QSPR of antioxidant phenolic compounds using quantum chemical descriptors

References

• Koutsilieri , E. , Scheller , C. , Grünblatt , E. , Nara , K. , Li , J. and Riederer , P. 2002 . Free radicals in Parkinson's disease . J. Neurol. , 249 : II/1 – II/5 .
   Google Scholar
• Prasad , K.N. , Cole , W.C. and Kumar , B. 1999 . Multiple antioxidants in the prevention and treatment of Parkinson's disease . J. Am. Coll. Nutr. , 18 : 413 – 423 .
   PubMed Web of Science ®Google Scholar
• Nuttall , S.L. , Kendall , M.J. and Martin , U. 1999 . Antioxidant therapy for the prevention of cardiovascular disease . Q. J. Med. , 92 : 239 – 244 .
   Google Scholar
• Dizdaroglu , M. , Jaruga , P. , Birincioglu , M. and Rodriguez , H. 2002 . Free radical-induced damage to DNA: Mechanisms and measurement . Free Radic. Biol. Med. , 32 : 1102 – 1115 .
   PubMed Web of Science ®Google Scholar
• Ozawa , T. 1999 . Understanding the Process of Aging , Edited by: Cadenas , E. and Packer , L. 265 – 292 . New York : Marcel Dekker .
   Google Scholar
• Grishko , V. , Solomon , M. , Wilson , G.L. , LeDoux , S.P. and Gillespie , M.N. 2001 . Oxygen radical-induced mitochondrial DNA damage and repair in pulmonary vascular endothelial cell phenotypes . Am. J. Physiol. Lung Cell Mol. Physiol. , 280 : L1300 – L1308 .
   PubMed Web of Science ®Google Scholar
• Genestra , M. 2007 . Oxyl radicals, redox-sensitive signalling cascades and antioxidants . Cell Signal. , 19 : 1807 – 1809 .
   PubMed Web of Science ®Google Scholar
• Hubbard , R.C. , Ogushi , F. , Fells , G.A. , Cantin , A.M. , Jallat , S. , Courtney , M. and Crystal , R.G. 1987 . Oxidants spontaneously released by alveolar macrophages of cigarette smokers can inactivate the active site of alpha 1-antitrypsin, rendering it ineffective as an inhibitor of neutrophil elastase . J. Clin. Invest. , 80 : 1289 – 1295 .
   PubMed Web of Science ®Google Scholar
• Ames , B.N. , Shigenaga , M.K. and Hagen , T.M. 1993 . Oxidants, antioxidants, and the degenerative diseases of aging . Proc. Natl Acad. Sci. USA , 90 : 7915 – 7922 .
   PubMed Web of Science ®Google Scholar
• Gutteridge , J.M.C. and Halliwell , B. 1994 . Antioxidants in Nutrition, Health and Disease , Oxford : Oxford University Press .
   Google Scholar
• Halliwell , B. 1997 . Antioxidants and human disease: A general introduction . Nutr. Rev. , 55 : S44 – S49 .
   Web of Science ®Google Scholar
• Wright , J.S. , Johnson , E.R. and DiLabio , G.A. 2001 . Predicting the activity of phenolic antioxidants: Theoretical method, analysis of substituent effects, and application to major families of antioxidants . J. Am. Chem. Soc. , 123 : 1173 – 1183 .
   PubMed Web of Science ®Google Scholar
• Vafiadis , A.P. and Bakalbassis , E.G. 2005 . A DFT study on the deprotonation antioxidant…step of ortho-substituted phenolic cation radicals . Chem. Phys. , 316 : 195 – 204 .
   Web of Science ®Google Scholar
• Musialik , M. and Litwinienko , G. 2005 . Scavenging of DPPH.: Radicals by vitamin E is accelerated by its partial ionization: The role of sequential proton loss electron transfer . Org. Lett. , 7 : 4951 – 4954 .
   PubMed Web of Science ®Google Scholar
• Pokorny , J. 1991 . Natural antioxidants for food use: A re-view . Trends Food Sci. Technol. , 2 : 223 – 227 .
   Google Scholar
• Judith , Z. and John , C. 2002 . The Cardiovascular Cure: How to Strengthen your Self-defense Against Heart Attack and Stroke , New York : Broadway Books .
   Google Scholar
• Serafini , M. , Laranjinha , J.A. , Almeida , L.M. and Maiani , G. 2000 . Inhibition of human LDL lipid peroxidation by phenol-rich beverages and their impact on plasma total antioxidant capacity in humans . J. Nutr. Biochem. , 11 : 585 – 590 .
