Molecular modeling studies of a ferric hexadentate 3-hydroxy-2(l#)-pyridinone complex and an analogue by molecular mechanics, molecular dynamics, and free energy perturbation simulations

Journal of Physical Chemistry

Volumn 100, Issue 6, 1996, Pages 2345-2352

  Xiao, Gaoyi ^a,b   Van Helm, Dick Der ^a   Hider, Robert C ^a   Rai, Bejeya L ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

^b KING'S COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001496644     PISSN: 00223654     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp942640s     Document Type: Article

References (51)

1. Weatherall, D. J.; Clegg, J. B. The Tlialassaemia Syndromes, 3rd ed.; Blackwell Scientific Publications: Oxford, 1981.
2. Halliwell, B.; Gutteridge, J. M. C. Biochem. J. 1984, 219, 1.
3. Sephton-Smith, R. Br. Med. J. 1962, 2, 1577.
4. Modell, B.; Letsky, E. A.; Flynn, D. M.; Peto, R.; Weatherall, D. J. Br. Med. J. 1982, 284, 1081.
5. Porter, J. B.; Huehns, E. R.; Hider, R. C. In Bailliere's Clinical Haematohgy; Hershko, C., Ed.; Bailliese Tindall: London, 1989; Vol. 2, pp 257-292.
6. Rodgers, S. J.; Lee, Chi-Woo; Ng, C. Y.; Raymond, K. N. Inorg. Chem. 1987, 26, 1622.
7. Bergeron, R. J.; Wiegand, J.; McManis, J. S.; Perumal, P. T. J. Med. Chem. 1991,34, 3182.
8. Martell, A. E.; Motekaitis, R. J.; Clarke, E. T.; Harrison, J. J. Can. J. Chem. 1986, 64, 449.
9. Hider, R. C. Structure and Bonding; Neilands, J. B., Ed.; Springer Verlag: Berlin, 1984; Vol. 58, pp 25-87.
10. Hider, R. C.; Hall, A. D. Progress in Med. Chem.; Ellis, G. P.; West, G. B., Eds.; Elsevier: New York, 1991; Vol. 28, pp 41-173.
11. Summers, J. B.; Gunn, B. P.; Martin, J. G.; Mazdiyasni, H.; Stewart, A. O.; Young, P. R.; Goetze, A. M.; Bouska, J. B.; Dyer, R. D.; Brooks, D. W.; Carter, G. W. J. Med. Chem. 1988, 31, 3.
12. Hershko, C.; Link, G.; Pinson, A.; Avramovia-Grisaru, S.; Sarel, S.; Peter, H. H.; Hider, R. C.; Grady, R. W. Ann. N. Y. Acad. Sei. 1990, 612, 351.
13. Streater, M.; Taylor, P. D.; Hider, R. C.; Porter, J. B. J. Med. Chem. 1990, 33, 1749.
14. Porter, J. B.; Gyparaki, M.; Burke, L. C.; Huehns, E. R.; Sarpong, P.; Saez, V.; Hider, R. C. Blood 1988, 72, 1479.
15. Martell, A. E. Adv. Chem. Ser. 1967, 62, 272.
16. Hider, R. C.; Kontoghiorghes, G.; Silver, J.; Stockham, M. A. UK Patent GB21469898B, 1983.
17. White, D. L.; Durbin, P. W.; Jeung, N.; Raymond, K. N. J. Med. Chem. 1988, 31, 11.
18. Miyamoto, S.; Kollman, P. A. J. Am. Chem. Soc. 1992,114,3668.
19. Karpishin, T. B.; Dewey, T. M.; Raymond, K. N. J. Am. Chem. Soc. 1993, 115, 1842.
20. Stack, T. D. P.; Hou, Z.; Raymond, K. N. J.Am. Chem. Soc. 1993, 115, 6466.
21. Trueblood, K. N.; Knobler, C. B.; Maverick, E.; Helgeson, R. C.; Brown, S. B.; Cram, D. J. J. Am. Chem. Soc. 1981, 103, 5594.
