Discovery of novel SERCA inhibitors by virtual screening of a large compound library

European Journal of Medicinal Chemistry

Volumn 46, Issue 5, 2011, Pages 1512-1523

  Elam, Christopher ^a   Lape, Michael ^a   Deye, Joel ^a   Zultowsky, Jodie ^a   Stanton, David T ^b   Paula, Stefan ^a  

^a NORTHERN KENTUCKY UNIVERSITY   (United States)

^b Procter and Gamble   (United States)

Author keywords

Calcium pump; Enzyme inhibition; Hydroquinones; Ligand docking; Recursive partitioning; Structure activity relationship; Virtual screening

Indexed keywords

ADENOSINE TRIPHOSPHATASE INHIBITOR; ANTINEOPLASTIC AGENT; PHENYL GROUP; SARCOPLASMIC RETICULUM CALCIUM TRANSPORTING ADENOSINE TRIPHOSPHATASE; SARCOPLASMIC RETICULUM CALCIUM TRANSPORTING ADENOSINE TRIPHOSPHATASE INHIBITOR; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; ARTICLE; BIOASSAY; CANCER CHEMOTHERAPY; CONCENTRATION RESPONSE; DRUG POTENCY; DRUG SCREENING; DRUG TARGETING; ENZYME INHIBITION; MOLECULAR DOCKING; NONHUMAN; PROTEIN INTERACTION; STRUCTURE ACTIVITY RELATION;

CRYSTALLOGRAPHY, X-RAY; DRUG DISCOVERY; ENZYME ACTIVATION; ENZYME INHIBITORS; HIGH-THROUGHPUT SCREENING ASSAYS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; SARCOPLASMIC RETICULUM CALCIUM-TRANSPORTING ATPASES; SMALL MOLECULE LIBRARIES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 79953167791     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.01.069     Document Type: Article

References (62)

