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Volumn 68, Issue 5, 2014, Pages 697-713

QSAR modeling of aromatase inhibition by flavonoids using machine learning approaches

Author keywords

Anti cancer; Aromatase; Breast cancer; Data mining; Flavonoids; Structure activity relationship

Indexed keywords


EID: 84896860327     PISSN: 03666352     EISSN: 13369075     Source Type: Journal    
DOI: 10.2478/s11696-013-0498-2     Document Type: Article
Times cited : (14)

References (55)
  • 1
    • 0035671735 scopus 로고    scopus 로고
    • Effects of phytoestrogens and synthetic combinatorial libraries on aromatase, estrogen biosynthesis, and metabolism
    • DOI: 10.1111/j.1749-6632.2001.tb03986.x
    • Brueggemeier, R. W., Gu, X. J., Mobley, J. A., Joomprabutra, S., Bhat, A. S., & Whetstone, J. L. (2001). Effects of phytoestrogens and synthetic combinatorial libraries on aromatase, estrogen biosynthesis, and metabolism. Annals of the New York Academy of Sciences, 948, 51-66. DOI: 10.1111/j.1749-6632.2001.tb03986.x.
    • (2001) Annals of the New York Academy of Sciences , vol.948 , pp. 51-66
    • Brueggemeier, R.W.1    Gu, X.J.2    Mobley, J.A.3    Joomprabutra, S.4    Bhat, A.S.5    Whetstone, J.L.6
  • 2
    • 18844443185 scopus 로고    scopus 로고
    • Aromatase inhibitors in the treatment of breast cancer
    • DOI: 10.1210/er.2004-0015
    • Brueggemeier, R. W., Hackett, J. C., & Diaz-Cruz, E. S. (2005). Aromatase inhibitors in the treatment of breast cancer. Endocrine Reviews, 26, 331-345. DOI: 10.1210/er.2004-0015.
    • (2005) Endocrine Reviews , vol.26 , pp. 331-345
    • Brueggemeier, R.W.1    Hackett, J.C.2    Diaz-Cruz, E.S.3
  • 3
    • 34249753618 scopus 로고
    • Support-vector network
    • DOI: 10.1007/bf00994018
    • Cortes, C., & Vapnik, V. (1995). Support-vector network. Machine Learning, 20, 273-297. DOI: 10.1007/bf00994018.
    • (1995) Machine Learning , vol.20 , pp. 273-297
    • Cortes, C.1    Vapnik, V.2
  • 4
    • 48049086830 scopus 로고    scopus 로고
    • Aromatase inhibitors: Past, present and future in breast cancer therapy
    • DOI: 10.1007/s12032-007-9019-x
    • Dutta, U., & Pant, K. (2008). Aromatase inhibitors: past, present and future in breast cancer therapy. Medical Oncology, 25, 113-124. DOI: 10.1007/s12032-007-9019-x.
    • (2008) Medical Oncology , vol.25 , pp. 113-124
    • Dutta, U.1    Pant, K.2
  • 5
    • 7244250182 scopus 로고    scopus 로고
    • Data mining in bioinformatics using Weka
    • DOI: 10.1093/bioinformatics/bth261
    • Frank, E., Hall, M., Trigg, L., Holmes, G., & Witten, I. H. (2004). Data mining in bioinformatics using Weka. Bioinformatics, 20, 2479-2481. DOI: 10.1093/bioinformatics/bth261.
    • (2004) Bioinformatics , vol.20 , pp. 2479-2481
    • Frank, E.1    Hall, M.2    Trigg, L.3    Holmes, G.4    Witten, I.H.5
  • 7
    • 33746712854 scopus 로고    scopus 로고
    • Lead optimization providing a series of flavone derivatives as potent nonsteroidal inhibitors of the cytochrome P450 aromatase enzyme
    • DOI: 10.1021/jm060186y
    • Gobbi, S., Cavalli, A., Rampa, A., Belluti, F., Piazzi, L., Paluszcak, A., Hartmann, R. W., Recanatini, M., & Bisi, A. (2006). Lead optimization providing a series of flavone derivatives as potent nonsteroidal inhibitors of the cytochrome P450 aromatase enzyme. Journal of Medicinal Chemistry, 49, 4777-4780. DOI: 10.1021/jm060186y.
    • (2006) Journal of Medicinal Chemistry , vol.49 , pp. 4777-4780
    • Gobbi, S.1    Cavalli, A.2    Rampa, A.3    Belluti, F.4    Piazzi, L.5    Paluszcak, A.6    Hartmann, R.W.7    Recanatini, M.8    Bisi, A.9
  • 9
    • 0033628605 scopus 로고    scopus 로고
    • Use of artificial neural networks in a QSAR study of anti-HIV activity for a large group of HEPT derivatives
