Controlling ligand substitution reactions of organometallic complexes: Tuning cancer cell cytotoxicity

Proceedings of the National Academy of Sciences of the United States of America

Volumn 102, Issue 51, 2005, Pages 18269-18274

  Wang, Fuyi ^a   Habtemariam, Abraha ^a   Van Der Geer, Erwin P L ^a   Fernández, Rafael ^a   Melchart, Michael ^a   Deeth, Robert J ^b   Aird, Rhona ^a   Guichard, Sylvie ^a   Fabbiani, Francesca P A ^a   Lozano Casal, Patricia ^a   Oswald, Iain D H ^a   Jodrell, Duncan I ^a   Parsons, Simon ^a   Sadler, Peter J ^a  

^a UNIVERSITY OF EDINBURGH   (United Kingdom)

^b UNIVERSITY OF WARWICK   (United Kingdom)

Author keywords

Anticancer; Bioorganometallic; Hydrolysis; Kinetics; Ruthenium complexes

Indexed keywords

3,5 DICHLOROPYRIDINE DERIVATIVE; ANTINEOPLASTIC AGENT; AZIDE; CHLORIDE; DNA; ETHYLENEDIAMINE DERIVATIVE; GUANOSINE PHOSPHATE; HALIDE; HEXAMETHYLBENZENE DERIVATIVE; ORGANOMETALLIC COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON; PYRIDINE DERIVATIVE; RUTHENIUM COMPLEX; THIOL DERIVATIVE; THIOPHENOLATE DERIVATIVE; UNCLASSIFIED DRUG; WATER;

ABSORPTION SPECTROSCOPY; ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL REACTION KINETICS; CONTROLLED STUDY; CRYSTAL STRUCTURE; DENSITY FUNCTIONAL THEORY; DRUG CYTOTOXICITY; ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; HYDROLYSIS; LIGAND BINDING; OVARY CANCER; PARTITION COEFFICIENT; PRIORITY JOURNAL; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

5'-GUANYLIC ACID; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; DRUG DESIGN; FEMALE; HUMANS; HYDROLYSIS; INHIBITORY CONCENTRATION 50; KINETICS; LIGANDS; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OVARIAN NEOPLASMS; RUTHENIUM;

EID: 29444455073     PISSN: 00278424     EISSN: None     Source Type: Journal    
DOI: 10.1073/pnas.0505798102     Document Type: Article

References (45)

