbamate derivatives for the treatment of cancer: Solution chemistry, DNA binding, and hemolytic properties

Journal of Medicinal Chemistry

Volumn 49, Issue 5, 2006, Pages 1648-1657

  Ronconi, Luca ^a   Marzano, Christine ^a   Zanello, Piero ^b   Corsini, Maddalena ^b   Miolo, Giorgia ^a   Maccà, Carlo ^a   Trevisan, Andrea ^a   Fregona, Dolores ^a  

^a UNIVERSITY OF PADOVA   (Italy)

^b UNIVERSITY OF SIENA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CISPLATIN; DITHIOCARBAMIC ACID DERIVATIVE; GOLD COMPLEX;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CYTOTOXICITY; DNA SYNTHESIS; DRUG DNA BINDING; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMICAL ANALYSIS; HEMOLYSIS; MACROMOLECULE; MOUSE; NONHUMAN; OXIDATION; RNA SYNTHESIS;

ANIMALS; ANTINEOPLASTIC AGENTS; CATTLE; CELL LINE, TUMOR; CISPLATIN; CROSS-LINKING REAGENTS; DNA; DRUG RESISTANCE, NEOPLASM; DRUG SCREENING ASSAYS, ANTITUMOR; HEMOLYSIS; HYDROLYSIS; KINETICS; MICE; ORGANOGOLD COMPOUNDS; SOLUTIONS; STRUCTURE-ACTIVITY RELATIONSHIP; THIOCARBAMATES; THYMIDINE; TRITIUM; URIDINE;

EID: 33644855554     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0509288     Document Type: Article

References (53)