    • DOI: 10.1021/ci990314+
    • Jalali-Heravi, M., & Parastar, F. (2000). Use of artificial neural networks in a QSAR study of anti-HIV activity for a large group of HEPT derivatives. Journal of Chemical Information and Computer Sciences, 40, 147-154. DOI: 10.1021/ci990314+.
    • (2000) Journal of Chemical Information and Computer Sciences , vol.40 , pp. 147-154
    • Jalali-Heravi, M.1    Parastar, F.2
  • 10
    • 0031915796 scopus 로고    scopus 로고
    • Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study
    • DOI: 10.1289/ehp.9810685
    • Kao, Y. C., Zhou, C. B., Sherman, M., Laughton, C. A., & Chen, S. (1998). Molecular basis of the inhibition of human aromatase (estrogen synthetase) by flavone and isoflavone phytoestrogens: A site-directed mutagenesis study. Environmental Health Perspectives, 106, 85-92. DOI: 10.1289/ehp.9810685.
    • (1998) Environmental Health Perspectives , vol.106 , pp. 85-92
    • Kao, Y.C.1    Zhou, C.B.2    Sherman, M.3    Laughton, C.A.4    Chen, S.5
  • 11
    • 0035808202 scopus 로고    scopus 로고
    • Chalcones are potent inhibitors of aromatase and 17β-hydroxysteroid dehydrogenase activities
    • DOI: 10.1016/s0024-3205(00)00974-7
    • Le Bail, J. C., Pouget, C., Fagnere, C., Basly, J. P., Chulia, A. J., & Habrioux, G. (2001). Chalcones are potent inhibitors of aromatase and 17β-hydroxysteroid dehydrogenase activities. Life Sciences, 68, 751-761. DOI: 10.1016/s0024-3205(00)00974-7.
    • (2001) Life Sciences , vol.68 , pp. 751-761
    • Le Bail, J.C.1    Pouget, C.2    Fagnere, C.3    Basly, J.P.4    Chulia, A.J.5    Habrioux, G.6
  • 12
    • 84870218113 scopus 로고    scopus 로고
    • Developing phytoestrogens for breast cancer prevention
    • DOI: 10.2174/187152012803833062
    • Liu, M. M., Huang, Y., & Wang, J. (2012). Developing phytoestrogens for breast cancer prevention. Anti-Cancer Agents in Medicinal Chemistry, 12, 1306-1313. DOI: 10.2174/187152012803833062.
    • (2012) Anti-Cancer Agents in Medicinal Chemistry , vol.12 , pp. 1306-1313
    • Liu, M.M.1    Huang, Y.2    Wang, J.3
  • 15
    • 33646531814 scopus 로고    scopus 로고
    • Effect of hop (Humulus lupulus L.) flavonoids on aromatase (estrogen synthase) activity
    • DOI: 10.1021/jf053162t
    • Monteiro, R., Becker, H., Azevedo, I., & Calhau, C. (2006). Effect of hop (Humulus lupulus L.) flavonoids on aromatase (estrogen synthase) activity. Journal of Agricultural and Food Chemistry, 54, 2938-2943. DOI: 10.1021/jf053162t.
    • (2006) Journal of Agricultural and Food Chemistry , vol.54 , pp. 2938-2943
    • Monteiro, R.1    Becker, H.2    Azevedo, I.3    Calhau, C.4
  • 16
    • 79959795631 scopus 로고    scopus 로고
    • QSAR treatment on a new class of triphenylmethylcontaining compounds as potent anticancer agents
    • DOI: 10.1016/j.chemolab.2011.04.011
    • Mullen, L. M. A., Duchowicz, P. R., & Castro, E. A. (2011). QSAR treatment on a new class of triphenylmethylcontaining compounds as potent anticancer agents. Chemometrics and Intelligent Laboratory Systems, 107, 269-275. DOI: 10.1016/j.chemolab.2011.04.011.
    • (2011) Chemometrics and Intelligent Laboratory Systems , vol.107 , pp. 269-275
    • Mullen, L.M.A.1    Duchowicz, P.R.2    Castro, E.A.3
  • 18
    • 46049095881 scopus 로고    scopus 로고
    • Pharmacophore mapping of flavone derivatives for aromatase inhibition
    • DOI: 10.1007/s11030-008-9077-9
    • Nagar, S., Islam, M. A., Das, S., Mukherjee, A., & Saha, A. (2008). Pharmacophore mapping of flavone derivatives for aromatase inhibition. Molecular Diversity, 12, 65-76. DOI: 10.1007/s11030-008-9077-9.
    • (2008) Molecular Diversity , vol.12 , pp. 65-76
    • Nagar, S.1    Islam, M.A.2    Das, S.3    Mukherjee, A.4    Saha, A.5
  • 19
    • 31444441573 scopus 로고    scopus 로고
