Pharmacophore mapping of arylbenzothiophene derivatives for MCF cell inhibition using classical and 3D space modeling approaches

Journal of Molecular Graphics and Modelling

Volumn 26, Issue 5, 2008, Pages 884-892

  Mukherjee, Subhendu ^a   Nagar, Shuchi ^a   Mullick, Sanchita ^a   Mukherjee, Arup ^a   Saha, Achintya ^a  

^a UNIVERSITY OF CALCUTTA   (India)

Author keywords

Arylbenzothiophene; MCF cell line inhibition; Pharmacophore mapping; QSAR study; Space modeling

Indexed keywords

BIOLOGICAL ORGANS; DERIVATIVES; MOLECULAR MODELING; ONCOLOGY; THREE DIMENSIONAL;

ARYLBENZOTHIOPHENE; KETONIC LINKAGES; PHARMACOPHORE MAPPINGS; PIPERIDINE RINGS; QSAR STUDY;

KETONES;

4 [4 METHYL 2 [4 [2 (1 PIPERIDINYL)ETHOXY]PHENYL] 7 PIVALOYLOXY 2H 1 BENZOPYRAN 3 YLPHENYL] PIVALATE; 4 HYDROXYTAMOXIFEN; ACOLBIFENE; BAZEDOXIFENE; BENZOTHIOPHENE DERIVATIVE; CELECOXIB; CLOMIFENE; DIETHYLSTILBESTROL; EPHEDRINE; ETOPOSIDE; GEFITINIB; GENISTEIN; HYDROXYL GROUP; LASOFOXIFENE; LETROZOLE; LUTEOLIN; MORPHINE; NAFOXIDINE; NORGESTREL; ORPHENADRINE; PHENYTOIN; PIPERIDINE; PROPRANOLOL; QUERCETIN; RALOXIFENE; STANOZOLOL; TANGERETIN; TESTOSTERONE; TETRAHYDROISOQUINOLINE; UNINDEXED DRUG;

ARTICLE; BREAST CANCER; CONTROLLED STUDY; DRUG MECHANISM; DRUG STRUCTURE; HUMAN; HUMAN CELL; HYDROPHOBICITY; MOLECULAR MODEL; PHARMACOPHORE; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION;

ANIMALS; CELL LINE, TUMOR; CRYSTALLOGRAPHY, X-RAY; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; INHIBITORY CONCENTRATION 50; MODELS, MOLECULAR; PIPERIDINES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RALOXIFENE; RATS; RECEPTORS, ESTROGEN; THIOPHENES;

EID: 36749034303     PISSN: 10933263     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jmgm.2007.06.003     Document Type: Article

References (54)

