2D autocorrelation modelling of the anti-HIV HEPT analogues using multiple linear regression approaches

References

• Gabuzda , D.H. and Hirsch , M.S. 1987 . Neurologic manifestations of infection with human immunodeficiency virus clinical features and pathogenesis . Ann. Intern. Med. , 107 : 383 – 391 .
   PubMed Web of Science ®Google Scholar
• Barton , L.L. and Friedman , N.R. 2008 . The Neurological Manifestations of Pediatric Infectious Diseases and Immunodeficiency Syndromes , Totowa, NJ : Humana Press .
   Google Scholar
• UNAIDS, Report on the global AIDS epidemic, XV International AIDS Conference, Bangkok, 2004.
   Google Scholar
• Schinazi , R.F. 1993 . Competitive inhibitors of human immunodeficiency virus reverse transcriptase . Perspect. Drug Discov. Des. , 1 : 151 – 180 .
   Google Scholar
• Garg , R.K. 1999 . HIV infection and seizures . Post. Grad. Med. J. , 75 : 387 – 390 .
   PubMed Web of Science ®Google Scholar
• Fernandez , M. and Caballero , J. 2006 . Modeling of activity of cyclic urea HIV-1 protease inhibitors using regularized-artificial neural networks . Bioorg. Med. Chem. , 14 : 280 – 294 .
   PubMed Web of Science ®Google Scholar
• Baba , M. , Debyser , Z. , Shigeta , S. and DeClercq , E. 1992 . Highly potent and selective inhibition of human immunodeficiency virus type I (HIV-I) by the HIV-I-specific reverse transcriptase inhibitors . Drugs Fut. , 17 : 891 – 897 .
   Google Scholar
• DeClercq , E. 1994 . Trends in drug development for the treatment of AIDS compounds interfering with the initial stages of the HIV replicative cycle . Eur. J. Pharm. Sci. , 2 : 4 – 6 .
   Web of Science ®Google Scholar
• DeClercq , E. 1995 . Toward improved anti-HIV chemotherapy: Therapeutic strategies for intervention with HIV infections . J. Med. Chem. , 38 : 2491 – 2517 .
   PubMed Web of Science ®Google Scholar
• Mitsuya , H. , Yarchoan , R. and Broder , S. 1990 . Molecular targets for AIDS therapy . Science , 249 : 1533 – 1544 .
   PubMed Web of Science ®Google Scholar
• Sandberg , J.A. and Slikker , W. 1995 . Developmental pharmacology and toxicology of anti-HIV therapeutic agents: Dideoxynucleosides . FASEB J. , 9 : 1157 – 1163 .
   PubMed Web of Science ®Google Scholar
• Jacobo-Molina , A. , Ding , J. , Nanni , R.G. , Clark , A.D. , Lu , X. , Tantillo , C. , Williams , R.L. , Kamer , G. , Ferris , A.L. , Clerck , P. , Hizi , A. , Huges , S. and Arnold , E. 1993 . Crystal structure of human immunodeficiency virus type 1 reverse transcriptase complexed with double-stranded DNA at 3.0 Å resolution shows bent DNA . Proc. Natl Acad. Sci. USA , 90 : 6320 – 6324 .
   PubMed Web of Science ®Google Scholar
• Miyasaka , T. , Tanaka , H. , Baba , M. , Hayakawa , H. , Walker , R.T. , Balzarini , J. and DeClercq , E. 1989 . A novel lead for specific anti-HIV-1 agents: 1-[(2-Hydroxyethoxy) methyl]-6-(phenylthio) thymine . J. Med. Chem. , 32 : 2507 – 2509 .
   PubMed Web of Science ®Google Scholar
• Tanaka , H. , Baba , M. , Hayakawa , H. , Sakamaki , T. , Miyasaka , T. , Ubasawa , M. , Takashima , H. , Sekiya , K. , Nitta , I. , Shigeta , S. , Walker , R.T. , Balzarini , J. and DeClercq , E. 1991 . A new class of HIV-1-specific 6-substituted acyclouridine derivatives: Synthesis and anti-HIV-1 activity of 5- or 6-substituted analogues of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) . J. Med. Chem. , 34 : 349 – 357 .
   PubMed Web of Science ®Google Scholar
• Tanaka , H. , Baba , M. , Ubasawa , M. , Takashima , H. , Sekiya , K. , Nitta , I. , Shigeta , S. , Walker , R.T. and Miyasaka , T. 1991 . Synthesis and antiviral activity of deoxy analogs of 1-[(2-hydroxyethoxy)-methyl]-6-(phenylthio)thymine (HEPT) as potent and selective anti-HIV-1 agents . J. Med. Chem. , 34 : 1394 – 1399 .
   PubMed Web of Science ®Google Scholar
• Tanaka , H. , Takashima , H. , Ubasawa , M. , Sekiya , K. , Nitta , I. , Baba , M. , Shigeta , S. , Walker , R.T. , DeClercq , E. and Miyasaka , T. 1992 . Structure–activity relationships of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine analogs: Effect of substitutions at the C-6 phenyl ring and at the C-5 position on anti-HIV-1 activity . J. Med. Chem. , 35 : 337 – 345 .
