Development of the β-lactam type molecular scaffold for selective estrogen receptor α modulator action: synthesis and cytotoxic effects in MCF-7 breast cancer cells

References

• Ferlay J, Shin HR, Bray F, et al Estimates of worldwide burden of cancer in 2008: GLOBOCAN 2008. Int J Cancer 2010;127:2893–917
   PubMed Web of Science ®Google Scholar
• Ferlay J, Steliarova-Foucher E, Lortet-Tieulent J, et al Cancer incidence and mortality patterns in Europe: estimates for 40 countries in 2012. Eur J Cancer 2013;49:1374–403
   PubMed Web of Science ®Google Scholar
• European Network of Cancer Registries ENCR Factsheets Breast Cancer (BC) Factsheet September 2014. 2014. Available from: http://www.encr.eu/images/docs/factsheets/ENCR_Factsheet_Breast_2014.pdf
   Google Scholar
• Cancer in Ireland. 2013: Annual report of the National Cancer Registry
   Google Scholar
• Berry DA, Cirrincione C, Henderson IC, et al Estrogen-receptor status and outcomes of modern chemotherapy for patients with node-positive breast cancer. JAMA 2006;295:1658–67
   PubMed Web of Science ®Google Scholar
• Jordan VC. Chemoprevention of breast cancer with selective oestrogen-receptor modulators. Nat Rev Cancer 2007;7:46–53
   PubMed Web of Science ®Google Scholar
• Vogel VG, Costantino JP, Wickerham DL, et al Update of the national surgical adjuvant breast and bowel project study of tamoxifen and raloxifene (STAR) P-2 trial: preventing breast cancer. Cancer Prev Res (Phila) 2010;3:696–706
   PubMed Web of Science ®Google Scholar
• Desta Z, Ward BA, Soukhova NV, Flockhart DA. Comprehensive evaluation of tamoxifen sequential biotransformation by the human cytochrome P450 system in vitro: prominent roles for CYP3A and CYP2D6. J Pharmacol Exp Ther 2004;310:1062–75
   PubMed Web of Science ®Google Scholar
• Hoskins JM, Carey LA, McLeod HL. CYP2D6 and tamoxifen: DNA matters in breast cancer. Nat Rev Cancer 2009;9:576–86
   PubMed Web of Science ®Google Scholar
• Lim YC, Desta Z, Flockhart DA, Skaar TC. Endoxifen (4-hydroxy-N-desmethyl-tamoxifen) has anti-estrogenic effects in breast cancer cells with potency similar to 4-hydroxy-tamoxifen. Cancer Chemother Pharmacol 2005;55:471–8
   PubMed Web of Science ®Google Scholar
• Lv W, Liu J, Lu D, et al Synthesis of mixed (E,Z)-, (E)-, and (Z)-norendoxifen with dual aromatase inhibitory and estrogen receptor modulatory activities. J Med Chem 2013;56:4611–18
   PubMed Web of Science ®Google Scholar
• Ahmed NS, Elghazawy NH, ElHady AK, et al Design and synthesis of novel tamoxifen analogues that avoid CYP2D6 metabolism. Eur J Med Chem 2016;112:171–9
   PubMed Web of Science ®Google Scholar
• Moen MD, Keating GM. Raloxifene: a review of its use in the prevention of invasive breast cancer. Drugs 2008;68:2059–83
   PubMed Web of Science ®Google Scholar
• Brzozowski AM, Pike AC, Dauter Z, et al Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 1997;389:753–8
   PubMed Web of Science ®Google Scholar
• Jordan VC. Antiestrogens and selective estrogen receptor modulators as multifunctional medicines. 2. Clinical considerations and new agents. J Med Chem 2003;46:1081–111
   PubMed Web of Science ®Google Scholar
• Goss PE, Ingle JN, Martino S, et al A randomized trial of letrozole in postmenopausal women after five years of tamoxifen therapy for early-stage breast cancer. N Engl J Med 2003;349:1793–802
   PubMed Web of Science ®Google Scholar
• Howell A, Cuzick J, ATAC Trialists' Group, et al Results of the ATAC (Arimidex, Tamoxifen, alone or in combination) trial after completion of 5 years' adjuvant treatment for breast cancer. Lancet 2005;365:60–2
   PubMed Web of Science ®Google Scholar