1. Guo, Z.; Sadler, P. J. Medicinal inorganic chemistry. Adv. Inorg. Chem. 2000, 49, 183-306.
2. Kean, W. F.; Forestier, F.; Kassam, Y.; Buchanan, W. W.; Rooney, P. J. The history of gold therapy in rheumatoid disease. Semin. Arthritis Rheum. 1985, 14, 180-186.
3. Shaw, C. F., III. Gold-based therapeutic agents. Chem. Rev. 1999, 99, 2589-2600.
4. Ward, J. R. Role of disease-modifying antirheumatic drugs versus cytotoxic agents in the therapy of rheumatoid arthritis. Am. J. Med. 1988, 85, 39-44.
5. Tiekink, E. R. T. Gold derivatives for the treatment of cancer. Crit. Rev. Oncol. Hematol. 2002, 42, 225-248.
6. Messori, L.; Marcon, G. Gold complexes as antitumor agents. Met. Ions Biol. Syst. 2004, 42, 385-424.
7. Messori, L.; Marcon, G.; Orioli, P. Gold(III) compounds as a new family of anticancer drugs. Bioinorg. Chem. Appl. 2003, 1, 177-187.
8. Calamai, P.; Carotti, S.; Guerri, A.; Mazzei, T.; Messori, L.; Mini, E.; Orioli, P.; Speroni, G. P. Cytotoxic effects of gold(III) complexes on established human tumor cell lines sensitive and resistant to cisplatin. Anti-Cancer Drug Des. 1998, 13, 67-80.
9. Novelli, F.; Recine, M.; Sparatore, F.; Juliano, C. Gold complexes as antimicrobial agents. Farmaco 1999, 54, 232-236.
10. Crooke, S. T.; Mirabelli, C. K. Molecular mechanisms of action of auranofin and other gold complexes as related to their biological activities. Am. J. Med. 1983, 75, 109-113.
11. Marcon, G.; Messori, L.; Orioli, P. Gold(III) complexes as a new family of cytotoxic and antitumor agents. Expert Rev. Anticancer Ther. 2002, 2, 337-346.
12. Fregona, D.; Ronconi, L.; Marzano, C. Complessi ditiocarbammici di oro(III) e loro impiego come antitumorali. Italian Patent No. MI2003A000600, March 26, 2003.
13. Ronconi, L.; Giovagnini, L.; Marzano, C.; Bettìo, F.; Graziani, R.; Pilloni, G.; Fregona, D. Gold dithiocarbamate derivatives as potential antineoplastic agents: design, spectroscopic properties and in vitro antitumor activity. Inorg. Chem. 2005, 44, 1867-1881.
14. Forghieri, F.; Preti, C.; Tassi, L.; Tosi, G. Preparation, properties and reactivity of gold complexes with some heterocyclic dithiocarbamates as ligands. Polyhedron 1988, 7, 1231-1237.
15. Mestroni, G.; Alessio, E.; Sava, G.: Pacor, S.; Coluccia, M.; Boccarelli, A. Water-soluble ruthenium(III)-dimethyl sulfoxide complexes: chemical behavior and pharmaceutical properties. Met.-Based Drugs 1994, 1, 41-63.
16. Messori, L.; Abbate, F.; Marcon, G.; Orioli, P.; Fontani, M.; Mini, E.; Mazzei, T.; Carotti, S.; O'Connell, T.; Zanello, P. Gold(III) complexes as potential antitumor agents: solution chemistry and cytotoxic properties of some selected gold(III) compounds. J. Med. Chem. 2000, 43, 3541-3548.
17. Marcon, G.; Carotti, S.; Coronnello, M.; Messori, L.; Mini, E.; Orioli, P.; Mazzei, T.; Cinellu, M. A.; Minghetti, G. Gold(III) complexes with bipyridyl ligands: solution chemistry, cytotoxicity and DNA binding properties. J. Med. Chem. 2002, 45, 1672-1677.
18. Calamai, P.; Guerri, A.; Messori, L.; Orioli, P.; Speroni, G. P. Structure and DNA binding properties of the gold(III) complex [AuC12(esal)]. Inorg. Chim. Acta 1999, 285, 309-312.
19. Buck, R. P. Theory and Principles of Membrane Electrodes. In Ion-Selective Electrodes in Analytical Chemistry; Freiser, H., Ed.; Plenum Press: New York, 1978; p 93.
20. Maccà, C.; Soldà, L. pH-Static techniques in volumetric analysis. I. A theoretical reappraisal of pH-static acid-base titrations. Electroanalysis 2002, 14, 57-62.
21. Fernàndez, E. J.; Lopez-de-Luzuriaga, J. M.; Monge, M.; Olmos, E. Dithiocarbamate ligands as building-blocks in the coordination chemistry of gold. Inorg. Chem. 1998, 37, 5532-5536.
22. 2]. Organometallics 1994, 13, 3415-3419.
23. 2. Inorg. Chem. 1988, 27, 836-842.
24. Koelle, U.; Laguna, A. Electrochemistry of Au-complexes. Inorg. Chim. Acta 1999, 290, 44-50.
25. Ferrali, M.; Bambagioni, S.; Ceccanti, A.; Donati, D.; Giorgi, G.; Fontani, M.; Laschi, F.; Zanello, P.; Casolaro, M.; Pietrangelo, A. Design, synthesis, and physicochemical and biological characterization of a new iron chelator of the family of hydroxychromenes. J. Med. Chem. 2002, 45, 5776-5785.
26. 4(DMSO)(Im)], NAMI-A. Dalton Trans. 2004, 15 2347-2351.
27. Åkerström, S. The N,N-dialkyldithiocarbamates of the univalent coinage metals. Arkiv Kemi 1959, 14, 387-401.