1. Smith E.P., Boyd J., Frank G.R., Takahashi H., Cohen R.M., Specker B., Williams T.C., Lubahn D.B., and Korach K.S. Estrogen resistance caused by a mutation in the estrogen-receptor gene in a man. N. Engl. J. Med. 331 (1994) 1056-1061
2. Ciocca D.R., and Vargas R.L.M. Estrogen receptors in human non-target tissues: biological and clinical implications. Endocrinol. Rev. 16 (1995) 35-62
3. Lindsay R. Select steroids in the pathogenesis and prevention of osteoporosis. In: Riggs B.L., and Melton L.J. (Eds). Osteoporosis: Etiology, Diagnosis, and Management (1988), Raven Press, New York 333-358
4. Ross R.K., Pike M.C., Mack T.M., and Henderson B.E. Oestrogen replacement therapy and cardiovascular disease. In: Drife J.O., and Studd J.W.W. (Eds). HRT and Osteoporosis (1990), Springer-Verlag, London 209-222
5. Dutertre M., and Smith C.L. Molecular mechanisms of selective estrogen receptor modulator (SERM) action. J. Pharmacol. Exp. Ther. 295 (2000) 431-437
6. Rosati R.L., Jardine P.D.S., Cameron K.O., Thompson D.D., and Ke H.Z. Discovery and preclinical pharmacology of a novel, potent, nonsteroidal estrogen receptor agonist/antagonist, CP-336156, a diaryltetrahydronaphthalene. J. Med. Chem. 41 (1998) 2928-2931
7. Shao W., and Brown M. Advances in estrogen receptor biology: Prospects for improvements in targeted breast cancer therapy. Breast Cancer Res. 6 (2004) 39-52
8. Burger H.G. Selective oestrogen receptor modulators. Hormone Res. 53 (2000) 25-29
9. Goldstein S.R., Siddhanti S., Ciaccia A.V., and Plouffe L. A pharmacological review of selective oestrogen receptor modulators. Human Reprod. Update 6 (2000) 212-224
10. Grese T.A., and Dodge J.A. Estrogen receptor modulators: effects in non-traditional target tissues. Annu. Rep. Med. Chem. 31 (1998) 181-190
11. Kauffman R.F., and Bryant H.U. Selective estrogen receptor modulators. Drug News Perspect. 8 (1995) 531-539
12. Evans G.L., and Turner R.T. Tissue-selective actions of estrogen analogs. Bone 17 (1995) 181S-190S
13. Jordan V.C., Gapstur S., and Morrow M. Selective estrogen receptor modulation and reduction in risk of breast cancer, osteoporosis, and coronary heart disease. J. Natl. Cancer Inst. 93 (2001) 1449-1457
14. Jordan V.C., and Morrow M. Raloxifene as a multifunctional medicine? Current trials will show whether it is effective in both osteoporosis and breast cancer. Br. Med. J. 319 (1999) 331-332
15. Jordan V.C. Estrogen, selective estrogen receptor modulation, and coronary heart disease: something or nothing. J. Natl. Cancer Inst. 93 (2001) 2-4
16. Guner O.F. Pharmacophore Perception, Development, and Use in Drug Design (2000), International University Line, California
17. da Cunha E.F.F., Martins R.C.A., Albuquerque M.G., and de Alencastro R.B. LIV-3D-QSAR model for estrogen receptor ligands. J. Mol. Modell. 10 (2004) 297-304
18. Schmidt J.M., Mercure J., Tremblay G.B., Page M., Feher M., Dunn-Dufault R., Peter M.G., and Redden P.R. De novo design, synthesis and evaluation of a non-steroidal diphenylnapthyl propylene ligand for the estrogen receptor. Bioorg. Med. Chem. 11 (2003) 1389-1396
19. Mortensen D.S., Rodriguez A.L., Carlson K.E., Sun J., Katzenellenbogen B.S., and Katzenellenbogen J.A. Synthesis and biological evaluation of a novel series of furans: Ligands selective for estrogen receptor α. J. Med. Chem. 44 (2001) 3838-3848
20. Henke B.R., Consler T.G., Go N., Hale R.L., Hohman D.R., Jones S.A., Lu A.T., Moore L.B., Moore J.T., Orband-Miller L.A., Robinett R.G., Shearin J., Spearing P.K., Stewart E.L., Turnbull P.S., Weaver S.L., Williams S.P., Wisely G.B., and Lambert M.H. A new series of estrogen receptor modulators that display selectivity for estrogen receptor β. J. Med. Chem. 45 (2002) 5492-5505
21. Zong-Ru G., Xiang Y., and Zhi-Bin X. Molecular simulation of interactions between estrogen receptor and selective estrogen receptor modulators. Acta Pharmacol. Sin. 23 (2002) 208-212
22. Schuster D., Laggner C., Steindl T.M., Palusczak A., Hartmann R.W., and Langer T. Pharmacophore modeling and in silico screening for new p450 19 (aromatase) inhibitors. J. Chem. Inf. Model. 46 (2006) 1301-1311
23. Lopez-Rodrýguez M.L., Benhamu B., de la Fuente T., Sanz A., Pardo L., and Campillo M. A three-dimensional pharmacophore model for 5-hydroxytryptamine6 (5- HT6) receptor antagonists. J. Med. Chem. 48 (2005) 4216-4219
24. Taha M.O., Qandil A.M., Zaki D.D., and Aidamen M.A. Ligand-based assessment of factor Xa binding site flexibility via elaborate pharmacophore exploration and genetic algorithm based QSAR modeling. Eur. J. Med. Chem. 40 (2005) 701-727
25. Catalyst, version 4.11, Accelrys, Inc., San Diego, CA, 2005.
26. Barnum D., Greene J., Smellie A., and Sprague P. Identification of common functional configurations among molecules. J. Chem. Inf. Comput. Sci. 36 (1996) 563-571
27. Jones G., Willett P., and Glen R.C. A genetic algorithm for flexible molecular overlay and pharmacophore elucidation. J. Comput. Aided Mol. Des. 9 (1995) 532-549
