Titanocene-phosphine derivatives as precursors to cytotoxic heterometallic TiAu 2 and TiM (M = Pd, Pt) compounds. Studies of their interactions with DNA

Inorganic Chemistry

Volumn 50, Issue 21, 2011, Pages 11099-11110

  González Pantoja, Jose F ^a   Stern, Michael ^a   Jarzecki, Andrzej A ^a   Royo, Eva ^b   Robles Escajeda, Elisa ^c   Varela Ramírez, Armando ^c   Aguilera, Renato J ^c   Contel, María ^a  

^a CITY UNIVERSITY OF NEW YORK   (United States)

^b UNIVERSITY OF ALCALÁ   (Spain)

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

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; CALF THYMUS DNA; DNA; ORGANOMETALLIC COMPOUND; PALLADIUM; PHOSPHINE DERIVATIVE; PLATINUM; TITANIUM; TITANOCENE;

ANIMAL; ARTICLE; CATTLE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; CIRCULAR DICHROISM; CONFORMATION; DRUG EFFECT; FEMALE; HUMAN; IC 50; INFRARED SPECTROPHOTOMETRY; MALE; METABOLISM; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PATHOLOGY; PROSTATE TUMOR; STRUCTURE ACTIVITY RELATION; SYNTHESIS; TUMOR CELL LINE; UTERINE CERVIX TUMOR;

ANIMALS; ANTINEOPLASTIC AGENTS; CATTLE; CELL LINE, TUMOR; CELL SURVIVAL; CHEMISTRY, PHARMACEUTICAL; CIRCULAR DICHROISM; DNA; FEMALE; HUMANS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MALE; MODELS, MOLECULAR; NUCLEIC ACID CONFORMATION; ORGANOMETALLIC COMPOUNDS; PALLADIUM; PHOSPHINES; PLATINUM; PROSTATIC NEOPLASMS; SPECTROPHOTOMETRY, INFRARED; STRUCTURE-ACTIVITY RELATIONSHIP; TITANIUM; UTERINE CERVICAL NEOPLASMS;

EID: 80155151873     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic201647h     Document Type: Article

References (106)

