A new entry to asymmetric platinum(IV) complexes via oxidative chlorination

Inorganic Chemistry

Volumn 53, Issue 17, 2014, Pages 9326-9335

  Ravera, Mauro ^a   Gabano, Elisabetta ^a   Pelosi, Giorgio ^b   Fregonese, Federico ^a   Tinello, Stefano ^a   Osella, Domenico ^a  

^a UNIVERSITY OF EASTERN PIEDMONT   (Italy)

^b UNIVERSITY OF PARMA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE; PLATINUM DERIVATIVE;

CHEMICAL STRUCTURE; CHEMISTRY; ELECTROSPRAY MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION REDUCTION REACTION; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

CHLORINE; CRYSTALLOGRAPHY, X-RAY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; OXIDATION-REDUCTION; PLATINUM COMPOUNDS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 84906862041     PISSN: 00201669     EISSN: 1520510X     Source Type: Journal    
DOI: 10.1021/ic501446b     Document Type: Article

References (65)

1. Skeel, R. T. Antineoplastic Drugs and Biologic Response Modifiers: Classification, Use, and Toxicity of Clinically Useful Agents. In Handbook of Cancer Chemotherapy; 7 th ed.; Skeel, R. T., Ed.; Lippincott Williams & Wilkins: Philadelphia, PA, 2007; Section II-Chemotherapeutic and Biotherapeutic Agents and Their Use, Ch 4.
2. Gabano, E.; Ravera, M.; Osella, D. Curr. Med. Chem. 2009, 16, 4544-4580
3. Hall, M. D.; Hambley, T. W. Coord. Chem. Rev. 2002, 232, 49-67
4. Hall, M. D.; Alderden, R. A.; Zhang, M.; Beale, P. J.; Cai, Z.; Lai, B.; Stamp, A. P. J.; Hambley, T. W. J. Struct. Biol. 2006, 155, 38-44
5. Graf, N.; Lippard, S. J. Adv. Drug Delivery Rev. 2012, 64, 993-1004
6. Wang, X.; Guo, Z. Chem. Soc. Rev. 2013, 42, 202-224
7. Gaviglio, L.; Gross, A.; Metzler-Nolte, N.; Ravera, M. Metallomics 2012, 4, 260-266
8. Graf, N.; Mokhtari, T. E.; Papayannopoulos, I. A.; Lippard, S. J. J. Inorg. Biochem 2012, 110, 58-63
9. Abramkin, S.; Valiahdi, S. M.; Jakupec, M. A.; Galanski, M.; Metzler-Nolte, N.; Keppler, B. K. Dalton Trans. 2012, 41, 3001-3005
10. Mukhopadhyay, S.; Barnes, C. M.; Haskel, A.; Short, S. M.; Barnes, K. R.; Lippard, S. J. Bioconjugate Chem. 2008, 19, 39-49
11. Barnes, K. R.; Kutikov, A.; Lippard, S. J. Chem. Biol. (Oxford, U. K.) 2004, 11, 557-564
12. Barry, N. P. E.; Sadler, P. J. ACS Nano 2013, 7, 5654-5659
13. Butler, J. S.; Sadler, P. J. Curr. Opin. Chem. Biol. 2013, 17, 175-188
14. Zhang, J. Z.; Bonnitcha, P.; Wexselblatt, E.; Klein, A. V.; Najajreh, Y.; Gibson, D.; Hambley, T. W. Chem.-Eur. J. 2013, 19, 1672-1676
15. Chin, C. F.; Tian, Q.; Setyawati, M. I.; Fang, W.; Qing Tan, E. S.; Leong, D. T.; Ang, W. H. J. Med. Chem. 2012, 55, 7571-7582
