Gold complexes as prospective metal-based anticancer drugs

Histology and Histopathology

Volumn 23, Issue 1, 2008, Pages 101-108

  Milacic, V ^a   Fregona, D ^b   Dou, Q P ^a  

^a WAYNE STATE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^b UNIVERSITY OF PADOVA   (Italy)

Author keywords

Anticancer drugs; Gold complexes; Metal based drugs

Indexed keywords

MUS MUSCULUS;

ANTINEOPLASTIC AGENT; GOLD DERIVATIVE; PROTEASOME; UBIQUITIN;

ANIMAL; DRUG EFFECT; DRUG SCREENING; HUMAN; MOUSE; NEOPLASM; NUDE MOUSE; PHYSIOLOGY; REVIEW; SIGNAL TRANSDUCTION;

ANIMALS; ANTINEOPLASTIC AGENTS; GOLD COMPOUNDS; HUMANS; MICE; MICE, NUDE; NEOPLASMS; PROTEASOME ENDOPEPTIDASE COMPLEX; SIGNAL TRANSDUCTION; UBIQUITIN; XENOGRAFT MODEL ANTITUMOR ASSAYS;

EID: 35748937356     PISSN: 02133911     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Review

References (58)

1. Adams J. (2003). Potential for proteasome inhibition in the treatment of cancer. Drug Discov. Today 8, 307-315.
2. Adams J., Palombella V.J., Sausville E.A., Johnson J., Destree A., Lazarus D.D., Maas J., Pien C.S., Prakash S. and Elliott P.J. (1999). Proteasome inhibitors: a novel class of potent and effective antitumor agents. Cancer Res. 59, 2615-2622.
3. Alderden R.A., Hall M.D. and Hambley T.W. (2006). The discovery and development of cisplatin. J. Chem. Edu. 83, 728-734.
4. Almond J.B. and Cohen G.M. (2002). The proteasome: a novel target for cancer chemotherapy. Leukemia 16, 433-443.
5. An B., Goldfarb R.H., Siman R. and Dou Q.P. (1998). Novel dipeptidyl proteasome inhibitors overcome Bcl-2 protective function and selectively accumulate the cyclin dependent kinase inhibitor p27 and induce apoptosis in transformed, but not normal, human fibroblasts. Cell Death Differ. 5, 1062-1075.
6. Bodenner D.L., Dedon P.C., Keng P.C. and Borch R.F. (1986). Effect of diethyldithiocarbamate on cis-diamminedichloroplatinum(II)-induced cytotoxicity, DNA cross-linking, and gamma-glutamyl transpeptidase inhibition. Cancer Res. 46, 2745-2750.
7. Borch R.F., Dedon P.C., Gringeri A. and Montine T.J. (1988). Inhibition of platinum drug toxicity by diethyldithiocarbamate. In: Platinum and other metal coordination compounds in cancer chemotherapy. Nicolini M. (ed). Martinus Nijhoff. Boston. pp 216-227.
8. Bruni B., Guerri A., Marcon G., Messori L. and Orioli P. (1999). Structure and cytotoxic properties of some selected gold(III) complexes. Croatica Chemica Acta 72, 221-229.
9. Calamai P., Carotti S., Guerri A., Mazzei T., Messori L., Mini E., Orioli P. and Speroni G.P. (1998). Cytotoxic effects of gold(III) complexes on established human tumor cell lines sensitive and resistant to cisplatin. Anticancer Drug Res. 13, 67-80.
10. Ciechanover A. (1998). The ubiquitin-proteasome pathway: on protein death and cell life. EMBO J. 17, 7151-7160.
11. Ciechanover A. (2006). The ubiquitin proteolytic system: from a vague idea, through basic mechanisms, and onto human diseases and drug targeting. Neurology 66(2 Suppl 1), S7-S19.
12. Criado J.J., Manzano J.L. and Rodriguez-Fernandez E. (2003). New organotropic compounds. Synthesis, characterization and reactivity of Pt(II) and Au(III) complexes with bile acids: DNA interactions and 'in vitro' anticancer activity. J. Inorg. Biochem. 96, 311-320.
13. Crooke S.T. and Mirabelli C.K. (1983). Molecular mechanisms of action of auranofin and other gold complexes as related to their biologic activities. Am. J. Med. 75, 109-113.
14. Daniel K.G., Gupta P., Harbach R.H., Guida W.C. and Dou Q.P. (2004). Organic copper complexes as a new class of proteasome inhibitors and apoptosis inducers in human cancer cells. Biochem. Pharmacol. 67, 1139-1151.
15. Daniel K.G., Chen D., Orlu S., Cui Q.C., Miller F.R. and Dou Q.P. (2005). Clioquinol and pyrrolidine dithiocarbamate complex with copper to form proteasome inhibitors and apoptosis inducers in human breast cancer cells. Breast Cancer Res. 7, R897-R908.
