Mechanism-based categorization of aromatase inhibitors: A potential discovery and screening tool

SAR and QSAR in Environmental Research

Volumn 20, Issue 7-8, 2009, Pages 657-678

  Petkov, P I ^a   Temelkov, S ^a   Villeneuve, D L ^b   Ankley, G T ^b   Mekenyan, O G ^a  

^a ASSEN ZLATAROV UNIVERSITY   (Bulgaria)

^b U S ENVIRONMENTAL PROTECTION AGENCY   (United States)

Author keywords

Aromatase inhibitors; Categorization; Endocrine disruption; Mechanism; SAR

Indexed keywords

DECISION TREES; SCAFFOLDS; SCAFFOLDS (BIOLOGY);

AROMATASE; AROMATASE INHIBITORS; CATEGORIZATION; CYTOCHROMES P450; ENDOCRINE DISRUPTION; ENVIRONMENTAL CONTAMINANT; MECHANISM-BASED; OESTROGENS; SCREENING TOOL; STRUCTURE-ACTIVITY RELATIONSHIPS;

ANIMALS;

VERTEBRATA;

EID: 72149108995     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/10629360903438347     Document Type: Article

References (41)

1. W.R. Miller and S.P. Langdan, Steroid hormones and cancer: (III) Observations from human subjects, Eur. J. Surg. Oncol. 23 (1977), p. 163.
2. W.R. Miller, R.A. Hawkins, and A.P. Forrest, Significance of aromatase activity in human breast cancer, Cancer Res. 42 (1982), p. 3365.
3. L.R. Nelson and S.E. Bulun, Estrogen production and action, J. Am. Acad. Dermatol. 45 (2001), pp. 116-124.
4. Early Breast Cancer Trialists Collaborative Group, Tamoxifen for early breast cancer: An overview of the randomised trials, Lancet 351 (1998), pp. 1451-1467.
5. N. Murthy, A.R. Rao, and G.N. Sastry, Aromatase inhibitors: A new paradigm in breast cancer treatment, Curr. Med. Chem. - Anti-Cancer Agents 4 (2004), pp. 1-11.
6. A. Brodie, H.B. Brodie, G. Callard, C. Robinson, C. Roselli, and R. Santen, Recent advances in steroid biochemistry and molecular biology, J. Steroid Biochem. Molec. Biol. 44 (1993), pp. 321-695.
7. C.J. Corbin, S. Graham-Lorence, M. Mcphaul, J.J. Mason, C.R. Mendelson, and E.R. Simpson, Isolation of a full-length cDNA insert encoding human aromatase system cytochrome P-450 and its expression in nonsteroidogenic cells, Proc. Acad. Sci. USA 85 (1988), pp. 8948-8952.
8. D.W. Nebert, D.R. Nelson, M.J. Coon, R.W. Estabrook, R. Feyereisen, Y. Fujii-Kuriyama, F.J. Gonzalez, F.P. Guengerich, I.C. Gunsalus, and E.F. Johnson, The P450 superfamily: Update on new sequences, gene mapping, and recommended nomenclature, DNA Cell Biol. 10 (1991), pp. 1-14.
9. T. Damstra, S. Barlow, A. Bergman, R. Kavlock, and G.Van Der Kraak, Global assessment of the state-of-the-science of endocrine disruptors, International Program on Chemical Safety WHO/PCS/EDC/ (2002).
10. A.K. Hotchkiss, C.V. Rider, C.R. Blystone, V.S. Wilson, P.C. Hartig, G.T. Ankley, P.M. Foster, C.L. Gray, and L.E. Gray, Fifteen years after "Wingspread"-environmental endocrine disrupters and human and wildlife health: Where we are today and where we need to go, Toxicol. Sci. 105 (2008), pp. 235-259.
11. E.A. Thompson and P.K. Siiteri, The involvement of human placental microsomal cytochrome P-450 in aromatization, J. Biol. Chem. 249 (1974), pp. 5373-5378.
12. P.A. Cole and C.H. Robinson, Mechanism and inhibition of cytochrome P-450 aromatase, J. Med. Chem. 33 (1990), pp. 2933-2942.
13. J.N. Wright and M. Akhtar, Studies on estrogen biosynthesis using radioactive and stable isotopes, Steroids 55 (1990), pp. 142-151.
14. D.C. Johannessen, T. Engan, E. Disealle, M.G. Zurlo, J. Paolini, G. Ornati, G. Piscitelli, S. Kvinnsland, and P.E. Lonning, Endocrine and clinical effects of exemestane (PNU 155071) a novel steroidal aromatase inhibitor in postmenopausal breast cancer patients, Clin. Cancer Res. 3 (1997), p. 1101.
15. N. Zilembo, C. Noberasco, and E. Bajetta, Endocrinological and clinical evaluation of exemestane, a new steroidal aromatase inhibitor, Br. J. Cancer 72 (1995), pp. 1007-1012.
16. A. Hamilton and M. Piccart, The third-generation non-steroidal aromatase inhibitors: A review of their clinical benefits in the second-line treatment of advanced breast cancer, Ann. Oncol. 10 (1999), pp. 377-384.
17. M. Numazawa, A. Mutsumi, K. Hoshi, and R. Koike, 19-Hydroxy-4-androsten-17-one: Potential competitive inhibitor of estrogen biosynthesis, Biochem. Biophys. Res. Commun. 160 (1989), pp. 1009-1014.
18. M. Numazawa, A. Mutsumi, K. Hoshi, M. Oshibe, E. Ishikawa, and H. Kigawa, Synthesis and biochemical studies of 16- or 19-substituted androst-4-enes as aromatase inhibitors, J. Med. Chem. 34 (1991), pp. 2496-2504.
