Does electron-correlation has any role in the quantitative structure-activity relationships?

Journal of Molecular Graphics and Modelling

Volumn 42, Issue , 2013, Pages 7-16

  Vikas, ^a   Reenu, ^a   Chayawan, ^a  

^a PANJAB UNIVERSITY   (India)

Author keywords

Correlation energy; Density functional theory; Mutagenicity; QSAR; Quantum mechanical descriptors

Indexed keywords

CORRELATION ENERGY; DESCRIPTORS; LOWEST UNOCCUPIED MOLECULAR ORBITAL; MUTAGENICITY; NITRATED POLYCYCLIC AROMATIC HYDROCARBONS; QSAR; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIPS;

COMPUTATIONAL CHEMISTRY; DENSITY FUNCTIONAL THEORY; DYES; MOLECULAR GRAPHICS; POLYCYCLIC AROMATIC HYDROCARBONS; QUANTUM THEORY;

ELECTRONS;

POLYCYCLIC AROMATIC HYDROCARBON;

ARTICLE; CORRELATION COEFFICIENT; DENSITY FUNCTIONAL THEORY; ELECTRON; ELECTRON CORRELATION; ENERGY; HARTREE FOCK METHOD; MOLECULAR DYNAMICS; NITRATION; PREDICTIVE VALIDITY; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM MECHANICS; THEORETICAL MODEL;

ELECTRONS; MODELS, CHEMICAL; MUTAGENESIS; MUTAGENICITY TESTS; NITRO COMPOUNDS; POLYCYCLIC HYDROCARBONS, AROMATIC; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUANTUM THEORY;

EID: 84874933968     PISSN: 10933263     EISSN: 18734243     Source Type: Journal    
DOI: 10.1016/j.jmgm.2013.02.005     Document Type: Article

References (38)

