Nanosecond photoreduction of cytochrome P450cam by channel-specific Ru-diimine electron tunneling wires

Journal of the American Chemical Society

Volumn 125, Issue 41, 2003, Pages 12450-12456

  Dunn, Alexander R ^a   Dmochowski, Ivan J ^a   Winkler, Jay R ^a   Gray, Harry B ^a  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS;

ELECTRON TUNNELING; ENZYME KINETICS; HYDROPHOBICITY; MOLECULAR STRUCTURE; PHOTOCHEMICAL REACTIONS; REDOX REACTIONS; REDUCTION;

BIOCHEMISTRY;

2,2' BIPYRIDINE; 4,4' DIMETHYLBIPYRIDINE; 4,4',5,5' TETRAMETHYLBIPYRIDINE; ADAMANTANE; BIPYRIDINE DERIVATIVE; CYTOCHROME P450; IMIDAZOLE; RUTHENIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; BINDING KINETICS; CHEMICAL INTERACTION; COMPLEX FORMATION; ELECTRON TRANSPORT; ENZYME SUBSTRATE; FLUORINATION; HYDROPHOBICITY; MOLECULAR MODEL; OXIDATION REDUCTION REACTION; REACTION ANALYSIS; SYNTHESIS;

CAMPHOR 5-MONOOXYGENASE; ELECTRONS; HEME; IMINES; KINETICS; LUMINESCENT MEASUREMENTS; MODELS, MOLECULAR; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; PHOTOCHEMISTRY; RUTHENIUM; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0141919816     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0294111     Document Type: Article

References (61)

