Pharmacophore mapping of flavone derivatives for aromatase inhibition

Molecular Diversity

Volumn 12, Issue 1, 2008, Pages 65-76

  Nagar, Shuchi ^a   Islam, Md Ataul ^a   Das, Suvadra ^a   Mukherjee, Arup ^a   Saha, Achintya ^a  

^a UNIVERSITY OF CALCUTTA   (India)

Author keywords

Aromatase inhibitor; CoMFA; CoMSIA; Flavonoids; QSAR; Space modeling

Indexed keywords

4 [4 METHYL 2 [4 [2 (1 PIPERIDINYL)ETHOXY]PHENYL] 7 PIVALOYLOXY 2H 1 BENZOPYRAN 3 YLPHENYL] PIVALATE; AROMATASE; BAZEDOXIFENE; CYCLOFENIL; EPHEDRINE; FLAVONE DERIVATIVE; GEFITINIB; GENISTEIN; HYDROXYFLAVONE; HYDROXYTAMOXIFENE; HYDROXYTOREMIFENE; HYDROXYTRIOXIFENE; IDOXIFENE; IMIDAZOLE; LASOFOXIFENE; LETROZOLE; NAFOXIDINE; NORGESTREL; QUERCETIN; SIMVASTATIN; STANOZOLOL; TAMOXIFEN DERIVATIVE; TANGERETIN; TESTOSTERONE; TETRAHYDROISOQUINOLINE; TOREMIFENE; TRIOXIFENE;

ARTICLE; COMPARATIVE MOLECULAR FIELD ANALYSIS; DRUG ACTIVITY; DRUG INHIBITION; ENZYME ACTIVITY; ENZYME INHIBITION; PHARMACOPHORE; PRIORITY JOURNAL; STEREOSPECIFICITY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

AROMATASE; AROMATASE INHIBITORS; DRUG DESIGN; FLAVONES; MODELS, MOLECULAR; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; SUBSTRATE SPECIFICITY;

EID: 46049095881     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-008-9077-9     Document Type: Article

References (50)

