First crystal structures of human carbonic anhydrase II in complex with dual aromatase-steroid sulfatase inhibitors

Biochemistry

Volumn 44, Issue 18, 2005, Pages 6858-6866

  Lloyd, Matthew D ^a   Thiyagarajan, Nethaji ^a   Ho, Yaik T ^b   Woo, L W Lawrence ^a   Sutcliffe, Oliver B ^a   Purohit, Atul ^b   Reed, Michael J ^b   Acharya, K Ravi ^a   Potter, Barry V L ^a  

^a University of Bath   (United Kingdom)

^b ST MARY S HOSPITAL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

BIOCHEMISTRY; CATALYSIS; COMPLEXATION; CRYSTAL STRUCTURE; DRUG PRODUCTS; HYDRATION; TUMORS;

ANTICANCER THERAPY; CARBONIC ANHYDRASE (CA); CYANOPHENYL GROUPS; PH BALANCE;

ENZYMES;

4 [(3 BROMO 4 O SULFAMOYLBENZYL)(4 CYANOPHENYL)AMINO] 4H [1,2,4]TRIAZOLE; 4 [(4 O SULFAMOYLBENZYL)(4 CYANOPHENYL)AMINO] 4H [1,2,4]TRIAZOLE; AMINO ACID; AROMATASE; CARBONATE DEHYDRATASE; CARBONATE DEHYDRATASE II; ENZYME INHIBITOR; NITROGEN; STERYL SULFATASE; TRIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ZINC ION;

ANTINEOPLASTIC ACTIVITY; ARTICLE; BINDING AFFINITY; BINDING SITE; CRYSTAL STRUCTURE; DRUG DESIGN; DRUG PROTEIN BINDING; DRUG STABILITY; DRUG TARGETING; GEOMETRY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

AROMATASE INHIBITORS; BINDING SITES; CARBONIC ANHYDRASE II; CRYSTALLIZATION; CRYSTALLOGRAPHY, X-RAY; DIMETHYL SULFOXIDE; DRUG STABILITY; ENZYME STABILITY; ESTRONE; HUMANS; LIGANDS; RECOMBINANT PROTEINS; SOLVENTS; STERYL-SULFATASE;

EID: 18244398670     PISSN: 00062960     EISSN: None     Source Type: Journal    
DOI: 10.1021/bi047692e     Document Type: Article

References (31)