1. Ortiz de Montellano, P. R. Cytochrome P450: Structure, Mechanism and Biochemistry, 2 ed.; Plenum Press: New York, 1995; p 652.
2. Fisher, M. T.; Sligar, S. G. J. Am. Chem. Soc, 1985, 107, 5018-5019.
3. (a) Davydov, R.; Makris, T. M.; Kofman, V.; Werst, D. E.; Sligar, S, G.; Hoffman, B. M. J, Am. Chem. Soc. 2001, 123, 1403-1415.
4. (b) Schlichting, I.; Berendzen, J.; Chu, K.; Stock, A. M.; Maves, S. A.; Benson, D. E.; Sweet, R. M.; Ringe, D.; Petsko, G. A.; Sligar, S. G. Science 2000, 287, 1615-1622.
5. Groves, J. T.; McClusky, G, A.; White, R. E.; Coon, M. J. Biochem. Biophys. Res. Commun, 1978, 81, 154-160.
6. Dmochowski, I. J.; Crane, B. R.; Wilker, J. J.; Winkler, J. R.; Gray, H. B. Proc. Natl. Acad. Sci. U.S.A. 1999, 96, 12987-12990.
7. Wilker, J. J.; Dmochowski, I. J.; Dawson, J. H.; Winkler, J, R.; Gray, H, B. Angew. Chem., Int. Ed. 1999, 38, 90-92.
8. Dmochowski, I. J. Probing cytochrome P450 with sensitizer-linked substrates; California Institute of Technology: Pasadena. CA, 2000, p 305.
9. Roundhill, D. M. Photochemistry and Photophysics of Metal Complexes; Plenum Press: New York. 1994.
10. van Houten, J.; Watts, R. J. J. Am. Chem. Soc. 1976, 98, 4853-4858.
11. Cook, M. J.; Lewis, A. P.; McAuliffe, G. S. G.; Skarda, V.; Thomson, N. J.; Glasper, J. L.; Robbins, D. J. J. Chem. Soc., Perkin Trans. 2 1984, 1293-1301.
12. Dawson, J. H.; Andersson, L. A.; Sono, M. J. Biol. Chem. 1983, 258, 13637-13645.
13. Dmochowski, I. J.; Winkler, J. R.; Gray. H. B. J. Inorg. Biochem. 2000, 81, 221-228.
14. Low, D. W.; Winkler, J. R.; Gray, H. B. J. Am. Chem. Soc. 1996, 118, 117-120.
15. Dunn, A. R.; Hays, A.-M. A.; Goodin, D. B.; Stout, C. D.; Chiu. R.; Winkler, J. R.; Gray, H. B. J. Am. Chem. Soc. 2002, 124, 10254-10255.
16. Kotkar, D.; Joshi, V.; Ghosh, P. K. J. Chem. Soc., Chem. Commun. 1987, 1, 4-6.
17. Miller, R. R.; Brandt, W. W.; Puke, M. J. Am. Chem. Soc. 1955, 77, 3178-3180.
18. Demas, J. N. Excited State Lifetime Measurements; Academic Press: New York, 1983.
19. Wu, P.; Brand, L. Anal. Biochem. 1994, 218, 1-13.
20. Opperman, K. A.; Mecklenburg, S. L.; Meyer, T. J. Inorg. Chem. 1994, 33, 5295-5301.
21. Dawson, J. H.; Andersson, L. A.; Sono, M. J. Biol. Chem. 1982, 257, 3606-3617.
22. 3+ does not oxidize these nearby residues. Tyrosine oxidation by Ru-diimine complexes has been previously observed: (a) Sjodin, M.; Styring, S.; Akermark, B.; Sun, L. C.; Hammarström, L. J. Am. Chem. Soc. 2000, 122, 3932-3936.
23. (b) Magnuson, A.; Berglund, H.; Korall, P.; Hammarström, L.; Åkermark. B.; Styring, S.; Sun, L. C. J. Am. Chem. Soc. 1997, 119, 10720-10725.
24. 3+ decays through multiple pathways in aqueous solution: (a) Brune, S. N.; Bobbitt, D. R. Talanta 1991, 38, 419-424.
25. (b) Ledney, M.; Dutta, P. K. J. Am. Chem. Soc. 1995, 117, 7687-7695.
26. (c) Ghosh, P. K.; Brunschwig, B. S.; Chou, M.; Creutz, C.; Sutin, N. J. Am. Chem. Soc. 1984, 106, 4772-4783.
27. (d) Arce-Sagues, J. A.; Gillard, R. D.; Lancashire, R. J.; Williams, P. A. J. Chem. Soc., Dalton Trans. 1979, 1, 193-198.
28. 8bp-Im, as judged by transient absorption at 445 nm. Thus, the processes leading to the long-lived ferrous heme constitute a minor side reaction compared to the initial forward and back electron transfer.
29. Eisenberg, D.; McLachlan, A. D. Nature 1986. 319, 199-203.
30. Dunn, A. R.; Dmochowski, I. J.; Bilwes, A. M.; Gray, H. B.; Crane, B. R. Proc. Natl. Acad. Sci. U.S.A. 2001, 98, 12420-12425.
31. Marcus, R. A. J. Chem. Phys. 1956, 24, 966-989.