• Robertson JF. Faslodex (ICI 182, 780), a novel estrogen receptor downregulator-future possibilities in breast cancer. J Steroid Biochem Mol Biol 2001;79:209–12
   PubMed Web of Science ®Google Scholar
• Pike ACW. Lessons learnt from structural studies of the oestrogen receptor. Best Pract Res Clin Endocrinol Metab 2006;20:1–14
   PubMed Web of Science ®Google Scholar
• Ruff M, Gangloff M, Wurtz JM, Moras D. Estrogen receptor transcription and transactivation: structure-function relationship in DNA- and ligand-binding domains of estrogen receptors. Breast Cancer Res 2000;2:353–9
   PubMed Web of Science ®Google Scholar
• Sun J, Meyers MJ, Fink BE, et al Novel ligands that function as selective estrogens or antiestrogens for estrogen receptor-alpha or estrogen receptor-beta. Endocrinology 1999;140:800–4
   PubMed Web of Science ®Google Scholar
• Pike AC, Brzozowski AM, Hubbard RE, et al Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist. Embo J 1999;18:4608–18
   PubMed Web of Science ®Google Scholar
• Blizzard TA. Selective estrogen receptor modulator medicinal chemistry at Merck. A review. Curr Top Med Chem 2008;8:792–812
   PubMed Web of Science ®Google Scholar
• Gennari L, Merlotti D, Martini G, Nuti R. Lasofoxifene: a third-generation selective estrogen receptor modulator for the prevention and treatment of osteoporosis. Expert Opin Investig Drugs 2006;15:1091–103
   PubMed Web of Science ®Google Scholar
• Blizzard TA, Morgan JD, II Mosley RT, et al 2-Phenylspiroindenes: a novel class of selective estrogen receptor modulators (SERMs). Bioorg Med Chem Lett 2003;13:479–83
   PubMed Web of Science ®Google Scholar
• Stauffer SR, Coletta CJ, Tedesco R, et al Pyrazole ligands: structure-affinity/activity relationships and estrogen receptor-alpha-selective agonists. J Med Chem 2000;43:4934–47
   PubMed Web of Science ®Google Scholar
• Croisy-Delcey M, Croisy A, Carrez D, et al Diphenyl quinolines and isoquinolines: synthesis and primary biological evaluation. Bioorg Med Chem 2000;8:2629–41
   PubMed Web of Science ®Google Scholar
• Labrie F, Labrie C, Belanger A, et al EM-652 (SCH 57068), a third generation SERM acting as pure antiestrogen in the mammary gland and endometrium. J Steroid Biochem Mol Biol 1999;69:51–84
   PubMed Web of Science ®Google Scholar
• Kim S, Wu JY, Birzin ET, et al Estrogen receptor ligands. II. Discovery of benzoxathiins as potent, selective estrogen receptor alpha modulators. J Med Chem 2004;47:2171–5
   PubMed Web of Science ®Google Scholar
• Barrett I, Meegan MJ, Hughes RB, et al Synthesis, biological evaluation, structural-activity relationship, and docking study for a series of benzoxepin-derived estrogen receptor modulators. Bioorg Med Chem 2008;16:9554–73
   PubMed Web of Science ®Google Scholar
• Jain N, Xu J, Kanojia RM, et al Identification and structure-activity relationships of chromene-derived selective estrogen receptor modulators for treatment of postmenopausal symptoms. J Med Chem 2009;52:7544–69
   PubMed Web of Science ®Google Scholar
• O'Boyle NM, Pollock JK, Carr M, et al beta-Lactam estrogen receptor antagonists and a dual-targeting estrogen receptor/tubulin ligand. J Med Chem 2014;57:9370–82
   PubMed Web of Science ®Google Scholar
• Palomo C, Aizpurua JM, Ganboa I, Oiarbide M. Asymmetric synthesis of β-Lactams through the Staudinger reaction and their use as building blocks of natural products. Curr Med Chem 2004;11:1837–72
   PubMed Web of Science ®Google Scholar
• Banik BK, Banik I, Becker FF. Stereocontrolled synthesis of anticancer beta-lactams via the Staudinger reaction. Bioorg Med Chem 2005;13:3611–22
   PubMed Web of Science ®Google Scholar
