449
Views
3
CrossRef citations to date
0
Altmetric
Research Article

Descriptor analysis of estrogen receptor β-selective ligands using 2-phenylquinoline, tetrahydrofluorenone and 3-hydroxy 6H-benzo[c]chromen-6-one scaffolds

, , , &
Pages 831-842 | Received 06 Mar 2010, Accepted 19 Feb 2011, Published online: 25 Mar 2011

References

  • Katzenellenbogen BS. Estrogen receptors: bioactivities and interactions with cell signaling pathways. Biol Reprod 1996;54:287–293.
  • Kuiper GG, Enmark E, Pelto-Huikko M, Nilsson S, Gustafsson JA. Cloning of a novel receptor expressed in rat prostate and ovary. Proc Natl Acad Sci USA 1996;93:5925–5930.
  • Mosselman S, Polman J, Dijkema R. ER beta: identification and characterization of a novel human estrogen receptor. FEBS Lett 1996;392:49–53.
  • Enmark E, Pelto-Huikko M, Grandien K, Lagercrantz S, Lagercrantz J, Fried G et al. Human estrogen receptor beta-gene structure, chromosomal localization, and expression pattern. J Clin Endocrinol Metab 1997;82:4258–4265.
  • Tremblay GB, Tremblay A, Copeland NG, Gilbert DJ, Jenkins NA, Labrie F et al. Cloning, chromosomal localization, and functional analysis of the murine estrogen receptor beta. Mol Endocrinol 1997;11:353–365.
  • Malamas MS, Manas ES, McDevitt RE, Gunawan I, Xu ZB, Collini MD et al. Design and synthesis of aryl diphenolic azoles as potent and selective estrogen receptor-beta ligands. J Med Chem 2004;47:5021–5040.
  • Imamov O, Shim GJ, Warner M, Gustafsson JA. Estrogen receptor beta in health and disease. Biol Reprod 2005;73:866–871.
  • Koehler KF, Helguero LA, Haldosén LA, Warner M, Gustafsson JA. Reflections on the discovery and significance of estrogen receptor beta. Endocr Rev 2005;26:465–478.
  • Vedani A, Smiesko M, Spreafico M, Peristera O, Dobler M. VirtualToxLab - in silico prediction of the toxic (endocrine-disrupting) potential of drugs, chemicals and natural products. Two years and 2,000 compounds of experience: a progress report. Altex 2009;26:167–176.
  • Cao Q, Garib V, Yu Q, Connell DW, Campitelli M. Quantitative structure-property relationships (QSPR) for steroidal compounds of environmental importance. Chemosphere 2009;76:453–459.
  • Roncaglioni A, Piclin N, Pintore M, Benfenati E. Binary classification models for endocrine disrupter effects mediated through the estrogen receptor. SAR QSAR Environ Res 2008;19:697–733.
  • Li H, Ung CY, Yap CW, Xue Y, Li ZR, Chen YZ. Prediction of estrogen receptor agonists and characterization of associated molecular descriptors by statistical learning methods. J Mol Graph Model 2006;25:313–323.
  • Boriani E, Spreafico M, Benfenati E, Novic M. Structural features of diverse ligands influencing binding affinities to estrogen alpha and estrogen beta receptors. Part I: Molecular descriptors calculated from minimal energy conformation of isolated ligands. Mol Divers 2007;11:153–169.
  • Spreafico M, Boriani E, Benfenati E, Novic M. Structural features of diverse ligands influencing binding affinities to estrogen alpha and estrogen beta receptors. Part II. Molecular descriptors calculated from conformation of the ligands in the complex resulting from previous docking study. Mol Divers 2007;11:171–181.
  • Hillisch A, Peters O, Kosemund D, Müller G, Walter A, Schneider B et al. Dissecting physiological roles of estrogen receptor alpha and beta with potent selective ligands from structure-based design. Mol Endocrinol 2004;18:1599–1609.
