Chemical behavior and in vitro activity of mixed phosphine gold(I) compounds on melanoma cell lines

Journal of Medicinal Chemistry

Volumn 51, Issue 6, 2008, Pages 1584-1591

  Caruso, Francesco ^a   Pettinari, Claudio ^b   Paduano, Francesco ^d   Villa, Raffaella ^d   Marchetti, Fabio ^b   Monti, Elena ^e   Rossi, Miriam ^c  

^a CATHOLIC UNIVERSITY   (Italy)

^b UNIVERSITY OF CAMERINO   (Italy)

^c VASSAR COLLEGE   (United States)

^d NATIONAL CANCER INSTITUTE   (Italy)

^e UNIVERSITY OF INSUBRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,2 BIS(DIPHENYLPHOSPHINO)ETHANE; CATION; CHLOROTRIPHENYLPHOSPHINE 1,3 BIS(DIPHENYLPHOSPHINO)PROPANEGOLD(I); DIMETHYL SULFOXIDE; ETHANE; GOLD; HYPOCHLORITE; PHOSPHINE; PHOSPHINE OXIDE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ANIMAL CELL; ARTICLE; CONTROLLED STUDY; DECOMPOSITION; DENSITY FUNCTIONAL THEORY; DOSE RESPONSE; DRUG ACTIVITY; DRUG OXIDATION; DRUG STRUCTURE; ELECTROSPRAY MASS SPECTROMETRY; GEOMETRY; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MELANOMA CELL; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

CELL LINE, TUMOR; CELL PROLIFERATION; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; MELANOMA; MODELS, MOLECULAR; MOLECULAR STRUCTURE; ORGANOGOLD COMPOUNDS; PHOSPHINES; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 41149164834     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm700978a     Document Type: Article

References (63)

