Synthesis of apoptosis-inducing iminophosphorane organogold(III) complexes and study of their interactions with biomolecular targets

Inorganic Chemistry

Volumn 48, Issue 4, 2009, Pages 1577-1587

  Shaik, Neha ^a   Martínez, Alberto ^a   Augustin, Idline ^a   Giovinazzo, Hugh ^b   Varela Ramírez, Armando ^b   Sanaú, Mercedes ^c   Aguilera, Renato J ^b   Contel, María ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF TEXAS AT EL PASO   (United States)

^c UNIVERSITY OF VALENCIA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CYTOCHROME C; LIGAND; ORGANOGOLD COMPOUND; PHOSPHORANE DERIVATIVE; THIOREDOXIN REDUCTASE;

APOPTOSIS; ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; DRUG STABILITY; HUMAN; SOLUBILITY; SYNTHESIS; TUMOR CELL LINE; DRUG EFFECTS;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CYTOCHROMES C; DRUG STABILITY; HUMANS; LIGANDS; MOLECULAR STRUCTURE; ORGANOGOLD COMPOUNDS; PHOSPHORANES; SOLUBILITY; THIOREDOXIN-DISULFIDE REDUCTASE;

EID: 64349103236     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic801925k     Document Type: Article

References (62)

1. Kelland. L. Nat. Rev. 2007, 7, 573.
2. Bruijnincx, P. CA.; Sadler. P. J. Curr. Opin. Chem. Biol. 2008, 12, 197.
3. Reedijk, J. Platinum Met. Rev. 2008, 52 (1), 2.
4. Lippert, B. Cisplatin: chemistry and biochemistry of a leading anticancer drug; Wiley-VCH: Zurich, 1999.
5. Lippert. B. Coord. Chem. Rev. 1999, 182, 263.
6. Jamieson, E. R.; Lippard, S. J. Chem. Rev. 1999, 99, 2467.
7. Dong, Y.; Berners-Price, S. J.; Thorburn, D. R.; Antalis, T.; Dickinson, J.; Hurst. T.; Qiu, L.; Khoo, S. K.; Parsons, P. C. Biochem. Pharmacol. 1997, .55, 1673.
8. Guo, Z.; Sadler, P. J. Angew. Chem., Int. Ed. 1999, 38, 1512.
9. Parish, R. V.; Cottrill, S. M. Gold Bull. 1987, 20, 3; and references therein.
10. Tiekink. E. R. T. Bioinorg. Chem. Appl. 2003, 1, 53.
11. Shaw. C. F., III Chem. Rev. 1999, 99, 2589.
12. Tiekink, E. R. T. Inflammopharmacology. 2008, 16, 138.
13. Wang, X.; Guo, Z. Dalton Trans. 2008, 1521.
14. Casini, A.; Hartinger, C.; Gabbiani, C.; Mini, E.; Dyson, P. J.; Keppler, B. K.; Messori, L. J. Inorg. Biochem. 2008, 102, 564.
15. Milacic, V.; Fregona, D.; Dou, Q. P. Histol. Histopathol. 2008, 23, 101.
16. Sun, W.-Y.; Ma, D.-L.; Wong, E. L.-H.; Che, C.-M. Dalton Trans. 2007, 4884.
17. Gabbiani. C.; Casini. A.; Messori, L. Gold Bull. 2007, 40, 73.
18. Barnard, P. J.; Berners-Price, S. J. Coord. Client. Rev. 2007, 251, 1889.
19. Messori, L.; Chiara. G. Met. Compd. Cancer Chemother. 2005, 355.
20. Tiekink, E. R. Gold Bull. 2003, 36, 117.
21. Hickey, J. L.; Ruhayel, R. A.; Barnard, P. J.; Baker, M. V.; Berners-Price. S.; Filipovska, A. J. Am. Chem. Soc. 2008, 138, 12570.
