Homology modelling of the enzyme P450 17α-hydroxylase/ 17,20-lyase - a target for prostate cancer chemotherapy - from the crystal structure of P450BM-3

Anti-Cancer Drug Design

Volumn 12, Issue 2, 1997, Pages 113-123

  Burke, David F ^b   Laughton, Charles A ^a,b   Neidle, Stephen ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b INSTITUTE OF CANCER RESEARCH   (United Kingdom)

Author keywords

Chemotherapy; Homology modelling; P450BM 3; P450c17; Prostate cancer

Indexed keywords

ANTINEOPLASTIC AGENT; CYTOCHROME P450; STEROID; STEROID 17,20 LYASE; STEROID 17ALPHA MONOOXYGENASE;

ARTICLE; BINDING AFFINITY; COMPARATIVE STUDY; CRYSTAL STRUCTURE; DRUG TARGETING; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME STRUCTURE; HUMAN; MOLECULAR MODEL; NONHUMAN; PRIORITY JOURNAL; PROSTATE CANCER;

AMINO ACID SEQUENCE; ANIMALS; ANTINEOPLASTIC AGENTS; BACTERIAL PROTEINS; BINDING SITES; CAMPHOR 5-MONOOXYGENASE; CATTLE; CHICKENS; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; HUMANS; MALE; MIXED FUNCTION OXYGENASES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; PREDICTIVE VALUE OF TESTS; PROSTATIC NEOPLASMS; PROTEIN STRUCTURE, SECONDARY; RATS; SEQUENCE HOMOLOGY, AMINO ACID; STEROID 17-ALPHA-HYDROXYLASE;

EID: 0030945393     PISSN: 02669536     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (37)