1. Zhang, C. X.; Lippard, S. J. New metal complexes as potential therapeutics. Curr. Opin. Chem. Biol. 2003, 7, 481-489.
2. Guo, Z.; Sadler, P. J. Medicinal inorganic chemistry. Adv. Inorg. Chem. 2000, 49, 183-306.
3. Shaw, C. F., III. Gold-based therapeutic agents. Chem. Rev. 1999, 99, 2589-2600.
4. Tiekink, E. R. T. Gold derivatives for the treatment of cancer. Crit. Rev. Oncol. Hematol. 2002, 42, 225-248.
5. Simon, T. M.; Kunishima, D. H.; Vibert, G. J.; Lorber, A. Screening trial with the coordinated gold compound auranofin using mouse lymphocytic leukemia P388. Cancer Res. 1981, 41, 94-97.
6. Mirabelli, C. K.; Johnson, R. K.; Sung, C.-M.; Faucette, L. F.; Muirheard, K.; Crooke, S. T. Evaluation of the in vivo antitumor activity and in vitro cytotoxic properties of Auranofin, a coordinated gold coumpound, in murine tumor models. Cancer Res. 1985, 45, 32-39.
7. Mirabelli, C. K.; Johnson, R. K.; Hill, D. T.; Faucette, L. F.; Girard, G. R.; Kuo, G. Y.; Sung, C.-M.; Crooke, S. T. Correlation of the in vitro cytotoxic and in vivo antitumor activities of Gold (I) coordination complexes. J. Med. Chem. 1986, 29, 218-223.
8. Berners-Price, S. J.; Girard, G. R.; Hill, D. T.; Sutton, B. M.; Jarret, P. S.; Faucette, L. F.; Johnson, R. K.; Mirabelli, C. K.; Sadler, P. J. Cytotoxicity and antitumor activity of some tetrahedral bis. (diphosphino)gold(I) chelates. J. Med. Chem. 1990, 33, 1386-1392.
9. Rigobello, P.; Messori, L.; Marcon, G.; Cinellu, A. M.; Bragadin, M.; Folda, A.; Scutari, G.; Bindoli, A. Gold complexes inhibit mitochondrial thioredoxin reductase: Consequences on mitochondrial functions. J. Inorg. Biochem. 2004, 98, 1634-1641.
10. Rigobello, P.; Scutari, G.; Folda, A.; Bindoli, A. Mitochondrial thioredoxin reductase inhibition by gold(I) compounds and concurrent stimulation of permeability transition and release of cytochrome c. Biochem. Pharmacol. 2004, 67, 689-696.
11. Hoke, G. D.; Rush, G. F. Mechanism of alterations in isolated rat liver mitochondrial function induced by gold complexes of bidentate phosphines. J. Biol. Chem. 1988, 263, 11203-11210.
12. Barnard, P. J.; Baker, M. V.; Berners-Price, S. J.; Day, D. A. Mitochondrial permeability transition induced by dinuclear gold(I)-carbene complexes: Potential new antimitochondrial antitumour agents. J. Inorg. Biochem. 2004, 98, 1642-1647.
13. McKeage, M. J. Gold opens mitochondrial pathways to apoptosis. Br. J. Pharmacol. 2002, 136, 1081-1082.
14. Ly, J. D.; Grubb, D. R.; Lawen, A. The mitochondrial membrane potential (deltapsi. (m)) in apoptosis; An update. Apoptosis 2003, 8, 115-128.
15. Zhou, L. L.; Zhou, L. Y.; Luo, K. Q.; Chang, D. C. Smac/DIABLO and cytochrome c are released from mitochondria through a similar mechanism during UV-induced apoptosis. Apoptosis 2005, 10, 289-299.
16. Garber, K. Targeting mitochondria emerges as therapeutic strategy. J. Natl. Cancer Inst. 2005, 97, 1800-1801.
17. Bras, M.; Queenan, B.; Susin, S. A. Programmed cell death via mitochondria: Different modes of dying. Biochemistry 2005, 70, 231-239.
18. Mohamad, N.; Gutierrez, A.; Nunez, M.; Cocca, C.; Martin, G.; Cricco, G.; Medina, V.; Rivera, E.; Bergoc, R. Mitochondrial apoptotic pathways. Biocell 2005, 29, 149-161.
19. Caruso, F.; Rossi, M.; Tanski, J.; Pettinari, C.; Marchetti, F. Antitumor activity of the mixed phosphine gold species chlorotriphenylphosphine-1,3-bis. (diphenylphosphino)propanegold(I). J. Med. Chem. 2003, 46, 1737-1742.
20. Caruso, F.; Villa, R.; Rossi, M.; Pettinari, C.; Paduano, F.; Pennati, M.; Daidone, M. G.; Zaffaroni, N. Mitochondria are primary targets in apoptosis induced by the mixed phosphine gold species chlorotriphenylphosphine-1,3-bis. (diphenylphosphino)propanegold(I) in melanoma cell lines. Biochem. Pharmacol. 2006, 6, 773-781.
