A computational approach to tuning the photochemistry of platinum(IV) anticancer agents

Chemistry - A European Journal

Volumn 18, Issue 34, 2012, Pages 10630-10642

  Tai, Hui Chung ^a   Zhao, Yao ^a   Farrer, Nicola J ^a   Anastasi, Anna E ^a   Clarkson, Guy ^a   Sadler, Peter J ^a   Deeth, Robert J ^a  

^a UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

antitumor agents; bioinorganic chemistry; computational chemistry; photochemistry; platinum

Indexed keywords

ANTI-CANCER AGENTS; ANTI-TUMOR AGENTS; ANTICANCER ACTIVITIES; BIOINORGANIC CHEMISTRY; COMPUTATIONAL APPROACH; COORDINATION ENVIRONMENT; ELECTRON-WITHDRAWING SUBSTITUENTS; ELECTRONIC TRANSITION; ELECTRONWITHDRAWING; EXPERIMENTAL STUDIES; H-BONDS; HALOGEN LIGANDS; INTENSE BANDS; LOW ENERGIES; LOW ENERGY REGIONS; N-LIGANDS; OPTIMISATIONS; PHOTO-ACTIVATED; PHOTO-REDUCTION; PHOTOACTIVITY; PHOTOPRODUCTS; PRODRUGS; SOLVENT MODEL; SPECTROSCOPIC DATA; TIME DEPENDENT DENSITY FUNCTIONAL THEORY; TRANS INFLUENCE; UV/VIS SPECTRA; VISIBLE REGION;

BIOCHEMISTRY; CHEMICAL REACTIONS; COMPUTATIONAL CHEMISTRY; COMPUTER AIDED DESIGN; DENSITY FUNCTIONAL THEORY; HALOGEN COMPOUNDS; IODINE; ISOMERS; LIGANDS; MOLECULAR ORBITALS; OPTIMIZATION; PHOTOCHEMICAL REACTIONS; PLATINUM; PYRIDINE;

PLATINUM COMPOUNDS;

ANTINEOPLASTIC AGENT; PLATINUM COMPLEX;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON SPIN RESONANCE; PHOTOCHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; ELECTRON SPIN RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; ORGANOPLATINUM COMPOUNDS; PHOTOCHEMICAL PROCESSES; STEREOISOMERISM;

EID: 84864979681     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201200782     Document Type: Article

References (63)

