Hypoxia-targeting copper bis(selenosemicarbazone) complexes: Comparison with their sulfur analogues

Journal of the American Chemical Society

Volumn 125, Issue 33, 2003, Pages 10040-10049

  Castle, Thomas C ^a   Maurer, Richard I ^b   Sowrey, Frank E ^a   Went, Michael J ^a   Reynolds, Christopher A ^b   McInnes, Eric J L ^c   Blower, Philip J ^a  

^a UNIVERSITY OF KENT   (United Kingdom)

^b UNIVERSITY OF ESSEX   (United Kingdom)

^c UNIVERSITY OF MANCHESTER   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; DRUG PRODUCTS; ELECTRONIC STRUCTURE; OXIDATION; POSITRONS; PROBABILITY DENSITY FUNCTION; REDUCTION; SELENIUM; SPECTROSCOPIC ANALYSIS; SULFUR; SYNTHESIS (CHEMICAL); TISSUE;

REDUCTION POTENTIALS;

CARBON;

COPPER BIS(SELENOSEMICARBAZONE); COPPER BIS(THIOSEMICARBAZONE); COPPER COMPLEX; GLYOXAL BIS(SELENOSEMICARBAZONE); LIGAND; METHYLGLYOXAL BIS(SELENOSEMICARBAZONE); SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ACCELERATION; ALKYLATION; ARTICLE; CALCULATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; ELECTROCHEMICAL ANALYSIS; HYPOXIA; METAL BINDING; OXIDATION; REDUCTION; SPECTROSCOPY; STRUCTURE ANALYSIS; SYNTHESIS; TISSUE PERFUSION;

COPPER; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE SPECTROSCOPY; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; SEMICARBAZONES; SPECTROPHOTOMETRY, ULTRAVIOLET; SULFUR COMPOUNDS;

EID: 0041519423     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja035737d     Document Type: Article

References (59)