21. Schmidbaur, H.; Dziwok, K.; Grohmann, A.; Mueller, G. Further evidence for attractive interactions between gold(I) centers in binuclear complexes. Chem. Ber. 1989, 122, 893-895.
22. (a) Elder, R. C.; Zeiher, E. H. K.; Onady, M.; Whittle, R. R. Nearly regular tetrahedral geometry in a gold(I)-phosphine complex. X-ray crystal structure of tetrakis. (methyldiphenylphosphine)-gold(I) hexafluorophosphate. J. Chem. Soc., Chem. Commun. 1981, 900-901.
23. 4]. J. Chem. Soc., Chem. Commun. 1980, 1031-1033.
24. (c) Parish, R. V.; Rush, J. D. Gold-197 Mössbauer spectra of two-, three-, and four-coordinate gold(I) complexes. Chem. Phys. Lett. 1979, 63, 37-39.
25. (d) Mays, M. J.; Vergnano, P. A. Structure and bonding in gold(I) compounds. A phosphorus-31 nuclear magnetic study of the structure of some gold(I) phosphine complexes in solution. J. Chem. Soc., Dalton Trans. 1979, 1112-1115.
26. 31P NMR study of tertiary phosphine complexes of gold(I). J. Chem. Soc., Chem. Commun. 1979, 218-219.
27. 1H} nuclear magnetic resonance spectroscopy. J. Chem. Soc., Dalton Trans. 1981, 2098-2104.
28. (g) Muir, J. A.; Muir, M. M.; Arias, S.; Campana, C. F.; Dwight, S. K. Structure of the monoclinic form of thiocyanato tris. (triphenylphosphine) gold(I) monohydrate. Acta Crystallogr. 1982, 38B, 2047-2049.
29. (h) Uson, R.; Laguna, A.; Vicente, J.; Garcia, J.; Jones, P. G.; Sheldrick, G. M. Preparation of three- and four-coordinate gold(I) complexes; crystal structure of bis[o-phenylenebis. (dimethylarsine)]gold(I) bis. (pentafluorophenyl)aurate(I). J. Chem. Soc., Dalton Trans. 1981, 655-657.
30. 2O. Inorg. Chim. Acta 1984, 81, 169-174.
31. 2O. Inorg. Chim. Acta 1984, 81, 151-154.
32. (b) Berners-Price, S. J.; Mazid, M. A.; Sadler, P. J. Stable gold(I) complexes with chelate rings: Solution studies of bis. (phosphino) ethane complexes and X-ray crystal structure of bis[1,2-bis. (diphenylphosphino)ethane] gold(I) hexafluoroantimoniate-acetone (1/1). J. Chem. Soc., Dalton Trans. 1984, 96, 9-974.
33. 2Cl: a chelated copper(I) complex with tetrahedral stereochemistry. Rate of inversion compared with those of isostructural silver(I) and gold(I) complexes. Inorg. Chem. 1986, 25, 596-599.
34. (d) Berners-Price, S. J.; Sadler, P. J. Gold(I) complexes with bidentate tertiary phosphine ligands: Formation of annular vs tetrahedral chelated complexes. Inorg. Chem. 1986, 25, 3822-3827.
35. + induced by thiols and blood Plasma. Inorg. Chem. 1987, 26, 3074-3077.
36. 4)]. Inorg. Chem. 2000, 39, 680-687.
37. (b) Bardaji', M.; Laguna, A.; Orera, V. M.; Villacampa, M. D. Synthesis, structural characterization, and luminescence studies of gold(I) and gold(III) complexes with a triphosphine ligand. Inorg. Chem. 1998, 37, 5125-5130.
38. (c) Bardaji', M.; Laguna, A.; Vicente, J.; Jones, P. G. Synthesis of luminescent gold(I) and gold(III) complexe with a triphosphine ligand. Inorg. Chem. 2001, 40, 2675-2681.
39. Cooper, M. K.; Mitchell, L. E.; Henrick, K.; McPartlin, M.; Scott, M. The synthesis and X-ray structure analysis of dichloro{1,3-bis. (diphenylphosphino)propane}digold(I). Inorg. Chim. Acta 1984, 84, L9-L10.
40. Babior, B. M.; Kipnes, R. S.; Curnutte, J. T. Biological defense mechanisms. The production by leukocytes of superoxide, a potential bactericidal agent. J. Clin. Invest. 1973, 52, 741-744.
41. Attar, S.; Nelson, J. H.; Bearden, W. H.; Alcock, N. W.; Solujic, L.; Milosavljevic, E. B. Phosphole complexes of gold(III) halides: Synthesis, structure, electrochemistry and ligand redistribution reactions. Polyhedron 1991, 10, 1939-1949.
42. Serafimova, I. M.; Hoggard, P. E. The photochemistry of chloro. (triphenylphosphine)gold(I) and trichlorotriphenylphosphine)gold(III) in chloroform. Inorg. Chim. Acta 2002, 338, 105-110.
43. Bayler, A.; Schier, A.; Schmidbaur, H. Four-coordinate gold(I), silver(I), and copper(I) complexes with a large-span chiral ditertiary phosphine ligand. Inorg. Chem. 1998, 37, 4353-4359.