1. S. Paula, J. Abell, J. Deye, C. Elam, M. Lape, J. Purnell, R. Ratliff, K. Sebastian, J. Zultowsky, and R.J. Kempton Design, synthesis, and biological evaluation of hydroquinone derivatives as novel inhibitors of the sarco/endoplasmic reticulum calcium ATPase Bioorg. Medicinal Chemistry 17 2009 6613 6619
2. 2+-ATPases Trends Pharmacol. Sci. 19 1998 131 135 (Pubitemid 28218535)
3. S.R. Denmeade, and J.T. Isaacs The SERCA pump as a therapeutic target: making a "smart bomb" for prostate cancer, Cancer Biol. Ther. 4 2005 14 22 (Pubitemid 41350924)
4. S.R. Denmeade, C.M. Jakobsen, S. Janssen, S.R. Khan, E.S. Garrett, H. Lilja, S.B. Christensen, and J.T. Isaacs Prostate-specific antigen-activated thapsigargin prodrug as targeted therapy for prostate cancer J. Natl. Cancer Inst. 95 2003 990 1000 (Pubitemid 36896716)
5. J. Isaacs New strategies of the medical treatment of prostate cancer BJU Int. 96 2005 35 40 (Pubitemid 43041975)
6. J. Deye, C. Elam, M. Lape, R. Ratliff, K. Evans, and S. Paula Structure-based virtual screening for novel inhibitors of the sarco/endoplasmic reticulum calcium ATPase and their experimental evaluation Bioorg. Medicinal Chemistry 17 2009 1353 1360
7. 2+ ATPase. Stereoselectivity and important functional groups FEBS Lett. 335 1993 345 348 (Pubitemid 23355959)
8. S.F. Nielsen, O. Thastrup, R. Pedersen, C.E. Olsen, and S.B. Christensen Structure-activity relationships of analogues of thapsigargin modified at O-11 and O-12 J. Med. Chem. 38 1995 272 276
9. E. Norup, U.W. Smitt, and S.B. Christensen The potencies of thapsigargin and analogues as activators of rat peritoneal mast cells, Planta Med. 52 1986 251 255 (Pubitemid 16030190)
10. 2+-ATPase inhibitory activity of a locked analogue of thapsigargin Bioorg. Medicinal Chemistry Letters 4 1994 657 660
11. M. Ball, S.P. Andrews, F. Wierschem, E. Cleator, M.D. Smith, and S.V. Ley Total synthesis of thapsigargin, a potent SERCA pump inhibitor Org. Lett. 9 2007 663 666
12. S.V. Ley, A. Antonello, E.P. Balskus, D.T. Booth, S.B. Christensen, E. Cleator, H. Gold, K. Hogenauer, U. Hunger, R.M. Myers, S.F. Oliver, O. Simic, M.D. Smith, H. Sohoel, and A.J. Woolford Synthesis of the thapsigargins Proc. Natl. Acad. Sci. U S A 101 2004 12073 12078 (Pubitemid 39145399)
13. 2+-transport ATPase in rat skeletal muscle sarcoplasmic reticulum vesicles Biochem. Pharmacol. 37 1988 978 981 (Pubitemid 18058475)
14. 2+-ATPases by cyclopiazonic acid J. Biol. Chem. 272 1997 2794 2800 (Pubitemid 27053324)
15. 2+-ATPase of sarcoplasmic reticulum J. Biol. Chem. 264 1989 17816 17823 (Pubitemid 19279247)
16. 2+-dependent conformational states of the sarcoplasmic reticulum ATPase. Implication for the enzyme turnover Biochemistry 37 1998 4266 4274 (Pubitemid 28166449)
17. G. Appendino, S. Prosperini, C. Valdivia, M. Ballero, G. Colombano, R.A. Billington, A.A. Genazzani, and O. Sterner SERCA-inhibiting activity of C-19 terpenolides from Thapsia garganica and their possible biogenesis J. Nat. Prod. 68 2005 1213 1217 (Pubitemid 41291265)
18. 2+ binding and favoring the E2 conformation J. Biol. Chem. 281 2006 9547 9551 (Pubitemid 43864672)
19. L.R. Benzaquen, C. Brugnara, H.R. Byers, S. Gatton-Celli, and J.A. Halperin Clotrimazole inhibits cell proliferation in vitro and in vivo Nat. Med. 1 1995 534 540
20. L. Snajdrova, A. Xu, and N. Narayanan Clotrimazole, an antimycotic drug, inhibits the sarcoplasmic reticulum calcium pump and contractile function in heart muscle J. Biol. Chem. 273 1998 28032 28039 (Pubitemid 28496096)
21. 2+-ATPase of skeletal muscle sarcoplasmic reticulum Biochemistry 42 2003 3556 3566 (Pubitemid 36368650)
22. S. Hoving, M. Bar-Shimon, J.J. Tijmes, R. Goldshleger, D.M. Tal, and S.J. Karlish Novel aromatic isothiouronium derivatives which act as high affinity competitive antagonists of alkali metal cations on Na/K-ATPase J. Biol. Chem. 270 1995 29788 29793 (Pubitemid 26001647)
23. 2+ ATPase by 1,3-dibromo-2,4,6-tris(methylisothiouronium) benzene J. Biol. Chem. 280 2005 17579 17583 (Pubitemid 41388991)
24. 2+ ATPase (SERCA) inhibition J. Bioenerg. Biomembr 37 2005 365 368 (Pubitemid 43725159)
25. 2+ homeostasis Toxicol Vitro 22 2008 943 952
26. 2+ pump Biochem. J. 408 2007 407 415
27. 2+ pumps by curcumin. Curcumin putatively stabilizes the interaction between the nucleotide-binding and phosphorylation domains in the absence of ATP Eur. J. Biochem. 268 2001 6318 6327 (Pubitemid 33132054)
28. 2+ pump isoforms 1, 2, and 3 to thapsigargin and other inhibitors J. Biol. Chem. 281 2006 6970 6976 (Pubitemid 43847459)
29. 2+-ATPase: separate binding sites for dihydroxybenzenes and sesquiterpene lactones Biochemistry 34 1995 14385 14393 (Pubitemid 3000707)
30. 2+ sequestration FEBS Lett. 224 1987 331 336 (Pubitemid 18008187)
31. 2+-ATPase by trilobolide and 2,5-di(tert-butyl)-1,4-benzohydroquinone, Biochem. Biophys. Res. Commun. 199 1994 916 921
32. M. Lape, C. Elam, M. Versluis, R. Kempton, and S. Paula Molecular determinants of sarco/endoplasmic reticulum calcium ATPase inhibition by hydroquinone-based compounds Proteins 70 2008 639 649 (Pubitemid 351161926)
33. 2+ Proc. Natl. Acad. Sci. U S A 102 2005 14489 14496 (Pubitemid 41457085)