22. Shi, P.; Jiang. Q.; Lin. J.; Zhao. Y.; Lin, L.; Guo, Z. J. Inorg. Biochem. 2006, 100, 939.
23. Palanichamy, K.; Ontko, A. C. Inorg. Chim. Acta 2006, 359, 44.
24. Marcon. G.; Carotti, S.; Coronnello, M.; Messori. L.; Mini, E.; Orioli, P.: Mazzei, T.; Cinellu. M. A.; Minghetti, G. J. Med. Chem. 2002, 45, 1672.
25. Wang, Y.; He, Q.-Y.; Sun, R. W.-Y.; Che. C.-M.; Chiu, J.-F. Eur. J. pharmacol. 2007, 554, 113.
26. Che. C.-M.; Sun, R. W.-Y.; Ko, C. B.; Zhu, N.; Sun, H. Chem. Commun. 2003, 1718.
27. Aldinucci, D.; Lorenzon. D.; Stefani, L.; Giovagnini, L.; Colombatti. A.; Fregona, D. Anti-Cancer Drugs 2007, 18, 323.
28. Ronconi, L.; Marzano, C.; Zanello, P.; Corsini, M.; Macca, C.; Trevisan, A.; Fregona, D. J. Med. Chem. 2006, 49, 1648.
29. Ronconi, L.; Giovagnini, L.; Marzano, C.; Bettio, F.; Grziani, R.; Pilloni, G.; Fregona. D. Inorg. Chem. 2005, 44, 1867.
30. Kilpin. K. J.; Henderson, W.; Nicholson, B. K. Polyhedron 2007, 26, 434.
31. Kilpin, K. J.; Henderson, W.; Nicholson. B. K. Polyhedron 2007, 26, 204.
32. Casas, J. S.; Castaño, M. V.; Cifuentes, M. C.; Gareía-Monteagudo, J. C.; Sánchez. A.; Soldo, J.; Abram, U. J. Inorg. Biochem. 2004, 98, 1009.
33. Fang, D.; Yang, C.-T.; Ranford, J. D.; Lee, P. F.; Vittal, J. J. Dalton Trans. 2003, 2680.
34. Goss, C. H. A.; Henderson, W.; Wilkins, A. L.; Evans, C. J. Organomet. Chem. 2003, 679, 194.
35. Messori, L.; Abbate, F.; Marcon, G.; Orioli, P.; Fontani, M.; Mini, E.; Mazzei, T.; Carotti, S.; O'Connell, T.; Zanello, P. J. Med. Chem. 2000, 43, 3541.
36. Bucklev, R.; Elsome, A.; Flicker. S.; Henderson, G.; Theobald, B.; Parish, R.; Howe. B.; Kelland. L. J. Med. Chem. 1996, 39, 5208.
37. Li, C. K.-L.; Sun. R. W.-Y.; Kui. S. C.-F.; Zhu, N.; Che, C.-M. Chem. - Eur. J. 2006, 12, 5253.
38. Criado, J. J.; Manzano. J. L.; Rodriguez-Fernández. E. J. Inorg. Biochem. 2003, 96, 311.
39. Carrasco, J.; Criado, J. J.; Macias, R. I.; Manzano, J. L.; Marin, J. J.; Medarde, M.; Rodriguez, E. J. Inore. Biochem. 2001, 84, 287.
40. Cuadrado. J. A.: Zhang. W.; Hang, W.: Majidi, V. J. Environ. Monit. 2000, 2, 355.
41. Carotti, S.; Marcon, G.; Marussich, M.; Mazzei, T.; Messori, L.; Mini, E.; Orioli, P. Chem. Biol. Interact. 2000, 125, 29.
42. Casini, A.; Cinellu. M. A.; Minghetti, G.; Gabbiani, C.; Coronnello, M.; Mini, E.; Messori, L. J. Med. Chem. 2006, 49, 5524.
43. Gabbiani, C.; Casini, A.; Messori, L.; Guerri, A.; Cinellu, M. A.; Minghetti, G.; Corsini, M.; Rosani. C.; Zanello. P.; Arca. M. Inorg. Chem. 2008, 47, 2368.
44. Saggioro, D.; Rigobello, M. P.; Paloschi, L.; Folda, L.; Moggach, S. A.; Parsons. S.; Ronconi. L.; Fregona, D.; Bindoli. A. Chem. Biol. 2007, 14, 1128.
