An efficient steroid pharmacophore-based strategy to identify new aromatase inhibitors

European Journal of Medicinal Chemistry

Volumn 44, Issue 10, 2009, Pages 4121-4127

  Neves, Marco A C ^a   Dinis, Teresa C P ^b   Colombo, Giorgio ^c   Sá e Melo, M Luisa ^a  

^a UNIVERSITY OF COIMBRA   (Portugal)

^b UNIVERSITY OF COIMBRA   (Portugal)

^c CNR   (Italy)

Author keywords

Aromatase inhibitors; Breast cancer; Pharmacophore modeling; Virtual screening

Indexed keywords

ALIPHATIC COMPOUND; ALKYL GROUP; AMINOGLUTETHIMIDE; ANDROSTENEDIONE DERIVATIVE; AROMATASE INHIBITOR; CYTOCHROME P450; FORMESTANE; PHENYL GROUP;

AB INITIO CALCULATION; ARTICLE; BREAST CANCER; CATALYSIS; CONCENTRATION RESPONSE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DATA BASE; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; ENZYME INHIBITION; ENZYME KINETICS; ENZYME SUBSTRATE; HUMAN; HUMAN TISSUE; HYDROPHOBICITY; IN VITRO STUDY; PHARMACOPHORE; VIRTUAL REALITY;

ANDROSTENEDIONE; ANTINEOPLASTIC AGENTS, HORMONAL; AROMATASE; AROMATASE INHIBITORS; BREAST NEOPLASMS; DRUG DESIGN; FEMALE; HUMANS; MODELS, MOLECULAR; PLACENTA; PREGNANCY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 67651154131     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2009.05.003     Document Type: Article

References (48)

