Anticancer steroid sulfatase inhibitors: synthesis of a potent fluorinated second-generation agent, in vitro and in vivo activities, molecular modeling, and protein crystallography
Anticancer steroid sulfatase inhibitors: synthesis of a potent fluorinated second-generation agent, in vitro and in vivo activities, molecular modeling, and protein crystallography(644 views) Woo LWL, Fischer DS, Sharland CM, Trusselle M, Foster PA, Chander SK, Di Fiore A, Supuran CT, De Simone G, Purohit A, Reed MJ, Potter BVL
Mol Cancer Ther (ISSN: 1535-7163, 1538-8514electronic), 2008 Sep; 7(8): 2435-2444.
Keywords: 3 Hydroxy N 3, 3 Trifluoropropyl 16, 17 Seco Estra 1, 5(10) Triene 16, 17 Imide, 3 Sulfamoyloxy N 3, 667 Coumarin, Antineoplastic Agent, Estrone, Estrone 3 O Sulfamic Acid, Stx 64, Unclassified Drug, Animal Experiment, Animal Model, Antineoplastic Activity, Article, Binding Site, Breast Cancer, Controlled Study, Crystallization, Crystallography, Drug Synthesis, Female, Hydrogen Bond, Hydrophobicity, Molecular Model, Nonhuman, Priority Journal, Protein Interaction, Single Drug Dose, Chromatography, Liquid, X-Ray, Enzyme Inhibitors, Fluorine, Magnetic Resonance Spectroscopy, Protein Conformation, Wistar, Spectrometry, Electrospray Ionization, Steryl-Sulfatase, 5 (10) Triene 16,
Affiliations: *** IBB - CNR ***
Department of Pharmacy and Pharmacology, Sterix Ltd., University of Bath, Bath, United Kingdom
Department of Endocrinology and Metabolic Medicine, Imperial College London, St. Mary's Hospital, London, United Kingdom
Istituto di Biostrutture e Bioimmagini-CNR, Naples, Italy
Università degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Florence, Italy
Universit degli Studi di Firenze, Polo Scientifico, Laboratorio di Chimica Bioinorganica, Florence, Italy
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Lloyd, M.D., Thiyagarajan, N., Ho, Y.T., First crystal structures of human carbonic anhydrase II in complex with dual aromatase-steroid sulfatase inhibitors (2005) Biochemistry, 44, pp. 6858-6866
Leese, M.P., Jourdan, F., Gaukroger, K., Structure-activity relationships of C-17 cyanated estratrienes as anti-cancer agents (2008) J Med Chem, 51, pp. 1295-1308
Reed, M. J., Purohit, A., Woo, L. W. L., Newman, S. P., Potter, B. V. L., Steroid sulfatase: Molecular biology, regulation, and inhibition (2005) Endocr Rev, 26, pp. 171-20
Stanway, S. J., Purohit, A., Woo, L. W. L., Phase I study of STX 64 (667 Coumate) in breast cancer patients: The first study of a steroid sulfatase inhibitor (2006) Clin Cancer Res, 12, pp. 1585-1592
Foster, P. A., Newman, S. P., Chander, S. K., In vivo efficacy of STX213, a second-generation steroid sulfatase inhibitor, for hormone-dependent breast cancer therapy (2006) Clin Cancer Res, 12, pp. 5543-5549
Foster, P. A., Chander, S. K., Parsons, M. F., Efficacy of three potent steroid sulfatase inhibitors: Pre-clinical investigations for their use in the treatment of hormone-dependent breast cancer (2008) Breast Cancer Res Treat, 111, pp. 129-138
Stanway, S. J., Delavault, P., Purohit, A., Steroid sulfatase: A new target for the endocrine therapy of breast cancer (2007) Oncologist, 12, pp. 370-374
Fischer, D. S., Woo, L. W. L., Mahon, M. F., Purohit, A., Reed, M. J., Potter, B. V. L., D-ring modified estrone derivatives as novel potent inhibitors of steroid sulfatase (2003) Bioorg Med Chem, 11, pp. 1685-1700
Fischer, D. S., Chander, S. K., Woo, L. W. L., Novel D-ring modified steroid derivatives as potent, non-estrogenic, steroid sulfatase inhibitors with in vivo activity (2003) J Steroid Biochem Mol Biol, 84, pp. 343-349
57: 79-88Jones, G., Willett, P., Glen, R. C., Leach, A. R., Taylor, R., Development and validation of a genetic algorithm for flexible docking (1997) J Mol Biol, 267, pp. 727-748
Eriksson, A. E., Jones, T. A., Liljas, A., Refined structure of human carbonic anhydrase II at 2. 0 A resolution (1988) Proteins, 4, pp. 274-282