32. Marcus, R. A.; Sutin, N. Biochim. Biophys. Acta 1985, 811, 265-322.
33. heme falls between 0.7 and 1.2 eV (Winkler, J. R.; Wittung-Stafshede, P.; Leckner, J.; Malmstrom, B. G.; Gray, H. B. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 4246-4249).
34. (a) Scott, J. R.; Willie, A.; McLean, M.; Stayton, P. S.; Sligar, S. G.; Durham, B.; Millett, F. J. Am. Chem. Soc. 1993, 115, 6820-6824.
35. (b) Turro, C.; Zaleski, J. M.; Karabatsos, Y. M.; Nocera, D. G. J. Am. Chem. Soc. 1996, 118, 6060-6067.
36. (a) Gould, I. R.; Moser, J. E.; Armitage, B.; Farid, S.; Goodman, J. L.; Herman, M. S. J. Am. Chem. Soc. 1989, 111, 1917-1919.
37. (b) Wasielewski, M. R.; Niemczyk, M. P.; Svec, W. A.; Pewitt, E. B. J. Am. Chem. Soc. 1985, 107, 1080-1082.
38. (c) Ohno, T.; Yoshimura, A.; Mataga, N. J. Phys. Chem. 1986, 90, 3295-3297.
39. (d) Chen, P.; Duesing, R.; Tapolsky, G.; Meyer, T. J. J. Am. Chem. Soc. 1989, 111, 8305-8306.
40. (e) Closs, G. L.; Miller. J. R. Science 1988, 240, 440-447.
41. (f) Fox, L. S.; Kozik, M.; Winkler, J. R.; Gray, H. B. Science 1990, 247, 1069-1071.
42. Beitz, J. V.; Miller, J. R. J. Chem. Phys. 1979, 71, 4579-4595.
43. (a) Mines, G. A.; Bjerrum, M. J.; Hill, M. G.; Casimiro, D. R.; Chang, I.-J.; Winkler. J. R.; Gray, H. B. J. Am. Chem. Soc. 1996, 118. 1961-1965.
44. (b) Makinen, M. W.; Churg, A. K. Structural and analytical aspects of the electronic spectra of heme proteins. In Iron Porphyrins; Lever, A. B. P., Gray, H. B., Eds.; Addison-Wesley: Reading, MA, 1983; Vol. 1, pp 141-236.
45. Daizadeh, I.; Medvedev, E. S.; Stuchebrukhov, A. A. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 3703-3708.
46. Langen, R.; Colon, J. L.; Casimiro, D. R.; Karpishin, T. B.; Winkler, J. R.; Gray, H. B. J. Biol. Inorg. Chem. 1996, 1, 221-225.
47. Beratan, D. N.; Skourtis, S. S. Curr. Opin. Chem. Biol. 1998, 2, 235-243.
48. (a) Winkler, J. R. Curr. Opin. Chem. Biol. 2000, 4, 192-198.
49. (b) Onuchic, J. N.; Beratan, D. N.; Winkler, J. R.; Gray, H. B. Annu. Rev. Biophys. Biomol. Struct. 1992, 21, 349-377.
50. (c) Beratan, D. N.; Onuchic, J. N.; Winkler, J. R.; Gray, H. B. Science 1992, 258, 1740-1741.
51. (a) Gunsalus, I. C.; Meeks, J. R.; Lipscomb, J. D. Ann. N.Y. Acad. Sci. 1973, 212, 107-121.
52. (b) Sligar, S. G.; Gunsalus, I. C. Proc. Natl. Acad. Sci. U.S.A. 1976, 73, 1078-1082.
53. Elliott, C. M.; Freitag, R. A.; Blaney, D. D. J. Am. Chem. Soc. 1985, 107, 4647-4655.
54. (a) Smalley, J. F.; Feldberg, S. W.; Chidsey, C. E. D.; Linford, M. R.; Newton, M. D.; Liu, Y.-P. J. Phys. Chem. 1995, 99, 13141-13149.
55. (b) Warman, J. M.; Smit, K. J.; de Haas, M. P.; Jonker, S. A.; Paddon-Row, M. N.; Oliver, A. M.; Kroon, J.; Oevering, H.; Verhoeven, J. W. J. Phys. Chem. 1991, 95, 1979-1987.
56. (c) Langen, R.; Chang, I.-J.; Germanas, J. P.; Richards, J. H.; Winkler, J. R.; Gray, H. B. Science 1995, 268, 1733-1735.
57. (d) Creager, S.; Yu, C. J.; Bamdad, C.; O'Connor, S.; MacLean, T.; Lam, E.; Chong, Y.; Olsen, G. T.; Luo, J. Y.; Gozin, M.; Kayyem, J. F. J. Am. Chem. Soc. 1999, 121, 1059-1064.
58. (e) Sikes, H. D.; Smalley, J. F.; Dudek, S. P.; Cook, A. R.; Newton, M. D.; Chidsey, C. E. D.; Feldberg, S. W. Science 2001, 291, 1519-1523.
59. (f) Pollard, W. T.; Felts, A. K.; Friesner, R. A. Adv. Chem. Phys. 1996, 93, 77-134.
60. (g) Davis, W. B.; Wasielewski, M. R.; Ratner, M. A.; Mujica, V.; Nitzan. A. J. Phys. Chem. A 1997, 101, 6158-6164.
61. (h) McConnell, H. M. J. Chem. Phys. 1961, 35, 508-515.