   PubMed Web of Science ®Google Scholar
• Jang , M. , Cai , L. , Udeani , G.O. , Slowing , K.V. , Thomas , C.F. , Beecher , C.W.W. , Fong , H.H.S. , Farnsworth , N.R. , Kinghorn , A.D. , Mehta , R.G. , Moon , R.C. and Pezzuto , J.M. 1997 . Cancer chemopreventive activity of resveratrol, a natural product derived from grapes . Science , 275 : 218 – 220 .
   PubMed Web of Science ®Google Scholar
• Vieira , O. , Escargueil-Blanc , I. , Meilhac , O. , Basile , J.P. , Laranjinha , J. , Almeida , L. , Salvayre , R. and Negre-Salvayre , A. 1998 . Effect of dietary phenolic compounds on apoptosis of human cultured endothelial cells induced by oxidized LDL . Br. J. Pharmacol. , 123 : 565 – 573 .
   PubMed Web of Science ®Google Scholar
• Magalhães , P.J. , Carvalho , D.O. , Cruz , J.M. , Guido , L.F. and Barros , A.A. 2009 . Fundamentals and health benefits of xanthohumol, a natural product derived from hops and beer . Nat. Prod. Commun. , 4 : 591 – 610 .
   PubMed Web of Science ®Google Scholar
• Frankel , E.N. 2005 . Lipid Oxidation , Bridgewater, UK : Oily Press .
   Google Scholar
• Frankel , E.N. 2007 . Antioxidants in Food and Biology , Bridgewater, UK : Oily Press .
   Google Scholar
• Nagamine , I. , Sakurai , H. , Nguyen , H.T.T. , Miyahara , M. , Parkányiová , J. , Réblová , Z. and Pokorný , J. 2004 . Vegetable oils and amino acids . Czech J. Food Sci. , 22 : 155S – 158S .
   Google Scholar
• Pokorný , J. 2006 . Natural Antioxidant Phenols , Edited by: Boskou , D. Trivandrum, India : Synpost .
   Google Scholar
• Kajiyama , T. and Ohkatsu , Y. 2002 . Effect of meta-substituents of phenolic antioxidants-proposal of secondary substituent effect . Polym. Degrad. Stab. , 75 : 535 – 542 .
   Google Scholar
• Vasileva , T. , Stanulov , K. and Nenkova , S. 2008 . Phenolic antioxidants for fuels . J. Univ. Chem. Technol. Metall. , 43 : 65 – 68 .
   Google Scholar
• Liu , P. and Long , W. 2009 . Current mathematical methods used in QSAR/QSPR studies . Int. J. Mol. Sci. , 10 : 1978 – 1998 .
   PubMed Web of Science ®Google Scholar
• Helguera , A.M. , Combes , R.D. , Gonzalez , M.P. and Cordeiro , M.N. 2008 . Applications of 2D descriptors in drug design: A DRAGON tale . Curr. Top. Med. Chem. , 8 : 1628 – 1655 .
   PubMed Web of Science ®Google Scholar
• Zhao , M. , Li , Z. , Wu , Y. , Tang , Y.R. , Wang , C. , Zhang , Z. and 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 .
   PubMed Web of Science ®Google Scholar
• Calgarotto , A.K. , Miotto , S. , Honorio , K.M. , Da Silva , A.B.F. , Marangoni , S. , Silva , J.L. , Comar , M. Jr. , Oliveirad , K.M.T. and Da Silva , S.L. 2007 . A multivariate study on flavonoid compounds scavenging the peroxynitrite free radical . J. Mol. Struct.: Theochem. , 808 : 25 – 33 .
   Web of Science ®Google Scholar
• Khlebnikov , A.I. , Schepetkin , I.A. , Domina , N.G. , Kirpotina , L.N. and 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 .
   PubMed Web of Science ®Google Scholar
• Ray , S. , Sengupta , C. and Roy , K. 2007 . QSAR modeling of antiradical and antioxidant activities of flavonoids using electrotopological state atom (E-state) parameters . Cent. Eur. J. Chem. , 5 : 1094 – 1113 .
   Web of Science ®Google Scholar
• Gupta , S. , Matthew , S. , Abreu , P.M. and Aires-de-Sousa , J. 2006 . QSAR analysis of phenolic antioxidants using MOLMAP descriptors of local properties . Bioorg. Med. Chem. , 14 : 1199 – 1206 .
   PubMed Web of Science ®Google Scholar
• Mitra , I. , Saha , A. and Roy , K. 2009 . QSAR modeling of antioxidant activities of hydroxybenzalacetones using quantum chemical, physicochemical and spatial descriptors . Chem. Biol. Drug Des. , 73 : 526 – 536 .