    • Quantitative prediction of imprinting factor of molecularly imprinted polymers by artificial neural network
    • DOI 10.1007/s10822-005-9004-4
    • Nantasenamat, C., Naenna, T., Isarankura-Na-Ayudhya, C., & Prachayasittikul, V. (2005). Quantitative prediction of imprinting factor of molecularly imprinted polymers by artificial neural network. Journal of Computer-Aided Molecular Design, 19, 509-524. DOI 10.1007/s10822-005-9004-4.
    • (2005) Journal of Computer-Aided Molecular Design , vol.19 , pp. 509-524
    • Nantasenamat, C.1    Naenna, T.2    Isarankura-Na-Ayudhya, C.3    Prachayasittikul, V.4
  • 20
    • 34248574742 scopus 로고    scopus 로고
    • Quantitative structureimprinting factor relationship of molecularly imprinted polymers
    • DOI: 10.1016/j.bios.2007.01.017
    • Nantasenamat, C., Isarankura-Na-Ayudhya, C., Naenna, T., & Prachayasittikul, V. (2007a). Quantitative structureimprinting factor relationship of molecularly imprinted polymers. Biosensors and Bioelectronics, 22, 3309-3317. DOI: 10.1016/j.bios.2007.01.017.
    • (2007) Biosensors and Bioelectronics , vol.22 , pp. 3309-3317
    • Nantasenamat, C.1    Isarankura-Na-Ayudhya, C.2    Naenna, T.3    Prachayasittikul, V.4
  • 24
    • 77953707142 scopus 로고    scopus 로고
    • Advances in computational methods to predict the biological activity of compounds
    • DOI: 10.1517/17460441.2010.492827
    • Nantasenamat, C., Isarankura-Na-Ayudhya, C., & Prachayasittikul, V. (2010). Advances in computational methods to predict the biological activity of compounds. Expert Opinion on Drug Discovery, 5, 633-654. DOI: 10.1517/17460441.2010.492827.
    • (2010) Expert Opinion on Drug Discovery , vol.5 , pp. 633-654
    • Nantasenamat, C.1    Isarankura-Na-Ayudhya, C.2    Prachayasittikul, V.3
  • 25
    • 84861931691 scopus 로고    scopus 로고
    • Exploring the physicochemical properties of templates from molecular imprinting literature using interactive text mining approach
    • DOI: 10.1016/j.chemolab.2012.05.006
    • Nantasenamat, C., Li, H., Isarankura-Na-Ayudhya, C., & Prachayasittikul, V. (2012). Exploring the physicochemical properties of templates from molecular imprinting literature using interactive text mining approach. Chemometrics and Intelligent Laboratory Systems, 116, 128-136. DOI: 10.1016/j.chemolab.2012.05.006.
    • (2012) Chemometrics and Intelligent Laboratory Systems , vol.116 , pp. 128-136
    • Nantasenamat, C.1    Li, H.2    Isarankura-Na-Ayudhya, C.3    Prachayasittikul, V.4
  • 30
    • 84899455738 scopus 로고    scopus 로고
    • OpenEye Scientific Software. Santa Fe, NM, USA: OpenEye Scientific Software
    • OpenEye Scientific Software (2013). VIDA, Version 4.2.1 [computer software]. Santa Fe, NM, USA: OpenEye Scientific Software.
    • (2013) VIDA, Version 4.2.1 [Computer Software]
  • 36
    • 0037041192 scopus 로고    scopus 로고
    • New aromatase inhibitors. Synthesis and inhibitory activity of pyridinyl-substituted flavanone derivatives
    • DOI: 10.1016/s0960-894x(02)00072-0
    • Pouget, C., Fagnere, C., Basly, J. P., Habrioux, G., & Chulia, A. J. (2002b). New aromatase inhibitors. Synthesis and inhibitory activity of pyridinyl-substituted flavanone derivatives. Bioorganic & Medicinal Chemistry Letters, 12, 1059-1061. DOI: 10.1016/s0960-894x(02)00072-0.
    • (2002) Bioorganic & Medicinal Chemistry Letters , vol.12 , pp. 1059-1061
    • Pouget, C.1    Fagnere, C.2    Basly, J.P.3    Habrioux, G.4    Chulia, A.J.5
  • 38
    • 75749143457 scopus 로고    scopus 로고
    • Elucidating the structure-activity relationships of the vasorelaxation and antioxidation properties of thionicotinic acid derivatives
    • DOI: 10.3390/molecules15010198