45. Milacic, V.; Chen, D.; Ronconi. L.; Landis-Piwowar, K. R.; Fregona, D.; Dou. Q. P. Cancer Res. 2006, 66, 21.
46. Wang, Y.; He, Q.-Y.; Che, C.-H.; Tsa, S. W.; Sun, R. W.-Y.; Chiu, J.-F. Biochem. Pharmacol. 2008, 75, 1282.
47. Casini, A.; Guerri. A.; Gabbiani, C.; Messori. L. J.Inorg. Biochem. 2008, 102, 995.
48. Aguilar. D.; Contel, M.; Navarro, R.: Urriolabeitia. E. P. Organometallics 2007, 26, 4604.
49. Brown. S. D. J.; Henderson, W.: Kilpin. K. J.; Nicholson, B. K. Inorg. Chim. Acta 2007, 360, 1310.
50. Parish, R. V.; Howe. B. P.; Wright. J. P.; Mack. J.; Pritchard, R. G. Inorg. Chem. 1996, 35, 1659.
51. 2]: 45.1 (s) ppm (to be reported elsewhere).
52. 2O): δ [AuCl(TPPS)]: 33.4 (s) ppm. Sanz, S.; Jones, L. A.; Mohr, F.; Laguna, M. Organometallics 2007, 26, 952.
53. Miranda, S.: Vergara. E.; Mohr, F.; de Vos. D.; Cerrada, E.; Media. A.; Laguna. M. Inorg. Chem. 2008, 47, 5641.
54. 1H} NMR (d6-DMSO): δ [AuCl(PTA)]: -51.4 (s) ppm. Assefa, Z.; McBurnett, G.; Staples, R. J.; Fickler, J. P., Jr.; Assman, B.; Angermaler, K.; Schmidbaur, H. Inorg. Chem. 1995, 34, 75.
55. Montoya, J.; Varela-Ramirez, A.; Estrada, A.; Martinez, L. E.; Garza, K.; Aguilera, R. J. Biochem. Biophys. Res. Commun. 2004, 325, 1517.
56. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D.; Warren, J. T.; Bokesch, H.; Kenney. S.; Boyd, M. R. J. Natl. Cancer. Inst. 1990, 82 (13), 1107.
57. Alley, M. C.; Scudiero, D. A.; Monks, A.; Hursey, M. L.; Czerwinski, M. J.: Fine. D. L.: Abbott. B. J.; Mayo, J. G.; Shoemaker. R. H.; Boyd. M. R. Cancer Res. 1988, 48, 589.
58. Giovagnini, L.; Sitran, S.; Montpoli, M.; Caparrotta, L.; Corsini, M.; Rosani, C.; Zanello, P.; Dou. Q. P.; Fregona, D. Inorg. Chem. 2008, 47, 6336.
59. Wang, Y.; He, Q.-Y.: Sun, R. W.-Y.; Che, C.-M.; Chiu, J.-F. Eur. J. Pharmacol. 2007, 554, 113.
60. Similar spectroscopic changes for interactions of metals with serum proteins have been reported. Timerbaev, A. R.; Hartinger, C. G.; Aleksenko, S. S.; Keppler, B. K. Chem. Rev 2006, 106, 2224; and references therein.
61. We performed a titration of cytochrome c with dithiothreitol DTT (in mol ratios protein/DTT 1:1, 1:3, and 1:5, concentration of protein 5 μm) in buffer containing 0.1 mol % DMSO and the vis - UV spectra shows a shift of the Soret band of the hemo group at 409 to 415 nm but also two characteristic bands at 521 and 550 nm consistent with the reduction of Fe(III) to Fe(II) that we do not see in the experiment of titration of cytochrome c with 2.
62. Trynda-Lemiesz. L.; Keppler, B. K.; Kozlowski, H. J. Inorg. Biochem. 1999, 73, 123.