1. Bahr, G. Z. Anorg. Allg. Chem. 1952, 268, 351-363.
2. Bahr, G. Z. Anorg. Allg. Chem. 1953, 273, 325-332.
3. Bahr, G.; Schleitzer, E. Z. Anorg. Allg. Chem. 1955, 278, 136-154.
4. Petering, D. H. In Metal Ions in Biological Systems; Sigel, H., Ed.; Marcel Dekker: New York, 1980; Vol. 11, pp 197-229.
5. Wada, A.; Fujibayashi, Y.; Yokoyama, A. Arch. Biochem. Biophys. 1994, 310, 1-5.
6. Mathias, C. J.; Welch, M. J.; Raichle, M. E.; Mintun, M. A.; Lich, L. L. ; McGuire, A. H.; Zinn, K. R.; John, E.; Green, M. A. J. Nucl. Med. 1990, 31, 351-359.
7. Dearling, J. L. J.; Lewis, J. S.; McCarthy, D. W.; Welch, M. J.; Blower, P. J. Chem. Commun. 1998, 2531-2532.
8. Dearling, J. L. J.; Lewis, J. S.; Mullen, G. E. D.; Rae, M. T.; Zweit, J.; Blower, P. J. Eur. J. Nucl. Med. 1998, 25, 788-792.
9. Dearling, J. L. J.; Lewis, J. S.; Mullen, G. E. D.; Welch, M. J.; Blower, P. J. J. Biol. Inorg. Chem. 2002, 7, 249-259.
10. Chao, K. S. C.; Bosch, W. R.; Mutic, S.; Lewis, J. S.; Dehdashti, F.; Mintun, M. A.; Dempsey, J. F.; Perez, C. A.; Purdy, J. A.; Welch, M. J. Int. J. Radiat. Oncol., Biol., Phys. 2001, 49, 1171-1182.
11. Fujibayashi, Y.; Cutler, C. S.; Anderson, C. J.; McCarthy, D. W.; Jones, L. A.; Sharp, T.; Yonekura, Y.; Welch, M. J. Nucl. Med. Biol. 1999, 26, 117-121.
12. Fujibayashi, Y.; Taniuchi, H.; Yonekura, Y.; Ohtani, H.; Konishi, J.; Yokoyama, A. J. Nucl. Med. 1997, 38, 1155-1160.
13. Fujibayashi, Y.; Yoshimi, E.; Waki, A.; Takahashi, N.; Yonekura, Y. J. Nucl. Med. 1998, 38, 503P.
14. Lewis, J. S.; Laforest, R.; Buettner, T. L.; Song, S. K.; Fujibayashi, Y.; Connett, J. M.; Welch, M. J. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 1206-1211.
15. Lewis, J. S.; McCarthy, D. W.; McCarthy, T. J.; Fujibayashi, Y.; Welch, M. J. J. Nucl. Med. 1999, 40, 177-183.
16. Lewis, J. S.; Sharp, T. L.; Laforest, R.; Fujibayashi, Y.; Welch, M. J. J. Nucl. Med. 2001, 42, 655-661.
17. Lewis, J. S.; Welch, M. J. Q. J. Nucl. Med. 2001, 45, 183-188.
18. Lewis, J. S.; McCarthy, D. W.; McCarthy, T. J.; Fujibayashi, Y.; Welch, M. J. J. Nucl. Med. 1999, 40, 177-183.
19. Obata, A.; Yoshimi, E.; Waki, A.; Lewis, J. S.; Oyama, N.; Welch, M. J.; Saji, H.; Yonekura, Y.; Fujibayashi, Y. Ann. Nucl. Med. 2001, 15, 499-504.
20. Takahashi, N.; Fujibayashi, Y.; Yonekura, Y.; Welch, M. J.; Waki, A.; Tsuchida, T.; Sadato, N.; Sugimoto, K.; Itoh, H. Ann. Nucl. Med. 2000, 14, 323-328.
21. Takahashi, N.; Fujibayashi, Y.; Yonekura, Y.; Welch, M. J.; Waki, A.; Tsuchida, T.; Sadato, N.; Sugimoto, K.; Nakano, A.; Lee, J. D.; Itoh, H. Ann. Nucl. Med. 2001, 15, 293-296.
22. Takahashi, N.; Fujibayashi, Y.; Yonekura, Y.; Welch, M. J.; Waki, A.; Tsuchida, T.; Nakamura, S.; Sadato, N.; Sugimoto, K.; Yamamoto, K.; Ishii, Y. J. Nucl. Med. 1998, 39, 53P.
23. Maurer, R. I.; Blower, P. J.; Dilworth, J. R.; Reynolds, C. A.; Zheng, Y. F.; Mullen, G. E. D. J. Med. Chem. 2002, 45, 1420-1431.
24. Dearling, J. L. J.; Mullen, G. E. D.; Lewis, J. S.; Welch, M. J.; Blower, P. J. J. Labelled Compd. Radiopharm. 1999, 42 (Suppl. 1), S276-S278.
25. Klayman, D. L.; Scovill, J. P.; Bartosevich, J. F.; Mason, C. J. Eur. J. Med. Chem. 1981, 16, 317-320.
26. Garg, B. S.; Kurup, M. R. P.; Jain, S. K.; Bhoon, Y. K. Transition Met. Chem. (London) 1988, 13, 92-95.
