Synthesis, properties, and antitumor effects of a new mixed phosphine gold(I) compound in human colon cancer cells

Journal of Inorganic Biochemistry

Volumn 124, Issue , 2013, Pages 78-87

  Lupidi, Giulio ^a   Avenali, Luca ^a   Bramucci, Massimo ^a   Quassinti, Luana ^a   Pettinari, Riccardo ^a   Khalife, Hala K ^b   Gali Muhtasib, Hala ^c   Marchetti, Fabio ^d   Pettinari, Claudio ^a  

^a Faculty of Pharmacy   (Italy)

^b AMERICAN UNIVERSITY OF BEIRUT   (Lebanon)

^c LEBANESE UNIVERSITY   (Lebanon)

^d Chemistry Section   (Italy)

Author keywords

Antineoplastic activity; DNA fragmentation; Gold complexes; Phoshine; Spectroscopy

Indexed keywords

ANTINEOPLASTIC AGENT; CASPASE 3; CHLORO[TRIS(TERTBUTYL)PHOSPHINE][CIS 1,2 BIS(DIPHENYLPHOSPHINO)ETHENE]GOLD(I); CISPLATIN; CYTOCHROME C; GOLD COMPLEX; PHOSPHINE; REACTIVE OXYGEN METABOLITE; THIOREDOXIN REDUCTASE; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; COLON CANCER; CONTROLLED STUDY; COVALENT BOND; CYTOTOXICITY; DNA FRAGMENTATION; DRUG SYNTHESIS; G1 PHASE CELL CYCLE CHECKPOINT; HUMAN; HUMAN CELL; IC 50; MITOCHONDRION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; SOLID STATE;

ANTINEOPLASTIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CISPLATIN; COLONIC NEOPLASMS; CYTOTOXINS; GOLD COMPOUNDS; HUMANS; INSECTICIDES; OXIDATION-REDUCTION; PHOSPHINES; REACTIVE OXYGEN SPECIES;

EID: 84877061508     PISSN: 01620134     EISSN: 18733344     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2013.03.014     Document Type: Article

References (61)