1. 2 elimination, Annu. Rev. Physiol. 50, 695-717.
2. Recacha, R., Costanzo, M. J., Maryanoff, B. E., and Chattopadhyay, D. (2002) Crystal structure of human carbonic anhydrase II complexed with an anti-convulsant sugar sulphamate, Biochem. J. 361, 437-441.
3. Casini, A., Scozzafava, A., Mincione, F., Menabuoni, L., Starnotti, M., and Supuran, C. T. (2003) Carbonic anhydrase inhibitors: Topically acting antiglaucoma sulfonamides incorporating esters and amides of 3- and 4-carboxybenzolamide, Bioorg. Med. Chem. Lett. 13, 2867-2873.
4. Türeci, Ö., Sahin, E., Vollmar, E., Siemer, S., Göttert, E., Seitz, G., Parkkila, A.-K., Shah, G. N., Grubb, J. H., Pfreundschuh, M., and Sly, W. S. (1998) Human carbonic anhydrase XII: cDNA cloning, expression, and chromosomal localization of a carbonic anhydrase gene that is over-expressed in some renal cell cancers, Proc. Natl. Acad. Sci. U.S.A. 95, 7608-7613.
5. Wykoff, C. C., Beasley, N. J. P., Watson, P. H., Turner, K. J., Pastorek, J., Sibtain, A., Wilson, G. D., Turley, H., Talks, K. L., Maxwell, P. H., Pugh, C. W., Ratcliffe, P. J., and Harris, A. L. (2000) Hypoxia-inducible expression of tumor-associated carbonic anhydrases, Cancer Res. 60, 7075-7083.
6. Loncaster, J. A., Harris, A. L., Davidson, S. E., Logue, J. P., Hunter, R. D., Wycoff, C. C., Pastorek, J., Ratcliffe, P. J., Stratford, I. J., and West, C. M. L. (2001) Carbonic anhydrase (CA IX) expression, a potential new intrinsic marker of hypoxia: Correlations with tumor oxygen measurements and prognosis in locally advanced carcinoma of the cervix, Cancer Res. 61, 6394-6399.
7. Supuran, C. T. (2003) Carbonic anhydrase inhibitors in the treatment and prophylaxis of obesity, Expert Opin. Ther. Pat. 13, 1545-1550.
8. Ho, Y. T., Purohit, A., Vicker, N., Newman, S. P., Robinson, J. J., Leese, M. P., Ganeshapillai, D., Woo, L. W. L., Potter, B. V. L., and Reed, M. J. (2003) Inhibition of carbonic anhydrase II by steroidal and non-steroidal sulphamates, Biochem. Biophys. Res. Commun. 305, 909-914.
9. Abbate, F., Winum, J.-Y., Potter, B. V. L., Casini, A., Montero, J.-L., Scozzafava, A., and Supuran, C. T. (2004) Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with EMATE, a dual inhibitor of carbonic anhydrase and steroid sulfatase, Bioorg. Med. Chem. Lett. 14, 231-234.
10. Supuran, C. T., Scozzafava, A., and Casini, A. (2003) Carbonic anhydrase inhibitors, Med. Res. Rev. 23, 146-189.
11. Woo, L. W. L., Purohit, A., Malini, B., Reed, M. J., and Potter, B. V. L. (2000) Potent active site-directed inhibition of steroid sulphatase by tricyclic coumarin-based sulphamates, Chem. Biol 7, 773-791.
12. Woo, L. W. L., Sutcliffe, O. B., Bubert, C., Grasso, A., Chander, S. K., Purohit, A., Reed, M. J., and Potter, B. V. L. (2003) First dual aromatase-steroid sulfatase inhibitors, J. Med. Chem. 46, 3193-3196.
13. Wood, P. M., Woo, L. W. L., Humphreys, A., Chander, S. K., Purohit, A., Reed, M. J., and Potter, B. V. L. (2005) A letrozole based dual aromatase-sulphatase inhibitor with in vivo activity, J. Steroid Biochem. Mol. Biol. (in press).
14. Howarth, N. M., Purohit, A., Reed, M. J., and Potter, B. V. L. (1994) Estrone sulfamates: Potent inhibitors of estrone sulfatase with therapeutic potential, J. Med. Chem. 37, 219-221.
15. Woo, L. W. L., Howarth, N. M., Purohit, A., Hejaz, H. A. M., Reed, M. J., and Potter, B. V. L. (1998) Steroidal and non-steroidal sulfamates as potent inhibitors of steroid sulfatase, J. Med. Chem. 41, 1068-1083.
16. Purohit, A., Williams, G. J., Howarth, N. M., Potter, B. V. L., and Reed, M. J. (1995) Inactivation of steroid sulfatase by an active site-directed inhibitor, estrone 3-O-sulfamate, Biochemistry 34, 11508-11514.
17. Vicker, N. J., Ho, Y. T., Robinson, J. J., Woo, L. W. L., Purohit, A., Reed, M. J., and Potter, B. V. L. (2003) Docking studies of sulphamate inhibitors of estrone sulphatase in human carbonic anhydrase II, Bioorg. Med. Chem. Lett. 13, 863-865.
18. Ireson, C. R., Chander, S. K., Purohit, A., Parish, D. A., Woo, L. W. L., Potter, B. V. L., and Reed, M. J. (2004) Pharmacokinetics of the non-steroidal steroid sulfatase inhibitor 667-coumate and its sequestration into red blood cells, Br. J. Cancer 91, 1399-1404.
19. Lloyd, M. D., Pederick, R. L., Natesh, R., Woo, L. W. L., Purohit, A. P., Reed, M. J., Acharya, K. R., and Potter, B. V. L. (2005) Crystal structure of human carbonic anhydrase II at 1.95 Å resolution in complex with 667-coumate, a novel anti-cancer agent, Biochem. J. 385, 715-720.
20. Nair, S. K., Calderone, T. L., Christianson, D. W., and Fierke, C. A. (1991) Altering the mouth of a hydrophobic pocket. Structure and kinetics of carbonic anhydrase II mutants at residue Val-121, J. Biol. Chem. 266, 17320-17325.
21. Otwinowski, Z., and Minor, W. (1997) in Methods in Enzymology (Carter, C. W., Jr., and Sweet, R. M., Eds.) pp 307-326, Academic Press, New York.
22. Scolnick, L. R., and Christianson, D. W. (1996) X-ray crystallographic studies of alanine-65 variants of carbonic anhydrase II reveal the structural basis of compromised proton transfer in catalysis, Biochemistry 35, 16429-16434.
23. Brünger, A. T., Adams, P. D., Clore, G. M., DeLano, W. L., Gros, P., Grosse-Kunstleve, R. W., Jiang, J.-S., Kuszewski, J., Nilges, N., Pannu, N. S., Read, R. J., Rice, L. M., Simonson, T., and Warren, G. L. (1998) Crystallography and NMR system (CNS): A new software system for macromolecular structure determination, Acta Crystallogr. D54, 905-921.
24. Jones, T. A., Zou, J.-Y., Cowan, S. W., and Kjeldgaard, M. (1991) Improved methods for building protein models in electron density maps and the location of errors in these models, Acta Crystallogr. A47, 110-119.
25. Hejaz, H. A. M., Woo, L. W. L., Purohit, A., Reed, M. J., and Potter, B. V. L. (2004) Synthesis, in vitro and in vivo activity of benzophenone-based inhibitors of steroid sulfatase, Bioorg. Med. Chem. 12, 2759-2772.
26. Purohit, A., Vernon, K. A., Hummelinck, A. E. W., Woo, L. W. L., Hejaz, H. A. M., Potter, B. V. L., and Reed, M. J. (1998) The development of a-ring modified analogues of oestrone-3-O-sulphamate as potent steroid sulphatase inhibitors with reduced oestrogenicity, J. Steroid Biochem. Mol. Biol. 64, 269-275.
27. Abbate, F., Coetzee, A., Casini, A., Ciantini, S., Scozzafava, A., and Supuran, C. T. (2004) Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with the antipsychotic drug sulpiride, Bioorg. Med. Chem. Lett. 14, 377-341.
28. Abbate, F., Casini, A., Owa, T., Scozzafava, A., and Supuran, C. T. (2004) Carbonic anhydrase inhibitors: E7070, a sulfonamide anticancer agent, potently inhibits cytosolic isozymes I and II, and transmembrane, tumour-associated isozyme IX, Bioorg. Med. Chem. Lett. 14, 217-223.
29. Abbate, F., Casini, A., Scozzafava, A., and Supuran, C. T. (2004) Carbonic anhydrase inhibitors: X-ray crystallographic structure of the adduct of human isozyme II with a topically acting antiglaucoma sulfonamide, Bioorg. Med. Chem. Lett. 14, 2357-2361.
30. Merritt, E. A., and Bacon, D. J. (1997) in Methods in Enzymology (Carter, C. W., Jr., and Sweet, R. M., Eds.) pp 505-524, Academic Press, New York.
31. Esnouf, R. M. (1997) An extensively modified version of Molscript that includes greatly enhanced colouring capabilities, J. Mol. Graphics 15, 132-134.