   PubMed Web of Science ®Google Scholar
• Tanaka , H. , Takashima , H. , Ubasawa , M. , Sekiya , K. , Nitta , I. , Baba , M. , Shigeta , S. , Walker , R.T. , DeClercq , E. and Miyasaka , T. 1992 . Synthesis and antiviral activity of deoxy analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT) as potent and selective anti-HIV-1 agents . J. Med. Chem. , 35 : 4713 – 4719 .
   PubMed Web of Science ®Google Scholar
• Barreca , M.L. , Balzarini , J. , Chimirri , A. , De Clercq , E. , De Luca , L. , De Höltje , H. , Höltje , M. , Monforte , A.M. , Monforte , P. , Pannecouque , C. , Rao , A. and Zappalà , M. 2002 . Design, synthesis, structure–activity relationships, and molecular modeling studies of 2,3-diaryl-1,3-thiazolidin-4-ones as potent anti-HIV agents . J. Med. Chem. , 45 : 5410 – 5413 .
   PubMed Web of Science ®Google Scholar
• Rawal , R.K. , Prabhakar , Y.S. , Katti , S.B. and De Clercq , E. 2005 . 2-(Aryl)-3-furan-2-ylmethyl-thiazolidin-4-ones as selective HIV-RT inhibitors . Bioorg. Med. Chem. , 13 : 6771 – 6776 .
   PubMed Web of Science ®Google Scholar
• Mao , C. , Sudbeck , E.A. , Venkatachalam , T.K. and Uckun , F.M. 1999 . Structure-based design of non-nucleoside reverse transcriptase inhibitors of drug-resistant human immunodeficiency virus . Antivir. Chem. Chemother. , 10 : 233 – 240 .
   PubMed Web of Science ®Google Scholar
• Tintori , C. , Manetti , F. , Veljkovic , N. , Perovic , V. , Vercammen , J. , Hayes , S. , Massa , S. , Witvrouw , M. , Debyser , Z. , Veljkovic , V. and Botta , M. 2007 . Novel virtual screening protocol based on the combined use of molecular modeling and electron–ion interaction potential techniques to design HIV-1 integrase inhibitors . J. Chem. Inf. Model. , 47 : 1536 – 1544 .
   PubMed Web of Science ®Google Scholar
• Bhhataraj , B. and Garg , R. 2005 . From SAR to comparative QSAR: Role of hydrophobicity in the design of 4-hydroxy-5,6-dihydropyran-2-ones HIV-1 protease inhibitors . Bioorg. Med. Chem. , 13 : 4078 – 4084 .
   PubMed Web of Science ®Google Scholar
• Kellenberger , E. , Springael , J.Y. , Parmentier , M. , Haas , M.H. , Galzi , J.L. and Rognan , D. 2007 . Identification of nonpeptide CCR5 receptor agonists by structure-based virtual screening . J. Med. Chem. , 50 : 1294 – 1303 .
   PubMed Web of Science ®Google Scholar
• Mandal , A.S. and Roy , K. 2009 . Predictive QSAR modeling of HIV reverse transcriptase inhibitor TIBO derivatives . Eur. J. Med. Chem. , 44 : 1509 – 1524 .
   PubMed Web of Science ®Google Scholar
• Buolamwini , J.K. and Assefa , H. 2002 . CoMFA and CoMSIA 3D QSAR and docking studies on conformationally-restrained cinnamoyl HIV-1 integrase inhibitors: Exploration of a binding mode at the active site . J. Med. Chem. , 45 : 841 – 852 .
   PubMed Web of Science ®Google Scholar
• R. Todeschini, Milano Chemometrics and QSAR Group; software available at http://www.talete.mi.it
   Google Scholar
• Moreau , G. and Broto , P. 1980 . The autocorrelation of a topological structure: A new molecular descriptor . Nouv. J. Chim. , 4 : 359 – 360 .
   Google Scholar
• Moran , P.A.P. 1950 . Notes on continuous stochastic phenomena . Biometrika , 37 : 17 – 23 .
   PubMed Web of Science ®Google Scholar
• Geary , R.F. 1954 . The contiguity ratio and statistical mapping . Statistician , 5 : 115 – 141 .
   Google Scholar
• Broto , P. , Moreau , G. and Vandycke , C. 1984 . Molecular structures: Perception, autocorrelation descriptor and SAR studies . Eur. J. Med. Chem. , 19 : 66 – 70 .
   Web of Science ®Google Scholar
• Fernández , M. and Caballero , J. 2006 . Modeling of activity of cyclic urea HIV-1 protease inhibitors using regularized-artificial neural networks . J. Bioorg. Med. Chem. , 14 : 280 – 294 .