1. Harding, M. M.; Mokdsi, G. Curr. Med. Chem. 2000, 7, 1289 and references cited therein
2. Köpf-Maier, P.; Köpf, H. Angew. Chem., Int. Ed. Engl. 1979, 18, 477
3. Berdel, W. E.; Schmoll, H. J.; Scheulen, M. E.; Korfel, A.; Knoche, M. F.; Harstrick, A.; Bach, F.; Sa, G. J. Cancer Res. Clin. Oncol. 1994, 120 (Suppl) R172
4. Abeysinghe, P. M.; Harding, M. M. Dalton Trans. 2007, 3474 and references cited therein
5. Olszewski, U.; Hamilton, G. Anti-Cancer Agents Med. Chem. 2010, 10, 320 and references cited therein
6. Lummen, G.; Sperling, H.; Lubolt, H.; Otto, T.; Rubben, H. Cancer Chemother. Pharmacol. 1998, 42, 415
7. Kroger, N.; Kleeberg, U. R.; Mross, K.; Edler, L.; Sab, G.; Hossfeld, D. Onkologie 2000, 23, 288
8. Chen, X.; Zhou, L. J. Mol. Struct. 2010, 940, 45
9. Ravera, M.; Cassino, C.; Monti, E.; Gariboldi, M.; Osella, D. J. Inorg. Biochem. 2005, 99, 2264
10. Chen, P.; Wu, Q.-S.; Ding, Y.-P.; Chu, M.; Huang, Z.-M.; Hu, W. Eur. J. Pharm. Biopharm. 2010, 76, 413
11. Guo, M.; Sun., H.; McArdle, H. J.; Gambling, L.; Sadler, P. J. Biochemistry 2000, 39, 10023
12. Guo, M.; Sadler, P. Dalton Trans. 2000, 7
13. Parker Siburt, C. J. P.; Lin, E. M.; Brandt, S. J.; Tinoco, A. D.; Valentine, A. M.; Crumbliss, A. L. J. Inorg. Biochem. 2010, 104, 1006
14. Tinoco, A. D.; Incarvito, C. D.; Valentine, A. M. J. Am. Chem. Soc. 2007, 129, 3444
15. Sarsam, S. W.; Nutt, D. R.; Strohfeldt, K.; Kimberly, A. Metallomics: Int. Biomet. Sci. 2011, 3, 152
16. Deng, C.; Zhou, L. Struct. Chem. 2010, 21, 735
17. Erxleben, A.; Claffey, J.; Tacke, M. J. Inorg. Biochem. 2010, 104, 390
18. Strohfeldt, K.; Tacke, M. Chem. Soc. Rev. 2008, 37, 1174
19. Caruso, F.; Rossi, M. Mini-Rev. Med. Chem. 2004, 4, 49 and references cited therein
20. Meléndez, E. Crit. Rev. Oncol. Hematol. 2002, 42, 309 and references cited therein
21. Cuffe, S.; Dowling, C. M.; Claffey, J.; Pampillon, C.; Hogan, M.; Fitzpatrick, J. M.; Carty, M. P.; Tacke, M.; Watson, R. W. G. Prostate 2010, DOI: 10.1002/pros.21227
22. Pizarro, A. M.; Habtemariam, A.; Sadler, P. J. Top. Organomet. Chem. 2010, 32, 21
23. Allen, O. R.; Croll, L.; Gott, A. L.; Knox, R. J.; McGowan, P. C. Organometallics 2004, 23, 60
24. Kaluderovic, G. N.; Tayurska, V.; Paschke, R.; Prashar, S.; Fajardo, M.; Gómez-Ruíz, S. Appl. Organomet. Chem. 2010, 24, 656
25. Kaluderovic, G. N.; Pérez-Quintanilla, D.; Sierra, I.; Prashar, S.; del Hierro, I.; Zizak, Z.; Juranic, Z. D.; Fajardo, M.; Gómez- Ruíz, S. J. Mater. Chem. 2010, 20, 806
26. Oberschmidt, O.; Hanauske, A. R.; Pampillón, C.; Sweeney, N. J.; Strohfeldt, K.; Tacke, M. Anti-Cancer Drugs 2007, 18, 317
27. Beckhove, P.; Oberschmidt, O.; Hanauske, A. R.; Pampillón, C.; Schirrmacher, V.; Sweeney, N. J.; Strohfeldt, K.; Tacke, M. Anti-Cancer Drugs 2007, 18, 311