Brunger, A. T., Adams, P. D., Clore, G. M., Crystallography & NMR system: A new software suite for macromolecular structure determination (1998) Acta Crystallogr D Biol Crystallogr, 54, pp. 905-921
Jones, T. A., Zou, J. Y., Cowan, S. W., Kjeldgaard, M., Improved methods for building protein models in electron density maps and the location of errors in these models (1991) Acta Crystallogr A, 47, pp. 110-119
Laskowski, R. A., MacArthur, M. W., Moss, D. S., Thornton, J. M., PROCHECK - a program to check the stereochemical quality of protein structures (1993) J Appl Crystallogr, 26, pp. 283-291
Park, B. K., Kitteringham, N. R., O'Neill, P. M., Metabolism of fluorine-containing drugs (2001) Annu Rev Pharmacol Toxicol, 41, pp. 443-470
Woo, L. W. L., Bubert, C., Sutcliffe, O. B., Dual aromatase-steroid sulfatase inhibitors (2007) J Med Chem, 50, pp. 3540-3560
Howard, J. A. K., Hoy, V. J., O'Hagan, D., Smith, G. T., How good is fluorine as a hydrogen bond acceptor? (1996) Tetrahedron, 52, pp. 12613-12622
Barbarich, T. J., Rithner, C. D., Miller, S. M., Anderson, O. P., Strauss, S. H., Significant inter- and intramolecular O-H F-C hydrogen bonding (1999) J Am Chem Soc, 121, pp. 4280-4281
Bohm, H. J., Banner, D., Bendels, S., Fluorine in medicinal chemistry (2004) ChemBioChem, 5, pp. 637-643
Boivin, R. P., Luu-The, V., Lachance, R., Labrie, F., Poirier, D., Structure-activity relationships of 17 -derivatives of estradiol as inhibitors of steroid sulfatase (2000) J Med Chem, 43, pp. 4465-4478
Woo, L. W. L., Howarth, N. M., Purohit, A., Hejaz, H. A., Reed, M. J., Potter, B. V. L., Steroidal and nonsteroidal sulfamates as potent inhibitors of steroid sulfatase (1998) J Med Chem, 41, pp. 1068-1083
Woo, L. W. L., Purohit, A., Malini, B., Reed, M. J., Potter, B. V. L., Potent active site-directed inhibition of steroid sulphatase by tricyclic coumarin-based sulphamates (2000) Chem Biol, 7, pp. 773-791
Chander, S. K., Purohit, A., Woo, L. W. L., Potter, B. V. L., Reed, M. J., The role of steroid sulphatase in regulating the oestrogenicity of oestrogen sulphamates (2004) Biochem Biophys Res Commun, 322, pp. 217-222
Ho, Y. T., Purohit, A., Vicker, N., Inhibition of carbonic anhydrase II by steroidal and non-steroidal sulphamates (2003) Biochem Biophys Res Commun, 305, pp. 909-914
Leese, M. P., Leblond, B., Smith, A., 2-Substituted estradiol bis-sulfamates, multitargeted antitumor agents: Synthesis, in vitro SAR, protein crystallography, and in vivo activity (2006) J Med Chem, 49, pp. 7683-7696
Ireson, C. R., Chander, S. K., Purohit, A., Pharmacokinetics of the nonsteroidal steroid sulphatase inhibitor 667 COUMATE and its sequestration into red blood cells in rats (2004) Br J Cancer, 91, pp. 1399-1404
Lloyd, M. D., Pederick, R. L., Natesh, R., Crystal structure of human carbonic anhydrase II at 1. 95 A resolution in complex with 667-coumate, a novel anti-cancer agent (2005) Biochem J, 385, pp. 715-720
Lloyd, M. D., Thiyagarajan, N., Ho, Y. T., First crystal structures of human carbonic anhydrase II in complex with dual aromatase-steroid sulfatase inhibitors (2005) Biochemistry, 44, pp. 6858-6866
Leese, M. P., Jourdan, F., Gaukroger, K., Structure-activity relationships of C-17 cyanated estratrienes as anti-cancer agents (2008) J Med Chem, 51, pp. 1295-1308
Anticancer steroid sulfatase inhibitors: synthesis of a potent fluorinated second-generation agent, in vitro and in vivo activities, molecular modeling, and protein crystallography
Anticancer steroid sulfatase inhibitors: synthesis of a potent fluorinated second-generation agent, in vitro and in vivo activities, molecular modeling, and protein crystallography
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Anticancer steroid sulfatase inhibitors: synthesis of a potent fluorinated second-generation agent, in vitro and in vivo activities, molecular modeling, and protein crystallography