1. Smith I.E., and Dowsett M. N. Engl. J. Med. 348 (2003) 2431-2442
2. Meunier B., de Visser S.P., and Shaik S. Chem. Rev. 104 (2004) 3947-3980
3. Shimizu Y., Yarborough C., and Osawa Y. J. Steroid Biochem. Mol. Biol. 44 (1993) 651-656
4. Brueggemeier R.W. Breast Cancer Res. Treat. 30 (1994) 31-42
5. Coombes R.C., Hall E., Gibson L.J., Paridaens R., Jassem J., Delozier T., Jones S.E., Alvarez I., Bertelli G., Ortmann O., Coates A.S., Bajetta E., Dodwell D., Coleman R.E., Fallowfield L.J., Mickiewicz E., Andersen J., Lonning P.E., Cocconi G., Stewart A., Stuart N., Snowdon C.F., Carpentieri M., Massimini G., and Bliss J.M. N. Engl. J. Med. 350 (2004) 1081-1092
6. Goss P.E., Powles T.J., Dowsett M., Hutchison G., Brodie A.M.H., Gazet J.C., and Coombes R.C. Cancer Res. 46 (1986) 4823-4826
7. Numazawa M., Oshibe M., Yamaguchi S., and Tachibana M. J. Med. Chem. 39 (1996) 1033-1038
8. Numazawa M., Oshibe M., and Yamaguchi S. Steroids 62 (1997) 595-602
9. Numazawa M., and Yamaguchi S. J. Steroid Biochem. Mol. Biol. 67 (1998) 41-48
10. Numazawa M., and Yamaguchi S. Steroids 64 (1999) 187-196
11. Numazawa M., Shelangouski M., and Nagasaka M. Steroids 65 (2000) 871-882
12. Brueggemeier R.W., Hackett J.C., and Diaz-Cruz E.S. Endocr. Rev. 26 (2005) 331-345
13. Rowland P., Blaney F.E., Smyth M.G., Jones J.J., Leydon V.R., Oxbrow A.K., Lewis C.J., Tennant M.G., Modi S., Eggleston D.S., Chenery R.J., and Bridges A.M. J. Biol. Chem. 281 (2006) 7614-7622
14. Williams P.A., Cosme J., Sridhar V., Johnson E.F., and Mcree D.E. J. Inorg. Biochem. 81 (2000) 183-190
15. Williams P.A., Cosme J., Ward A., Angova H.C., Vinkovic D.M., and Jhoti H. Nature 424 (2003) 464-468
16. Williams P.A., Cosme J., Vinkovic D.M., Ward A., Angove H.C., Day P.J., Vonrhein C., Tickle I.J., and Jhoti H. Science 305 (2004) 683-686
17. Favia A.D., Cavalli A., Masetti M., Carotti A., and Recanatini M. Proteins 62 (2006) 1074-1087
18. Karkola S., Holtje H.D., and Wahala K. J. Steroid Biochem. Mol. Biol. 105 (2007) 63-70
19. Loge C., Le Borgne M., Marchand P., Robert J.M., Le Baut G., Palzer M., and Hartmann R.W. J. Enzyme Inhib. Med. Chem. 20 (2005) 581-585
20. Neves M.A.C., Dinis T.C.P., Colombo G., and Melo M.L.S. ChemMedChem 2 (2007) 1750-1762
21. Cepa M., Correia-Da-Silva G., da Silva E.J.T., Roleira F.M.F., Hong Y.Y., Chen S., and Teixeira N.A. Biol. Chem. 389 (2008) 1183-1191
22. Jackson T., Woo L.W.L., Trusselle M.N., Purohit A., Reed M.J., and Potter B.V.L. ChemMedChem 3 (2008) 603-618
23. Gobbi S., Cavalli A., Rampa A., Belluti F., Piazzi L., Paluszcak A., Hartmann R.W., Recanatini M., and Bisi A. J. Med. Chem. 49 (2006) 4777-4780
24. Leonetti F., Favia A., Rao A., Aliano R., Paluszcak A., Hartmann R.W., and Carotti A. J. Med. Chem. 47 (2004) 6792-6803
25. Recanatini M., and Cavalli A. Bioorg. Med. Chem. 6 (1998) 377-388
26. Cavalli A., Greco G., Novellino E., and Recanatini M. Bioorg. Med. Chem. 8 (2000) 2771-2780
27. Schuster D., Laggner C., Steindl T.M., Palusczak A., Hartmann R.W., and Langer T. J. Chem. Inf. Model. 46 (2006) 1301-1311
28. Clement O.O., and Mehl A.T. In: Güner O.F. (Ed). Pharmacophore Perception, Development, and Use in Drug Design (2000), International University Line, La Jolla, CA 69-84
29. Catalyst, Release Version 4.11, Accelrys Software Inc, 2007,www.accelrys.com.
30. Barnum D., Greene J., Smellie A., and Sprague P. J. Chem. Inf. Comput. Sci. 36 (1996) 563-571
31. Schleinkofer K., Sudarko, Winn P.J., Ludemann S.K., and Wade R.C. EMBO Rep. 6 (2005) 584-589
32. Developmental Therapeutics Program, NCI/NIH, 2008,http://dtp.nci.nih.gov.
33. Irwin J.J., and Shoichet B.K. J. Chem. Inf. Model. 45 (2005) 177-182
34. Lipinski C.A., Lombardo F., Dominy B.W., and Feeney P.J. Adv. Drug Deliv. Rev. 23 (1997) 3-25
35. MDL CrossFire Commander, Release Version 7.0SP2, Elsevier MDL, 2005,www.mdli.com.
36. PubChem Compound database, 2008, available at: http://www.ncbi.nlm.nih.gov/sites/entrez/.
37. Kitz R., and Wilson I.B. J. Biol. Chem. 237 (1962) 3245-3249
38. Instant JChem, Release Version 2.0.0, ChemAxon, 2008, www.chemaxon.com.
39. Ryan K.J. J. Biol. Chem. 234 (1959) 268-272
40. Siiteri P.K., and Thompson E.A. J. Steroid Biochem. 6 (1975) 317-322
41. Neves M.A.C., Dinis T.C.P., Colombo G., and Melo M.L.S. J. Steroid Biochem. Mol. Biol. 110 (2008) 10-17
42. MAESTRO, Release Version 8.0.314, Schrodinger, 2008, www.schrodinger.com.
43. Goodman J.M., and Still W.C. J. Comput. Chem. 12 (1991) 1110-1117
44. Mohamadi F., Richards N.G.J., Guida W.C., Liskamp R., Lipton M., Caufield C., Chang G., Hendrickson T., and Still W.C. J. Comput. Chem. 11 (1990) 440-467
45. Halgren T.A. J. Comput. Chem. 17 (1996) 490-519
46. Clark Still W., Tempczyk A., Hawley R.C., and Hendrickson T. J. Am. Chem. Soc. 112 (1990) 6127-6129
47. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, V.G. Zakrzewski, J.A. Montgomery Jr., R.E. Stratmann, J.C. Burant, S. Dapprich, J.M. Millam, A.D. Daniels, K.N. Kudin, M.C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P.M.W. Gill, B.G. Johnson, W. Chen, M.W. Wong, J.L. Andres, M. Head-Gordon, E.S. Replogle, J.A. Pople, Gaussian 98, Revision A.7, Gaussian, Inc., Pittsburgh, PA, USA, 1998, www.gaussian.com.
48. Schaftenaar G., and Noordik J.H. J. Comput.-Aided Mol. Des. 14 (2000) 123-134