QSAR modeling of anxiolytic activity taking into account the presence of keto- and enol-tautomers by balance of correlations with ideal slopes

• Autorzy: Alla. Toropova , Andrey Toropov , Emilio Benfenati , Giuseppina Gini , Danuta Leszczynska , Jerzy Leszczynski
• Języki publikacji: EN

Abstrakty

EN

Optimal descriptors calculated with simplified molecular input line entry system (SMILES) have been examined as a tool for prediction of anxiolytic activity. Descriptors calculated with SMILES (a) of keto-isomers; (b) of enol-isomers; and (c) of both keto-isomers together with enol-isomers have been studied. Three approaches have been compared: 1. classic’ training-test’ system 2. balance of correlations and 3. balance of correlations with ideal slopes. The best statistical characteristics for the external validation set took place for optimal descriptors calculated with SMILES of both keto-form and enol-form (i.e., molecular structure was represented in the format: ’sMILES of keto-form. SMILES of enol-form’) by means of balance of correlations with ideal slopes. The predictive potential of this model was checked with three random splits. [...]

Słowa kluczowe

EN

QSAR; SMILES; Tautomerism; Anxiolytic activity; Balance of correlation

• Czasopismo: Open Chemistry
• Rocznik: 2011
• Tom: 9
• Numer: 5
• Strony: 846-854

Daty

wydano

2011-10-01

online

2011-07-24

Twórcy

autor

Alla. Toropova

• Institute of Pharmacological Researches “Mario Negri”, 20156, Milan, Italy

autor

Andrey Toropov

• Institute of Pharmacological Researches “Mario Negri”, 20156, Milan, Italy,

autor

Emilio Benfenati

• Institute of Pharmacological Researches “Mario Negri”, 20156, Milan, Italy

autor

Giuseppina Gini

• Department of Electronics and Information, Polytechnical Institute of Milan, 20133, Milan, Italy

autor

Danuta Leszczynska

• Interdisciplinary Nanotoxicity Center, Department of Civil and Environmental Engineering, Jackson State University, Jackson, MS, 39217-0510, USA

autor

Jerzy Leszczynski

• Interdisciplinary Nanotoxicity Center, Department of Chemistry and Biochemistry, Jackson State University, Jackson, MS, 39217, USA