   PubMed Web of Science ®Google Scholar
• Caballero , J. , Garriga , M. and Fernández , M. 2006 . 2D autocorrelation modeling of the negative inotropic activity of calcium entry blockers using Bayesian-regularized genetic neural networks . Bioorg. Med. Chem. , 14 : 3330
   PubMed Web of Science ®Google Scholar
• Fernández , M. and Caballero , J. 2006 . Bayesian-regularized genetic neural networks applied to the modeling of non-peptide antagonists for the human luteinizing hormone-releasing hormone receptor . J. Mol. Graph. Model. , 25 : 410 – 422 .
   PubMed Web of Science ®Google Scholar
• Fernández , M. , Caballero , J. and Tundidor-Camba , A. 2006 . Linear and nonlinear QSAR study of N-hydroxy-2-[(phenylsulfonyl)amino]acetamide derivatives as matrix metalloproteinase inhibitors . Bioorg. Med. Chem. , 14 : 4137 – 4150 .
   PubMed Web of Science ®Google Scholar
• Caballero , J. , Tundidor-Camba , A. and Fernández , M. 2007 . Modeling of the inhibition constant (Ki) of some cruzain ketone-based inhibitors using 2D spatial autocorrelation vectors and data-diverse ensembles of Bayesian-regularized genetic neural networks . QSAR Comb. Sci. , 26 : 27 – 40 .
   Google Scholar
• Fernández , M. and Caballero , J. 2007 . QSAR modeling of matrix metalloproteinase inhibition by N-hydroxy-α-phenylsulfonylacetamide derivatives . J. Bioorg. Med. Chem. , 15 : 6298 – 6310 .
   PubMed Web of Science ®Google Scholar
• Urra , L.S. , Gonzáleza , M.P. and Teijeira , M. 2007 . 2D-autocorrelation descriptors for predicting cytotoxicity of naphthoquinone ester derivatives against oral human epidermoid carcinoma . J. Bioorg. Med. Chem. , 15 : 3565 – 3571 .
   PubMed Web of Science ®Google Scholar
• Luco , J.M. and Ferretti , F.H. 1997 . QSAR based on multiple linear regression and PLS methods for the anti-HIV activity of a large group of HEPT derivatives . J. Chem. Inf. Comput. Sci. , 37 : 392 – 401 .
   PubMedGoogle Scholar
• Jalali-Heravi , M. and Parastar , F. 2000 . Use of artificial neural networks in a QSAR study of anti-HIV activity for a large group of HEPT derivatives . J. Chem. Inf. Comput. Sci. , 40 : 147 – 154 .
   PubMedGoogle Scholar
• Bazoui , H. , Zahouily , M. , Boulajaaj , S. , Sebti , S. and Zakarya , D. 2002 . QSAR for anti-HIV activity of HEPT derivatives . SAR QSAR Environ. Res. , 13 : 567 – 577 .
   PubMed Web of Science ®Google Scholar
• Douali , L. , Villemin , D. and Cherqaoui , D. 2003 . Neural networks: Accurate nonlinear QSAR model for HEPT derivatives . J. Chem. Inf. Comput. Sci. , 43 : 1200 – 1207 .
   PubMedGoogle Scholar
• Arakawa , M.M. , Hasegawa , K. and Funatsu , K. 2006 . QSAR study of anti-HIV HEPT analogues based on multi-objective genetic programming and counter-propagation neural network . Chem. Intel. Lab. Syst. , 83 : 91 – 98 .
   Web of Science ®Google Scholar
• Guo , W. , Hu , X. , Chu , N. and Yin , C. 2006 . Quantitative structure–activity relationship studies on HEPTs by supervised stochastic resonance . J. Bioorg. Med. Chem. , 16 : 2855 – 2859 .
   Web of Science ®Google Scholar
• Afantitis , A. , Melagraki , G. , Sarimveis , H. , Koutentis , A. , Markopoulos , J. and Igglessi-Markopoulou , O. 2006 . A novel simple QSAR model for the prediction of anti-HIV activity using multiple linear regression analysis . Mol. Diversity , 10 : 405 – 414 .
   PubMed Web of Science ®Google Scholar
• Kubinyi , H. , Hamprecht , F.A. and Mietzner , T. 1998 . Three-dimensional quantitative similarity–activity relationships (3D QSiAR) from SEAL similarity matrices . J. Med. Chem. , 41 : 2553 – 2564 .
   PubMed Web of Science ®Google Scholar
• Walker , J.D. , Jaworska , J. , Comber , M.H.I. , Schultz , T.W. and Dearden , J.C. 2003 . Guidelines for developing and using quantitative structure–activity relationships . Environ. Toxicol. Chem. , 22 : 1653 – 1665 .
   PubMed Web of Science ®Google Scholar
• Eriksson , L. , Jaworska , J. , Worth , A.P. , Cronin , M.T.D. , 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
• Hawkins , D.M. , Basak , S.C. and Mills , D. 2003 . Assessing model fit by cross-validation . J. Chem. Inf. Comput. Sci. , 43 : 579 – 586 .
   PubMedGoogle 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
• 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
• Willett , P. 2006 . Similarity-based virtual screening using 2D fingerprints . Drug Discov. Today , 11 : 1046 – 1053 .
   PubMed Web of Science ®Google Scholar