   PubMed Web of Science ®Google Scholar
• Mitra , I. , Roy , K. and Saha , A. 2009 . QSAR of anti-lipid peroxidative activity of substituted benzodioxoles using chemometric tools . J. Comput. Chem. , 30 : 2712 – 2722 .
   PubMed Web of Science ®Google Scholar
• Mitra , I. , Saha , A. and Roy , K. 2010 . Pharmacophore mapping of arylamino substituted benzo[b]thiophenes as free radical scavengers . J. Mol. Model. , 16 : 1585 – 1596 .
   Google Scholar
• Kajiyama , T. and Ohkatsu , Y. 2001 . Effect of para-substituents of phenolic antioxidants . Polym. Degrad. Stab. , 71 : 445 – 452 .
   Web of Science ®Google Scholar
• Matsuura , T. and Ohkatsu , Y. 2000 . Phenolic antioxidants: Effect of o-benzyl substituents . Polym. Degrad. Stab. , 70 : 59 – 63 .
   Google Scholar
• 2003 . GaussView3.0 , Pittsburgh, PA, USA : Semichem Inc., Gaussian Inc. .
   Google Scholar
• Frisch , M.J. , Trucks , G.W. , Schlegel , H.B. , Scuseria , G.E. , Robb , M.A. , Cheeseman , J.R. , Montgomery , J.A.J , Vreven , J.T , Kudin , K.N , Burant , J.C , Millam , J.M , Iyengar , S.S , Tomasi , J , Barone , V , Mennucci , B , Cossi , M , Scalmani , G , Rega , N , Petersson , G.A , Nakatsuji , H , Hada , M , Ehara , M , Toyota , K , Fukuda , R , Hasegawa , J , Ishida , M , Nakajima , T , Honda , Y , Kitao , O , Nakai , H , Klene , M , Li , X , Knox , J.E , Hratchian , H.P , Cross , J.B , Adamo , C , Jaramillo , J , Gomperts , R , Stratmann , R.E , Yazyev , O , Austin , A.J , Cammi , R , Pomelli , C , Ochterski , J.W , Ayala , P.Y , Morokuma , K , Voth , G.A , Salvador , P , Dannenberg , J.J , Zakrzewski , V.G , Dapprich , S , Daniels , A.D , Strain , M.C , Farkas , O , Malick , D.K , Rabuck , A.D , Raghavachari , K , Foresman , J.B , Ortiz , J.V , Cui , Q , Baboul , A.G , Clifford , S , Cioslowski , J , Stefanov , B.B , Liu , G , Liashenko , A , Piskorz , P , Komaromi , I , Martin , R.L , Fox , D.J , Keith , T , Al-Laham , M.A , Peng , C.Y , Nanayakkara , A , Challacombe , M , Gill , P.M.W , Johnson , B , Chen , W , Wong , M.W , Gonzalez , C and Pople , J.A . 2003 . GAUSSIAN 03, Revision B.05 , Pittsburgh, PA : Gaussian Inc. .
   Google Scholar
• Roy , K. and Popelier , P.L.A. 2009 . Predictive QSPR modeling of acidic dissociation constant (pKa) of phenols in different solvents . J. Phys. Org. Chem. , 22 : 186 – 196 .
   Web of Science ®Google Scholar
• Roy , K. and Popelier , P.L.A. 2008 . Exploring predictive QSAR models using quantum topological molecular similarity (QTMS) descriptors for toxicity of nitroaromatics to Saccharomyces cerevisiae . QSAR Comb. Sci. , 27 : 1006 – 1012 .
   Google Scholar
• Popelier , P.L.A. 1999 . Quantum molecular similarity. 1. BCP space . J. Phys. Chem. A , 103 : 2883 – 2890 .
   Web of Science ®Google Scholar
• Bader , R.F.W. and Preston , H.J.T. 1969 . The kinetic energy of molecular…molecular stability . Int. J. Quantum Chem. , 3 : 327 – 347 .
   Web of Science ®Google Scholar
• Howard , S.T. and Lamarche , O. 2003 . Description of covalent bond orders using the charge density topology . J. Phys. Org. Chem. , 16 : 133 – 141 .
   Google Scholar
• Bader , R.F.W. , Slee , T.S. , Cremer , D. and Kraka , E. 1983 . Description of conjugation and hyperconjugation in terms of electron distributions . J. Am. Chem. Soc. , 105 : 5061 – 5068 .
