Abstract:
Inhibition of HER2 (human epidermal growth factor receptor 2) expression and function is required in several cancer treatments. Numerous compounds with very different molecular structures have been suggested as HER2 inhibitors. Here we perform quantitative structure-activity relationship (QSAR) analysis on 444 of such compounds to investigate the molecular properties that may influence its efficiency. Models based on 1D and 2D flexible molecular descriptors are proposed to develop simple models based solely on constitutional and topological molecular features. A large number of non-conformational descriptors (17974) was used to thoroughly explore the structural characteristics that influence the HER2 inhibitory activity. Three different approaches were explored using: 1) Molecular Descriptors, 2) Flexible Molecular Descriptors, and 3) Hybrid Descriptors. A QSAR model for HER2 inhibitors was successfully developed. Some properties such as electronegativity, aromatic character, and the presence of amino groups appear as molecular characteristics that may have influence in the HER2 inhibitory activity. © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Registro:
Documento: |
Artículo
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Título: | Conformation-Independent QSAR Study on Human Epidermal Growth Factor Receptor-2 (HER2) Inhibitors |
Autor: | Duchowicz, P.R.; Fioressi, S.E.; Castro, E.; Wróbel, K.; Ibezim, N.E.; Bacelo, D.E. |
Filiación: | Instituto de Investigaciones Fisicoquímicas Teóricas y Aplicadas INIFTA (CCT La Plata-CONICET, UNLP), Diag. 113 y 64, Sucursal 4, C.C. 16, La Plata, 1900, Argentina Departamento de Química, Facultad de Ciencias Exactas y Naturales, Universidad de Belgrano, Villanueva 1324, Buenos Aires, CP 1426, Argentina Medical University of Lodz, Kosciuszki 4, Lodz, 90-419, Poland Department of Computer Education, University of Nigeria, Nsukka, Nigeria
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Palabras clave: | Cancer; HER2; QSAR; Tyrosine kinase protein |
Año: | 2017
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Volumen: | 2
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Número: | 13
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Página de inicio: | 3725
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Página de fin: | 3731
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DOI: |
http://dx.doi.org/10.1002/slct.201700436 |
Título revista: | ChemistrySelect
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Título revista abreviado: | ChemistrySelect
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ISSN: | 23656549
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Registro: | https://bibliotecadigital.exactas.uba.ar/collection/paper/document/paper_23656549_v2_n13_p3725_Duchowicz |
Referencias:
- Arteaga, C.L., Engelman, J.A., (2014) Cancer Cell, 25, pp. 282-303
- Schlessinger, J., (2000) Cell, 103, pp. 211-225
- Engel, R.H., Kaklamani, V.G., (2007) Drugs, 67, pp. 1329-1341
- Signoretti, S., Montironi, R., Manola, J., Altimari, A., Tam, C., Bubley, G., Balk, S., Hahnfeldt, P., (2000) J. Natl. Cancer Inst., 92, pp. 1918-1925