28. Bannon, J. H.; Fitchner, I.; O'Neill, A.; Pampillón, C.; Sweeney, N. J.; Strohfeldt, K.; Watson, R. W.; Tacke, M.; McGee, M. M. Br. J. Cancer 2007, 97, 1234
29. Fichtner, I.; Pampillón, C.; Sweeney, N. J.; Strohfeldt, K.; Tacke, M. Anti-Cancer Drugs 2006, 17, 333
30. Hogan, M.; Gleeson, B.; Tacke, M. Lett. Drug Des. Discovery 2010, 7, 310
31. O'Connor, K.; Gill, C.; Tacke, M.; Rehmann, F.-J. K.; Strohfeldt, K.; Sweeney, N.; Fitzpatrick, J. M.; Watson, R. W. G. Apoptosis 2006, 11, 1205
32. Hogan, M.; Gleeson, B.; Tacke, M. Organometallics 2010, 29, 1032
33. Claffey, J.; Mueller-Bunz, H.; Tacke, M. J. Organomet. Chem. 2010, 695, 2105
34. Immel, T. A.; Martin, J. T.; Duerr, C. J.; Groth, U.; Huhn, T. J. Inorg. Biochem. 2010, 104, 863
35. Eger, S.; Immel, T. A.; Claffey, J.; Muller-Bunz, H.; Tacke, M.; Groth, U.; Hunh, T. Inorg. Chem. 2010, 49, 1292
36. Claffey, J.; Hogan, M.; Muller-Bunz, H.; Pampillon, C.; Tacke, M. ChemMedChem. 2008, 3, 729
37. Claffey, J.; Deally, A.; Gleeson, B.; Patil, S.; Tacke, M. Appl. Organomet. Chem. 2010, 24, 675
38. Gao, L. M.; Vera, J. L.; Matta, J.; Meléndez, E. J. Biolog. Inorg. Chem. 2010, 15, 851
39. Zhang, J.; Wang, L.; Xing, Z.; Liu, D.; Sun, J.; Li, X.; Zhang, Y. Anti-Cancer Agents Med. Chem. 2010, 10, 272
40. Mattsson, J.; Govindaswamy, P.; Renfrew, A. K.; Dyson, P. J.; Stepnicka, P.; Suss-Fink, G.; Therrien, B. Organometallics 2009, 28, 4350
41. Therrien, B.; Suss-Fink, G.; Govindaswamy, P.; Renfrew, A. K.; Dyson, P. J. Angew. Chem., Int. Ed. 2008, 47, 3773
42. Schmitt, F.; Govindaswamy, P.; Suss-Fink, G.; Ang, W. H.; Dyson, P. J.; Juillerat-Jeanneret, L.; Therrien, B. J. Med. Chem. 2008, 51, 1811
43. Mendoza-Ferri, M. G.; Hartinger, C. G.; Eichinger, R. E.; Stolyarova, N.; Severin, K.; Jakupec, M. A.; Nazarov, A. A.; Keppler, B. K. Organometallics 2008, 27, 2405
44. 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
45. de Hoog, P.; Boldron, C.; Gamez, P.; Sliedregt-Bol, K.; Roland, I.; Pitie, M.; Kiss, R.; Meunier, B.; Reedijk, J. J. Med. Chem. 2007, 50, 3148
46. Pelletier, F.; Comte, V.; Massard, A.; Wenzel, M.; Toulot, S.; Richard, P.; Picquet, M.; Le Gendre, P.; Zava, O.; Edafe, F.; Casini, A.; Dyson, P. J. J. Med. Chem. 2010, 53, 6923
47. Wedgwood, J. L.; Kresinski, R. A.; Merry, S.; Platt, A. W. G. J. Inorg. Biochem. 2003, 95, 149
48. Berners-Price, S. Angew. Chem., Int. Ed. 2011, 50, 804
49. Wheate, N. J.; Walker, S.; Craig, G. E.; Oun, R. Dalton Trans. 2010, 39, 8113
50. Mangrum, J. B.; Farrell, N. P. Chem. Commun. 2010, 46, 6640
51. Olszewski, U.; Hamilton, G. Anti-Cancer Agents Med. Chem. 2010, 10, 293
52. Gibson, D. Dalton Trans. 2009, 10681
53. For example, see: Kozelka, J. I.; Segal, E.; Bois, C. J. Inorg. Biochem. 1992, 47, 67 and references cited therein