1. ABOLA, E., BERNSTEIN, F.C., BRYANT, S.H., KOETZLE, T.F. & WENG, J. (1987). Protein Data Bank. In Crystallographic Databases - Information Content, Software Systems, Scientific Applications. Allen, F.H., Bergerhoff, G. and Sievers, R. (eds), pp 107-132. Bonn, Cambridge, Chester: Data Commision of the International Union of Crystallography.
2. ANGELASTRO, M.R., LAUGHLIN, M.E., SCHATZMAN, G.L., BEY, P. & BLOHN, T.R. (1989). 17β-(cyclopropylamino)-andros-5-en-3β-ol, a selective mechanism based inhibitor of cytochrome P45017α (steroid 17α-hydroxylase/C17-20 lyase). Biochemical and Biophysical Research Communications, 162, 1571.
3. BARRIE, S E., POTTER, G.A., GODDARD, P.M., HAYNES, B.P., DOWSETT, M. & JARMAN, M. (1994). Pharmacology of novel steroidal inhibitors of cytochrome P450(17-α) (17-α-hydroxylase C17-20 lyase). Journal of Steroid Biochemistry and Molecular Biology, 50, 267.
4. BARTON, G.J. (1990) Protein multiple sequence alignment and flexible pattern matching. Methods in Enzymology, 183, 403.
5. CHUNG, B-C., PICARDO-LEONARD, J. HANNUI M., BIENKOWSKI M., HALL, P.F., SHIVELY J.E. & MILLER W.L. (1987). Cytochrome P450c17 cloning of human adrenal and testis cDNAs indicates the same gene is expressed in both tissues. Proceedings of the National Academy of Science, USA, 84 407.
6. CUPP-VICKERY, J.R., LI, H. & POULOS, T.L. (1994). Preliminary crystallographic analysis of an enzyme involved in erythromycin biosynthesis cytochrome P450eryF. Proteins, 20, 197.
7. FERRIN, T.E., HUANG, C.C, JARVIS, L.E. & LANGRIDGE, R. (1988). The MIDAS display system. Journal of Molecular Graphics, 6,13.
8. GRAHAM-LORENCE, S., AMARNEH, B., WHITE, R.E., PETERSON, J.A. & SIMPSON, E.R (1995). A three dimensional model of aromatase cytochrome P450. Protein Science, 4 , 1065.
9. GOTOH, O. (1992). Substrate recognition sites in cytochrome P450 family 2 (CYP2) proteins inferred from comparative analyses of amino acid and coding nucleotide sequences. Journal of Biological Chemistry, 267, 83.
10. HASEMANN, C A., RAVICHANDRAN, K.G., PETERSON, J.A. & DEISENHOFER, J. (1994). Crystal Structure and refinement of cytochrome P450terp at 2.3Å resolution. Journal of Molecular Biology, 236 1169.
11. HASEMANN, C.A., KURUMBAIL, R G., BODDUPALLI, S.S., PETERSON, J.A. & DEISENHOFER, J. (1995). Structure and function of cytochromes P450: a comparative analysis of three crystal structures. Structure, 2, 41.
12. IWASAKI, M., DARDEN, T.A, PEDERSON, L.G., DAVIS, D.G., JUVONEN, R.O., SUEYOSHI, T. & NEGISHI, M. (1993). Engineering mouse P450coh to a novel corticosterone 15α-hydroxylase and modelling steroid binding orientation in the substrate binding pocket. Journal of Biological Chemistry, 268, 759.
13. KAGIMOTO, M., WINTER, J.S.D., KAGIMOTO, K, SIMPSON, E.R. & WATERMAN, M.R. (1988). Structural characterisation of normal and mutant human steroid 17α-hydroxylase genes: molecular basis of one example of combined 17α-hydroxylase/17,20 lyase deficiency. Molecular Endocrinology, 2, 564.
14. KITAMURA, M., BUCZKO, E. & DUFAU, M.L. (1991). Dissociation of hydroxylase and lyase activities by site directed mutagenesis of the rat P450-17. Molecular Endocrinology, 5, 1373.
15. KUHN-VELTEN, W.N., BUNSE, T & FORSTER, M.E.C. (1991). Enzyme kinetic and inhibition analyses of cytochrome P450XVII, a protein with a bifunctional catalytic site. Journal of Biological Chemistry, 266, 6291.
16. LASKOWSKI, R.A., MACARTHUR, M.W., MOSS, D.S. & THORNTON, J.M. (1993). PROCHECK: a program to check the stereochemical quality of protein structures. Journal of Applied Crystallography, 26, 283-291.
17. LAUGHTON, C.A. (1994). Prediction of protein side-chain conformations from local three-dimensional homology relationships. Journal of Molecular Biology, 235 1088.
18. LAUGHTON, C.A., ZVELEBIL, M.J.J.M, NEIDLE, S & STERNBERG, M.J.E. (1990). A molecular model for the enzyme cytochrome P45017α - a major target for the chemotherapy of prostatic cancer. Biochemical and Biophysical Research Communications, 171, 1160.
19. LEWIS, D. F. & MOEREELS, H. (1992). The sequence homologies of cytochromes P-450 and active-site geometries. Journal of Computer Aided Molecular Design, 6, 235.
20. 106 → Proline causes 17α-hydroxylase deficiency. Journal of Biological Chemistry, 266, 15992.
21. LIN, D., ZHANG, L-H., CHIAO, E. & MILLER, W. (1994). Modelling and mutagenesis of the active site of human P450c17. Molecular Endocrinology, 8, 392.
22. MASAMURA, S., ADLERCREUTZ, H., HARVEY, H., LIPTON, A., DEMERS, L.M. SANTEN, R. J. & SANTNER, S. J (1995). Aromatase inhibitor development for treatment of breast-cancer. Breast Cancer Research And Treatment, 33, 19.
23. MONNO, S., OGAWA, H., DATE, T., MOTOJI, F., MILLER, W.L. & KOBAYASHI, M. (1993). Mutation of histidine 373 to leucine in cytochrome P450c17 causes 17-hydroxylase deficiency. Journal of Biological Chemistry, 268, 25811.
24. NAKAHARA, H., SHOUN, H., ADACHI, S-I., IIZUKA, T. & SHIRO, Y (1994). Crystallization and preliminary-X-ray diffraction studies of nitric-oxide reductase cytochrome P450nor from fusarium-oxysporum. Journal of Molecular Biology, 239, 158.
25. OUZOUNIS, C., SANDER, C., SCHARF, M. & SCHNEIDER, R (1993). Prediction of protein structure by evaluation of sequence structure fitness. Aligning sequences to contact profiles derived from three dimensional structures. Journal of Molecular Biology, 232, 805.
26. PEARLMAN, D.A., CASE, D.A., CALDWELL, J.C., SEIBEL, G.L., CHANDRA SINGH, U , WEINER, P. & KOLLMAN, P.A. (1991) AMBER 4.0. University of California, San Francisco.
27. PICADO-LEONARD, J. & MILLER, W.L. (1988). Homologous sequences in steroidogenic enzymes, steroid receptors and a steroid binding protein suggest a concensus steroid binding sequence. Molecular Endocrinology , 2, 1145.
28. PICKETT, S., SAQI, M.A.S. & STERNBERG, M.J.E. (1987). Evaluation of the sequence template method for protein structure prediction. Journal of Molecular Biology, 228, 170.
29. POULOS, T.L., FINZEL, B.C. & HOWARD, A.L. (1986). Crystal structure of substrate-free Pseudomonas putida P450. Biochemistry, 25, 5314.
30. RAVICHANDRAN, K.G., BODDUPALLI, S.S., HASEMAN, C.A., PETERSON, J.A. & DEISENHOFER, J. (1993) Crystal structure of hemoprotein domain of P450bm3, a prototype for microsomal P450's. Science, 261, 731.
31. ROST, B. & SANDER, C. (1992) Jury returns on structure prediction. Nature, 360, 540.
32. RUAN, K.H., WANG, L.H., WU, K.K. & KULMACZ, R.J. (1993). Amino-terminal topology of thromboxane synthase in the endoplasmic reticulum. Journal of Biological Chemistry, 268, 19483.
33. SZKLARZ, G.D., ORNSTEIN, R.L. & HALPERT, J.R. (1994). Application of 3-dimensional homology modelling of cytochrome P450-2b1 for interpretation of site-directed mutagenesis results. Journal of Biomolecular Structure and Dynamics, 12, 61.
34. TRACHTENBERG, J. (1984). Ketoconazole therapy in advanced prostatic cancer. Journal of Urology, 132, 61.
35. VAN WAUWE, J.P & JANSSEN, P.A.J. (1989). Is there a case for P-450 inhibitors in cancer treatment? Journal of Medical Chemistry, 32, 2231.
36. YANASE, T., KAGIMOTO, M., SUZUKI, S., HASHIBA, K., SIMPSON, E.R. & WATERMAN, M.R. (1989). Deletion of a phenylalanine in the N-terminal region of human cytochrome P45017 results in partial combined 17α-hydroxylase/17-20 lyase deficiency. Journal of Biological Chemistry, 264, 18076.
37. ZVELEBIL, M.J.J.M., WOLF, C.R & STERNBERG, M.J.E. (1991). A predicted three dimensional structure of human cytochrome P450: implications for substrate specificity. Protein Engineering, 4, 271.