- Steffensen, K.D., Waldstrom, M., Jeppesen, U., Jakobsen, E., Brandslund, I., Jakobsen, A., (2007) Int. J. Gynecol. Cancer, 17, pp. 798-807
- Sakai, K., Mori, S., Kawamoto, T., Taniguchi, S., Kobori, O., Morioka, Y., Kuroki, T., Kano, K., (1986) J. Natl. Cancer Inst., 77, pp. 1047-1052
- Orman, J.S., Perry, C.M., (2007) Drugs, 67, pp. 2781-2789
- Liang, K., Esteva, F.J., Albarracin, C., Stemke-Hale, K., Lu, Y., Bianchini, G., Yang, C.Y., Mills, G.B., (2010) Cancer Cell, 18, pp. 423-435
- Curran, M.P., (2010) Drugs, 70, pp. 1411-1422
- Kroep, J.R., Linn, S.C., Boven, E., Bloemendal, H.J., Baas, J., Mandjes, I.A., van den Bosch, J., Vermeulen, G.J., (2010) Neth. J. Med., 68, pp. 371-376
- Gazit, A., Osherov, N., Posner, I., Yaish, P., Poradosu, E., Gilon, C., Levitzki, A., (1991) J. Med. Chem., 34, pp. 1896-1907
- Gazit, A., Osherov, N., Posner, I., Bar-Sinai, A., Gilon, C., Levitzki, A., (1993) J. Med. Chem., 36, pp. 3556-3564
- Levitzki, A., Gazit, A., (1995) Science, 267, pp. 1782-1788
- Yarden, Y., (2001) Eur. J. Cancer, 37, pp. 3-8
- Ferguson, K.M., Berger, M.B., Mendrola, J.M., Cho, H.S., Leahy, D.J., Lemmon, M.A., (2003) Molecular Cell, 11, pp. 507-517
- Fink, B.E., Vite, G.D., Mastalerz, H., Kado, J.F., Kim, S.H., Leavitt, K.J., Du, K., Tokarski, J., (2005) Bioorg. Med. Chem. Lett., 15, pp. 4774-4779
- Llauger, L., He, H., Kim, J., Aguirre, J., Rosen, N., Peters, U., Davies, P., Chiosis, G., (2005) J. Med. Chem., 48, pp. 2892-2905
- He, H., Zatorska, D., Kim, J., Aguirre, J., Llauger, L., She, Y., Wu, N., Chiosis, G., (2006) J. Med. Chem., 49, pp. 381-390
- Mastalerz, H., Chang, M., Chen, P., Dextraze, P., Fink, B.E., Gavai, A., Goyal, B., Zhang, G., (2007) Bioorg. Med. Chem. Lett., 17, pp. 2036-2042
- Mastalerz, H., Chang, M., Gavai, A., Johnson, W., Langley, D., Lee, F.Y., Marathe, P., Zhang, G., (2007) Bioorg. Med. Chem. Lett., 17, pp. 2828-2833
- Mastalerz, H., Chang, M., Chen, P., Fink, B.E., Gavai, A., Han, W.C., Johnson, W., Zhang, G., (2007) Bioorg. Med. Chem. Lett., 17, pp. 4947-4954
- Cheng, Z.Y., Li, W.J., He, F., Zhou, J.M., Zhu, X.F., (2007) Bioorg. Med. Chem., 15, pp. 1533-1538
- Lippa, B., Kauffman, G.S., Arcari, J., Kwan, T., Chen, J., Hungerford, W., Bhattacharya, S., Pustilnik, L., (2007) Bioorg. Med. Chem. Lett., 7, pp. 3081-3086
- Hughes, T.V., Xu, G., Wetter, S.K., Connolly, P.J., Emanuel, S.L., Karnachi, P., Pollack, S.R., Greenberger, L.M., (2008) Bioorg. Med. Chem. Lett., 18, pp. 4896-4899
- Xu, G., Abad, M.C., Connoll, P.J., Neeper, M.P., Struble, G.T., Springer, B.A., Emanuel, S.L., Moreno-Mazza, S., (2008) Bioorg. Med. Chem. Lett., 18, pp. 4615-4619
- Xu, G., Searle, L.L., Hughes, T.V., Beck, A.K., Connolly, P.J., Abad, M.C., Neeper, M.P., Gruninger, R.H., (2008) Bioorg. Med. Chem. Lett., 18, pp. 3495-3499
- Cai, X., Zhai, H.X., Wang, J., Forrester, J., Qu, H., Yin, L., Lai, C.J., Qian, C., (2010) J. Med. Chem., 53, pp. 2000-2009
- Li, H.Q., Yan, T., Yang, Y., Shi, L., Zhou, C.F., Zhu, H.L., (2010) Bioorg. Med. Chem., 18, pp. 305-313
- Fidanze, S.D., Erickson, S.A., Wang, G.T., Mantei, R., Clark, R.F., Sorensen, B.K., Bamaung, N.Y., Hubbard, R.D., (2010) Bioorg. Med. Chem. Lett., 20, pp. 2452-2455