   Web of Science ®Google Scholar
• Leonard , J.T. and Roy , K. 2006 . On selection of training and test sets for the development of predictive QSAR models . QSAR Comb. Sci. , 25 : 235 – 251 .
   Google Scholar
• SPSS, standard version 1998, is statistical software of SPSS Inc., Chicago, IL; software available at http://www.spss.com.
   Google Scholar
• Rogers , D. and 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 .
   Google Scholar
• Fraser , A. 1957 . Simulation of genetic systems by automatic digital computers. I. Introduction . Aust. J. Biol. Sci. , 10 : 484 – 491 .
   Google Scholar
• Wold , S. , Sjostrom , M. and Eriksson , L. 2001 . PLS-regression: A basic tool of chemometrics . Chemom. Intell. Lab. Syst. , 58 : 109 – 130 .
   Web of Science ®Google Scholar
• Snedecor , G.W. and Cochran , W.G. 1967 . Statistical Methods , New Delhi : Oxford & IBH .
   Google Scholar
• Golbraikh , A. and Tropsha , A. 2002 . Beware of q2! . J. Mol. Graph. Model. , 20 : 269 – 276 .
   PubMed Web of Science ®Google Scholar
• Roy , P.P. and Roy , K. 2008 . On some aspects of variable selection for partial least squares regression models . QSAR Comb. Sci. , 27 : 302 – 313 .
   Google Scholar
• Wold , S. and Eriksson , L. 1995 . “ Validation tools ” . In Chemometric Methods in Molecular Design , Edited by: van de Waterbeemd , H. 312 – 317 . Weinheim : VCH .
   Google Scholar
• Debnath , A.K. 2001 . “ Quantitative structure–activity relationship (QSAR): A versatile tool in drug design ” . In Combinatorial Library Design and Evaluation , Edited by: Ghose , A.K. and Viswanadhan , V.N. 73 – 129 . New York : Marcel Dekker .
   Google Scholar
• Roy , K. 2007 . On some aspects of validation of predictive QSAR models . Expert Opin. Drug Discov. , 2 : 1567 – 1577 .
   PubMed Web of Science ®Google Scholar
• Roy , P.P. and Roy , K. 2008 . Comparative QSAR studies of CYP1A2 inhibitor flavonoids using 2D and 3D descriptors . Chem. Biol. Drug Des. , 72 : 370 – 382 .
   PubMed Web of Science ®Google Scholar
• Roy , P.P. , Paul , S. , Mitra , I. and Roy , K. 2009 . On two novel parameters for validation of predictive QSAR models . Molecules , 14 : 1660 – 1701 .
   PubMed Web of Science ®Google Scholar
• Toropov , A.A. , Toropova , A.P. and Benfenati , E. 2009 . QSPR modeling bioconcentration factor (BCF) by balance of correlations . Eur. J. Med. Chem. , 44 : 2544 – 2551 .
   PubMedGoogle Scholar
• Lu , P. , Wei , X. and Zhang , R. 2010 . CoMFA and CoMSIA 3D-QSAR studies on quionolone caroxylic acid derivatives inhibitors of HIV-1 integrase . Eur. J. Med. Chem. , 45 : 3413 – 3419 .
   PubMed Web of Science ®Google Scholar
• Mitra , I. , Saha , A. and Roy , K. 2010 . Exploring quantitative structure–activity relationship (QSAR) studies of antioxidant phenolic compounds obtained from traditional Chinese medicinal plants . Mol. Simul. , 36 : 1067 – 1079 .
   Web of Science ®Google Scholar
• Gramatica , P. 2007 . Principles of QSAR models validation: Internal and external . QSAR Comb. Sci. , 26 : 694 – 701 .
   Google Scholar
• Eriksson , L. , Jaworska , J. , Worth , A.P. , Cronin , M.T. , McDowell , R.M. and Gramatica , P. 2003 . Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs . Environ. Health Perspect , 111 : 1361 – 1375 .
   PubMed Web of Science ®Google Scholar
• Zhang , L. , Zhu , H. , Oprea , T. , Golbraikh , A. and Tropsha , A. 2008 . QSAR modeling of the blood–brain barrier permeability for diverse organic compounds . Pharm. Res. , 25 : 1902 – 1914 .
   PubMed Web of Science ®Google Scholar
• SIMCA-P version 10.0.2.0, 2002, is a product of UMETRICS, Umea, Sweden, [email protected], www.umetrics.com.
   Google Scholar
• ChemDraw Ultra version 5.0, 1999, is a product of Cambridge soft Corporation, Cambridge, MA 02140, USA; available at http://www.camsoft.com/support.html.
   Google Scholar