Estrone 3-sulfate mimics, inhibitors of estrone sulfatase activity: Homology model construction and docking studies

Biochemistry

Volumn 41, Issue 50, 2002, Pages 14801-14814

  Howarth, Nicola M ^a,c   Purohit, Atul ^b   Robinson, James J ^a   Vicker, Nigel ^a   Reed, Michael J ^b   Potter, Barry V L ^a  

^a University of Bath   (United Kingdom)

^b ST MARY S HOSPITAL   (United Kingdom)

^c HERIOT WATT UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; BIOLOGICAL ORGANS; BIOSYNTHESIS; CATALYSIS; ENDOCRINOLOGY; ENZYME KINETICS; HYDROPHOBICITY; ISOMERS; SUBSTRATES; TUMORS;

ENDOCRINE THERAPY;

BIOCHEMISTRY;

ASPARTIC ACID; ESTRONE; ESTRONE 3 4 TOLUENE SULFONATE; ESTRONE 3 O METHYLTHIOPHOSPHONATE; ESTRONE 3 O SULFAMATE; ESTRONE SULFATASE; ESTRONE SULFATE; GLUTAMINE; GLYCINE; LYSINE; MAGNESIUM ION; SULFATASE; UNCLASSIFIED DRUG;

ARTICLE; BREAST CANCER; CANCER HORMONE THERAPY; CATALYSIS; CHIRALITY; DIASTEREOISOMER; DRUG BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROPHOBICITY; MOLECULAR MODEL; PARTICLE SIZE; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

ANIMALS; BINDING SITES; BREAST NEOPLASMS; CROTALID VENOMS; DRUG SCREENING ASSAYS, ANTITUMOR; ENZYME INHIBITORS; ESTRONE; HUMANS; MODELS, CHEMICAL; MODELS, MOLECULAR; MOLECULAR MIMICRY; PHOSPHONIC ACIDS; SEQUENCE HOMOLOGY, AMINO ACID; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; SULFATASES; TETRAHYDRONAPHTHALENES; TUMOR CELLS, CULTURED;

EID: 2242438074     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi020543g     Document Type: Article

References (56)