34. M. Takahashi, Y. Kondou, and C. Toyoshima Interdomain communication in calcium pump as revealed in the crystal structures with transmembrane inhibitors Proc. Natl. Acad. Sci. U S A 104 2007 5800 5805 (Pubitemid 47175614)
35. M.H.J. Seifert, K. Wolf, and D. Vitt Virtual high-throughput in silico screening Biosilico 1 2003 143 149 (Pubitemid 40416767)
36. W.P. Walters, M.T. Stahl, and M.A. Murcko Virtual screening - an overview Drug Discov. Today 3 1998 160 178 (Pubitemid 128715971)
37. C.N. Cavasotto, and A.J. Orry Ligand docking and structure-based virtual screening in drug discovery Curr. topics Medicinal Chemistry 7 2007 1006 1014 (Pubitemid 47040528)
38. H. Sun Pharmacophore-based virtual screening Curr. Medicinal Chemistry 15 2008 1018 1024 (Pubitemid 351736404)
39. A.S. Reddy, S.P. Pati, P.P. Kumar, H.N. Pradeep, and G.N. Sastry Virtual screening in drug discovery - a computational perspective Curr. protein Peptide Science 8 2007 329 351 (Pubitemid 47317040)
40. F.L. Stahura, and J. Bajorath New methodologies for ligand-based virtual screening Curr. Pharmaceutical Design 11 2005 1189 1202 (Pubitemid 40403377)
41. C.N. Cavasotto, M.A. Ortiz, R.A. Abagyan, and F.J. Piedrafita In silico identification of novel EGFR inhibitors with antiproliferative activity against cancer cells Bioorg. Medicinal Chemistry Letters 16 2006 1969 1974 (Pubitemid 43267390)
42. A.J. Dooley, N. Shindo, B. Taggart, J.G. Park, and Y.P. Pang From genome to drug lead: identification of a small-molecule inhibitor of the SARS virus Bioorg. Medicinal Chemistry Letters 16 2006 830 833 (Pubitemid 43059832)
43. V. Carbone, S. Ishikura, A. Hara, and O. El-Kabbani Structure-based discovery of human L-xylulose reductase inhibitors from database screening and molecular docking Bioorg. Medicinal Chemistry 13 2005 301 312 (Pubitemid 39642914)
44. S.P. Gupta Quantitative structure-activity relationships of carbonic anhydrase inhibitors, Progress in drug research Fortschritte der Arzneimittelforschung 60 2003 171 204 (Pubitemid 36538116)
45. S.P. Gupta Quantitative structure-activity relationships of renin inhibitors Mini Reviews Medicinal Chemistry 3 2003 315 321
46. A. Rusinko 3rd, M.W. Farmen, C.G. Lambert, P.L. Brown, and S.S. Young Analysis of a large structure/biological activity data set using recursive partitioning J. Chem. Inf. Comput. Sci. 39 1999 1017 1026 (Pubitemid 129579834)
47. A. Rusinko 3rd, S.S. Young, D.H. Drewry, and S.W. Gerritz Optimization of focused chemical libraries using recursive partitioning Comb. Chem. High Throughput Screen. 5 2002 125 133 (Pubitemid 34475164)
48. I. Choi, S.Y. Kim, H. Kim, N.S. Kang, M.A. Bae, S.E. Yoo, J. Jung, and K.T. No Classification models for CYP450 3A4 inhibitors and non-inhibitors Eur. J. Med. Chem. 44 2009 2354 2360
49. E. Dubus, I. Ijjaali, F. Petitet, and A. Michel In silico classification of HERG channel blockers: a knowledge-based strategy ChemMedChem 1 2006 622 630 (Pubitemid 44105788)
50. D.R. Jones, S. Ekins, L. Li, and S.D. Hall Computational approaches that predict metabolic intermediate complex formation with CYP3A4 (+b5) Drug Metab. Dispos 35 2007 1466 1475 (Pubitemid 47296037)
51. C. Lamanna, M. Bellini, A. Padova, G. Westerberg, and L. Maccari Straightforward recursive partitioning model for discarding insoluble compounds in the drug discovery process J. Med. Chem. 51 2008 2891 2897 (Pubitemid 351711191)
52. G. Jones, P. Willett, and R.C. Glen Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation J. Mol. Biol. 245 1995 43 53
53. G. Jones, P. Willett, R.C. Glen, A.R. Leach, and R. Taylor Development and validation of a genetic algorithm for flexible docking J. Mol. Biol. 267 1997 727 748 (Pubitemid 27170693)
54. P. Van Veldhoven, and G. Mannaerts Inorganic and organic phosphate measurements in the nanomolar range Anal. Biochem. 161 1987 45 48 (Pubitemid 17036687)
55. 2+ homeostasis & Sertoli TM4 cell viability Chem. Biol. Interact 176 2008 220 226
56. L.B. Kier, and L.H. Hall An electrotopological-state index for atoms in molecules Pharm. Res. 7 1990 801 807 (Pubitemid 20332531)
57. L.B. Kier, and L.H. Hall Molecular structure description: the electrotopological state 1999 Academic Press New York
58. D.S. Goodsell, and A.J. Olson Automated docking of substrates to proteins by simulated annealing Proteins 8 1990 195 202 (Pubitemid 20363304)
59. M. Lape, C. Elam, and S. Paula Comparison of current docking tools for the simulation of inhibitor binding by the transmembrane domain of the sarco/endoplasmic reticulum calcium ATPase Biophys. Chem. 150 2010 88 97
60. C.A. Baxter, C.W. Murray, D.E. Clark, D.R. Westhead, and M.D. Eldridge Flexible docking using Tabu search and an empirical estimate of binding affinity Proteins 33 1998 367 382 (Pubitemid 28516342)
61. M.D. Eldridge, C.W. Murray, T.R. Auton, G.V. Paolini, and R.P. Mee Empirical scoring functions: I. The development of a fast empirical scoring function to estimate the binding affinity of ligands in receptor complexes J. Comput. Aided Mol. Des 11 1997 425 445 (Pubitemid 127505895)
62. D.H. MacLennan Purification and properties of an adenosine triphosphatase from sarcoplasmic reticulum J. Biol. Chem. 245 1970 4508 4518