44. Thompson, J. F.; Scolyer, R. A.; Kefford, R. F. Cutaneous melanoma. Lancet 2005, 365, 687-701.
45. Grossman, D.; Altieri, D. C. Drug resistance in melanoma: mechanisms apoptosis and new potential therapeutic targets. Cancer Metastasis Rev. 2001, 20, 3-11.
46. Berners-Price, S. J.; Bowen, R. J.; Galettis, P.; Healy, P. C.; McKeage, M. J. Structural and solution chemistry of gold(I) and silver(I) complexes with bidentate pyridil phosphines: Selective antitumor agents. Coord. Chem. Rev. 1999, 185-186, 823-826.
47. Mirabelli, C. K.; Hill, D. T.; Faucette, L. F.; McCabe, F. L.; Girard, G. R.; Bryan, D. B.; Sutton, B. M.; Barus, J. O.; Crooke, S. T.; Johnson, R. K. Antitumor activity of bis. (diphenylphosphino)alkanes, their gold(I) coordination complexes, and related compounds. J. Med. Chem. 1987, 30, 2181-2190.
48. Berners-Price, S. J.; Mirabelli, C. K.; Johnson, R. K.; Mattern, M. R.; McCabe, F. L.; Faucette, L. F.; Sung, C.-M.; Mong, S.-M.; Sadler, P. J.; Crooke, S. T. In vivo antitumor activity and in vitro cytotoxic properties of bis[1,2-bis. (diphenylphosphino)-ethane]gold(I) chloride. Cancer Res. 1986, 46, 5486-5493.
49. Struck, R. F.; Shealy, Y. F. Tertiary phosphines and phosphine oxides containing a 2-haloethyl group. J. Med. Chem. 1966, 9, 414-416.
50. Ronconi, L.; Marzano, C.; Zanello, P.; Corsini, M.; Miolo, G.; Macca, C.; Trevisan, A.; Fregona, D. Gold (III) dithiocarbamate derivatives for the treatment of cancer: Solution chemistry, DNA binding, and hemolytic properties. J. Med. Chem. 2006, 49, 1648-1657.
51. De Wall, S. L.; Painter, C.; Stone, J. D.; Bandaranayake, R.; Wiley, D. C.; Mitchison, T. J.; Stern, L. J.; DeDecker, B. S. Noble metals strip peptides from class II MHC proteins. Nat. Chem. Biol. 2006, 2, 197-201.
52. Goebel, C.; Kubicka-Muranyi, M.; Tonn, T.; Gonzalez, J.; Gleichmann, E. Phagocytes render chemicals immunogenic: Oxidation of gold(I) to the T cell-sensitizing gold(III) metabolite generated by mononuclear phagocytes. Arch. Toxicol. 1995, 69, 450-459.
53. - in the formation of gold metabolites. Metal Based Drugs 1994, 1, 351-362.
54. Senko, M. W. IsoPro isotopic abundance simulator, v. 2.1; National High Magnetic Field Laboratory, Los Alamos National Laboratory: Los Alamos, NM.
55. Camalli, M.; Spagna, R. CAOS program. J. Appl. Crystallogr. 1994, 27, 861-862.
56. Delley, B. An all-electron numerical method for solving the local density functional for polyatomic molecules. J. Chem. Phys. 1990, 92, 508-517.
57. Caruso, F.; Rossi, M.; Opazo, C.; Pettinari, C. Structural features of antitumor gold(I)-phosphine derivatives analyzed with theoretical methods. J. Argen. Chem. Soc. 2004, 92, 119-124.
58. Perdew, J. P.; Chevary, J. A.; Vosko, S. H.; Jackson, K. A.; Pederson, M. R.; Singh, D. J.; Fiolhais, C. Atoms, molecules, solids, and surfaces: applications of the generalized gradient approximation for exchange and correlation. Phys. Rev. B 1992, 46, 6671-6687.
59. Delley, B. Fast calculation of electrostatics in crystals and large molecules. J. Phys. Chem. 1996, 100, 6107-6110.
60. Badaracco, G.; Corsi, A.; Maisto, A.; Natali, P. G.; Storace, G.; Zupi, G. Expression of tumor-associated antigens and kinetic profile of two melanoma cell lines. Cytometry 1981, 2, 63-69.
61. Supino, R.; Mapelli, E.; Sanfilippo, O.; Silvestro, L. Biological and enzymatic features of human melanoma clones with different invasive potential. Melanoma Res. 1992, 2, 377-384.
62. Formelli, F.; Rossi, C.; Supino, R.; Parmiani, G. In vivo characterization of a doxorubicin resistant B16 melanoma cell line. Br. J. Cancer 1986, 54, 223-33.
63. Perez, R. P.; Godwin, A. K.; Handel, L. M.; Hamilton, T. C. A comparison of clonogenic, microtetrazolium and sulforodamine B assays for determination of cisplatin cytotoxicity in human ovarian carcinoma cell lines. Eur. J. Cancer 1993, 29A, 395-399.