    • Prachayasittikul, S., Wongsawatkul, O., Worachartcheewan, A., Nantasenamat, C., Ruchirawat, S., & Prachayasittikul, V. (2010). Elucidating the structure-activity relationships of the vasorelaxation and antioxidation properties of thionicotinic acid derivatives. Molecules, 15, 198-214. DOI: 10.3390/molecules15010198.
    • (2010) Molecules , vol.15 , pp. 198-214
    • Prachayasittikul, S.1    Wongsawatkul, O.2    Worachartcheewan, A.3    Nantasenamat, C.4    Ruchirawat, S.5    Prachayasittikul, V.6
  • 39
    • 84876968058 scopus 로고    scopus 로고
    • The development of endocrine therapy for women with breast cancer
    • DOI: 10.1016/j.ctrv.2012.07.006
    • Sainsbury, R. (2013). The development of endocrine therapy for women with breast cancer. Cancer Treatment Reviews, 39, 507-517. DOI: 10.1016/j.ctrv.2012. 07.006.
    • (2013) Cancer Treatment Reviews , vol.39 , pp. 507-517
    • Sainsbury, R.1
  • 47
    • 38049109784 scopus 로고    scopus 로고
    • The red clover (Trifolium pratense) isoflavone biochanin A inhibits aromatase activity and expression
    • DOI: 10.1017/s0007114507811974
    • Wang, Y., Gho, W. M., Chan, F. L., Chen, S., & Leung, L. K. (2008). The red clover (Trifolium pratense) isoflavone biochanin A inhibits aromatase activity and expression. British Journal of Nutrition, 99, 303-310. DOI: 10.1017/s0007114507811974.
    • (2008) British Journal of Nutrition , vol.99 , pp. 303-310
    • Wang, Y.1    Gho, W.M.2    Chan, F.L.3    Chen, S.4    Leung, L.K.5
  • 48
    • 0037342322 scopus 로고    scopus 로고
    • Phytoestrogens inhibit aromatase but not 17β-hydroxysteroid dehydrogenase (HSD) type 1 in human granulosa-luteal cells: Evidence for FSH induction of 17β-HSD
    • DOI: 10.1093/humrep/deg125
    • Whitehead, S. A., & Lacey, M. (2003). Phytoestrogens inhibit aromatase but not 17β-hydroxysteroid dehydrogenase (HSD) type 1 in human granulosa-luteal cells: evidence for FSH induction of 17β-HSD. Human Reproduction, 18, 487-494. DOI: 10.1093/humrep/deg125.
    • (2003) Human Reproduction , vol.18 , pp. 487-494
    • Whitehead, S.A.1    Lacey, M.2
  • 52
    • 84879603996 scopus 로고    scopus 로고
    • QSAR study of amidino bis-benzimidazole derivatives as potent antimalarial agents against Plasmodium falciparum
    • DOI: 10.2478/s11696-013-0398-5
    • Worachartcheewan, A., Nantasenamat, C., Isarankura-Na-Ayudhya, C., & Prachayasittikul, V. (2013). QSAR study of amidino bis-benzimidazole derivatives as potent antimalarial agents against Plasmodium falciparum. Chemical Papers, 67, 1462-1473. DOI: 10.2478/s11696-013-0398-5.
    • (2013) Chemical Papers , vol.67 , pp. 1462-1473
    • Worachartcheewan, A.1    Nantasenamat, C.2    Isarankura-Na-Ayudhya, C.3    Prachayasittikul, V.4
  • 54
    • 79955618401 scopus 로고    scopus 로고
    • Lead optimization of 4-imidazolylflavans: New promising aromatase inhibitors
    • DOI: 10.1016/j.ejmech.2011.03.043
    • Yahiaoui, S., Pouget, C., Buxeraud, J., Chulia, A. J., & Fagnère, C. (2011). Lead optimization of 4-imidazolylflavans: New promising aromatase inhibitors. European Journal of Medicinal Chemistry, 46, 2541-2545. DOI: 10.1016/j.ejmech.2011.03.043.
    • (2011) European Journal of Medicinal Chemistry , vol.46 , pp. 2541-2545
    • Yahiaoui, S.1    Pouget, C.2    Buxeraud, J.3    Chulia, A.J.4    Fagnère, C.5
  • 55
    • 34548139737 scopus 로고    scopus 로고
    • QSAR study of oxazolidinone antibacterial agents using artificial neural networks
    • DOI: 10.1080/08927020601188528
    • Zou, C., & Zhou, L. (2007). QSAR study of oxazolidinone antibacterial agents using artificial neural networks. Molecular Simulation, 33, 517-530. DOI: 10.1080/08927020601188528.
    • (2007) Molecular Simulation , vol.33 , pp. 517-530
    • Zou, C.1    Zhou, L.2


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