  • Vu AT, Cohn ST, Manas ES, Harris HA, Mewshaw RE. ERbeta ligands. Part 4: Synthesis and structure-activity relationships of a series of 2-phenylquinoline derivatives. Bioorg Med Chem Lett 2005;15:4520–4525.
  • Wilkening RR, Ratcliffe RW, Tynebor EC, Wildonger KJ, Fried AK, Hammond ML et al. The discovery of tetrahydrofluorenones as a new class of estrogen receptor beta-subtype selective ligands. Bioorg Med Chem Lett 2006;16:3489–3494.
  • Sun W, Cama LD, Birzin ET, Warrier S, Locco L, Mosley R et al. 6H-Benzo[c]chromen-6-one derivatives as selective ERbeta agonists. Bioorg Med Chem Lett 2006;16:1468–1472.
  • Trossini GH, Guido RV, Oliva G, Ferreira EI, Andricopulo AD. Quantitative structure-activity relationships for a series of inhibitors of cruzain from Trypanosoma cruzi: molecular modeling, CoMFA and CoMSIA studies. J Mol Graph Model 2009;28:3–11.
  • Leonard JT, Roy K. Exploring molecular shape analysis of styrylquinoline derivatives as HIV-1 integrase inhibitors. Eur J Med Chem 2008;43:81–92.
  • Hu QN, Liang YZ, Yin H, Peng XL, Fang KT. Structural interpretation of the topological index. 2. The molecular connectivity index, the kappa index, and the atom-type E-state index. J Chem Inf Comput Sci 2004;44:1193–1201.
  • Ullrich JW, Unwalla RJ, Singhaus RR Jr, Harris HA, Mewshaw RE. Estrogen receptor beta ligands: design and synthesis of new 2-phenyl-isoindole-1,3-diones. Bioorg Med Chem Lett 2007;17:118–122.
  • Umamatheswari S, Balaji B, Ramanathan M, Kabilan S. Synthesis, antimicrobial evaluation and QSAR studies of novel piperidin-4-yl-5-spiro-thiadiazoline derivatives. Bioorg Med Chem Lett 2010;20:6909–6914.
  • Hansch C, Verma RP. A QSAR study for the cytotoxic activities of taxoids against macrophage (MPhi)-like cells. Eur J Med Chem 2009;44:274–279.
  • Strike, version 1.8, Schrödinger, LLC, New York, NY, 2009.
  • Roy K. On some aspects of validation of predictive quantitative structure–activity relationship models. Expert Opin Drug Discov 2007;2:1567–1577.
  • LigPrep, version 2.3, Schrödinger, LLC, New York, NY, 2009.
  • Pike AC, Brzozowski AM, Hubbard RE, Bonn T, Thorsell AG, Engström O 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;18:4608–4618.
  • Maestro, version 9.0, Schrödinger, LLC, New York, NY, 2009.
  • Prime, version 2.1, Schrödinger, LLC, New York, NY, 2009.
  • Glide, version 5.5, Schrödinger, LLC, New York, NY, 2009.
  • Pike AC. Lessons learnt from structural studies of the oestrogen receptor. Best Pract Res Clin Endocrinol Metab 2006;20:1–14.
  • Manas ES, Unwalla RJ, Xu ZB, Malamas MS, Miller CP, Harris HA et al. Structure-based design of estrogen receptor-beta selective ligands. J Am Chem Soc 2004;126:15106–15119.
  • Fang H, Tong W, Shi LM, Blair R, Perkins R, Branham W et al. Structure-activity relationships for a large diverse set of natural, synthetic, and environmental estrogens. Chem Res Toxicol 2001;14:280–294.
  • Chang HJ, Kim HJ, Chun HS. Quantitative structure-activity relationship (QSAR) for neuroprotective activity of terpenoids. Life Sci 2007;80:835–841.
  • Hansch C, Verma RP, Kurup A, Mekapati SB. The role of QSAR in dopamine interactions. Bioorg Med Chem Lett 2005;15:2149–2157.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.