1. E. Wong, C. M. Giandomenico, Chem. Rev. 1999, 99, 2451-2466
2. L. Kelland, Nat. Rev. Cancer 2007, 7, 573-584.
3. K. Harrap, Cancer Treat. Rev. 1985, 12, 21-33
4. R. J. Knox, F. Friedlos, D. A. Lydall, J. J. Roberts, Cancer Res. 1986, 46, 1972-1979.
5. L. Kelland, Cancer Res. 1993, 53, 2581-2586
6. L. Kelland, Exp. Opin. Invest. Drugs 2000, 9, 1373-1382.
7. L. R. Kelland, Cancer Res. 1992, 52, 3857-3864
8. D. Gately, S. Howell, Br. J. Cancer 1993, 67, 1171-1176
9. S. Ishida, J. Lee, D. J. Thiele, I. Herskowitz, Proc. Natl. Acad. Sci. USA 2002, 99, 14298-14302
10. P. Mistry, L. R. Kelland, G. Abel, S. Sidhar, K. R. Harrap, Br. J. Cancer 1991, 64, 215-220
11. M. Dabholkar, F. Bostick-Bruton, C. Weber, V. A. Bohr, C. Egwuagu, E. Reed, J. Natl. Cancer Inst. 1992, 84, 1512-1517
12. G. Gifford, J. Paul, P. Vasey, S. Kaye, R. Brown, Clin. Cancer Res. 2004, 10, 4420-4426.
13. Y. Jung, S. J. Lippard, Chem. Rev. 2007, 107, 1387-1407.
14. F. Kratz, I. Mueller, C. Ryppa, A. Warnecke, ChemMedChem 2008, 3, 20-53.
15. S. C. White, P. Lorigan, G. P. Margison, J. M. Margison, F. Martin, N. Thatcher, H. Anderson, M. Ranson, Br. J. Cancer 2006, 95, 822-828
16. T. Dragovich, D. Mendelson, S. Kurtin, K. Richardson, D. Von Hoff, A. Hoos, Cancer Chemother. Pharmacol. 2006, 58, 759-764
17. J. M. Rademaker-Lakhai, C. Terret, S. B. Howell, C. M. Baud, R. F. de Boer, D. Pluim, J. H. Beijnen, J. H. M. Schellens, J. P. Droz, Clin. Cancer Res. 2004, 10, 3386-3395.
18. P. J. Bednarski, F. S. Mackay, P. J. Sadler, Anti-Cancer Agents Med. Chem. 2007, 7, 75-93
19. S. B. Brown, E. A. Brown, I. Walker, Lancet Oncol. 2004, 5, 497-508.
20. N. J. Farrer, P. J. Sadler, Aust. J. Chem. 2008, 61, 669-674.
21. P. J. Bednarski, R. Grunert, M. Zielzki, A. Wellner, F. S. Mackay, P. J. Sadler, Chem. Biol. 2006, 13, 61-67
22. J. Kasparkova, P. Heringova, V. Brabec, F. Mackay, P. J. Sadler, Metal Ions in Biology and Medicine 2008, 10, 463-469
23. J. Kasparkova, F. S. Mackay, V. Brabec, P. J. Sadler, J. Biol. Inorg. Chem. 2003, 8, 741-745
24. N. A. Kratochwil, A. I. Ivanov, M. Patriarca, J. A. Parkinson, A. M. Gouldsworthy, P. D. Murdoch, P. J. Sadler, J. Am. Chem. Soc. 1999, 121, 8193-8203
25. F. S. Mackay, J. Woods, H. Moseley, P. J. Sadler, Br. J. Dermatol. 2005, 152, 857-858
26. F. S. Mackay, J. A. Woods, P. Heringova, J. Kasparkova, A. M. Pizarro, S. A. Moggach, S. Parsons, V. Brabec, P. J. Sadler, Proc. Natl. Acad. Sci. USA 2007, 104, 20743-20748
27. F. S. Mackay, J. A. Woods, H. Moseley, J. Ferguson, A. Dawson, S. Parsons, P. J. Sadler, Chem. Eur. J. 2006, 12, 3155-3161
28. P. Müller, B. Schroder, J. A. Parkinson, N. A. Kratochwil, R. A. Coxall, A. Parkin, S. Parsons, P. J. Sadler, Angew. Chem. 2003, 115, 349-353
29. Angew. Chem. Int. Ed. 2003, 42, 335-339
30. H. I. A. Phillips, L. Ronconi, P. J. Sadler, Chem. Eur. J. 2009, 15, 1588-1596.
31. C. E. Wayne, R. P. Wayne, Photochemistry, 1 st ed., Oxford University Press, New York, 1996.
32. L. Brancaleon, H. Moseley, Lasers Med. Sci. 2002, 17, 173-186.
33. A. Y. Sokolov, H. F. Schaefer III, Dalton Trans. 2011, 40, 7571.
34. J. E. Huheey, E. A. Keiter, R. L. Keiter, Inorganic Chemistry: Principles of Structure and Reactivity, 4 th ed., Harper Collins, New York, 1993.
35. M. Hall, T. Hambley, Coord. Chem. Rev. 2002, 232, 49-67.
36. M. D. Hall, H. R. Mellor, R. Callaghan, T. W. Hambley, J. Med. Chem. 2007, 50, 3403-3411.
37. F. S. Mackay, S. A. Moggach, A. Collins, S. Parsons, P. J. Sadler, Inorg. Chim. Acta 2009, 362, 811-819.
38. M. J. G. Peach, P. Benfield, T. Helgaker, D. J. Tozer, J. Chem. Phys. 2008, 128, 044118-044118.
39. H. Petzold, J. J. Xu, P. J. Sadler, Angew. Chem. 2008, 120, 3050-3053
40. Angew. Chem. Int. Ed. 2008, 47, 3008-3011.
41. M. R. Detty, S. L. Gibson, S. J. Wagner, J. Med. Chem. 2004, 47, 3897-3915.
42. B. M. Still, P. G. A. Kumar, J. R. Aldrich-Wright, W. S. Price, Chem. Soc. Rev. 2007, 36, 665-686
43. P. S. Pregosin, Coord. Chem. Rev. 1982, 44, 247-291
44. N. J. Farrer, J. A. Woods, L. Salassa, Y. Zhao, K. S. Robinson, G. Clarkson, F. S. Mackay, P. J. Sadler, Angew. Chem. 2010, 122, 9089-9092
45. Angew. Chem. Int. Ed. 2010, 49, 8905-8908.
46. D. Loganathan, H. Morrison, Photochem. Photobiol. 2006, 82, 237-247.
47. A. Klamt, J. Phys. Chem. 1995, 99, 2224-2235.
48. R. S. Butler, P. Cohn, P. Tenzel, K. A. Abboud, R. K. Castellano, J. Am. Chem. Soc. 2009, 131, 623-633.
49. P. S. Wagenknecht, P. C. Ford, Coord. Chem. Rev. 2011, 255, 591-616.
50. R. S. Mulliken, J. Chem. Phys. 1955, 23, 1833-1840.
51. G. te Velde, F. M. Bickelhaupt, E. J. Baerends, C. Fonseca Guerra, S. J. A. van Gisbergen, J. G. Snijders, T. Ziegler, J. Comput. Chem. 2001, 22, 931-967.
52. E. van Lenthe, R. van Leeuwen, E. J. Baerends, J. G. Snijders, Int. J. Quantum Chem. 1996, 57, 281-293
53. E. van Lenthe, A. Ehlers, E. J. Baerends, J. Chem. Phys. 1999, 110, 8943-8953.
54. K. Morokuma, J. Chem. Phys. 1971, 55, 1236-1244
55. T. Ziegler, A. Rauk, Theor. Chem. Acc. 1977, 46, 1-10
56. F. M. Bickelhaupt, E. J. Baerends, in Reviews in Computational Chemistry, Vol. 15 (Eds.:, K. B. Lipkowitz, D. B. Boyd,), Wiley-VCH, Weinheim, 2000, pp. 1-86
57. G. Frenking, N. Frohlich, Chem. Rev. 2000, 100, 717-774.
58. P. R. T. Schipper, O. V. Gritsenko, S. J. A. van Gisbergen, E. J. Baerends, J. Chem. Phys. 2000, 112, 1344-1352.
59. F. Wang, T. Ziegler, J. Chem. Phys. 2005, 123, 194102.
60. H. E. Gottlieb, V. Kotlyar, A. Nudelman, J. Org. Chem. 1997, 62, 7512-7515.
61. L. Mackenzie, W. Frainbel, Br. J. Dermatol. 1973, 89, 251-264.
62. H. J. Kuhn, S. E. Braslavsky, R. Schmidt, Pure Appl. Chem. 2004, 76, 2105-2146
63. S. L. Murov, G. L. Hug, I. Carmichael, Handbook of Photochemistry, 2 nd ed., M. Dekker, New York, 1993.