28. Durkin, W. J.; Ghanta, V. K.; Balch, C. M.; Davis, D. W.; Hiramoto, R. N. A methodological approach to the prediction of anticancer drug effects in humans. Cancer Res. 1979, 39, 402-407.
29. Tashiro, T.; Kawada, Y.; Sakurai, Y.; Kidani, Y. Antitumor activity of a new platinum complex, oxalato(trans-1-1,2-diaminocyclohexane)-platinum(II): new experimental data. Biomed. Pharmacother. 1989, 43, 251-260.
30. Pil, P.; Lippard, S. J. Cisplatin and Related Drugs. In Encyclopedia of Cancer, Bertino, J. R., Ed.; Academic Press: San Diego, 1997: vol. 1, pp 392-410.
31. Umezawa, N.; Arakane, K.; Ryu, A.; Mashiko, S.; Hirobe, M.; Nagano, T. Participation of reactive oxygen species in phototoxicity induced by quinolone antibacterial agents. Arch. Biochem. Biophys. 1997, 542, 275-281.
32. Eastman, A. The Mechanism of Action of Cisplatin: from Adducts to Apoptosis. In Cisplatin. Chemistry and Biochemistry of a Leading Anticancer Drug; Lippert, B., Ed.; Wiley VCH: Zurich, 1999; pp 111-134.
33. Coluccia, M.; Boccarelli, A.; Mariggio, M. A.; Cardellicchio, N.; Caputo, P.; Intini, F. P.; Natile, G. Platinum(II) complexes containing iminoethers: a trans platinum antitumour agent. Chem.-Biol. Interact 1995, 98, 251-266.
34. Mirabelli, C. K.; Zimmerman, J. P.; Bartus, H. R.; Sung, C. M.; Crooke, S. T. Inter-strand cross-links and single-strand breaks produced by gold(I) and gold(III) coordination complexes. Biochem. Pharmacol. 1986, 35, 1435-1443.
35. Mirabelli, C. K.; Johnson, R. K.; Hill, D. T. Correlation of the in vitro cytotoxic and in vivo antitumor activities of gold(I) coordination complexes. J. Med. Chem. 1986, 29, 218-223.
36. Kohn, K. W. Principles and practice of DNA filter elution. Pharmacol. Ther. 1991, 49, 55-77.
37. Robertson, M. L.; Eastmond, D. A.; Smith, M. T. Two benzene metabolites, catechol and hydroquinone, produce a synergistic induction of micronuclei and toxicity in cultured human lymphocytes. Mutat. Res. 1991, 249, 201-209.
38. Ronconi, L.; Maccato, C.; Barreca, D.; Saini, R.; Zancato, M.; Fregona, D. Gold(III) dithiocarbamate derivatives of N-methylglycine: an experimental and theoretical investigation. Polyhedron 2005, 24, 521-531.
39. Wang, X.; Zhang, Z.; Li, X. Role of survivin on the apoptosis of lung cancer cell line induced by chemotherapeutic drugs. Zhongguo Yaolixue Tongbao 2002, 18, 144-148.
40. Clarke, M. J. Oncological Implications of the Chemistry of Ruthenium. In Metal Ions in Biological Systems; Siegel, H., Ed.; Marcel Dekker Inc.: New York, 1980; vol. 11, pp 231-283.
41. Schafer, F. Q.; Buettner, G. R. Redox environment of the cell as viewed through the redox state of the glutathione disulfide/glutathione couple. Free Radical Biol. Med. 2001, 30, 1191-1212.
42. Marzano, C.; Baccichetti, F.; Trevisan, A.; Giovagnini, L.; Fregona, D. Cytotoxicity and DNA damage induced by a new Pt(II) complex with pyridine and dithiocarbamate. Chem.-Biol. Interact. 2002, 140, 215-219.
43. Minko, I. G.; Zou, Y.; Lloyd, R. S. Incision of DNA-protein crosslinks by UvrABC nuclease suggests a potential repair pathway involving nucleotide excision repair. Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 1905-1909.
44. 2]Cl with human blood plasma, red cells, and lipoproteins. J. Inorg. Biochem. 1987, 31, 267-281.
45. Smith, W. E.; Reglinski, J.; Hoey, S.; Brown, D. H.; Sturrock, R. D. Action of sodium gold(I) thiomalate on erythrocyte membrane. Inorg. Chem. 1990, 29, 5190-5196.
46. Zhang, Y.; Hess, E. V.; Pryhuber, K. G.; Dorsey, J. G.; Tepperman, K.; Elder, R. C. Gold binding in red blood cells. Inorg. Chim. Acta 1995, 229, 271-280.
47. Metal Complexes in Cancer Chemotherapy; Keppler, B., Ed.; VCH: Weinheim, 1993.
48. Orvig, C.; Abrams, M. J. Medicinal Inorganic Chemistry. Chem. Rev. 1999, 99 (Special Issue), 2201-2842.
49. Gran, G. Determination of the equivalence point in potentiometric titrations. II. Analyst 1952, 77, 661-671.
50. Midgley, D.; Torrance, K. Potentiometric Water Analysis, 2nd ed.; John Wiley & Sons: Chichester, 1991.
51. Maccà, C.; Soldà, L. pH-Static techniques in volumetric analysis. 11. Experimental study of pH-static acid-base titrations. Electroanalysis 2002, 14, 63-70.
52. 2(phen)(dbm) (phen = 1, 10-phenanthroline; dbm = dibutyl maleate): (spectro)electrochemistry and theoretical considerations. J. Chem. Soc., Dalton Trans. 1999, 6, 965-970.
53. Valenzeno, D. P.; Arriaga, E.; Trank, J.; Tarr, M. Membrane potential can influence the rate of membrane photomodification. Photochem. Photobiol. 1993, 57, 996-999.