Molecular orbital study of porphyrin-substrate interactions in cytochrome P450 catalysed aromatic hydroxylation of substituted anilines

Biophysical Chemistry

Volumn 73, Issue 3, 1998, Pages 189-203

  Zakharieva, Olga ^a,b   Grodzicki, Michael ^c   Trautwein, Alfred X ^c   Veeger, Cees ^a   Rietjens, Ivonne M C M ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

^b UNIVERSITY OF SOFIA   (Bulgaria)

^c UNIVERSITY OF LÜBECK   (Germany)

Author keywords

Cytochrome P450; Hydroxylation; Molecular orbital calculations

Indexed keywords

ANILINE DERIVATIVE; CYTOCHROME P450; FLUOROBENZENE;

ARTICLE; CALCULATION; ELECTRON TRANSPORT; ENZYME ACTIVITY; ENZYME BINDING; HYDROXYLATION; IN VITRO STUDY; MOLECULAR MODEL; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032572570     PISSN: 03014622     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0301-4622(98)00111-2     Document Type: Article

References (41)

1. Zakharieva O., Grodzicki M., Trautwein A.X., Veeger C., Rietjens I.M.C.M. ARTICLE TITLE. Biol. Inorg. Chem. 1:1996;192-204.
2. Korzekwa K.R., Trager W.F., Gouterman M., Spangler D., Loew G.H. ARTICLE TITLE. J. Am. Chem. Soc. 107:1985;4273-4279.
3. Korzekwa K.R., Swinney D.C., Trager W.F. ARTICLE TITLE. Biochemistry. 28:1989;9019-9027.
4. Vervoort J., Rietjens I.M.C.M., van Berkel W.J.H., Veeger C. ARTICLE TITLE. Eur. J. Biochem. 206:1992;479-484.
5. Rietjens I.M.C.M., Soffers A.E.M.F., Veeger C., Vervoort J. ARTICLE TITLE. Biochemistry. 32:1993;4801-4812.
6. P.R. Ortiz de Montellano (Ed.), Oxygen activation and transfer, in: Cytochrome P-450: Structure, Mechanism and Biochemistry, Plenum Press, New York, 1986, pp. 217-271.
7. Guengerich F.P., MacDonald T.L. ARTICLE TITLE. FASEB J. 4:1990;2453.
8. Du P., Loew G. ARTICLE TITLE. Int. J. Quant. Chem. 44:1992;251-261.
9. J. Koerts, S.J. Boeren, J. Vervoort, R. Weiss, C. Veeger, I.M.C.M. Rietjens, Chem. Biol. Interact. 1996, p. 99.
10. Cnubben N.H.P., Vervoort J., Veeger C., Rietjens I.M.C.M. ARTICLE TITLE. Chem.-Biol. Interact. 85:1992;151-172.
11. Son O.S., Everett D.W., Fiala E.S. ARTICLE TITLE. Xenobiotica. 10:1980;457-468.
12. Daly J.W., Guroff G., Udenfriend S., Witkop B. ARTICLE TITLE. Biochem. Pharmacol. 17:1968;31-36.
13. Cheever K.L., Richards D.E., Plotnic H.B. ARTICLE TITLE. Toxicol. Appl. Pharmacol. 56:1980;361-369.
14. K.E. Wade, J. Troke, C.M. MacDonald, I.D. Wilson, J.K. Nicholson, Bioanalysis of Drugs and Metabolites, E. Reid, J.D. Robinson, I. Wilson (Eds.), Plenum Publishing Corporation, New York, 1988, pp. 383-388.
15. Boeren S., Tyrakowska B., Vervoort J., de Hoffman E., Teunis K., van Veldhuizen A., Rietjens I.M.C.M. ARTICLE TITLE. Xenobiotica. 22:1992;1403-1423.
