Influence of ligand structure on Fe(II) spin-state and redox rate in cytotoxic tripodal chelators

Journal of Inorganic Biochemistry

Volumn 102, Issue 1, 2008, Pages 150-156

  Childers, Matt L ^a   Cho, Joonhyung ^a   Regino, Celeste A S ^b   Brechbiel, Martin W ^b   DiPasquale, Antonio G ^c   Rheingold, Arnold L ^c   Torti, Suzy V ^d   Torti, Frank M ^d   Planalp, Roy P ^a  

^a University of New Hampshire   (United States)

^b NATIONAL INSTITUTES OF HEALTH   (United States)

^c UNIVERSITY OF CALIFORNIA   (United States)

^d WAKE FOREST UNIVERSITY HEALTH SCIENCES   (United States)

Author keywords

Antitumor agent; Fe(II); Ligand design; Redox reaction; Tripodal chelator

Indexed keywords

CHELATING AGENT; IRON COMPLEX; LIGAND; N,N',N'' TRIS(3 METHOXY 2 PYRIDYLMETHYL) 1,3,5 TRIAMINOCYCLOHEXANE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHELATION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CONTROLLED STUDY; DEHYDROGENATION; DRUG CYTOTOXICITY; HELA CELL; HUMAN; HUMAN CELL; OXIDATION; OXIDATION REDUCTION REACTION; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ANALYSIS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

AMINOPYRIDINES; CYCLOHEXYLAMINES; FERROUS COMPOUNDS; IRON CHELATING AGENTS; LIGANDS; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PYRIDINES;

EID: 37049031427     PISSN: 01620134     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jinorgbio.2007.07.039     Document Type: Article

References (34)

1. Shannon R. Acta Crystallogr., Sect. A A32 (1976) 751-767
2. Ghisletta M., Jalett H.-P., Gerfin T., Gramlich V., and Hegetschweiler K. Helv. Chim. Acta 75 (1992) 2233-2242
3. Hegetschweiler K. Chem. Soc. Rev. 28 (1999) 239-249
4. Park G., Przyborowska A.M., Ye N., Tsoupas N., Bauer C.B., Broker G.A., Rogers R.D., Brechbiel M.W., and Planalp R.P. J. Chem. Soc., Dalton Trans. (2003) 318-324
5. Zhao R., Planalp R.P., Ma R., Greene B., Jones B., Brechbiel M., Torti F.M., and Torti S.V. Biochem. Pharmacol. 67 (2004) 1677-1688
6. Torti S.V., Torti F.M., Whitman S.P., Brechbiel M.W., Park G., and Planalp R.P. Blood 92 (1998) 1384-1389
7. Turner J., Koumenis C., Kute T.E., Planalp R.P., Brechbiel M.W., Beardsley D., Cody B., Brown K.D., Torti F.M., and Torti S.V. Blood 106 (2005) 3191-3199
8. Buss J.L., Greene B.T., Turner J., Torti F.M., and Torti S.V. Curr. Top. Med. Chem. 4 (2004) 1623-1635
9. Childers M., Su F., Przyborowska A.M., Biswokarma B., Park G., Broker G.A., Alexander J.S., Brechbiel M.W., Ruhlandt-Senge K., Torti S.V., Torti F.M., and Planalp R.P. Eur. J. Inorg. Chem. (2005) 3971-3982
10. Torti S.V., Ma R., Venditto V.J., Torti F.M., Planalp R.P., and Brechbiel M.W. Bioorg. Med. Chem. 13 (2005) 5961-5967
11. Park G., Lu F., Ye N., Brechbiel M., Torti S., Torti F., and Planalp R. JBIC. J. Biol. Inorg. Chem. 3 (1998) 449-457
12. Symons M.C.R. Free Radicals and Iron: Chemistry, Biology, and Medicine (1998), Oxford University Press, Oxford
13. Keene F.R. Coord. Chem. Rev. 187 (1999) 121-149
14. Planalp R.P., Przyborowska A.M., Park G., Ye N., Lu F.H., Rogers R.D., Broker G.A., Torti S.V., and Brechbiel M.W. Biochem. Soc. Trans. 30 (2002) 758-762
15. Ma D., Lu F., Overstreet T., Milenic D.E., and Brechbiel M.W. Nucl. Med. Biol. 29 (2002) 91-105
16. Toftlund H., and Yde-Andersen S. Acta. Chem. Scand., Series A 35 (1981) 575-585
17. Hancock R.D., and McDougall G.J. J. Chem. Soc., Dalton Trans. (1977) 67-70
18. J.H. Cho, R.P. Planalp, unpublished.
19. Goto M., Koga N., Ohse Y., Kurosaki H., Komatsu T., and Kuroda Y. J. Chem. Soc., Chem. Commun. (1994) 2015-2016
20. Holanda M.I.D., Krumholz P., and Chum H.L. Inorg. Chem. 15 (1976) 890-893
21. Toma H.E., and Stadler E. Inorg. Chim. Acta 119 (1986) 49-53
22. Ugalde-Saldivar V.M., Sosa-Torres M.E., and Gonzalez I. Eur. J. Inorg. Chem. (2003) 978-987
23. Bernhard P., Bull D.J., Buergi H.-B., Osvath P., Raselli A., and Sargeson A.M. Inorg. Chem. 36 (1997) 2804-2815
24. Gomez J., Garcia-Herbosa G., Cuevas J.V., Arnaiz A., Carbayo A., Munoz A., Falvello L., and Fanwick P.E. Inorg. Chem. 45 (2006) 2483-2493
25. Keene F., Ridd M., and Snow M. J. Am. Chem. Soc. 105 (1983) 7075-7081
26. Liu S., Lee S., Wang S., Yeh A., Gau H.M., and Shao M.Y. Inorg. Chem. 40 (2001) 6139-6143
27. Ridd M., and Keene F. J. Am. Chem. Soc. 103 (1981) 5733-5740
28. Graf E., Mahoney J., Bryant R., and Eaton J. J. Biol. Chem. 259 (1984) 3620-3624
29. Bernal I., Jensen I.M., Jensen K.B., Mckenzie C.J., Toftlund H., and Tuchagues J.P. J. Chem. Soc., Dalton Trans. (1995) 3667-3675
30. Butcher R.J., and Addison A.W. Inorg. Chim. Acta 158 (1989) 211-215
31. Christiansen L., Hendrickson D.N., Toftlund H., Wilson S.R., and Xie C.-L. Inorg. Chem. 25 (1986) 2813-2818
32. Greenaway A.M., and Sinn E. J. Am. Chem. Soc. 100 (1978) 8080-8085
33. Alcock N.W., Zhang D., and Busch D.H. Acta Crystallogr., Section C: Crystal Struct. Commun. C 55 (1999) 886-889
34. Mosmann T. J. Immunol. Methods 65 (1983) 55-63