27. Panell, L. K.; Fales, H. M.; Scovill, J. P.; Klayman, D. L.; West, D. X. ; Tate, R. L. Transition Met. Chem. (London) 1985, 10, 141-147.
28. Keiko, N. A.; Mamashvili, T. N.; Rassolova, G. V.; Kashik, T. V.; Kalikhman, I. D.; Voronkov, M. G. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1984, 33, 561-564.
29. Goddard, D. R.; Lodam, B. D.; Ajayi, S. O.; Campbell, M. J. J. Chem. Soc. A 1969, 506-512.
30. Gingras, B. A.; Suprunchuk, R. W.; Bayley, C. H. Can. J. Chem. 1965, 43, 1650-1655.
31. Sathyanarayana, D. N.; Volka, K.; Geetharani, K. Spectrochim. Acta, Part A 1977, 33, 517-522.
32. Blumberg, W. E.; Peisach, J. J. Chem. Phys. 1968, 49, 1793-1802.
33. Getz, D.; Silver, B. L. J. Chem. Phys. 1970, 52, 6449-6450.
34. Warren, E. L.; Flowers, J. M.; Hatfield, W. E. J. Chem. Phys. 1969, 51, 1270.
35. Warren, E. L.; Horner, S. M.; Hatfield, W. E. J. Am. Chem. Soc. 1972, 94, 6392-6396.
36. Antholine, W. E.; Basosi, R.; Hyde, J. S.; Lyman, S.; Petering, D. H. Inorg. Chem. 1984, 23, 3543-3548.
37. Campbell, M. J. M. Coord. Chem. Rev. 1975, 15, 279-319.
38. Campbell, M. J. M.; Collis, A. J.; Grzeskowiak, R. Bioinorg. Chem. 1976, 6, 305-311.
39. Ackerman, L. J.; Fanwick, P. E.; Green, M. A.; John, E.; Running, W. E.; Swearingen, J. K.; Webb, J. W.; West, D. X. Polyhedron 1999, 18, 2759-2767.
40. Bushnell, G. W.; Tsang, A. Y. Can. J. Chem. 1979, 57, 603-607.
41. John, E.; Fanwick, P. E.; McKenzie, A. T.; Stowell, J. G.; Green, M. A. Nucl. Med. Biol. 1989, 16, 791-797.
42. Taylor, M. R.; Gabe, E. J.; Glusker, J. P.; Minkin, J. A.; Patterson, A. L. J. Am. Chem. Soc. 1966, 88, 1845-1846.
43. Taylor, M. R.; Glusker, J. P.; Gabe, E. J.; Minkin, J. A. Bioinorg. Chem. 1974, 3, 189-205.
44. Cowley, A. R.; Dilworth, J. R.; Donnelly, P. S.; Labisbal, E.; Sousa, A. J. Am. Chem. Soc. 2002, 124, 5270-5271.
45. Castineiras, A.; Bermejo, E.; West, D. X.; El-Sawaf, A. K.; Swearingen, J. K. Polyhedron 1998, 17, 2751-2757.
46. McQuade, P.; Lewis, J. S.; Martin, K.; Blower, P. J.; Welch, M. J. Abstract Supplement of the Fifteenth International Symposium on Radiopharmaceutical Chemistry, August 2003, Sydney, Australia. J. Labelled Compd. Radiopharm., in press.
47. West, D. X.; Ives, J. S.; Bain, G. A.; Liberta, A. E.; Valdes-Martinez, J.; Ebert, K. H.; Hernandez-Ortega, S. Polyhedron 1997, 16, 1895-1905.
48. x2-y2 orbital in the HOMO.
49. Gingras, B. A.; Suprunchuk, R. W.; Bayley, C. H. Can. J. Chem. 1962, 40, 1053-1059.
50. Parr, R. G.; Yang, W. Density Functional Theory of Atoms and Molecules; Oxford University Press: New York, 1989.
51. Andezelm, J.; Wimmer, E. J. Chem. Phys. 1992, 96, 1280-1303.
52. Medawar Centre: Oxford, 2000.
53. Becke, A. D. Phys. Rev. A: At., Mol., Opt., Phys. 2001, 38, 3098-3100.
54. Lee, C. T.; Yang, W. T.; Parr, R. G. Phys. Rev. B 1988, 37, 785-789.
55. Godbout, N.; Salahub, D. R.; Andzelm, J.; Wimmer, E. Can. J. Phys. 1992, 70, 560-571.
56. Pople, J. A.; Nesbet, R. K. J. Chem. Phys. 1954, 22, 571-578.
57. Riddick, J. A.; Bunger, W. B.; Sakland, T. K. Organic Solvents: Physical Properties and Methods of Purification; Wiley: New York, 1986.
58. Mulliken, R. S. J. Chem. Phys. 1955, 23, 1833-1840.
59. Winn, P. J.; Ferenczy, G. G.; Reynolds, C. A. J. Phys. Chem. A 1997, 101, 5437-5445.