22. Cram, D. J.; Lein, G. M.; Kaneda, T.; Helgeson, R. C.; Knobler, C. B.; Maverick, E.; Trueblood, K. N. J. Am. Chem. Soc. 1981,103, 6228.
23. Lein, G. M.; Cram, D. J. J. Chem. Soc., Chem. Commun. 1982, 301.
24. Cram, D. J. Science 1986, 240, 760, and references therein.
25. Brubaker, G. R.; Johnson, D. W. Coord. Chem. Rev. 1984, 53, 1.
26. Hancock, R. D.; Martel, A. E. Chem. Rev. 1989, 90, 1875-1914.
27. Comba, P. Coord. Chem. Rev. 1993, 123, 1-48.
28. Kollman, P. A.; Wipff, G.; Singh, U. C. J. Am. Chem. Soc. 1985, 707, 2212, and references therein.
29. Shanzer, A.; Libman, J.; Lifson, S.; Felder, C. E. J. Am. Chem. Soc. 1986, 108, 7609, and references therein.
30. Tor, Y.; Libman, J.; Shanzer, A.; Felder, C. E.; Lifson, S. J. Ain. Chem. Soc. 1992, 114, 6601.
31. Fidelis, K. Ph.D. Thesis, University of Oklahoma, Norman, OK, 1989.
32. Bouraoui, A.; Fathallah, M.; Blaive, B.; Gallo, R.; Mhenni, F. J. Chem. Soc., Perkin Trans. 1990, 2, 121L
33. Xiao, G.; van der Helm, D.; Hider, R. C.; Dobbin, P. S. Inorg. Chem. 1995, 34, 1268.
34. Pearlman, D. A.; Case, D. A.; Caldwell, J. C.; Seibel, G. L.; Singh, U. C.; Weiner, P.; Kollman, P. A. AMBER 4.0; University of California: San Francisco, CA, 1991.
35. Weiner, S. J.; Kollman, P. A.; Case, D. A.; Singh, U. C.; Ghio, C; Alagona, G.; Profeta, S.; Weiner, P. J. Am. Chem. Soc. 1984, 106, 765.
36. Rappe, A. K.; Casewit, C. J.; Cohvell, K. S.; Goddard, W. A.; Skiff, W. M. J. Am. Chem. Soc. 1992, 114, 10024.
37. Scarrow, R. C.; Raymond, K. N. Inorg. Chem. 1988, 27, 4140.
38. Stewart, J. J. P. MOP AC 5.0.; Frank J. Seiler Research Laboratory, United States Air Force Academy: Colorado Springs, CO, 1988.
39. Besler, B. H.; Merz, K. M., Jr.; Kollman, P. A. J. Comput. Chem. 1990. //, 431.
40. Jorgenson, W. L.; Chandrasekhar, J.; Madura, J. D. J. Chem. Phys. 1983, 79, 926.
41. Brunger, A. T.; Clore, G. M.; Gronenborn, A. M.; Karplus, M. Proc. Natl. Acad. Sei. U.SA. 1986, 83, 3801.
42. Kirkwood, J. G. J. Chem. Phys. 1935, 3, 300.
43. Zwanzig, R. W. J. Chem. Phys. 1954, 22, 1420.
44. Fleischman, S. H.; Brooks, C. L. J. Chem. Phys. 1987, 87, 3029.
45. Hamor, T. A.; Watkin, D. J. J. Chem. Soc., Chem. Commun. 1969, 440.
46. Anderson, B. F.; Buckingham, D. A.; Robertson, G. B.; Webb, J. Acta Crystallogr. 1982, B28, 1927.
47. van der Helm, D.; Baker, J. R.; Eng-Wilmot, D. K.; Hossain, M. B.; Loghry, R. A. J. Am. Chem. Soc. 1980, 702, 4224.
48. Bulls, A. R.; Pippin, C. G.; Hahn, F. E.; Raymond, K. N. J. Am. Chem. Soc. 1990, 112, 2627.
49. Hahn, F. E. Angew. Chem., Int. Ed. Engl. 1993, 32, 650.
50. Hermans, J.; Berendsen, H. J. C.; van Gunsteren, W. F.; Postma, J. P. M. Biopolymers 1984, 23, 1513-1519.
51. Scarrow, R. C.; Ecker, D. J.; Ng, C.; Liu, S.; Raymond, K. N. Inorg. Chem. 1991, 30, 900.