2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity(931 views) Leese MP, Leblond B, Smith A, Newman SP, Di Fiore A, De Simone G, Supuran CT, Purohit A, Reed MJ, Potter BVL
J Med Chem (ISSN: 0022-2623print, 0022-2623linking, 1520-4804), 2006 Dec 28; 49(26): 7683-7696.
Keywords: Animals, Antineoplastic Agents, Chemical Synthesis, Chemistry, Pharmacology, Binding Sites, Breast Neoplasms, Drug Therapy, Carbonic Anhydrase Ii, Metabolism, Carcinoma, Lewis Lung, Blood Supply, Cell Proliferation, Drug Effects, Crystallography, X-Ray, Estradiol, Analogs, Derivatives, Female, Humans, Nude, Models, Molecular, Neovascularization, Pathologic, Steryl-Sulfatase, Antagonists, Inhibitors, Structure-Activity Relationship, Sulfonic Acids, Survival Rate, Tumor Cells, Cultured, Xenograft Model Antitumor Assays, Zinc, 2 Ethylestradiol 3, 17 O, O Bisulfamate, 2 Methoxyestradiol 3, Carbonate Dehydratase Ii, Estradiol 17 O Sulfamate, Estradiol Derivative, Steryl Sulfatase, Unclassified Drug, Animal Experiment, Animal Model, Antineoplastic Activity, Article, Breast Carcinoma, Cancer Inhibition, Controlled Study, Drug Binding, Drug Structure, Drug Synthesis, Human Cell, Lewis Carcinoma, Mouse, Nonhuman, Structure Activity Relation, Tumor Xenograft, X Ray Crystallography,
Affiliations: *** IBB - CNR ***
Medicinal Chemistry, Department of Pharmacy and Pharmacology & Sterix Ltd., University of Bath, Bath BA2 7AY, United Kingdom.,
Faculty of Medicine, Imperial College, St. Mary's Hospital, London W2 1NY, United Kingdom
Istituto di Biostrutture e Bioimmagini-CNR, Naples, Italy
Laboratorio di Chimica Bioinorganica, Università degli Studi di Firenze, Florence, Italy
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Reed, M. J., Purohit, A., Newman, S. P., Potter, B. V. L., Steroid sulfatase: Molecular biology, regulation and inhibition (2005) Endocr. Rev, 26, pp. 171-202
Stanway, S. J., Purohit, A., Woo, L. W. L., Sufi, S., Vigushin, D., Ward, R., Wilson, R., Coombs, R. C., Phase I study of STX64 (667 Coumate) in breast cancer patients: The first study of a steroid sulfatase inhibitor (2006) Clin. Cancer Res, 12, pp. 1585-1592
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
D'Amato, R. J., Lin, C. M., Flynn, E., Folkman, J., Hamel, E., 2-Methoxyestradiol, an endogenous mammalian metabolite, inhibits tubulin polymerization by interacting at the colchicine site (1994) Proc. Natl. Acad. Sci. U. S. A, 91, pp. 3964-3968
Mabjeesh, N. J., Escuin, D., LaVallee, T. M., Pribluda, V. S., Swartz, G. M., Johnson, M. S., Willard, M. T., Giannakakou, P., 2ME2 inhibits tumor growth and angiogenesis by disrupting microtubules and dysregulating HIF (2003) Cancer Cell, 3, pp. 363-375
Edsall, A. B., Mohanakrishnan, A. K., Yang, D. L., Fanwick, P. E., Hamel, E., Hanson, A. D., Agoston, G. E., Cushman, M., Effects of altering the electronics of 2-methoxyestradiol on cell proliferation, on cytotoxicity in human cancer cell cultures, and on tubulin polymerization (2004) J. Med. Chem, 47, pp. 5126-5139
Rao, P. N., Cessac, J. W., Tinley, T. L., Mooberry, S. L., Synthesis and antimitotic activity of novel 2-methoxyestradiol analogs (2002) Steroids, 67, pp. 1079-1089
Tinley, T. L., Leal, R. M., Randall-Hlubek, D. A., Cessac, J. W., Wilkens, L. R., Rao, P. N., Mooberry, S. L., Novel 2-methoxyestradiol analogues with antitumor activity (2003) Cancer Res, 63, pp. 1538-1549
Newman, S. P., Ireson, C. R., Tutill, H. J., Day, J. M., Parsons, M. F. C., Leese, M. P., Potter, B. V. L., Purohit, A., The role of 17 -hydroxysteroid dehydrogenases in modulating the activity of 2-methoxyestradiol in breast cancer (2006) Cancer Res, 66, pp. 324-330
Dahut, W. L., Lakhani, N. J., Kohn, E. C., Gulley, J., Arlen, P. M., Raggio, M., Wright, J., Figg, W. D., A phase I study of 2-methoxyestradiol (2ME2) in patients with solid tumors (2005) Proc. Am. Soc. Clin. Oncol, 2003
Leese, M. P., Hejaz, H. A. M., Mahon, M. F., Newman, S. P., Purohit, A., Reed, M., Potter, B. V. L., A-ring substituted estrogen sulfamates: Potent multi-targeted anti-cancer agents (2005) J. Med. Chem, 48, pp. 5243-5256
Newman, S. P., Leese, M. P., Purohit, A., James, D. R. C., Rennie, C. E., Potter, B. V. L., Reed, M. J., Inhibition of in vitro angiogenesis by 2-methoxy- and 2-ethyl-estrogen sulfamates (2004) Int. J. Cancer, 109, pp. 533-540