1. Halpern, J. (2001) Pure Appl. Chem. 73, 209-220.
2. Fish, R. H. & Jaouen, G. (2003) Organometallics 22, 2166-2177.
3. Köpf-Maier, P. & Köpf, H. (1987) Chem. Rev. 87, 1137-1152.
4. Sadler, P. J. (1991) Adv. Inorg. Chem. 36, 1-48.
5. Jaouen, G., Top, S., Vessieres, A. & Alberto, R. (2000) J. Organomet. Chem. 600, 23-36.
6. Howe-Grant, M. E. & Lippard, S. J. (1980) Met. Ions Biol. Syst. 11, 63-125.
7. Frey, U., Ranford, J. D. & Sadler, P. J. (1993) Inorg. Chem. 32, 1333-1340.
8. Barnham, K. J., Djuran, M. I., Murdoch, P. d. S., Ranford, J. D. & Sadler, P. J. (1996) Inorg. Chem. 35, 1065-1072.
9. Clarke, M. J. (2003) Coord. Chem. Rev. 236, 209-233.
10. Bennett, M. A., Byrnes, M. J. & Kovacik, I. (2004) J. Organomet. Chem. 689, 4463-4474.
11. Aird, R. E., Cummings, J., Ritchie, A. A., Muir, M., Morris, R. E., Chen, H., Sadler, P. J. & Jodrell, D. I. (2002) Br. J. Cancer 86, 1652-1657.
12. Morris, R. E., Aird, R. E., Murdoch, P. D., Chen, H. M., Cummings, J., Hughes, N. D., Parsons, S., Parkin, A., Boyd, G., Jodrell, D. I. & Sadler, P. J. (2001) J. Med. Chem. 44, 3616-3621.
13. Chen, H. M., Parkinson, J. A., Parsons, S., Coxall, R. A., Gould, R. O. & Sadler, P. J. (2002) J. Am. Chem. Soc. 124, 3064-3082.
14. Chen, H. M., Parkinson, J. A., Nováková, O., Bella, J., Wang, F. Y., Dawson, A., Gould, R., Parsons, S., Brabec, V. & Sadler, P. J. (2003) Proc. Natl. Acad. Sci. USA 100, 14623-14628.
15. Chen, H. M., Parkinson, J. A., Morris, R. E. & Sadler, P. J. (2003) J. Am. Chem. Soc. 125, 173-186.
16. Guo, Z. J. & Sadler, P. J. (2000) Adv. Inorg. Chem. 49, 183-306.
17. Tobe, M. L. & Burgess, J. (1999) Inorganic Reaction Mechanisms (Longman, New York).
18. Wang, F. Y., Chen, H. M., Parsons, S., Oswald, L. D. H., Davidson, J. E. & Sadler, P. J. (2003) Chem. Eur. J. 9, 5810-5820.
19. Velde, G. T., Bickelhaupt, F. M., Baerends, E. J., Guerra, C. F., Van Gisbergen, S. J. A., Snijders, J. G. & Ziegler, T. (2001) J. Comput. Chem. 22, 931-967.
20. Baerends, E. J., Bérces, A., Bo, C., Boerrigter, P. M., Cavallo, L., Deng, L., Dickson, R. M., Ellis, D. E., Fan, L., Fischer, T. H., et al. (2000) ADF 2000.01 (Free University, Amsterdam).
21. Baerends, E. J., Ros, P. & Ellis, D. E. (1972) Theor. Chim. Acta 27, 339-354.
22. Bennett, M. A., Huang, T. N., Matheson, T. W. & Smith, A. K. (1982) Inorg. Synth. 21, 74-78.
23. Bennett, M. A. & Smith, A. K. (1974) J. Chem. Soc. Dalton Trans., 233-241.
24. Zelonka, R. A. & Baird, M. C. (1972) Can. J. Chem. 50, 3063-3072.
25. Basolo, F. & Pearson, R. G. (1967) Mechanisms of Inorganic Reactions: A Study of Metal Complexes in Solution (Wiley, New York), 2nd Ed., pp. 124-246.
26. Broomhead, J. A. & Kane-Maguire, L. A. P. (1968) Inorg. Chem. 7, 2519-2523.
27. Hindmarsh, K., House, D. A. & Turnbull, M. M. (1997) Inorg. Chim. Acta 257, 11-18.
28. Hollebone, B. R. (1971) J. Chem. Soc. A, 481-486.
29. Carey, F. A. (1987) Organic Chemistry (MacGraw-Hill, London), pp. 430-467.
30. Chrystiuk, E. & Williams, A. (1987) J. Am. Chem. Soc. 109, 3040-3046.
31. Miller, S. E. & House, D. A. (1991) Inorg. Chim. Acta 187, 125-132.
32. Dadci, L., Elias, H., Frey, U., Hornig, A., Koelle, U., Merbach, A. E., Paulus, H. & Schneider, J. S. (1995) Inorg. Chem. 34, 306-315.
33. Fernández, R., Melchart, M., Habtemariam, A., Parsons, S. & Sadler, P. J. (2004) Chem. Eur. J. 10, 5173-5179.
34. Rapaport, I., Helm, L., Merbach, A. E., Bernhard, P. & Ludi, A. (1988) Inorg. Chem. 27, 873-879.
35. Steblerrothlisberger, M., Hummel, W., Pittet, P. A., Burgi, H. B., Ludi, A. & Merbach, A. E. (1988) Inorg. Chem. 27, 1358-1363.
36. Broomhead, J. A., Basolo, F. & Pearson, R. G. (1964) Inorg. Chem. 3, 826-832.
37. Bosnich, B. & Dwyer, F. P. (1966) Aust. J. Chem. 19, 2229-2233.
38. Wang, F. Y., Chen, H. M., Parkinson, J. A., Murdoch, P. D. & Sadler, P. J. (2002) Inorg. Chem. 41, 4509-4523.
39. Wang, F. Y., Bella, J., Parkinson, J. A. & Sadler, P. J. (2005) J. Biol. Inorg. Chem. 10, 147-155.
40. Wang, F. Y., Xu, J. J., Habtemariam, A., Bella, J. & Sadler, P. J. (2005) J. Am. Chem. Soc., in press.
41. Reedijk, J. (2003) Proc. Natl. Acad. Sci. USA 100, 3611-3616.
42. Hohmann, H., Hellquist, B. & Van Eldik, R. (1992) Inorg. Chem. 31, 345-351.
43. Jennerwein, M. & Andrews, P. A. (1995) Drug Metab. Dispos. 23, 178-184.
44. Novakova, O., Chen, H., Vrana, O., Rodger, A., Sadler, P. J. & Brabec, V. (2003) Biochemistry 42, 11544-11554.
45. Martin, R. B. (1999) in Cisplatin: Chemistry and Biochemistry of a Leading Anticancer Drug, ed. Lippert, B. (Wiley-VCH, Zurich), pp. 183-205.