Bibliografia

• [1] J. W. Zou, C.C. Luo, H-X. Zhang, J. Mol. Graph. Model. 26, 494 (2007) http://dx.doi.org/10.1016/j.jmgm.2007.03.002[Crossref]
• [2] P.P. Roy, K. Roy, QSAR Comb Sci. 27, 302 (2008) http://dx.doi.org/10.1002/qsar.200710043[Crossref]
• [3] A.A. Toropov, A.P. Toropova, E. Benfenati, Eur. J. Med. Chem. 45, 3581(2010) http://dx.doi.org/10.1016/j.ejmech.2010.05.002[Crossref]
• [4] P.R. Duchowicz, A. Talevi, L.E. Bruno-Blanch, E.A. Castro, Bioorg Med Chem. 16, 7944 (2008) http://dx.doi.org/10.1016/j.bmc.2008.07.067[Crossref]
• [5] A. Afantitis, G. Melagraki, H. Sarimveis, P.A. Koutentis, J. Markopoulos, O. Igglessi-Markopoulou, QSAR Comb Sci. 25, 928 (2006) http://dx.doi.org/10.1002/qsar.200530208[Crossref]
• [6] A. Afantitis, G. Melagraki, H. Sarimveis, P.A. Koutentis, J. Markopoulos, O. Igglessi-Markopoulou, Polymer 47, 3240 (2006) http://dx.doi.org/10.1016/j.polymer.2006.02.060[Crossref]
• [7] T. Puzyn, N. Suzuki, M. Haranczyk, J. Rak, J. Chem. Inform. Model. 48, 1174 (2008) http://dx.doi.org/10.1021/ci800021p[Crossref]
• [8] A.A. Toropov, B.F. Rasulev, D. Leszczynska, J. Leszczynski, Chem. Phys. Lett. 444, 209 (2007) http://dx.doi.org/10.1016/j.cplett.2007.07.024[Crossref]
• [9] A.A. Toropov, B.F. Rasulev, J. Leszczynski, Bioorg. Med. Chem. 16, 5999 (2008) http://dx.doi.org/10.1016/j.bmc.2008.04.055[Crossref]
• [10] C. Zhao, E. Boriani, A. Chana, A. Roncaglioni, E. Benfenati, Chemosphere 73, 1701 (2008) http://dx.doi.org/10.1016/j.chemosphere.2008.09.033[Crossref]
• [11] G. Gini, E. Benfenati, Int. J. Artif. Intell. T. 16, 243 (2007) http://dx.doi.org/10.1142/S0218213007003308[Crossref]
• [12] A.A. Toropov, A.P. Toropova, E. Benfenati, Eur. J. Med. Chem. 44, 2544 (2009) http://dx.doi.org/10.1016/j.ejmech.2009.01.023[Crossref]
• [13] A.A. Toropov, A.P. Toropova, E. Benfenati, Int. J. Mol. Sci. 10, 3106 (2009) http://dx.doi.org/10.3390/ijms10073106[Crossref]
• [14] A.A. Toropov, A.P. Toropova, J. Mol. Struct. (Theochem). 578, 129 (2002) http://dx.doi.org/10.1016/S0166-1280(01)00695-9[Crossref]
• [15] A.A. Toropov, E. Benfenati, Bioorg. Med. Chem. 14, 3923 (2006) http://dx.doi.org/10.1016/j.bmc.2006.01.038[Crossref]
• [16] A.A. Toropov, A.P. Toropova, E. Benfenati, Eur. J. Med. Chem. 45, 3581 (2010) http://dx.doi.org/10.1016/j.ejmech.2010.05.002[Crossref]
• [17] A.P. Toropova, A.A. Toropov, E. Benfenati, D. Leszczynska, J. Leszczynski, J. Math. Chem. 48, 959 (2010) http://dx.doi.org/10.1007/s10910-010-9719-x[Crossref]
• [18] D. Weininger, J. Chem. Inf. Comput. Sci. 28, 31 (1988) [Crossref]
• [19] D. Weininger, A. Weininger, J.L. Weininger, J. Chem. Inf. Comput. Sci. 29, 97 (1989) [Crossref]
• [20] D. Weininger, J. Chem. Inf. Comput. Sci. 30, 237 (1990) [Crossref]
• [21] A.A. Toropov, A.P. Toropova, E. Benfenati, Mol. Divers. 14, 183 (2010) http://dx.doi.org/10.1007/s11030-009-9156-6[Crossref]
• [22] B. Xia, W. Ma, B. Zheng, X. Zhang, B. Fan, Eur. J. Med. Chem. 43, 1489 (2008) http://dx.doi.org/10.1016/j.ejmech.2007.09.004[Crossref]
• [23] M.P. Freitas, Chemometr. Intell. Lab. 91, 173 (2008) [Crossref]
• [24] M.P. Freitasa, S.D. Brownb, J.A. Martinsa, J. Mol. Struct. 738, 149 (2005) http://dx.doi.org/10.1016/j.molstruc.2004.11.065[Crossref]
• [25] B. Costa, E. Da Pozzo, B. Chelli, N. Simola, M. Morelli, M. Luisi, M. Maccheroni, S. Taliani, F. Simorini, F. Da Settimo, C. Martini, Psychoneuroendocrino 36, 463 (2011) http://dx.doi.org/10.1016/j.psyneuen.2010.07.021[Crossref]
• [26] O. Grundmann, J-I. Nakajima, K. Kamata, S. Seo, V. Butterweck, Phytomedicine 16, 295 (2009) http://dx.doi.org/10.1016/j.phymed.2008.12.020[Crossref]
• [27] E. Ognibene, P. Bovicelli, W. Adriani, L. Saso, G. Laviola, Prog. Neuro-Psychoph. 32, 128 (2008) http://dx.doi.org/10.1016/j.pnpbp.2007.07.023[Crossref]
• [28] A. Zamilpa, M. Herrera-Ruiz, E. Del Olmo, J.L. Lopez-Pe’rez, J. Tortoriello, A. San Feliciano, Bioorg. Med. Chem. Lett. 17, 4016 (2007) http://dx.doi.org/10.1016/j.bmcl.2007.04.080[Crossref]

Identyfikatory

DOI

10.2478/s11532-011-0064-0