54. Nobili, S.; Mini, E.; Landini, I.; Gabbiani, C.; Casini, A.; Messori, L. Med. Res. Rev. 2010, 30, 550
55. Ronconi, L.; Aldinucci, D.; Dou, Q. P.; Fregona, D. Anti-Cancer Agents Med. Chem. 2010, 10, 283
56. Pacheco, E.; Tiekink, E.; Whitehouse, M. In Mohr, F., Ed. Gold Chemistry: Wiley-VCH: New York, 2009; Chapter 6, p 283.
57. Bindoli, A.; Rigobello, M. P.; Scutari, G.; Gabbiani, C.; Casini, A.; Messori, L. Coord. Chem. Rev. 2009, 253, 1692
58. Sun, R. W. Y.; Che, C. M. Coord. Chem. Rev. 2009, 253, 1682
59. Ott, I. Coord. Chem. Rev. 2009, 253, 1670
60. Shaik, N.; Martínez, A.; Augustin, I.; Giovinazzo, H.; Varela-Ramírez, A.; Aguilera, R. J.; Sanaú, M.; Contel, M. Inorg. Chem. 2009, 48, 1577
61. Vela, L.; Contel, M.; Palomera, L.; Azaceta, G.; Marzo, I. J. Inorg. Biochem. 2011, 105, 1306
62. Elie, B. T.; Levine, C.; Ubarretxena-Belandia, I.; Varela-Ramírez, A.; Aguilera, R. J.; Ovalle, R.; Contel, M. Eur. J. Inorg. Chem. 2009, 3421
63. Gao, E.; Zhu, M.; Liu, L.; Huang, Y.; Wang, L.; Shi, S.; Chuyue, Z.; Sun, W. Y. Inorg. Chem. 2010, 49, 3261
64. Prast-Nielsen, S.; Celbula, M.; Pader, I.; Arner, E. S. J. Free Radical Biol. Med. 2010, 49, 1765
65. Vrzal, R.; Starha, P.; Dvorak, Z.; Travniceck, Z. J. Inorg. Biochem. 2010, 1130
66. Spencer, J.; Casini, A.; Zava, O.; Rathnam, R. P.; Velhanda, S. K.; Pfeffer, M.; Callear, S. K.; Hursthouse, M. B.; Dyson, P. J. Dalton Trans. 2009, 10731 and references cited therein
67. 2Au derivatives was published online. Wenzel, M.; Bertrand, B.; Eymin, M.-J.; Comte, V.; Harvey, J. A.; Richard, P.; Groessl, M.; Zava, O.; Amrouche, H.; Harvey, P. D.; Le Gendre, P.; Picquet, M.; Casini, A. Inorg. Chem. doi: 10.1021/ic201155y.
68. LeBlanc, C.; Moise, C.; Maisonnat, A.; Poilblanc, R.; Charrier, C.; Mathey, F. J. Organomet. Chem. 1982, 231, C43
69. Graham, T. W.; Llamazares, A.; McDonald, R.; Cowie, M. Organometallics 1999, 18, 3490
70. Kettenbach, R. T.; Bonrath, W.; Butenschoen, H. Chem. Ber. 1993, 126, 1657
71. Cobley, C. J.; Pringle, P. G. Inorg. Chim. Acta 1997, 265, 107 and references cited therein
72. Delgado, E.; Forniés, J.; Hernández, E.; Lalinde, E.; Mansilla, N.; Moreno, M. T. J. Organomet. Chem. 1995, 494, 261
73. Graham, T. W.; Llamazares, A.; McDonald, R.; Cowie, M. Organometallics 1999, 18, 3502
74. Baker, J.; Jarzecki, A. A.; Pulay, P. J. Phys. Chem. A 1998, 1412
75. Modkdsi, G.; Harding, M. M. Met.-Based Drugs 1998, 5, 247
76. 50 obtained by Mosmann tests (MTT reduction). Carreira, M.; Sanaú, M.; Calvo Sanjuán, R.; Marzo, I.; Contel, M. Unpublished results.
77. Cardonna, J. P.; Kippard, S. J.; Gait, M. J.; Singh, M. J. Am. Chem. Soc. 1982, 104, 5793
78. Dabrowiak, J. C. Metals in Medicine; John Wiley and Sons: New York, 2009.
79. Liu, H.-K.; Sadler, P. Acc. Chem. Res. 2011, 44, 349
