Quantitative structure-activity relationship modeling of antioxidant activities of hydroxybenzalacetones using quantum chemical, physicochemical and spatial descriptors

Chemical Biology and Drug Design

Volumn 73, Issue 5, 2009, Pages 526-536

  Mitra, Indrani ^a   Saha, Achintya ^a   Roy, Kunal ^b  

^a UNIVERSITY OF CALCUTTA   (India)

^b JADAVPUR UNIVERSITY   (India)

Author keywords

Antioxidant; Physicochemical descriptors; QSAR; Quantum chemical parameters

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; ACETONE; ALKALOID; HYDROXYBENZALACETONE DERIVATIVE; OXYGEN; TERT BUTYL HYDROPEROXIDE; UNCLASSIFIED DRUG;

ANTIOXIDANT ACTIVITY; ARTICLE; GAMMA IRRADIATION; GENETIC ANALYSIS; GENETIC FUNCTION APPROXIMATION; LIPID PEROXIDATION; MATHEMATICAL ANALYSIS; NONHUMAN; PARTIAL LEAST SQUARES REGRESSION; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; QUANTUM CHEMISTRY; SURFACE CHARGE; VALIDATION PROCESS;

ALGORITHMS; ANTIOXIDANTS; BUTANONES; DRUG DESIGN; FREE RADICAL SCAVENGERS; GAMMA RAYS; LIPID PEROXIDATION; MODELS, CHEMICAL; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUANTUM THEORY; TERT-BUTYLHYDROPEROXIDE;

EID: 64249110197     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2009.00801.x     Document Type: Article

References (32)

1. Butler J. (1986) Free radicals molecular biology, aging and disease. Int J Radiat Biol 50 : 371 373.
2. Ozawa T. (1999) Oxidative damage and fragility of mitochondrial DNA. In : Cadenas E., Packer L., editors. Understanding the Process of Aging. New York : Marcel Dekker p. 265 292.
3. Bagchi K., Puri S. (1998) Free radicals and antioxidants in health and disease. East Mediterr Health J 4 : 350 360.
4. Gutteridge J.M.C., Halliwell B. (1994) Antioxidants in Nutrition, Health and Disease. Oxford : Oxford University Press.
5. Halliwell B. (1997) Antioxidants and human disease: a general introduction. Nutr Rev 55 : S44 S49.
6. Nuttall S.L., Kendall M.J., Martin U. (1999) Antioxidants therapy for prevention of cardiovascular disease. Q J Med 92 : 239 244.
7. Shahidi F., Wanasunadra P.K.J. (1992) Phenolic antioxidants. Crit Rev Food Sci Nutr 32 : 67 103.
8. Gao G., Sofic E., Prior R.L. (1997) Antioxidant and pro-oxidant behavior of flavonoids:structure-activity relationships. Free Rad Biol Med 22 : 749 760.
9. Chen Z.Y., Chan P.T., Ho K.Y., Fung K.P., Wang R. (1996) Antioxidant activity of natural flavonoids is governed by number and location of their aromatic hydroxyl groups. J Chem Phys Lipids 79 : 157 163.
10. Khlebnikov A.I., Schepetkin I.A., Domina N.G., Kirpotina L.N., Quinn M.T. (2007) Improved quantitative structure-activity relationship models to predict antioxidant activity of flavonoids in chemical, enzymatic, and cellular systems. Bioorg Med Chem 15 : 1749 1770.
11. Durand A.C., Farce A., Carato P., Dilly S., Yous S., Berthelot P., Chavatte P. (2007) Quantitative structure-activity relationships studies of antioxidant hexahydropyridoindoles and flavonoid derivatives. J Enzyme Inhib Med Chem 22 : 556 562.
12. Zhao M., Li Z., Wu Y., Tang Y.R., Wang C., Zhang Z., Peng S. (2007) Studies on log P, retention time and QSAR of 2-substituted phenylnitronyl nitroxides as free radical scavengers. Eur J Med Chem 42 : 955 965.
13. Ray S., Sengupta C., Roy K. (2007) QSAR modeling of antiradical and antioxidant activities of flavonoids using electrotopological state (E-State) atom parameters. Cent Eur J Chem 5 : 1094 1113.
14. Rastija V., Medic′-Šaric′ M. (2009) QSAR study of antioxidant activity of wine polyphenols. Eur J Med Chem 44 : 400 408.
15. Yamagami C., Motohashi N., Emoto T., Hamasaki A., Tanahashi T., Nagakuraa N., Takeuchib Y. (2004) Quantitative structure-activity analysis of antioxidant and free radical scavenging activities of hydroxybenzalacetones. Bioorg Med Chem Lett 14 : 5629 5633.
16. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Montgomery J.A. et al. (2003) gaussian 03, Revision B.05. Pittsburgh, PA : Gaussian Inc.
17. Hansch C., Leo A., Hoekman D. (1995) Exploring QSAR, Hydrophobic Electronic and Steric Constants. Washington, DC : American Chemical Society.
18. Kubiniyi H. (1995) Drug discovery technologies: the quantitative analysis of structure-activity relationships. In : Wolff M.E., editor. Burger's Medicinal Chemistry and Drug Discovery. New York : John Wiley & Sons p. 497 571.
19. Darlington R.B. (1990) Regression and Linear Models. New York : McGraw-Hill.
20. Snedecor G.W., Cochran W.G. (1967) Statistical Methods. New Delhi : Oxford & IBH.
21. Rogers D., Hopfinger A.J. (1994) Application of genetic function approximation to quantitative structure-activity relationship and quantitative structure-property relationship. J Chem Inf Comput Sci 34 : 854 866.
22. Fraser A., Burnell D. (1970) Computer Models in Genetics. New York : McGraw-Hill.
23. Fraser A. (1957) Simulation of genetic systems by automatic digital computers. I. Introduction. Aust J Biol Sci 10 : 484 491.
24. Wold S., Sjostrom M., Eriksson L. (2001) PLS-regression: a basic tool of chemometrics. Chemometrics Intell Lab Syst 58 : 109 130.
25. Dunn W.J., III., Rogers D. (1996) Genetic partial least squares in QSAR. In : Devillers J., editor. Genetic Algorithms in Molecular Modeling. London : Academic Press p. 109 130.
26. Wold S., Eriksson L. (1995) Validation tools. In : van de Waterbeemd H., editor. Chemometric Methods in Molecular Design. Weinheim : VCH p. 312 317.
27. Debnath A.K. (2001) Quantitative structure-activity relationships: a versatile toll in drug design. In : Ghose A.K., Viswanadhan V.N., editors. Combinatorial Library Design and Evaluation. New York : Marcel Dekker p. 73 129.
28. Roy K. (2007) On some aspects of validation of predictive quantitative structure-activity relationship models. Expert Opin Drug Discov 2 : 1567 1577.
29. Roy P.P., Roy K. (2008) On some aspects of variable selection for partial least squares regression models. QSAR Comb Sci 27 : 302 313.
30. Roy P.P., Roy K. (2008) Comparative QSAR studies of CYP1A2 inhibitor flavonoids using 2D and 3D descriptors. Chem Biol Drug Des 72 : 370 382.
31. Roy P.P., Leonard J.T., Roy K. (2008) Exploring the impact of the size of training sets for the development of predictive QSAR models. Chemometrics Intell Lab Syst 90 : 31 42.
32. Hawkins D.M., Basak S.C., Mills D. (2003) Assessing model fit by cross-validation. J Chem Inf Comput Sci 43 : 579 586.