16. Mailliet, P.; Bourrie, B.; Normand, A. French Patent FR 2 954 321 A1, July 15, 2010.
17. Choi, S.; Filotto, C.; Bisanzo, M.; Delaney, S.; Lagasee, D.; Whitworth, J. L.; Jusko, A.; Li, C. R.; Wood, N. A.; Willingham, J.; Schwenker, A.; Spaulding, K. Inorg. Chem. 1998, 37, 2500-2504
18. Chen, L.; Lee, P. F.; Ranford, J. D.; Vittal, J. J.; Wong, S. Y. J. Chem. Soc., Dalton Trans. 1999, 1209-1212
19. Zhang, J. Z.; Wexselblatt, E.; Hambley, T. W.; Gibson, D. Chem. Commun. 2012, 48, 847-849
20. Wexselblatt, E.; Gibson, D. J. Inorg. Biochem. 2012, 117, 220-229
21. Sinisi, M.; Intini, F. P.; Natile, G. Inorg. Chem. 2012, 51, 9694-9704
22. Wilson, J. J.; Lippard, S. J. Chem. Rev. 2014, 114, 4470-4495
23. Rendina, L. M.; Puddephatt, R. J. Chem. Rev. 1997, 97, 1735-1754
24. Gossage, R. A.; Ryabov, A. D.; Spek, A. L.; Stufkens, D. J.; van Beek, J. A. M.; van Eldik, R.; van Koten, G. J. Am. Chem. Soc. 1999, 121, 2488-2497
25. Margiotta, N.; Ranaldo, R.; Intini, F. P.; Natile, G. Dalton Trans. 2012, 41, 9689-9699
26. Giandomenico, C. M.; Abrams, M. J.; Murrer, B. A.; Vollano, J. F.; Rheinheimer, M. I.; Wyer, S. B.; Bossard, G. E.; Higgins, J. D., III Inorg. Chem. 1995, 34, 1015-1021
27. Galanski, M.; Keppler, B. K. Inorg. Chem. 1996, 35, 1709-1711
28. Whitfield, S. R.; Sanford, M. S. Organometallics 2008, 27, 1683-1689
29. Dunham, S. O.; Larsen, R. D.; Abbott, E. H. Inorg. Chem. 1993, 32, 2049-2055
30. Margiotta, N.; Ranaldo, R.; Intini, F. P.; Natile, G. Dalton Trans. 2011, 40, 12877-12885
31. Tamasi, G.; Cini, R.; Intini, F. P.; Sivo, M. F.; Natile, G. Angew. Chem. 2004, 116, 5191-5194
32. Lee, Y.; Yoo, K. H.; Jung, O. Inorg. Chem. Commun. 2003, 6, 249-251
33. Hall, M. D.; Dolman, R. C.; Hambley, T. W. Met. Ions Biol. Syst. 2004, 42, 297-322
34. Poon, G. K.; Raynaud, F. I.; Mistry, P.; Odell, D. E.; Kelland, L. R.; Harrap, K. R.; Barnard, C. F.; Murrer, B. A. J. Chromatogr., A 1995, 712, 61-66
35. Raynaud, F. I.; Odell, D. E.; Kelland, L. R. Br. J. Cancer 1996, 74, 380-386
36. Davies, M. S.; Hall, M. D.; Berners-Price, S. J.; Hambley, T. W. Inorg. Chem. 2008, 47, 7673-7680
37. Wexselblatt, E.; Yavin, E.; Gibson, D. Angew. Chem., Int. Ed. 2013, 52, 6059-6062
38. Washko, P.; Rotrosen, D.; Levine, M. Am. J. Clin. Nutr. 1991, 54, 1221S-1227S
39. Reiber, H.; Ruff, M.; Uhr, M. Clin. Chim. Acta 1993, 217, 163-173
40. Chen, Y.; Guo, Z.; Parsons, S.; Sadler, P. J. Chem.-Eur. J. 1998, 4, 672-676
41. Michelet, F.; Gueguen, R.; Leroy, P.; Wellman, M.; Nicolas, A.; Siest, G. Clin. Chem. 1995, 41, 1509-1517
42. Dabrowiak, J. C. Metals in Medicine; Wiley: Chichester, U.K., 2009.