28. Martin Y.C., Bures M.G., Danaher E.A., DeLazzer J., Lico I., and Pavlik P.A. A fast new approach to pharmacophore mapping and its application to dopaminergic and benzodiazepine agonists. J. Comput. Aided Mol. Des. 7 (1993) 83-102
29. Timothy A.G., Stephen C., Don R.F., Alexander G.G., Charles D.J., Charles W.L., Michael J.M., Ken M., Lewis D.P., Mark A.W., Adrian M.D., Harlan W.C., David E.M., Phillips D.L., Ellen R.R., Lorri L.S., Andrew L.G., and Henry U.B. Structure-activity relationships of selective estrogen receptor modulators: modifications to the 2-arylbenzothiophene core of raloxifene. J. Med. Chem. 40 (1997) 146-167
30. de Waterbeemd H.V., and Testa B. In: Testa B. (Ed). Advances in Drug Research vol. 16 (1987), Academic Press, New York 85-225
31. Atkins P.W. Physical Chemistry (1982), Freeman, New York
32. Wildman S.A., and Crippen G.M. Prediction of physicochemical parameters by atomic contributions. J. Chem. Inf. Comput. Sci. 39 (1999) 868-873
33. Williford C.J., and Stevens E.P. Strain energies as a steric descriptor in QSAR calculations. QSAR Combinatorial Sci. 23 (2004) 495-505
34. Wang B., and Ford G. Atomic charges derived from a fast and accurate method for electrostatic potentials based on modified AM1 calculations. J. Comp. Chem. 15 (1994) 200-207
35. McWeeny R. Coulson's Valence (1979), Oxford University Press, London
36. Dewar M.J.S. The Molecular Orbital Theory of Organic Chemistry (1969), McGraw-Hill, New York
37. House J.E. Fundamentals of Quantum Chemistry (2005), Elsevier Academic Press, California
38. Kier L.B. Methods and principles in medicinal chemistry. In: de Waterbeemd H.V. (Ed). Chemometric Methods in Molecular Design vol. 2 (1995), VCH Publishers, Weinheim 39-44
39. ETSA-CS, Cyber-Mate, Srirampur, W. Bengal, India, 2003.
40. TSAR 3D, version 3.3, Oxford Molecular Limited, Accelrys, Inc., San Diego, CA.
41. CAChe, version 6.1, Life Science and Material Science Division, Fujitsu Ltd., Chiba, Japan.
42. CS Chem3D Pro and CS MOPAC Pro, version 5.0, Cambridge Soft, Corporation, Cambridge, USA.
43. Statistica, version 5.0, StatSoft, Inc., Tulsa, USA.
44. Wold S., and Eriksson L. Methods and principles in medicinal chemistry. In: de Waterbeemd H.V. (Ed). Chemometric Methods in Molecular Design vol. 2 (1995), VCH Publishers, Weinheim 312
45. Snedecor G.W., and Cochran W.G. Statistical Methods. sixth ed. (1967), Iowa State University Press, Iowa
46. Brzozowski A.M., Pike A.C., Dauter Z., Hubbard R.E., Bonn T., Engstrom O., Ohman L., Greene G.L., Gustafsson J.A., and Carlquist M. Molecular basis of agonism and antagonism in the oestrogen receptor. Nature 389 (1997) 753-758
47. Pike A.C., Brzozowski A.M., Hubbard R.E., Bonn T., Thorsell A.G., Engstrom O., Ljunggren J., Gustafsson J.A., and Carlquist M. Structure of the ligand-binding domain of oestrogen receptor beta in the presence of a partial agonist and a full antagonist. EMBO J. 18 (1999) 4608-4618
48. Grese T.A., Sluka J.P., Bryant H.U., Cullian G.J., Glasebrook A.L., Jones C.D., Matsumoto K., Palkowitz A.D., Sato M., Termine J.D., Winter M.A., Yang M.A., and Dodge J.A. Molecular determinants of tissue selectivity in estrogen receptor modulators. Proc. Natl. Acad. Sci. 94 (1997) 14105-14110
49. Grese T.A., Sluka J.P., Bryant H.U., Cole H.W., Kim J.R., Magee D.E., Rowley E.R., and Sato M. Benzopyran selective estrogen receptor modulators (SERMs): Pharmacological effects and structural correlation with raloxifene. Bioorg. Med. Chem. Let. 6 (1996) 903-908
50. Verli H., Albuquerque M.G., Alencastro R.B., and Barreiro E.J. Local intersection volume: A new 3D descriptor applied to develop a 3D-QSAR pharmacophore model for benzodiazepine receptor ligands. Eur. J. Med. Chem. 37 (2002) 219-229
51. 2 receptor ligands. J. Braz. Chem. Soc. 13 (2002) 816-821
52. Gauthier S., Caron B., Cloutier J., Dory Y.L., Favre A., Larouche D., Mailhot J., Ouellet C., Schwerdtfeger A., Leblanc G., Martel C., Simard J., Merand Y., Belanger A., Labrie C., and Labrie F. (S)-(+)-4-[7-(2,2-Dimethyl-1-oxopropoxy)-4-methyl-2-[4-[2-(1-piperidinyl)-ethoxy]phenyl]-2H-1-benzopyran-3-yl]-phenyl-2,2-dimethylpropanoate (EM-800): a highly potent, specific, and orally active nonsteroidal antiestrogen. J. Med. Chem. 40 (1997) 2117-2122
53. Simard J., Sanchez R., Poirier D., Gauthier S., Singh S.M., Merand Y., Belanger A., Labrie C., and Labile F. Blockade of the stimulatory effect of estrogens, OH-tamoxifen, OH-toremifene, droloxifene, and raloxifene on alkaline phosphatase activity by the antiestrogen EM-800 in human endometrial adenocarcinoma Ishikawa cells. Cancer Res. 57 (1997) 3494-3497
54. Miller C.P., Collini M.D., Tran B.D., Harris H.A., Kharode Y.P., Marzolf J.T., Moran R.A., Henderson R.A., Bender R.H.W., Unwalla R.J., Greenberger L.M., Yardley J.P., Abou-Gharbia M.A., Lyttle C.R., and Komm B.S. Design, synthesis, and preclinical characterization of novel, highly selective indole estrogens. J. Med. Chem. 44 (2001) 1654-1657