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Original Article

Novel phenolic inhibitors of the sarco/endoplasmic reticulum calcium ATPase: identification and characterization by quantitative structure–activity relationship modeling and virtual screening

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Pages 1-8 | Received 27 Sep 2013, Accepted 28 Oct 2013, Published online: 11 Feb 2014

References

  • Moller JV, Juul B, le Maire M. Structural organization, ion transport, and energy transduction of P-type ATPases. Biochim Biophys Acta 1996;1286:1–51
  • Moller JV, Olesen C, Winther AM, Nissen P. The sarcoplasmic Ca2+-ATPase: design of a perfect chemi-osmotic pump. Quart Rev Biophy 2010;43:501–66
  • Michelangeli F, East JM. A diversity of SERCA Ca2+ pump inhibitors. Biochem Soc Trans 2011;39:789–97
  • Paula S. Progress in the Discovery of SERCA inhibitors. In: Colombia G, Ricci S, eds. Medicinal chemistry research progress. New York: Nova Science Publishers, Inc.; 2008:103--18
  • Treiman M, Caspersen C, Christensen SB. A tool coming of age: thapsigargin as an inhibitor of sarco-endoplasmic reticulum Ca2+-ATPases. Trends Pharmacol Sci 1998;19:131–5
  • Denmeade SR, Isaacs JT. The SERCA pump as a therapeutic target: making a “smart bomb” for prostate cancer. Cancer Biol Ther 2005;4:14–22
  • Isaacs J. New strategies of the medical treatment of prostate cancer. BJU Int. 2005;96:35–40
  • Obara K, Miyashita N, Xu C, et al. Structural role of countertransport revealed in Ca2+ pump crystal structure in the absence of Ca2+. Proc Natl Acad Sci USA 2005;102:14489–96
  • Moncoq K, Trieber CA, Young HS. The molecular basis for cyclopiazonic acid inhibition of the sarcoplasmic reticulum calcium pump. J Biol Chem 2007;282:9748–57
  • Laursen M, Bublitz M, Moncoq K, et al. Cyclopiazonic acid is complexed to a divalent metal ion when bound to the sarcoplasmic reticulum Ca2+-ATPase. J Biol Chem 2009;284:13513–18
  • Deye J, Elam C, Lape M, et al. Structure-based virtual screening for novel inhibitors of the sarco/endoplasmic reticulum calcium ATPase and their experimental evaluation. Bioorg Med Chem 2009;17:1353–60
  • Lape M, Elam C, Paula S. Comparison of current docking tools for the simulation of inhibitor binding by the transmembrane domain of the sarco/endoplasmic reticulum calcium ATPase. Biophys Chem 2010;150:88–97
  • Elam C, Lape M, Deye J, et al. Discovery of novel SERCA inhibitors by virtual screening of a large compound library. Eur J Med Chem 2011;46:1512–23
  • Puzyn T, Leszczynski J, Cronin M. Recent advances in QSAR studies: methods and applications. Challenges and advances in computational chemistry and physics, 2010 ed. New York: Springer; 2009
  • Hansch C, Leo A. Exploring QSAR: Volume 1: fundamentals and applications in chemistry and biology. Washington, DC: American Chemical Society; 1995
  • Lape M, Elam C, Versluis M, et al. Molecular determinants of sarco/endoplasmic reticulum calcium ATPase inhibition by hydroquinone-based compounds. Proteins 2008;70:639–49
  • Paula S, Abell J, Deye J, et al. Design, synthesis, and biological evaluation of hydroquinone derivatives as novel inhibitors of the sarco/endoplasmic reticulum calcium ATPase. Bioorg Med Chem 2009;17:6613–19
  • Leach A. Molecular modelling: principles and applications. Essex, England: Prentice-Hall; 2001:353–409
  • MacLennan DH. Purification and properties of an adenosine triphosphatase from sarcoplasmic reticulum. J Biol Chem 1970;245:4508–18
  • Van Veldhoven P, Mannaerts G. Inorganic and organic phosphate measurements in the nanomolar range. Anal Biochem 1987;161:45–8
  • Cheng Y, Prusoff WH. Relationship between the inhibition constant (K1) and the concentration of inhibitor which causes 50 per cent inhibition (I50) of an enzymatic reaction. Biochem Pharmacol 1973;22:3099–108
  • Woeste M, Steller J, Hofmann E, et al. Structural requirements for inhibitory effects of bisphenols on the activity of the sarco/endoplasmic reticulum calcium ATPase. Bioorg Med Chem 2013;21:3927--33
  • Ogunbayo OA, Michelangeli F. The widely utilized brominated flame retardant tetrabromobisphenol A (TBBPA) is a potent inhibitor of the SERCA Ca2+ pump. Biochem J 2007;408:407–15
  • Floreani M, Santi Soncin E, Carpenedo F. Effects of 2-methyl-1,4-naphthoquinone (menadione) on myocardial contractility and cardiac sarcoplasmic reticulum Ca-ATPase. Naunyn Schmiedebergs Arch Pharmacol 1989;339:448–55
  • Floreani M, Forlin A, Bellin S, Carpenedo F. Structure–activity relationship for the inhibition of cardiac sarcoplasmic reticulum Ca2+ ATPase activity by naphthoquinones. Biochem Mol Biol Int 1995;37:757–63
  • Floreani M, Carpenedo F. Modifications of cardiac contractility by redox cycling alkylating and mixed redox cycling/alkylating quinones. J Pharmacol Exp Ther 1991;256:243–8
  • Stanton DT. On the physical interpretation of QSAR models. J Chem Inf Comput Sci 2003;43:1423–33
  • Stanton DT. QSAR and QSPR model interpretation using partial least squares (PLS) analysis. Curr Comput-Aided Drug Des 2012;8:107–27

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