• O'Boyle NM, Carr M, Greene LM, et al Synthesis and evaluation of azetidinone analogues of combretastatin A-4 as tubulin targeting agents. J Med Chem 2010;53:8569–84
   PubMed Web of Science ®Google Scholar
• Greene TF, Wang S, Greene LM, et al Synthesis and biochemical evaluation of 3-phenoxy-1,4-diarylazetidin-2-ones as tubulin-targeting antitumor agents. J Med Chem 2016;59:90–113
   PubMed Web of Science ®Google Scholar
• Adlington RM, Baldwin JE, Becker GW, et al Design, synthesis, and proposed active site binding analysis of monocyclic 2-azetidinone inhibitors of prostate specific antigen. J Med Chem 2001;44:1491–508
   PubMed Web of Science ®Google Scholar
• Bisacchi GS, Slusarchyk WA, Bolton SA, et al Synthesis of potent and highly selective nonguanidine azetidinone inhibitors of human tryptase. Bioorg Med Chem Lett 2004;14:2227–31
   PubMed Web of Science ®Google Scholar
• Mulchande J, Guedes RC, Tsang WY, et al Azetidine-2,4-diones (4-oxo-beta-lactams) as scaffolds for designing elastase inhibitors. J Med Chem 2008;51:1783–90
   PubMed Web of Science ®Google Scholar
• Meegan MJ, Carr M, Knox AJ, et al Beta-lactam type molecular scaffolds for antiproliferative activity: synthesis and cytotoxic effects in breast cancer cells. J Enzyme Inhib Med Chem 2008;23:668–85
   PubMed Web of Science ®Google Scholar
• Grammaticakis P, Texier H. Contribution a l'etude de l'absorption dans l'ultraviolet moyen et le visible de derives fonctionnels azotes de quelques aldehydes et cetones aromatiques. Bulletin De La Société Chimique De France 1971;4:1323–30
   Google Scholar
• Bidlack JM, Lockshin RA. Evolution of LDH isozymes during programmed cell death. Comp Biochem Physiol B 1976;55:161–6
   PubMed Web of Science ®Google Scholar
• Littlefield BA, Gurpide E, Markiewick L, et al A simple and sensitive microtiter plate estrogen bioassay based on stimulation of alkaline phosphatase in Ishikawa cells: estrogenic action of delta 5 adrenal steroids. Endocrinology 1990;127:2757–62
   PubMed Web of Science ®Google Scholar
• Shiau AK, Barstad D, Loria PM, et al The structural basis of estrogen receptor/coactivator recognition and the antagonism of this interaction by tamoxifen. Cell 1998;95:927–37
   PubMed Web of Science ®Google Scholar
• Lambert C, Leonard N, De Bolle X, Depiereux E. ESyPred3D: prediction of proteins 3D structures. Bioinformatics 2002;18:1250–6
   PubMed Web of Science ®Google Scholar
• Molecular Operating Environment (MOE). developed and distributed by Chemical Computing Group; 2011. Available from: http://wwwchemcompcom
   Google Scholar
• Chen AA, Pappu RV. Parameters of monovalent ions in the AMBER-99 forcefield: assessment of inaccuracies and proposed improvements. J Phys Chem B 2007;111:11884–7
   PubMed Web of Science ®Google Scholar
• OMEGA v2.1. developed and distributed by Openeye Scientific Software; 2010. Available from: http://wwweyesopencom
   Google Scholar
• FRED (version 2.11). Developed and distributed by Openeye Scientific Software; 2016. Available from: http://wwweyesopencom
   Google Scholar
• Knox AJ, Meegan MJ, Carta G, Lloyd DG. Considerations in compound database preparation-“hidden” impact on virtual screening results. J Chem Inf Model 2005;45:1908–19
   PubMed Web of Science ®Google Scholar
• Singh GS. Recent progress in the synthesis and chemistry of azetidinones. Tetrahedron 2003;59:7631–49
   Web of Science ®Google Scholar
• Bolognese A, Diurno MV, Mazzoni O, Giordano F. On the azetidin-2-one ring formation – a H-1-NMR investigation. Tetrahedron 1991;47:7417–28
   Web of Science ®Google Scholar