1. Hartmann RW, Ehmer PB, Haidar S et al (2002) Inhibition of CYP 17, a new strategy for the treatment of prostate cancer. Arch Pharm 335: 19-128
2. 119
3. Brueggemeier RW (2002) Aromatase inhibitors in breast cancer therapy. Anticancer Ther 2: 181-191
4. Brueggemeier RW, Richards JA, Joomprabutra S et al (2001) Molecular pharmacology of aromatase and its regulation by endogenous and exogenous agents. J Steroid Biochem Mol Biol 79: 75-84
5. Banting L, Nicholls PJ, Shaw MA, Smith HJ (1989) Recent developments in aromatase inhibition as a potential treatment for oestrogen-dependent breast cancer. Prog Med Chem 26: 253-298
6. Pasqualini JR (2004) The selective estrogen enzyme modulators in breast cancer: A review. Biochem Biophys Acta 21: 23-43
7. Miller WR (2003) Aromatase Inhibitor: mechanism of action and role in the treatment of breast cancer. Semin Oncol 30: 3-11
8. Howell A (2005) New developments in the treatment of postmenopausal breast cancer. Trends Endocrin Metab 9: 420-428
9. Carlo DG, Mascolo N, Izzo AA, Capasso F (1999) Flavonoids: old and new aspects of a class of natural therapeutic drugs. Life Sci 49: 337-353
10. Kao YC, Zhou C, Sherman M et al (1998) Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: a site-directed mutagenesis study. Environ Health Perspect 106: 85-92
11. Jeong HJ, Shin YG, Kim IH, Pezzuto JM (1999) Inhibition of aromatase activity by flavonoids. Arch Pharm Res 22: 309-312
12. Jordan VC, Mittal S, Gosden B et al (1985) Structure-activity relationships of estrogens. Environ Health Perspect 61: 97-110
13. Le Bail JC, Laroche T, Marre-Fournier F, Habrioux G (1998) Aromatase and 17β-hydroxysteroid dehydrogenase inhibition by flavonoids. Cancer Let 133: 101-106
14. Pouget C, Lauthier F, Alain Simon A et al (2001) Flavonoids: structural requirements for antiproliferative activity on breast cancer cells. Bioorg Med Chem Let 11: 3095-3097
15. Fallowfield L, Cella D, Cuzick J et al (2004) Quality of life of postmenopausal women in the arimidex, tamoxifen, alone or in combination (ATAC) adjuvant breast cancer trial. J Clin Oncol 21: 4261-4271
16. Montana JG, Dyke HJ (2002) Update on the therapeutic potential of PDE4 inhibitors. Expert Opin Invest Drugs 11: 1-13
17. Hertog MGL, Feskens EJM, Kromhout D et al (1993) Dietary antioxidant flavonoids and risk of coronary heart disease: the Zutphen Elderly Study. Lancet 342: 1007-1011
18. Kristam R, Gillet VJ, Lewis RA, Thorner D (2005) Comparison of conformational analysis techniques to generate pharmacophore hypotheses using catalyst. J Chem Inf Model 2: 461-476
19. Guner OF (2000) In pharmacophore perception, development, and use in drug design. International University Line, California
20. Gobbi S, Cavalli A, Rampa A et al (2006) Lead optimization providing a series of flavone derivatives as potent nonsteroidal inhibitors of the cytochrome P450 aromatase enzyme. J Med Chem 49: 4777-4780
21. Pouget C, Fagnere C, Basly JP et al (2002) Synthesis and aromatase inhibitory activity of flavanones. Pharma Res 19: 286-291
22. Snedecor GW, Cochran WG (1967) Statistical methods, 6th edn. Iowa State University Press, Iowa
23. Wold S, Albano C (1984) Multivariate data analysis in chemistry. In: Kowalski B (ed) CHEMOMETRICS: mathematics and statistics in chemistry, Reidel Dordrecht Netherlands
24. Hoskuldsson A (1987) PLS regression methods. J Chemometrics 2: 211-228
25. CS Chem3D Pro and CS MOPAC Pro 5.0, CambridgeSoft, Cambridge. www.camsoft.com
26. Kier LB, Hall LH (1990) An electrotopological-state index for atoms in molecules. Pharm Res 7: 801-807
27. ESI-MS (2007) Chemical Technology, Calcutta University, Kolkata. www.caluniv.ac.in
28. CAChe 6.1, Computer-aided chemistry for macintosh and windows, Fujitsu Systems Business of America Inc. Chiba, Japan. www.CACheSoftware.com
29. TSAR 3D 3.3, Oxford Molecular Limited, Accelrys, San Diego. www.accelrys.com
30. Statistica 5.0, StatSoft Inc, Tulsa. www.statsoft.com
31. Wold S, Eriksson L (1995) Chemometric methods in molecular design. In: de Waterbeemd HV (eds) Chemometric methods, vol 2. Weinheim, VCH Verlagsgesellschaft mbh, p 312
32. Cramer RD III, Patterson DE, Bunce JD (1989) Recent advances in comparative molecular field analysis (CoMFA). Prog Clin Biol Res 291: 161-165
33. Allen MS, Tan YC, Koehler KF et al (1990) Synthetic and computer-assisted analyses of the pharmacophore for the benzodiazepine receptor inverse agonist site. J Med Chem 33: 2343-2357
34. Klebe G, Abraham U, Mietzner T (1994) Molecular similarity indices in a comparative analysis (CoMSIA) of drug molecules to correlate and predict their biological activity. J Med Chem 37: 4130-4146
35. Cramer RD III, Patterson DE, Bunce JD (1988) Comparative molecular field analysis (CoMFA). Effect of shape on binding of steroids to carrier proteins. J Am Chem Soc 110: 5959-5967
36. Cramer RD III, Bunce JD, Patterson DE et al (1988) Cross-validation, bootstrapping, and partial least squares compared with multiple regression in conventional QSAR and QSPR studies. Quant Struct Act Relat 7: 18-25
37. Wehrens R, van der Linden WE (1997) Bootstrapping principal component regression models. J Chemom 11: 157-171
38. SYBYL 7.3, (2006) Tripos Inc, St. Louis. www.tripos.com
39. Kirkpatrick S, Gelatt CD, Vecchi MP Jr (1983) Optimization by simulated annealing. Science 220: 671-680
40. Streitwieser A (1961) Molecular orbital theory for organic chemists. Wiley, New York
41. Vinter JG, Davis A, Saunders MR (1987) Strategic approaches to drug design. I. An integrated software framework for molecular modeling. J Comp-Aided Mol Design 1: 31-51
42. White DNJ (1977) The principles and practice of molecular mechanics calculations. Comp Chem 1: 225-233
43. Catalyst 4.11 (2005) Accelrys Inc, San Diego, CA. www.accelrys.com
44. Schuster D, Laggner C, Steindl TM (2006) Pharmacophore modeling and in-silico screening for new P450 19 (aromatase) inhibitors. J Chem Inf Model 46: 1301-1311
45. Cavalli A, Bisi A, Bertucci C et al (2005) Enantioselective nonsteroidal aromatase inhibitors identified through a multidisciplinary medicinal chemistry approach. J Med Chem 48: 7282-7289
46. Recanatini M, Bisi A, Cavalli A et al (2001) 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: 672-680
47. Viswanadhan VN, Ghose AK, Revankar GR, Robins RK (1989) Atomic physicochemical parameters for three dimensional structure directed quantitative structure-activity relationships. 4. Additional parameters for hydrophobic and dispersive interactions and their application for an automated superposition of certain naturally occurring nucleoside antibiotics. J Chem Inf Comput Sci 29: 163-172
48. Favia AD, Cavalli A, Masetti M et al (2006) Three dimensional model of the human aromatase enzyme and density functional parameterization of the iron-containing protopophyrin IX for molecular dynamics study of heme-cysteinato cytochromes. Proteins 62: 1074-1087
49. Gauthier S, Caron B, Cloutier J et al (1997) (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: 2117-2122
50. Miller CP, Collini MD, Tran BD et al (2001) Design, synthesis, and preclinical characterization of novel, highly selective indole estrogens. J Med Chem 44: 1654-1657