- Lv, P.C., Zhou, C.F., Chen, J., Liu, P.G., Wang, K.R., Mao, W.J., Li, H.Q., Zhu, H.L., (2010) Bioorg. Med. Chem., 18, pp. 314-319
- Fink, B.E., Norris, D., Mastalerz, H., Chen, P., Goyal, B., Zhao, Y., Kim, S., Gavai, A., (2011) Bioorg. Med. Chem. Lett., 21, pp. 781-785
- Dearden, J.C., (2016) Inter. J. Quantitative Structure-Property Relationships, 1, pp. 1-44
- Roy, K., Kar, S., Das, R.N., (2015) A Primer on QSAR/QSPR Modeling: Fundamental Concepts, , Springer, New York
- Roy, K., Kar, S., Das, R.N., (2015) Understanding the basics of QSAR for applications in pharmaceutical sciences and risk assessment, , Academic Press, USA
- Zhu, L.L., Hou, T.J., Chen, L.R., Xu, X.J., (2001) J. Chem. Inf. Comp. Sci., 41, pp. 1032-1040
- Kamath, S., Buolamwini, J.K., (2003) J. Med. Chem., 46, pp. 4657-4668
- Awale, M., Mohan, C.G., (2008) J. Mol. Graph. Model., 267, pp. 1169-1178
- Chen, C.Y., Chen, C.Y., (2010) J. Mol. Graph. Model., 291, pp. 21-31
- Sun, M.F., Yang, S.C., Chang, K.W., Tsai, T.Y., Chen, H.Y., Tsai, F.J., Lin, J.G., Chen, C.Y., (2011) Molecular Simulation, 37, pp. 884-892
- Yang, S.C., Chang, S.S., Chen, C.Y., (2011) , PLoS One, 6, p. 28793. , pe
- Mirzaie, S., Monajjemi, M., Hakhamaneshi, M.S., Fathi, F., Jamalan, M., (2013) EXCLI J., 12, p. 130
- Zalloum, H., Tayyem, R., Bustanji, Y., Zihlif, M., Mohammad, M., Rjai, T.A., Mubarak, M.S., (2015) J. Mol. Graph. Model., 61, pp. 61-84
- Duchowicz, P.R., Comelli, N.C., Ortiz, E.V., Castro, E.A., (2012) Curr. Drug. Saf., 7, pp. 282-288
- Talevi, A., Bellera, C.L., Ianni, M.D., Duchowicz, P.R., Bruno-Blanch, L.E., Castro, E.A., (2012) Curr. Comput. Aided Drug. Des., 8, pp. 172-181
- Yap, C.W., (2011) J. Comput. Chem., 32, pp. 1466-1474
- (2016) PaDEL, , Accessed 2 May
- US EPA 2016 Estimation Programs Interface Suite™ for Microsoft® Windows, v 411 United States Environmental Protection Agency, , Washington, DC, USA
- Hong, H., Xie, Q., Ge, W., Qian, F., Fang, F., Shi, L., Su, Z., Tong, W., (2008) J. Chem. Info. Mod., 48, pp. 1337-1344
- (2016) Coral, , http//wwwinsilicoeu/coral, Accessed 2 May
- Toropov, A.A., Toropova, A.P., Benfenati, E., Gini, G., (2013) Curr Comput Aided Drug Des., 9, pp. 226-232
- (2017) Dassault Systèmes BIOVIA, Discovery Studio Modeling Environment, , Release, San Diego, Dassault Systèmes, 2016
- Toropova, A.P., Toropov, A.A., Martyanov, S.E., Benfenati, E., Gini, G., Leszczynska, D., Leszczynski, J., (2012) Chemometr. Intell. Lab. Syst., 110, pp. 177-181
- Rojas, C., Duchowicz, P.R., Tripaldi, P., Diez, R.P., (2015) Chemometr. Intell. Lab. Syst., 140, pp. 126-132
- Rojas, C., Duchowicz, P.R., Tripaldi, P., Diez, R.P., (2015) J. Chromatography A, 1422, pp. 277-288
- Rojas, C., Tripaldi, P., Duchowicz, P.R., (2016) Int. J. Quant. Struct. Prop. Relationsh., 1, pp. 76-90
- Duchowicz, P.R., Castro, E.A., Fernández, F.M., (2006) MATCH Commun. Math. Comput. Chem., 55, pp. 179-719
- Duchowicz, P.R., Castro, E.A., Fernández, F.M., González, M., (2005) Chem. Phys. Lett., 412, pp. 376-380
- Duchowicz, P.R., Talevi, A., Bruno-Blanch, L.E., Castro, E.A., (2008) Bioorg. Med. Chem. Lett., 16, pp. 7944-7955
- Goodarzi, M., Duchowicz, P.R., Wu, C.H., Fernández, F.M., Castro, E.A., (2009) J. Chem. Inf. Model., 49, pp. 1475-1485