• Alonso E, del Pozo C, Gonzalez J. Staudinger reactions of unsymmetrical cyclic ketenes: a synthetically useful approach to spiro β-lactams and derivatives. Reaction mechanism and theoretical studies. J Chem Soc Perkin Trans 1 2002;4:571–6
   Google Scholar
• Cardillo G, Fabbroni S, Gentilucci L, et al Highly regio- and diastereoselective palladium-catalyzed allylic substitution. Synthesis of 3-(2-aminobutylidene)-4-arylazetidin-2-ones. Adv Synth Catal 2005;347:833–8
   Web of Science ®Google Scholar
• Kirkup MP, Rizvi R, Shankar BB, et al (-)-SCH 57939: synthesis and pharmacological properties of a potent, metabolically stable cholesterol absorption inhibitor. Bioorg Med Chem Lett 1996;6:2069–72
   Web of Science ®Google Scholar
• Ojima I, Qiu X. Asymmetric alkylation of chiral.beta.-lactam ester enolates. A new approach to the synthesis of.alpha.-alkylated.alpha.-amino acids. J Am Chem Soc 1987;109:6537–8
   Web of Science ®Google Scholar
• Alcaide B, Almendros P. Selective bond cleavage of the β-lactam nucleus: application in stereocontrolled synthesis. Synlett 2002;3:381–93
   Google Scholar
• Shani J, Gazit A, Livshitz T, Biran S. Synthesis and receptor-binding affinity of fluorotamoxifen, a possible estrogen-receptor imaging agent. J Med Chem 1985;28:1504–11
   PubMed Web of Science ®Google Scholar
• Woong Seo J, Comninos JS, Dae Yoon C, et al Fluorine-substituted cyclofenol derivatives as estrogen receptor ligands: synthesis and structure-affinity relationship study of potential position emission tomography agents for imaging estrogen receptors in breast cancer. J Med Chem 2006;49:2496–511
   PubMed Web of Science ®Google Scholar
• Bardon S, Vignon F, Montcourrier P, Rochefort H. Steroid receptor-mediated cytotoxicity of an antiestrogen and an antiprogestin in breast cancer cells. Cancer Res 1987;47:1441–8
   PubMed Web of Science ®Google Scholar
• Seeger H, Huober J, Wallwiener D, Mueck AO. Inhibition of human breast cancer cell proliferation with estradiol metabolites is as effective as with tamoxifen. Horm Metab Res 2004;36:277–80
   PubMed Web of Science ®Google Scholar
• Reddel RR, Murphy LC, Sutherland RL. Effects of biologically active metabolites of tamoxifen on the proliferation kinetics of MCF-7 human breast cancer cells in vitro. Cancer Res 1983;42:4618–24
   Google Scholar
• Karami-Tehrani F, Salami S. Cell kinetic study of tamoxifen treated MCF-7 and MDA-MB 468 breast cancer cell lines. Iran Biomed J 2003;7:51–6
   Google Scholar
• Reddel RR, Murphy LC, Hall RE, Sutherland RL. Differential sensitivity of human breast cancer cell lines to the growth-inhibitory effects of tamoxifen. Cancer Res 1985;45:1525–31
   PubMed Web of Science ®Google Scholar
• Jones CD, Blaszczak LC, Goettel ME, et al Antiestrogens. 3.′ Estrogen receptor affinities and antiproliferative effects in MCF-7 cells in phenolic analogues of trioxifene, [3,4-dihydro-2-(4-methoxyphenyl)-1-naphthalenyl][4-[2-(1-pyrrolidinyl)ethyoxy]-phenyl]methanone. J Med Chem 1992;35:931–8
   PubMed Web of Science ®Google Scholar
• Khalkhali-Ellis Z, Christian AL, Kirschmann DA, et al Regulating the tumor suppressor gene maspin in breast cancer cells: a potential mechanism for the anticancer properties of tamoxifen. Clin Cancer Res 2004;10:449–54
   PubMed Web of Science ®Google Scholar
• Enmark E, Pelto-Huikko M, Grandien K, et al Human estrogen receptor beta-gene structure, chromosomal localization, and expression pattern. J Clin Endocrinol Metab 1997;82:4258–65
   PubMed Web of Science ®Google Scholar
• Bramlett KS, Burris TP. Target specificity of selective estrogen receptor modulators within human endometrial cancer cells. J Steroid Biochem Mol Biol 2003;86:27–34
   PubMed Web of Science ®Google Scholar