1. S. Wilson Electron Correlation in Molecules 1984 Clarendon Press Oxford
2. P.-O. Löwdin The historical development of the electron correlation problem International Journal of Quantum Chemistry 55 1995 77 102
3. A. Szabo, and N.S. Ostlund Modern Quantum Chemistry: Introduction to Advanced Electronic Structure Theory 1982 MacMillan New York
4. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart AM1: a new general purpose quantum mechanical molecular model Journal of the American Chemical Society 107 1985 3902 3909
5. G.B. Rocha, R.O. Freire, A.M. Simas, and J.J.P. Stewart RM1: a reparameterization of AM1 for H, C, N, O, P, S, F, Cl, Br, and I Journal of Computational Chemistry 27 2006 1101 1111
6. J.J.P. Stewart Optimization of parameters for semiempirical methods V: modification of NDDO approximations and application to 70 elements Journal of Molecular Modeling 13 2007 1173 1213
7. T. Puzyn, N. Suzuki, M. Haranczyk, and J. Rak Calculation of quantum-mechanical descriptors for QSPR at the DFT level: is it necessary? J. Chem. Inf. Model. 48 2008 1174 1180
8. M.A.A. Ibrahim Performance assessment of semiempirical molecular orbital methods in describing halogen bonding: quantum mechanical and quantum mechanical/molecular mechanical-molecular dynamics study J. Chem. Inf. Model. 51 2011 2549 2559
9. R.G. Parr, and W. Yang Density Functional Theory of Atoms and Molecules 1989 Oxford University Press New York
10. W. Koch, and M.C. Holthausen A Chemist Guide to Density Functional Theory 2000 Wiley-VCH Weinheim
11. M. Karleson Molecular Descriptors in QSAR/QSPR 2002 Wiley New York
12. E. Eroglu, and H. Türkmen A DFT-based quantum theoretic QSAR study of aromatic and heterocyclic sulfonamides as carbonic anhydrase inhibitors against isozyme, CA-II Journal of Molecular Graphics and Modelling 26 2007 701 708
13. G.L. Borosky Carcinogenic carbocyclic and heterocyclic aromatic amines: a DFT study concerning their mutagenic potency Journal of Molecular Graphics and Modelling 27 2008 459 465
14. K. Nikolic, and D. Agababa Design and QSAR study of analogs of γ-tocotrienol with enhanced antiproliferative activity against human breast cancer cells Journal of Molecular Graphics and Modelling 27 2009 777 783
15. R. Vijayaraj, V. Subramanian, and P.K. Chattaraj Comparison of global reactivity descriptors calculated using various density functionals: a QSAR perspective J. Chem. Theory Comput. 5 2009 2744 2753
16. L.T.F.M. Camargo, M.M. Sena, and A.J. Camargo A quantum chemical and chemometrical study of indolo[2,1-B] quinazoline and their analogues with cytotoxic activity against breast cancer cells SAR and QSAR in Environmental Research 20 2009 537 549
17. C.D. Sherrill, and H.F. Schaefer III The configuration interaction method: advances in highly correlated approaches Advances in Quantum Chemistry 34 1999 143 269
18. A.K. Debnath, R.L.L. de Compadre, G. Debnath, A.J. Shusterman, and C. Hansch Structure-activity relationship of mutagenic aromatic and heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity Journal of Medicinal Chemistry 34 1991 786 797
19. A.D. Becke Density-functional thermochemistry, III. The role of exact exchange Journal of Chemical Physics 98 1993 5648
20. MOPAC2012, Version 12.239W, J.J.P. Stewart, Stewart Computational Chemistry, 2012. http://OpenMOPAC.net.
21. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision D.01, Gaussian, Inc., Wallingford, CT, 2004.
22. N. Chirico, E. Papa, S. Kovarich, S. Cassani, P. Gramatica, QSARINS, Software for QSAR MLR model development and validation, QSAR Res. Unit in Environ. Chem. and Ecotox., University of Insubria, Varese, Italy, 2012. http://www.qsar.it.
23. P. Gramatica, P. Pilutti, and E. Papa Approaches for externally validated QSAR modelling of nitrated polycyclic aromatic hydrocarbon mutagenicity SAR and QSAR in Environmental Research 18 2007 169 178
24. P. Gramatica, E. Giani, and E. Papa Statistical external validation and consensus modeling: a QSPR case study for Koc prediction Journal of Molecular Graphics and Modelling 25 2007 755 766
25. R. Todeschini, A. Maiocchi, and V. Consonni The K correlation index: theory development and its application in chemometrics Chemometrics and Intelligent Laboratory Systems 46 1999 13 29
26. R. Benigni, and C. Bossa Predictivity of QSAR J. Chem. Inf. Model. 48 2008 971 980
27. 2 parameter for QSAR validation J. Chem. Inf. Model. 49 2009 1669 1678
28. N. Chirico, and P. Gramatica Real external predictivity of QSAR models: how to evaluate it? Comparison of different validation criteria and proposal of using the concordance correlation coefficient J. Chem. Inf. Model. 51 2011 2320 2335
29. L.M. Shi, H. Fang, W. Tong, J. Wu, R. Perkins, R.M. Blair, W.S. Branham, S.L. Dial, C.L. Moland, and D.M. Sheehan QSAR models using a large diverse set of estrogens Journal of Chemical Information and Computer Science 41 2001 186 195
30. A. Tropsha, P. Gramatica, and V.K. Gombar The importance of being earnest: validation is the absolute essential for successful application and interpretation of QSPR models QSAR Comb. Sci. 22 2003 69 77
31. G. Schüürmann, R. Ebert, J. Chen, B. Wang, and R. Kühne External validation and prediction employing the predictive squared correlation coefficients test set activity mean vs training set activity mean J. Chem. Inf. Model. 48 2008 2140 2145
32. 2 for the training set or low root mean square error of prediction for the test set? QSAR Comb. Sci. 24 2005 385 396
33. L.I.A. Lin Concordance correlation coefficient to evaluate reproducibility Biometrics 45 1989 255 268
34. P.K. Ojha, I. Mitra, R.N. Das, and K. Roy Further exploring rm 2 metrics for validation of QSPR models dataset Chemometrics and Intelligent Laboratory Systems 107 2011 194 205
35. N. Chirico, and P. Gramatica Real external predictivity of QSAR models. Part 2. New intercomparable thresholds for different validation criteria and the need for scatter plot inspection J. Chem. Inf. Model. 52 2012 2044 2058
36. M. Dehmer, K. Varmuza, and D. Bonchev Statistical Modelling of Molecular Descriptors in QSAR/QSPR first ed. 2012 Wiley-VCH Weinheim
37. C. Lee, W. Yang, and R.G. Parr Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Physical Review B 37 1988 785 789
38. S. Hirata Electronic structure theory: present and future challenges Theoretical Chemistry Accounts 131 2012 1071