- Pomilio, A.B., Giraudo, M.A., Duchowicz, P.R., Castro, E.A., (2010) Food Chem., 123, pp. 917-927
- Talevi, A., Goodarzi, M., Ortiz, E.V., Duchowicz, P.R., Bellera, C.L., Pesce, G., Castro, E.A., Bruno-Blanch, L.E., (2011) Eur. J. Med. Chem., 46, pp. 218-228
- Pasquale, G., Romanelli, G.P., Autino, J.C., García, J., Ortiz, E.V., Duchowicz, P.R., (2012) J. Agric. Food Chem., 60, pp. 692-697
- (2016) Matlab 70, , http://wwwmathworkscom, 29 July, Available online (accessed on 29 July)
- Golbraikh, A., Tropsha, A., (2002) J. Mol. Graphics Model., 20, pp. 269-276
- Wold, S., Eriksson, L., (1995) Statistical validation of QSAR results, Chemometrics Methods in Molecular Design, pp. 309-318. , (Eds., vdW H, VCH, Weinheim, p
- Roy, K., Das, R.N., Ambure, P., Aher, R.B., (2016) Chemometr. Intell. Lab. Syst., 152, pp. 18-33
- Roy, K., Ambure, P., Aher, R.B., (2017) Chemometr. Intell. Lab. Syst., 162, pp. 44-54
- XternalValidationPlus v.1.2, , http://dtclab.webs.com/software-tools, accessed on 15 February 2017)
- http://dtclab.webs.com/software-tools, Bias-Variance Estimator. Available online,, accessed on 15 February 2017); Gramatica, P., (2007) QSAR Comb. Sci., 26, pp. 694-701
- Gadaleta, D., Mangiatordi, G.F., Catto, M., Carotti, A., Nicolotti, O., (2016) Inter. J. Quantitative Structure-Property Relationships, 1, pp. 45-63
- Eriksson, L., Jaworska, J., Worth, A.P., Cronin, M.T., McDowell, R.M., Gramatica, P., (2003) Environ. Health Perspect., 111, pp. 1361-1375
- Roy, K., Kar, S., Ambure, P., (2015) Chemometr. Intell. Lab. Syst., 145, pp. 22-29
- http://dtclab.webs.com/software-tools, Applicability domain 1.0. Available online,, accessed on 15 February 2017); Verma, R.P., Hansch, C., (2005) Bioorg. Med. Chem., 13, pp. 4597-4621
- Roy, K., (2007) Expert Opinion on Drug Discovery, 2, pp. 1567-1577
- Singh, H., Kumar, R., Singh, S., Chaudhary, K., Gautam, A., Raghava, G.P., (2016) BMC Cancer, 16, p. 1
- Mercader, A.G., Duchowicz, P.R., Fernández, F.M., Castro, E.A., (2011) J. Chem. Inf. Model., 51, pp. 1575-1581
Citas:
---------- APA ----------
Duchowicz, P.R., Fioressi, S.E., Castro, E., Wróbel, K., Ibezim, N.E. & Bacelo, D.E.
(2017)
. Conformation-Independent QSAR Study on Human Epidermal Growth Factor Receptor-2 (HER2) Inhibitors. ChemistrySelect, 2(13), 3725-3731.
http://dx.doi.org/10.1002/slct.201700436---------- CHICAGO ----------
Duchowicz, P.R., Fioressi, S.E., Castro, E., Wróbel, K., Ibezim, N.E., Bacelo, D.E.
"Conformation-Independent QSAR Study on Human Epidermal Growth Factor Receptor-2 (HER2) Inhibitors"
. ChemistrySelect 2, no. 13
(2017) : 3725-3731.
http://dx.doi.org/10.1002/slct.201700436---------- MLA ----------
Duchowicz, P.R., Fioressi, S.E., Castro, E., Wróbel, K., Ibezim, N.E., Bacelo, D.E.
"Conformation-Independent QSAR Study on Human Epidermal Growth Factor Receptor-2 (HER2) Inhibitors"
. ChemistrySelect, vol. 2, no. 13, 2017, pp. 3725-3731.
http://dx.doi.org/10.1002/slct.201700436---------- VANCOUVER ----------
Duchowicz, P.R., Fioressi, S.E., Castro, E., Wróbel, K., Ibezim, N.E., Bacelo, D.E. Conformation-Independent QSAR Study on Human Epidermal Growth Factor Receptor-2 (HER2) Inhibitors. ChemistrySelect. 2017;2(13):3725-3731.
http://dx.doi.org/10.1002/slct.201700436