16. Tyrakowska B., Boern S., Geurtsen B., RietJens I.M.C.M. ARTICLE TITLE. Drug Metab. Dispos. 21:1993;508-519.
17. Goldblum A., Loew G.H. ARTICLE TITLE. J. Am. Chem. Soc. 107:1985;4265-4272.
18. Armstrong R.N. Enzyme-catalyzed detoxification reactions: mechanism and stereo chemistry. CRC Crit. Rev. Biochem. 22:1987;39-88.
19. Jerina D.M., Daly J.W. ARTICLE TITLE. Science. 185:1974;573-582.
20. Daly J.W., Jerina D.M., Witkop B. ARTICLE TITLE. Experientia. 28:1972;1129-1264.
21. Selander H.G., Jerina D.M., Piccolo D.E., Berchtold G.A. ARTICLE TITLE. J. Am. Chem. Soc. 97:1975;4428-4430.
22. Hanzlik R.P., Hogberg K., Judson C.M. ARTICLE TITLE. Biochemistry. 23:1984;3048-3055.
23. Rizk P.N., Hanzlik R.P. ARTICLE TITLE. Xenobiotica. 25:1995;143-150.
24. Grodzicki M. ARTICLE TITLE. J. Phys. B. 13:1980;2683-2692.
25. Grodzicki, M., Theorie und Anwendung der Self-Consistent-Charge-Xα Methode, Thesis of habilitation, Hamburg, 1985.
26. Habibollahzadeh D., Grodzicki M., Seminaro J.M., Politzer P. ARTICLE TITLE. J. Phys. Chem. 95:1991;7699-7702.
27. Grodzicki M., Seminaro J.M., Politzer P. ARTICLE TITLE. J. Chem. Phys. 94:1991;1668-1669.
28. M.J. Frisch et al., GAUSSIAN 90, Revision H, Gaussian Inc., Pittsburgh, PA, 1990.
29. Antony J., Grodzicki M., Trautwein A.X. ARTICLE TITLE. J. Phys. Chem. A. 101:1997;2692-2701.
30. Chen B.M.L., Tulinsky A. ARTICLE TITLE. J. Am. Chem. Soc. 94:1972;4144-4151.
31. Schappacher M., Weiss R., Montiel-Montoya R., Trautwein A., Tabard A. ARTICLE TITLE. J. Am. Chem. Soc. 107:1985;3736-3738.
32. Andersson L.A., Dawson J.H. ARTICLE TITLE. Struct. Bonding. 74:1990;1-40.
33. Ravichandran K.G., Boddupalli S.S., Hasemann C.A., Peterson J.A., Deisenhofer J. ARTICLE TITLE. Science. 261:1993;731-736.
34. J.P. Dahl, J. Avery (Eds.), Local Density Approximations in Quantum Chemistry and Solid State Physics, Plenum Press, New York and London, 1984.
35. R.G. Parr, W. Yang, Density-Functional Theory of Atoms and Molecules, Oxford University Press, New York, 1989.
36. J.K. Labanowski, J.W. Andzelm (Eds.), Density Functional Methods in Chemistry, Springer, New York, Berlin, Heidelberg, 1991.
37. Paulsen H., Ding X.-Q., Grodzicki M., Butzlaff Ch., Trautwein A.X., Hastung R., Wieghardt K. ARTICLE TITLE. Chem. Phys. 184:1994;149-162.
38. Paulsen H., Kröckel M., Grodzicki M., Bill E., Trautwein A.X., Leigh G.L., Paulsen H. ARTICLE TITLE. J. Inorg. Chem. 34:1995;6244-6249.
39. Grodzicki M., Flint H., Winkler H., Walker F.A., Trautwein A.X. ARTICLE TITLE. J. Phys. Chem. A. 101:1997;4202-4207.
40. Preston B.D., Miller J.A., Miller E.C. ARTICLE TITLE. J. Biol. Chem. 258:1983;8304-8311.
41. Tomaszewski J.E., Jerina D.M., Daly J.W. ARTICLE TITLE. Biochemistry. 14:1975;2024-2031.