Artículos de revistas
Chemometric And Molecular Modeling Study Of 1h-indole-3-acetic Acid Derivatives With Auxin Activity
Registration in:
Croatica Chemica Acta. , v. 78, n. 4, p. 541 - 549, 2005.
111643
2-s2.0-32244444604
Author
Kiralj R.
Ferreira M.M.C.
Institutions
Abstract
Quantitative Structure-Activity Relationship (QSAR) study on 22 1H-indole-3-acetic acid derivatives with auxin activity was performed by means of Principal Component Analysis (PCA), Hierarchical Cluster Analysis (HCA), Partial Least Squares Regression (PLS) and Multiple Linear Regression (MLR). Molecular geometry of the auxins was optimized at MMFF94 and ab initio B3LYP 6-31G** levels. Modeling of complexes of some auxin molecules with the auxin binding protein 1 (ABP1) was also carried out, Parsimonius PLS and MLR models for prediction of optimal and half-optimal auxin concentrations for Avena L. Sativa coleoptile elongation were obtained with 15 auxins in the training set. HCA and PCA on data for the half-optimal concentration exhibit auxin clustering with respect to substitutent type and position, biological activity, and the size of the active site pockets of ABP1. Molecular graphics of ABP1 - NAA derivative complexes and of the coordination spheres around NAA (1-naphthalenic acid) hydrogen atoms in the ABP1 - NAA complex agrees well with the chemometrics/QSAR results. 78 4 541 549 Arteca, R., (1996) Plant Growth Substances: Principles and Applications, , Chapman&Hall, New York Nigović, B., Antolić, S., Kojić-Prodić, B., Kiralj, R., Magnus, V., Salopek-Sondi, B., (2000) Acta Crystallogr., Sect. B, 56, pp. 94-111 Woo, E.J., Marshall, J., Bauly, J., Chen, J.G., Venis, M., Napier, R.M., Pickersgill, R.W., (2002) EMBO J., 21, pp. 2877-2885 Davies, D.T., (1995) Aromatic Heterocydic Chemistry, , Oxford University Press, Oxford, Chapter 7 Gilchrist, T.L., (1997) Heterocyclic Chemistry, 3rd Ed., , Addison-Wesley-Longman Publishing Co., Harlow, UK Antolić, S., Kojic-Prodić, B., Tomić, S., Nigović, B., Magnus, V., Cohen, J.D., (1996) Acta Crystallogr., Sect. B, 52, pp. 651-661 Beebe, K., Pell, R., Seasholtz, M.B., (1998) Chemometrics: A Practical Guide, , John Wiley & Sons, New York Ferreira, M.M.C., Kiralj, R., Métodos Quimiométricos em QSAR Proceedings of the First Brazilian Symposium on Medicinal Chemistry, , C. A. Montanari (Ed.), in press Ferreira, M.M.C., (2002) J. Braz. Chem. Soc., 13, pp. 742-753 Kiralj, R., Ferreira, M.M.C., (2003) J. Mol. Graphics Modell., 21, pp. 435-448 Allen, F.H., (2002) Acta Crystallogr., Sect. B, 58, pp. 380-388 Halgren, T.A., (1996) J. Comput. Chem., 17, pp. 490-519 (2000) Titan, Version 1, 13. , Wavefunction, Inc., Irvine, CA, USA Lobanov, V.S., (1996) MOPAC, Version 6.0 for Microsoft Windows, , University of Florida, USA (2000) WebLab ViewerPro, Version 4.0, , Accelrys, Inc., Burlington, MA, USA (2000) Chem3D Ultra, Version 6.0, , CambridgeSoft.Com, Cambridge, MA, USA Todeschini, R., Consonni, V., Mauri, A., Pavan, M., (2003) Dragon, Web Version 3.0, , Milano, Italy (2002) ALOGPS, Version 2.1., , http://146.107.217.178/lab/alogps/, Virtual Computational Chemistry Laboratory (2001) Matlab, Version 6.1.0.450 Release 12.1, , MathWorks, Inc., Natick, MA (2001) Pirouette, Version 3.01, , Infometrix, Inc., Woodinville, WA, USA Spek, A.L., (2000) PLATON - A Multipurpose Crystallographic Tool, Version 31000, , Utrecht University, Utrecht, The Netherlands Kiralj, R., Ferreira, M.M.C., (2003) J. Mol. Graphics Modell., 21, pp. 435-448 Randić, M., (1995) J. Chem. Inf. Comput. Sci., 35, pp. 372-382 Hemmer, M.C., Steinhauer, V., Gasteiger, J., (1999) Vib. Spectrosc., 19, pp. 151-164 Gramatica, P., Corradi, M., Consonni, V., (2000) Chemosphere, 41, pp. 763-777 Kiralj, R., Ferreira, M.M.C., Chemom. Intell. Lab. Syst., , submitted Antolić, S., Kojić-Prodić, B., Magnus, V., (2000) Acta Crystallogr., Sect. C, 56, pp. 1026-1027