16. Dinger M.B. and Henderson W. (1998a). Organogold(III) metallacyclic chemistry. Part 2. Synthesis and characterisation of the first gold(III) ureylene complexes. J. Organomet. Chem. 557, 231-241.
17. Dinger M.B. and Henderson W. (1998b). Organogold(III) metallacyclic chemistry. Part 4. Synthesis, characterisation, and biological activity of gold(III)-thiosalicylate and -salicylate complexes. J. Organomet Chem. 560, 233-243.
18. Dou Q.P. and Li B. (1999). Proteasome inhibitors as potential novel anticancer agents. Drug Resist. Update 2, 215-223.
19. Dou Q.P. and Nam S. (2000). Pharmacological proteasome inhibitors and their therapeutic potential. Exp. Opin. Ther. Patents 10, 1263-1272.
20. Eckhardt S. (2002). Recent progress in the development of anticancer agents. Curr. Med. Chem. Anticancer Agents 2, 419-439.
21. Forestier J. (1935). Rheumatoid arthritis and its treatment with gold salts - results of six years' experience. J. Lab. Clin. Med. 20, 827-840.
22. Fricker S.P. (1999). A screening strategy for metal antitumor agents as exemplified by gold(III) complexes. Metal Based Drugs. 6, 291-300.
23. Fricker S.P., Skerjl R., Cameron B.R., Mosi R. and Zhu Y. (2003). Recent developments in gold drugs 2003; AnorMED Inc, Langley BC, V2Y 1N5, Canada. GOLD 2003.
24. He X.M. and Carter D.C. (1992). Atomic structure and chemistry of human serum albumin. Nature 358, 209-215.
25. Huang H., Zhu L., Reid B.R., Drobny G.P. and Hopkins P.B. (1995). Solution structure of a cisplatin-induced DNA interstrand cross-link. Science 270, 1842-1845.
26. Kostova I. (2006). Gold coordination complexes as anticancer agents. Anticancer Agents Med. Chem. 6, 19-32.
27. Lopes U.G., Erhardt P., Yao R. and Cooper G.M. (1997). p53-dependent induction of apoptosis by proteasome inhibitors. J. Biol. Chem. 272, 12893-12896.
28. Marcon G., Carotti S., Coronnello M, Messori L., Mini E., Orioli P., Mazzei T., Cinellu M.A. and Minghetti G. (2002). Gold(III) complexes with bipyridyl ligands: solution chemistry, cytotoxicity, and DNA binding properties. J. Med. Chem. 45, 1672-1677.
29. Marcon G., Messori L, Orioli P., Cinellu M.A. and Minghetti G. (2003). Reactions of gold(III) complexes with serum albumin. Eur. J. Biochem. 270, 4655-4661.
30. Marzano C., Bettio F., Baccichetti F., Trevisan A., Giovagnini L. and Fregona D. (2004). Antitumor activity of a new platinum(II) complex with low nephrotoxicity and genotoxicity. Chem. Biol. Interact. 148, 37-48.
31. McKeage M.J., Maharaj L. and Berners-Price S.J. (2002). Mechanisms of cytotoxicity and antitumor activity of gold(I) phosphine complexes: the possible role of mitochondria. Coord. Chem. Rev. 232, 127-135.
32. Messori L., Abbate F., Marcon G., Orioli P., Fontani M., Mini E., Mazzei T., Carotti S., O'Connell T. and Zanello P. (2000). Gold(III) complexes as potential antitumor agents: solution chemistry and cytotoxic properties of some selected gold(III) compounds. J. Med. Chem. 43, 3541-3548.
33. Messori L., Marcon G. and Orioli P. (2003). Gold (III) compounds as a new family of anticancer drugs. Bioinorg. Chem. Appl 1, 177-187.
34. Milacic V., Chen D., Ronconi L., Landis-Piwowar K.R., Fregona D. and Dou Q.P. (2006). A novel anticancer gold(III) dithiocarbamate compound inhibits the activity of a purified 20S proteasome and 26S proteasome in human breast cancer cell cultures and xenografts. Cancer Res. 66, 10478-10486.
35. Mirabelli C.K., Johnson R.K., Hill D.T., Faucette L.F., Girard G.R., Kuo G.Y., Sung C.M. and Crooke S.T. (1986). Correlation of the in vitro cytotoxic and in vivo antitumor activities of gold(I) coordination complexes. J. Med. Chem. 29, 218-223.
36. Nalepa G., Rolfe M. and Harper J.W. (2006). Drug discovery in the ubiquitin-proteasome system. Nat. Rev. Drug Discov. 5, 596-613.
37. Ni Dhubhghail O.M. and Sadler P.J. (1993). Gold complexes in cancer chemotherapy. In: Metal complexes in cancer chemotherapy. Keppler B.K. (ed). VCH, Weinheim. pp 221-248.