1. James, V. H. T., and Reed, M. J. (1980) Prog. Cancer Res. Ther. 14, 471-487.
2. Lippman, M. E., Dickson, R. B., Gelmann, E. P., Rosen, N., Knabbe, C., Bates, S., Bronzert, D., Hoft, K., and Kasid, A. (1988) J. Steroid Biochem. 30, 53-61.
3. Bonney, R. C., Reed, M. J., Davidson, K., Beranek, P. A., and James, V. H. T. (1983) Clin. Endocrinol. 19, 727-739.
4. Van Landgeham, A. A. J., Poortman, J., Nabuurs, M., and Thijssen, J. H. H. (1985) Cancer Res. 45, 2900-2906.
5. Vermeulen, A., Deslypere, J. P., Pavidaens, R., Leclercq, G., Roy, F., and Henson, J. C. (1986) Eur. J. Cancer Clin. Oncol. 22, 515-525.
6. Fishman, J., Nisselbaum, J. S., Menendez-Butet, C. J., and Schwartz, M. K. (1977) J. Steroid Biochem. 8, 893-896.
7. Santner, S. J., Feil, P. D., and Santen, R. J. (1984) J. Clin. Endocrinol. Metab. 59, 29-33.
8. James, V. H. T., McNeill, J. M., Lai, L. C., Newton, C. J., Ghilchik, M. W., and Reed, M. J. (1987) Steroids 50, 269-279.
9. Noel, C. T., Reed, M. J., Jacobs, H. S., and Jones, V. H. T. (1981) J. Steroid Biochem. 14, 1101-1105.
10. Longcope, C., Layne, D. S., and Tait, J. F. (1968) J. Clin. Invest. 47, 93-106.
11. Lonning, P. E., Johannessen, D. C., and Thorsen, T. (1989) Br. J. Cancer 60, 107-111.
12. Dauvois, S., and Labrie, F. (1989) Breast Cancer Res. Treat. 13, 61-69.
13. Adams, J. B., Garcia, M., and Rochefort, H. (1981) Cancer Res. 41, 4720-4726.
14. Poulin, R., and Labrie, F. (1986) Cancer Res. 46, 4933-4937.
15. Poortman, J., Andriesse, R., Agama, A., Donker, G. H., Schwarz, F., and Thijssen, J. H. H. (1980) in Adrenal Androgens (Genazzani, A. R., Thijssen, J. H. H., and Siiteri, P. K., Eds.) pp 219-240, Raven Press, New York.
16. Purohit, A., Dauvois, S., Parker, M. G., Potter, B. V. L., Williams, G. J., and Reed, M. J. (1994) J. Steroid Biochem. Mol. Biol. 50, 101-104.
17. Carlstrom, K., Doberl, A., Gershagen, S., and Rannevik, G. (1984) Acta Obstet. Gynecol. Scand., Suppl. 123, 125-111.
18. Birnbock, H., and Von Angerer, E. (1990) Biochem. Pharmacol. 39, 1709-1713.
19. Li, P. K., Pillai, R., and Dibbelt, L. (1995) Steroids 60, 299-306.
20. Li, P. K., Pillai, R., Young, B. L., Bender, W. H., Martino, D. M., and Liu, F. T. (1993) Steroids 58, 106-111.
21. Anderson, C. J., Lucan, L. J. H., and Widlanski, T. S. (1995) J. Am. Chem. Soc. 117, 3889-3890.
22. (a) Anderson, C., Freeman, J., Lucas, L. H., Farley, M., Dalhoumi, H., and Widlanski, T. S. (1997) Biochemistry 36, 2586-2594;
23. (b) Li, P. K., Chu, G. H., Guo, J. P., Peters, A., and Selcer, K. W. (1998) Steroids 63, 425-432;
24. (c) Piorier, D., and Biovin, R. P. (1998) Bioorg. Med. Chem. Lett. 8, 1891-1896;
25. (d) Biovin, R. P., Luu-The, V., Lachance, R., Labrie, F., and Poirier, D. (2000) J. Med. Chem. 43, 4465-4478.
26. Howarth, N. M., Cooper, G., Purohit, A., Duncan, L., Reed, M. J., and Potter, B. V. L. (1993) Bioorg. Med. Chem. Lett. 3, 313-318.
27. Duncan, L., Purohit, A., Howarth, N. M., Potter, B. V. L., and Reed, M. J. (1993) Cancer Res. 53, 298-303.
28. Howarth, N. M., Purohit, A., Reed, M. J., and Potter, B. V. L. (1997) Steroids 62, 346-350.
29. Howarth, N. M., Purohit, A., Reed, M. J., and Potter, B. V. L. (1994) J. Med. Chem. 37, 219-221.
30. Woo, L. W. L., Howarth, N. M., Purohit, A., Hejaz, H. A. M., Reed, M. J., and Potter, B. V. L. (1998) J. Med. Chem. 41, 1068-1083.
31. Purohit, A., Williams, G. J., Howarth, N. M., Potter, B. V. L., and Reed, M. J. (1995) Biochemistry 34, 11508-11514.