Leese, M. P., Leblond, B., Newman, S. P., Purohit, A., Reed, M. J., Potter, B. V. L., Anti-cancer activities of novel D-ring modified 2-substituted estrogen-3-O-sulfamates (2005) J. Steroid Biochem. Mol. Biol, 94, pp. 239-251
Reed, J. E., Woo, L. W. L., Robinson, J. J., Leblond, B., Leese, M. P., Purohit, A., Reed, M. J., Potter, B. V. L., 2-Difluoromethyloestrone 3-O-sulphamate, a highly potent steroid sulphatase inhibitor (2004) Biochem. Biophys. Res. Commun, 317, pp. 169-175
Woo, L. W. L., Howarth, N. M., Purohit, A., Hejaz, H. A. M., Reed, M. J., Potter, B. V. L., Steroidal and non-steroidal sulfamates as potent inhibitors of steroid sulfatase (1998) J. Med. Chem, 41, pp. 1068-1083
Boyd, M. R., Paull, K. D., Some practical consideration and applications of the National Cancer Institute in vitro anticancer drug discovery screen (1995) Drug Dev. Res, 34, pp. 91-109
Paull, K. D., Lin, C. M., Malspeis, L., Hamel, E., Identification of novel antimitotic agents acting at the tubulin level by computer-assisted evaluation of differential cytotoxicity data (1992) Cancer Res, 52, pp. 3892-3900
Ireson, C. R., Chander, S. K., Purohit, A., Perera, S., Newman, S. P., Parish, D., Leese, M. P., Reed, M. J., Pharmacokinetics and efficacy of 2-methoxyoestradiol and 2-methoxyoestradiol- bis-sulphamate in vivo in rodents (2004) Br. J. Cancer, 90, pp. 932-937
Ravelli, R. B. G., Gigant, B., Curmi, P. A., Jourdain, I., Lachkar, S., Sobel, A., Knossow, M., Insight into tubulin regulation from a complex with colchicine and a stathmin-like domain (2004) Nature, 428, pp. 198-202
Ho, Y. T., Purohit, A., Vicker, N., Newman, S. P., Robinson, J. J., Leese, M. P., Ganeshapillai, D., Reed, M. J., Inhibition of carbonic anhydrase II by steroidal and non-steroidal sulphamates (2003) Biochem. Biophys. Res. Commun, 305, pp. 909-914
Lloyd, M. D., Pederick, R. L., Natesh, R., Woo, L. W. L., Purohit, A., Reed, M. J., Acharya, K. R., Potter, B. V. L., Crystal structure of human carbonic anhydrase II at 1. 95 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., Woo, L. W. L., Sutcliffe, O. B., Purohit, A., Reed, M. J., Potter, B. V. L., First crystal structures of human carbonic anhydrase II in complex with dual aromatase-steroid sulfatase inhibitors (2005) Biochemistry, 44, pp. 6858-6866
Eriksson, A. E., Jones, T. A., Liljas, A., Refined structure of human carbonic anhydrase II at 2. 0 resolution (1988) Proteins, 4, pp. 274-282
Nissink, J. W. M., Murray, C., Hartshorn, M., Verdonk, M. L., Cole, J. C., Taylor, R., A new test set for validating predictions of protein-ligand interaction (2002) Proteins, 49, pp. 457-471
Berman, H. M., Westbrook, J., Feng, Z., Gilliland, G., Bhat, T. N., Weissig, H., Shindyalov, I. N., Bourne, P. E., The Protein Data Bank (2000) Nucleic Acids Res, 28, pp. 235-242
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
2-substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity
Kim YH, Shin SW, Pellicano R, Fagoonee S, Choi IJ, Kim YI, Park B, Choi JM, Kim SG, Choi J, Park JY, Oh S, Yang HJ, Lim JH, Im JP, Kim JS, Jung HC, Ponzetto A, Figura N, Malfertheiner P, Choi IJ, Kook MC, Kim YI, Cho SJ, Lee JY, Kim CG, Park B, Nam BH, Bae SE, Choi KD, Choe J, Kim SO, Na HK, Choi JY, Ahn JY, Jung KW, Lee J, Kim DH, Chang HS, Song HJ, Lee GH, Jung HY, Seta T, Takahashi Y, Noguchi Y, Shikata S, Sakai T, Sakai K, Yamashita Y, Nakayama T, Leja M, Park JY, Murillo R, Liepniece-karele I, Isajevs S, Kikuste I, Rudzite D, Krike P, Parshutin S, Polaka I, Kirsners A, Santare D, Folkmanis V, Daugule I, Plummer M, Herrero R, Tsukamoto T, Nakagawa M, Kiriyama Y, Toyoda T, Cao X, Corral JE, Mera R, Dye CW, Morgan DR, Lee YC, Lin JT, Garcia Martin R, Matia Cubillo A, Lee SH, Park JM, Han YM, Ko WJ, Hahm KB, Leontiadis GI, Ford AC, Ichinose M, Sugano K, Jeong M, Park JM, Han YM, Park KY, Lee DH, Yoo JH, Cho JY, Hahm KB, Bang CS, Baik GH, Shin IS, Kim JB, Suk KT, Yoon JH, Kim YS, Kim DJ * Helicobacter pylori Eradication for Prevention of Metachronous Recurrence after Endoscopic Resection of Early Gastric Cancer(307 views) N Engl J Med (ISSN: 0028-4793, 0028-4793linking, 1533-4406electronic), 2015 Jun; 30642104201566393291: 749-756. Impact Factor:59.558 ViewExport to BibTeXExport to EndNote