38. Novelli F., Recine M., Sparatore F. and Juliano C. (1999). Gold complexes as antimicrobial agents. Farmaco. 54, 232-236.
39. Orlowski R.Z. and Dees E.C. (2002a). The role of the ubiquitination-proteasome pathway in breast cancer: Applying drugs that affect the ubiquitin-proteasome pathway to the therapy of breast cancer. Breast Cancer Res. 5, 1-7.
40. Orlowski R.Z., Eswara J.R., Lafond-Walker A., Grever M.R., Orlowski M. and Dang C.V. (1998). Tumor growth inhibition induced in a murine model of human Burkitt's lymphoma by a proteasome inhibitor. Cancer Res. 58, 4342-4348.
41. Orlowski R.Z., Stinchcombe T.E., Mitchell B.S., Shea T.C., Baldwin A.S., Stahl S., Adams J., Esseltine D.L., Elliott P.J., Pien C.S., Guerciolini R., Anderson J.K., Depcik-Smith N.D., Bhagat R., Lehman M.J., Novick S.C., O'Connor O.A. and Soignet SL. (2002b). Phase I trial of the proteasome inhibitor PS-341 in patients with refractory hematologic malignancies. J. Clin. Oncol. 20, 4420-4427.
42. Rigobello M.P., Scutari G., Folda A. and Bindoli A. (2004). Mitochondrial thioredoxin reductase inhibition by gold(I) compounds and concurrent stimulation of permeability transition and release of cytochrome c. Biochem. Pharmacol. 67, 689-696.
43. Ronconi L., Giovagnini L., Marzano C., Bettio F., Graziani R., Pilloni G. and Fregona D. (2005). Gold dithiocarbamate derivatives as potential antineoplastic agents: design, spectroscopic properties and in vitro antitumor activity. Inorg. Chem. 44, 1867-1881.
44. Ronconi L., Marzano C., Zanello P., Corsini M., Miolo G., Macca C., Trevisan A. and Fregona D. (2006). Gold (III) dithiocarbamate derivatives for the treatment of cancer: solution chemistry, DNA binding, and hemolytic properties. J. Med. Chem. 49, 1648-1657.
45. Sadler P.J. (1982). The comparative evaluation of the physical and chemical properties of gold compounds. J. Rheumatol. Suppl. 8, 71-78.
46. Sadler P.J. and Guo Z. (1998). Metal complexes in medicine: Design and mechanism of action. Pure Appl. Chem. 70, 863-871.
47. Sadler P.J. and Sue R.E. (1994). The chemistry of gold drugs. Metal Based Drugs 1, 107-144.
48. Seemuller E., Lupas A., Stock D., Lowe J., Huber R. and Baumeister W. (1995). Proteasome from Thermoplasma acidophilum: a threonine protease. Science 268, 579-582.
49. Simon T.M., Kunishima D.H., Vibert G.J. and Lorber A. (1979). Cellular antiproliferative action exerted by auranofin. J. Rheumatol. Suppl. 5, 91-97.
50. Shaw C.F. III (1999). The biochemistry of gold. In: Gold: Progress in chemistry, biochemistry and technology. Schmidbaur H. (ed) John Wiley & Sons. New York. pp 260-308.
51. Szweda P.A., Friguet B. and Szweda L.I. (2002). Proteolysis, free radicals, and aging. Free Radic. Biol. Med. 33, 29-36.
52. Tiekink E.R. (2003). Gold derivatives for cancer treatment. Bioinorg. Chem. Applns. 53, 1-9.
53. Troyano A., Fernandez C., Sancho P., de Blas E. and Aller P. (2001). Effect of glutathione depletion on antitumor drug toxicity (apoptosis and necrosis) in U-937 human promonocytic cells. The role of intracellular oxidation. J. Biol. Chem. 276, 47107-47115.
54. Wang Y., He Q.Y., Sun R.W., Che C.M. and Chiu J.F. (2005). Gold(III) porphyrin 1a induced apoptosis by mitochondrial death pathways related to reactive oxygen species. Cancer Res. 65, 11553-11564.
55. Ward J.R. (1988). Role of disease-modifying antirheumatic drugs versus cytotoxic agents in the therapy of rheumatoid arthritis. Am. J. Med. 85, 39-44.
56. Wong E. and Giandomenico C.M. (1999). Current status of platinum-based antitumor drugs. Chem Rev. 99, 2451-2466.
57. Zhu C., Raber J. and Eriksson L.A. (2005). Hydrolysis process of the second generation platinum-based anticancer drug cisamminedichlorocyclohexylamineplatinum(II). J. Phys. Chem B. 109, 12195-12205.
58. Zou J., Guo Z., Parkinson J.A., Chen Y. and Sadler P.J. (1999). Gold(III)-induced oxidation of glycine. Chem. Commun. 1359-1360.