1. L. Ronconi, and D. Fregona Dalton Trans. 2009 10670 10680
2. B. Köberle, M.T. Tomicic, S. Usanova, and B. Kaina Biochim. Biophys. Acta 1806 2010 172 182
3. J.M. Piulats, L. Jiménez, X. García del Muro, A. Villanueva, F. Viñals, and J.R. Germà-Lluch Clin. Transl. Oncol. 11 2009 780 786
4. S. Rafique, M. Idrees, A. Nasim, H. Akbar, and A. Athar Biotechnol. Mol. Biol. Rev. 5 2010 38 45
5. P.J. O'Dwyer, J.P. Stevenson, and S.W. Johnson Cisplatin B. Lippert, chemistry and biochemistry of leading anticancer drug: Clinical status of cisplatin, carboplatin and other platinum-based antitumor drugs 1999 Wiley-VCH Zürich 31 72
6. S. Berners-Price E. Alessio, Bioinorganic Medicinal Chemistry: Gold-Based Therapeutic Agents: A New Perspective 2011 Wiley-VCH Verlag GmbH & Co. KGaA Weinheim, Germany
7. I. Ott, and R. Gust Arch. Pharm. 340 2007 117 126
8. P. Köpf-Maier Eur. J. Clin. Pharmacol. 47 1994 1 16
9. X. Wang, and Z. Guo Dalton Trans. 2008 1521 1532
10. I. Kostova Anticancer Agents Med. Chem. 6 2006 19 32
11. C. Marzano, V. Gandin, A. Folda, G. Scutari, A. Bindoli, and M.P. Rigobello Free Radic. Biol. Med. 42 2007 872 881
12. K.P. Bhabak, and G. Mugesh Inorg. Chem. 48 2009 2449 2455
13. C. Chiellini, A. Casini, O. Cochet, C. Gabbiani, G. Ailhaud, C. Dani, L. Messori, and E.Z. Amri Chem. Biodivers. 5 2008 1513 1520
14. L. Oehninger, R. Rubbiani, and I. Ott Dalton Trans. 42 2013 3269 3284
15. A. Casini, and L. Messori Curr. Top. Med. Chem. 11 2011 2647 2660
16. M.J. McKeage, L. Maharaj, and S.J. Berners-Price Coord. Chem. Rev. 232 2002 127 135
17. A. Casini, C. Hartinger, C. Gabbiani, E. Mini, P.J. Dyson, B.K. Keppler, and L. Messori J. Inorg. Biochem. 102 2008 564 575
18. C.F. Shaw III Chem. Rev. 99 1999 2589 2600
19. J.C. Lima, and L. Rodriguez Anticancer Agents Med. Chem. 11 2011 921 928
20. C.K. Mirabelli, R.K. Johnson, D.T. Hill, L.F. Faucette, G.R. Girard, G.Y. Kuo, C.M. Sung, and S.T. Crooke J. Med. Chem. 29 1986 218 223
21. I. Ott Coord. Chem. Rev. 253 2009 1670 1681
22. P.J. Barnard, and S.J. Berners-Price Coord. Chem. Rev. 251 2007 1889 1902
23. M.P. Rigobello, L. Messori, G. Marcon, M.A. Cinellu, M. Bragadin, A. Folda, G. Scutari, and A. Bindoli J. Inorg. Biochem. 98 2004 1634 1641
24. R. Rubbiani, I. Kitanovic, H. Alborzinia, S. Can, A. Kitanovic, L.A. Onambele, M. Stefanopoulou, Y. Geldmacher, W.S. Sheldrick, G. Wolber, A. Prokop, S. Wölfl, and I. Ott J. Med. Chem. 53 2010 8608 8618
25. K.F. Tonissen, and G. Di Trapani Mol. Nutr. Food Res. 53 2009 87 103
26. A.B. Witte, K. Anestål, E. Jerremalm, H. Ehrsson, and E.S. Arnér Free Radic. Biol. Med. 39 2005 696 703
27. E.S. Arnér, H. Nakamura, T. Sasada, J. Yodoi, A. Holmgren, and G. Spyrou Free Radic. Biol. Med. 31 2001 1170 1178
28. K. Becker, C. Herold-Mende, J.J. Park, G. Lowe, and R.H. Schirmer J. Med. Chem. 44 2001 2784 2792
29. E. Vergara, A. Casini, F. Sorrentino, O. Zava, E. Cerrada, M.P. Rigobello, A. Bindoli, M. Laguna, and P.J. Dyson ChemMedChem 5 2010 96 102
30. M. Colonnello, E. Mini, B. Caciagli, M.A. Cinellu, A. Bindoli, C. Gabbiani, and L. Messori J. Med. Chem. 48 2005 6761 6765
31. F. Caruso, M. Rossi, J. Tanski, C. Pettinari, and F. Marchetti J. Med. Chem. 46 2003 1737 1742
32. F. Caruso, C. Pettinari, F. Paduano, R. Villa, F. Marchetti, E. Monti, and M. Rossi J. Med. Chem. 51 2008 1584 1591
33. W.J. Geary Coord. Chem. Rev. 7 1971 81 122
34. P. Diversi, A. Cuzzola, and F. Ghiotto Eur. J. Inorg. Chem. 2009 545 553
35. M.P. Rigobello, A. Folda, B. Dani, R. Menabò, G. Scutari, and A. Bindoli Eur. J. Pharmacol. 582 2008 26 34
36. O. Rackham, S.J. Nichols, P.J. Leedman, S.J. Berners-Price, and A.A. Filipovska Biochem. Pharmacol. 74 2007 992 1002
37. S. Kagawa, J. Gu, T. Honda, J.T. McDonnell, G.S. Swisher, A.J. Roth, and B. Fang Clin. Cancer Res. 7 2001 1474 1480
38. A.J. Sánchez-Alcázar, A. Khodjakov, and E. Schneider Cancer Res. 61 2001 1038 1044
39. Y. Wang, M. Liu, R. Cao, M. Yin, Q. Liu, and N. Huang J. Med. Chem. 56 2013 1455 1466
40. M.J. Matês, and M.F. Sânchez-Jiménez Int. J. Biochem. Cell Biol. 32 2000 157 170
41. S. Nafisi, and Z. Norouzi DNA Cell Biol. 28 2009 469 477
42. N. Ercal, H.N. Gurer-Orhan, and N. Aykin-Burns Curr. Top. Med. Chem. 1 2001 529 539
43. M. Schmid, S. Zimmermann, H.F. Krug, and B. Sures Environ. Int. 33 2007 385 390
44. R. Bera, B.K. Sahoo, K.S. Ghosh, and S. Dasgupta Int. J. Biol. Macromol. 42 2008 14 21
45. N. Akbay, Z. Seferoǧlu, and E. Gök J. Fluoresc. 19 2009 1045 1051
46. A. Alonso, M.J. Almendral, Y. Curto, J.J. Criado, E. RodrIguez, and J.L. Manzano Anal. Biochem. 355 2006 157 164
47. J.R. Lakowicz Principles of Fluorescence Spectroscopy 2nd ed. 1999 Kluwer Academic/Plenum Publishers New York
48. G. Lupidi, E. Camaioni, H. Khalifé, L. Avenali, E. Damiani, F. Tanfani, and A. Scirè J. Pharm. Sci. 101 2012 2564 2573
49. M.P. Rigobello, G. Scutari, R. Boscolo, and A. Bindoli Br. J. Pharmacol. 136 2002 1162 1168
50. K.M. Debatin, D. Poncet, and G. Kroemer Oncogene 21 2002 8786 8803
51. S. Tanida, T. Tsutomu Mizoshita, K. Ozeki, H. Tsukamoto, T. Kamiya, H. Kataoka, D. Sakamuro, and T. Joh Int. J. Surg. Oncol. 2012 1 8
52. A.M. Florea, and D. Büsselberg Cancers 3 2011 1351 1371
53. K. Hill, G.W. McCollum, M.E. Boeglin, and R.F. Burk Biochem. Biophys. Res. Commun. 234 1997 293 295
54. S. Gromer, L.D. Arscott, C.H. Williams Jr., R.H. Schirmer, and K. Becker J. Biol. Chem. 273 1998 20096 20101
55. M.P. Rigobello, G. Scutari, A. Folda, and A. Bindoli Biochem. Pharmacol. 67 2004 689 696
56. D.T. Lincon, E.M. Ali Emadi, K.F. Tonissen, and F.M. Clarke Anticancer. Res. 23 2003 2425 2433
57. M. Deponte, S. Urig, L.D. Arscott, K. Fritz-Wolf, R. Reau, H.-M.C. Christel, S. Koncarevic, M. Meyer, E. Davioud-Charvet, P.D. Ballou, H.C. Williams Jr., and K. Becker J. Biol. Chem. 280 2005 20628 20637
58. Y. Liu, Y. Li, and G. Zhao Curr. Drug Targets 13 2012 1432 1444
59. M. Page, N. Bejaoui, B. Cinq-Mars, and P. Lemieux Int. J. Immunopharmacol. 10 1988 785 793
60. I. Nicoletti, G. Migliorati, and M.C. Pagliacci J. Immunol. Methods 139 1991 271 279
61. C.P. LeBel, H. Ischiropoulos, and S.C. Bondy Chem. Res. Toxicol. 5 1992 227 231