43. Žák, F.; Turánek, J.; Kroutil, A.; Sova, P.; Mistr, A.; Poulová, A.; Mikolin, P.; Žák, Z.; Kašná, A.; Záluská, D.; Neča, J.; Šindlerová, L.; Kozubík, A. J. Med. Chem. 2004, 47, 761-763
44. Ravera, M.; Gabano, E.; Zanellato, I.; Bonarrigo, I.; Escribano, E.; Moreno, V.; Font-Bardia, M.; Calvet, T.; Osella, D. Dalton Trans. 2012, 41, 3313-3320
45. Lemma, K.; House, D. A.; Retta, N.; Elding, L. I. Inorg. Chim. Acta 2002, 331, 98-108
46. Monti, E.; Gariboldi, M.; Maiocchi, A.; Marengo, E.; Cassino, C.; Gabano, E.; Osella, D. J. Med. Chem. 2005, 48, 857-866
47. Amblard, M.; Fehrentz, J.-A.; Martinez, J.; Subra, G. In Fundamentals of Modern Peptide Synthesis in Peptide Synthesis, Applications (Methods in Molecular Biology Vol. 298); Howl, J., Ed.; Humana Press: Totowa, NJ, 2005, Ch 1, pp 3-24.
48. Gandin, V.; Marzano, C.; Pelosi, G.; Ravera, M.; Gabano, E.; Osella, D. ChemMedChem 2014, 9, 1299-1305
49. Ang, W. H.; Pilet, S.; Scopelliti, R.; Bussy, F.; Juillerat-Jeanneret, L.; Dyson, P. J. J. Med. Chem. 2005, 48, 8060-8069
50. Gabano, E.; Marengo, E.; Bobba, M.; Robotti, E.; Cassino, C.; Botta, M.; Osella, D. Coord. Chem. Rev. 2006, 250, 2158-2174
51. Freeman, W.; Pregosin, P. S. J. Magn. Reson. 1976, 22, 473-478
52. Appleton, T. G.; Hall, J. R.; Ralph, S. F. Inorg. Chem. 1985, 24, 4685-4693
53. Gramatica, P.; Papa, E.; Luini, M.; Monti, E.; Gariboldi, M. B.; Ravera, M.; Gabano, E.; Gaviglio, L.; Osella, D. J. Biol. Inorg. Chem. 2010, 15, 1157-1169
54. Ermondi, G.; Caron, G.; Ravera, M.; Gabano, E.; Bianco, S.; Platts, J. A.; Osella, D. Dalton Trans. 2013, 42, 3482-3489
55. Pichler, V.; Göschl, S.; Meier, S. M.; Roller, A.; Jakupec, M. A.; Galanski, M.; Keppler, B. K. Inorg. Chem. 2013, 52, 8151-8162
56. Pichler, V.; Heffeter, P.; Valiahdi, S. M.; Kowol, C. R.; Egger, A.; Berger, W.; Jakupec, M. A.; Galanski, M.; Keppler, B. K. J. Med. Chem. 2012, 55, 11052-11061
57. Tsipis, A. C.; Karapetsas, I. N. Dalton Trans. 2014, 43, 5409-5426
58. Dhara, S. C. Indian J. Chem. 1970, 8, 193-194
59. Harrison, R. C.; McAuliffe, C. A. Inorg. Chim. Acta 1980, 46, L15-L16
60. Rochon, F. D.; Gruia, L. M. Inorg. Chim. Acta 2000, 306, 193-204
61. Sheldrick, G. SADABS: Siemens Area Detector Absorption Correction Software; University of Goettingen: Goettingen, Germany, 1996.
62. Sheldrick, G. SHELXL97, Program for Structure Refinement; University of Goettingen: Goettingen, Germany, 1997.
63. Farrugia, L. J. J. Appl. Crystallogr. 1999, A32, 837-838
64. International Tables for X-Ray Crystallography; Kynoch Press: Birmingham, U.K., 1974, Vol. 4.
65. Johnson, C. K.; Burnett, M. N. ORTEPIII; Technical Report ORNL-6895 for the Oak Ridge National Laboratory: Oak Ridge, TN, 1996.