80. For example, see: Ruíz, J.; Cutillas, N.; Vicente, C.; Villa, M. D.; López, G.; Lorenzo, J.; Avilés, F. X.; Moreno, V.; Bautista, D. Inorg. Chem. 2005, 44, 7365
81. Mansori-Torshizi, H.; I-Moghaddam, M.; Divsalar, A.; Saboury, A.-A. Biorg. Med. Chem. 2008, 16, 9616
82. Quiroga, A. G.; Pérez, J. M.; López-Solera, I.; Masaguer, J. R.; Luque, A.; Roman, P.; Edwards, A.; Alonso, C.; Navarro-Ranninger, C. J. Med. Chem. 1998, 41, 1399
83. Paul, A. K.; Mansuri-Torshizi, H.; Srivastava, T. S.; Chavan, S. J.; Chitnis, M. P. J. Inorg. Biochem. 1993, 50, 9
84. Blank, C. E.; Dabrowaik, J. C. J. Inorg. Biochem. 1984, 21, 21
85. Harding, M. M.; Murray, J. H. J. Med. Chem. 1994, 37, 1936
86. Christodoulou, C. V.; Eliopoulos, A. G.; Young, L. S.; Hodgkins, L.; Ferry, D. R.; Kerr, D. J. Br. J. Cancer 1998, 77, 2088
87. Mascini, M.; Bagni, G.; Di Pietro, M. L.; Ravera, M.; Baracco, S.; Osella, D. BioMetals 2006, 19, 409
88. Ravera, M.; Gavbano, E.; Baracco, S.; Oselvla, D. Inorg. Chim. Acta 2009, 362, 1303
89. Kopf Maier, P. J. Struct. Biol. 1990, 105, 35
90. Mokdsi, G.; Harding, M. M. J. Organomet. Chem. 1998, 565, 29
91. Yang, P.; Guo, M. Coord. Chem. Rev. 1999, 185-186, 189
92. Guo, M. L.; Guo, Z. J.; Sadler, P. J. J. Biol. Inorg. Chem. 2001, 6, 698
93. Fox, K. Drug-DNA Interact. Protocols 1997, 90, 95
94. Moreno, V.; Lorenzo, J.; Aviles, F. X.; García, M. H.; Ribeiro, J. P.; Morais, T. S.; Florindo, P.; Robalo, M. P. Bioinorg. Chem. Appl. 2010, doi: 10.1155/2010/936834.
95. Martínez, A.; Rajapakse, C. S. K.; Sanchez-Delgado, R. A.; Varela-Ramírez, A.; Lema, C.; Aguilera, R. J. J. Inorg. Biochem. 2010, 104, 967
96. Macquet, J.-P.; Butour, J.-L. Eur. J. Biochem. 1978, 83, 375
97. Usón, R.; Laguna, A.; Laguna, M. Inorg. Synth. 1989, 26, 85
98. Drew, D.; Doyle, J. R.; Shaver, A. G. Inorg. Synth. 2007, 13, 52
99. Baker, M. V.; Brown, D. H.; Simpson, P. V.; Skelton, B. W.; White, A. H.; Williams, C. C. J. Organomet. Chem. 2006, 691, 5845
100. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, R.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E., Jr.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. N.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.
101. Peterson, K. A.; Puzzarini, C. Theor. Chem. Acc. 2005, 114, 283
102. Peterson, K. A.; Figgen, D.; Dolg, M.; Stoll, H. J. Chem. Phys. 2007, 126, 124101
103. Schuchardt, K. L.; Didier, B. T.; Elsethagen, T.; Sun, L.; Gurumoorthi, V.; Chase, J.; Li, J.; Windus, T. L. J. Chem. Inf. Model. 2007, 47, 1045
104. Lema, C.; Varela-Ramírez, A.; Aguilera, R. J. J. Curr. Cell. Biochem. 2011, 1, 1.
105. Varela-Ramírez, A.; Costanzo, M.; Carrasco, Y. P.; Pannell, K. H.; Aguilera, R. J. Cell Biol. Toxicol. 2011, 3, 159
106. Moody, D. E. Drug Chem. Toxicol. 1991, 14, 319