19. T. Oprea and A.E. Garcia, Three-dimensional quantitative-activity relationships of steroid aromatase inhibitors, J. Comp.-Aid. Mol. Des. 10 (1996), pp. 186-200.
20. M. Lang, C. Batzl, P. Furet, R. Bowman, A. Hausler, and A.S. Bhatnagar, Structure- activity relationships and binding model of novel aromatase inhibitors, J. Steroid Biochem. Mol. Biol. 44 (1993), pp. 421-428.
21. A. Cavelli, G. Greco, E. Novellino, and M. Recanatini, Linking CoMFA and protein homology models of enzyme-inhibitor interactions: An application to non-steroidal aromatase inhibitors, Bioorg. Med. Chem. 8 (2000), pp. 2771-2780.
22. P. Furet, C. Batzl, A. Bhathagar, E. Francotte, G. Rihs, and M. Lang, Aromatase inhibitors: Synthesis, biological activity, and binding mode of azole-type compounds, J. Med. Chem. 36 (1993), pp. 1393-1400.
23. M. Recanatini, Comparative molecular fields analysis of non-steroidal aromatase inhibitors related to fadrozole, J. Comp.-Aid. Mol. Des. 10 (1996), pp. 74-82.
24. H. Vanden Bossche, H. Moereels, and L.M. Koymans, Aromatase inhibitors-mechanisms for non-steroidal inhibitors, Br. Cancer Res. Treat. 30 (1994), pp. 43-55.
25. Y.C. Kao, L.L. Cam, C.A. Laughton, D. Zhou, and S. Chen, Binding characteristics of seven inhibitors of human aromatase: A site-directed mutagenesis study, Cancer Res. 56 (1996), pp. 3451-3460.
26. B.R. Babu and A.D. Vaz, A.D.N. 1,2,3-thiadiazole: A novel heterocyclic heme ligand for the design of cytochrome P450 inhibitors, Biochemistry 36 (1997), pp. 7209-7216.
27. A. Cavalli and M. Recanatini, Looking for selectivity among cytochrome P450s inhibitors, J. Med. Chem. 45 (2002), pp. 251-254.
28. M. Recanatini, A. Bisi, A. Cavalli, F. Belluti, S. Gobbi, A. Rampa, P. Valenti, M. Palzer, A. Palusczak, and R.W. Hartmann, A new class of nonsteroidal aromatase inhibitors: Design and synthesis of chromone and xanthone derivatives and inhibition of the P450 enzymes aromatase and 17 -Hydroxylase/C17,20-Lyase, J. Med Chem. 44 (2001), pp. 672-680.
29. Organisation for Economic Co-operation and Development, Guidance on Grouping of Chemicals No. 80, ENV/JM/MONO, 28, 2007.
30. ECHA, Guidance on Information Requirements and Chemical Safety Assessment, Chapter R.6: QSARs and Grouping of Chemicals, 2008.
31. E.A. Thompson and P.K. Siiteri, Utilization of oxygen and reduced nicotinamide adenine dinucleotide phosphate by human placental microsomes during aromatization of androstenedione, J. Biol. Chem 249 (1974), pp. 5364-5372.
32. A.S. Bhatnagar, A. Hausler, and K. Schieweck, Inhibition of aromatase in vitro and in vivo by aromatase inhibitors, J. Enzyme Inhib. 4 (1990), pp. 179-186.
33. S. Dimitrov, G. Dimitrova, T. Pavlov, N. Dimitrova, G. Patlewicz, J. Niemela, and O. Mekenyan, A stepwise approach for defining applicability domain of SAR and QSAR models, J. Chem. Inf. Mod. 45 (2005), pp. 839-849.
34. A. de Groot and W. Koert, 14. The Working Mechanism of Aromatase, Het Anabolenboek, Wageningen, 2007. Available at:http://www.ergogenics.org/anabolenboek/index14en.html.
35. M. Numazawa, M. Ando, Y. Watari, T. Tominaga, Y. Hayata, and A. Yoshimura, Structure- activity relationships of 2-, 4-, or 6-substituted estrogens as aromatase inhibitors, J. Steroid Biochem. Mol. Biol. 96 (2005), pp. 51-58.
36. J. Steward, MOPAC: a semiempirical molecular orbital program, J. Comput.-Aided Mol. Des. 4 (1990), pp. 1-105.
37. J. Steward, MOPAC 93 Fujitsu Limited, 9-3, Nakase 1-Chome, Mihama-ku. Chiba-City, Chiba 261, Japan and Stewart Computational Chemistry, 15210 Paddington Circle, Colorado Springs, CO (1993).
38. F. Leonetti, A. Favia, A. Rao, R. Aliano, A. Paluszcak, R.W. Hartmann, and A. Carotti, Design, synthesis, and 3D QSAR of novel potent and selective aromatase inhibitors, J. Med. Chem. 47 (2004), pp. 6792-6803.
39. J.T. Sanderson, J. Hordijk, M.S. Denison, M.F. Springsteel, M.H. Nantz, and M. Berg, Induction and inhibition of aromatase (CYP19) activity by natural and synthetic flavonoid compounds in H295R human adrenocortical carcinoma cells, Toxicol. Sci. 82 (2004), pp. 70-79.
40. R.F. Canton, J.T. Sanderson, R.J. Letcher, A. Bergman, and M. Berg, Inhibition and induction of aromatase (CYP19) activity by brominated flame retardants in H295r human adrenocortical carcinoma cells, Toxicol. Sci. 88 (2005), pp. 447-455.
41. Laboratory of Mathematical Chemistry (LMC), Mechanism-based categorization of aromatase inhibitors. Available at: http://oasis-lmc.org/?section=software&swid=14#Aromatase.