32. Elger, W., Schwarz, S., Hedden, A., Reddersen, G., and Schneider, B. (1995) J. Steroid Biochem. Mol. Biol. 55, 395-403.
33. Woo, L. W. L., Lightowler, M., Purohit, A., Reed, M. J., and Potter, B. V. L. (1996) J. Steroid Biochem. Mol. Biol. 57, 79-88; Williams, G. J., Woo, L. W. L., Mahon, M. F., Purohit, A., Reed, M. J., and Potter, B. V. L. (1996) Pharm. Sci. 2. 11-16.
34. Woo, L. W. L., Lightowler, M., Purohit, A., Reed, M. J., and Potter, B. V. L. (1996) J. Steroid Biochem. Mol. Biol. 57, 79-88; Williams, G. J., Woo, L. W. L., Mahon, M. F., Purohit, A., Reed, M. J., and Potter, B. V. L. (1996) Pharm. Sci. 2. 11-16.
35. Woo, L. W. L., Purohit, A. Malini, B., Reed, M. J., and Potter, B. V. L. (2000) Chem. Biol. 7, 773-732.
36. Perrin, D. D., and Armarego, W. L. F. (1988) Purification of Laboratory Chemicals, 3rd Ed., Pergamon Press. Oxford.
37. Still, W. C., Kahn, M., and Mitra, A. (1978) J. Org. Chem. 43, 2923-2925.
38. Cox, R. I., Hoskinson, R. M., and Wong, M. S. (1979) Steroids 33, 549-562.
39. Eckstein, F. (1985) Annu. Rev. Biochem. 54, 367-402.
40. Dudman, N. P., and Benkovic, S. J. (1977) J. Am. Chem. Soc. 99, 6113-6115.
41. Burgers, P. M. J., and Eckstein, F. (1978) Proc. Natl. Acad. Sci. U.S.A. 75, 4798-4800.
42. Garegg, P. J., Regberg, T., Stawinski, J., and Strömberg, R. (1986) Chem. Scr. 26, 59-62.
43. (a) Bond, C. S., Clements, P. R., Ashby, S. J., Collyer, C. A., Harrop, S. J., Hopwood, J. J., and Gus, J. M. (1997) Structure 5, 277-289; Lukatela, G., Krauss, N., Theis, K., Selmer, T., Gieselmann, V., von Figura, K., and Saenger, W. (1998) Biochemistry 37, 3654-3664;
44. (a) Bond, C. S., Clements, P. R., Ashby, S. J., Collyer, C. A., Harrop, S. J., Hopwood, J. J., and Gus, J. M. (1997) Structure 5, 277-289; Lukatela, G., Krauss, N., Theis, K., Selmer, T., Gieselmann, V., von Figura, K., and Saenger, W. (1998) Biochemistry 37, 3654-3664;
45. (b) Recksiek, M., Selmer, T., Dierks, T., Schmidt, B., and von Figura, K. (1998) J. Biol. Chem. 273, 6096-6103.
46. Van Bommel, T., Marsen, T., and Bojar, H. (1987) Anticancer Res. 7, 1217-1224.
47. Stein, C., Hille, A., Seidel, J., Rijnbout, S., Waheed, A., Schmidt, B., Geuze, H., and Von Figura, K. (1989) J. Biol. Chem. 264, 13865-13872.
48. Von Buelow, R., Schmidt, B., Dierks, T., Von Figura, K., and Uson, I. (2001) J. Mol. Biol. 305, 269-277.
49. Uhlhorn-Dierks, G., Kolter, T., and Sandhoff, K. (1998) Angew. Chem., Int. Ed. Engl. 37, 2453-2455.
50. Franco, B., Meroni, G., Parenti, G., Levilliers, J., Bernard, L., Gebbia, M., Cox, L., Maroteaux, P., Sheffield, L., Rappold, G. A., Andria, G., Petit, C., and Ballabio, A. (1995) Cell 81, 15-25; Parenti, G., Meroni, G., and Ballabio, A. (1997) Curr. Opin. Gen. Dev. 7, 386-391.
51. Franco, B., Meroni, G., Parenti, G., Levilliers, J., Bernard, L., Gebbia, M., Cox, L., Maroteaux, P., Sheffield, L., Rappold, G. A., Andria, G., Petit, C., and Ballabio, A. (1995) Cell 81, 15-25; Parenti, G., Meroni, G., and Ballabio, A. (1997) Curr. Opin. Gen. Dev. 7, 386-391.
52. Shi, J., Blundell, T., and Mizuguchi, K. (2001) J. Mol. Biol. 310, 243-257.
53. MOE-Molecular Operating Environment Chemical Information Software, Chemical Computing Group Inc., Quebec.
54. Halgren, T. A. (1996) J. Comput. Chem. 17, 490-519.
55. Flex X, Sybyl 6.8 Chemical Information Software (2002) Tripos Inc., St. Louis, MO.
56. Dibbelt, L., and Kuss, E. (1991) Biol. Chem. Hoppe-Seyler 372, 173-185.