Comparison of CoMFA Models for Salmonella Typhimurium TA98, TA100+TA98+S9 and TA100+S9 Mutagenicity of Nitroaromatics

References

• Kier , L. E. , Brusick , D. J. , Auletta , A. E. , Von Halle , E. S. , Brown , M. M. , Simmon , V. F. , Dunkel , V. , McCann , J. , Mortelmans , K. , Prival , M. , Rao , T. K. and Ray , V. 1986 . The Salmonella typhimurium/mammalian microsomal assay. A report of the U.S. Environmental Protection Agency Gene-Tox Program. . Mutat. Res. , 168 : 69 – 240 .
   PubMed Web of Science ®Google Scholar
• Maron , D. M. and Ames , B. N. 1983 . Revised methods for the Salmonella mutagenicity test. . Mutat. Res. , 113 : 173 – 215 .
   PubMed Web of Science ®Google Scholar
• Hadley , W. M. 1983 . “ A review of the literature on enzymatic reduction of nitrocompounds LMF-104 UC 48 ” . In National Technical Information Service , 1 – 20 . Springfield, VA : U.S. Department of Commerce, 5285 Port Royal Road . 22161
   Google Scholar
• Rosenkranz , H. S. and Mermelstein , R. 1983 . Mutagenicity and genotoxicity of nitroarenes. All nitro-containing chemicals were not created equal. . Mutat. Res. , 114 : 217 – 267 .
   PubMed Web of Science ®Google Scholar
• Rosenkranz , H. S. and Mermelstein , R. 1985 . The genotoxicity, metabolism and carcinogenicity of nitrated polycyclic aromatic hydrocarbons. . J. Environ. Sci. Health , C3 ( 2 ) : 221 – 272 .
   Google Scholar
• Fu , P. P. 1990 . Metabolism of nitro-polycyclic aromatic hydrocarbons . Drug Metab. Rev. , 22 ( 2, 3 ) : 209 – 268 .
   PubMedGoogle Scholar
• Zeiger , E. 1987 . Carcinogenicity of mutagens: Predictive capability of the Salmonella mutagenesis assay for rodent carcinogenicity. . Cancer Res. , 47 : 1287 – 1296 .
   PubMed Web of Science ®Google Scholar
• Lopez de Compadre , R. L. , Shusterman , A. J. and Hansch , C. 1988 . The role of hydrophobicity in the Ames test. The correlation of the mutagenicity of nitropolycyclic hydrocarbons with partition coefficients and molecular orbital indices. . Int. J. Quantum Chem. , 34 : 91 – 101 .
   Google Scholar
• Lopez de Compadre , R. L. , Kumar , A. K. , Shusterman , A. J. and Hansch , C. 1990 . LUMO energies and hydrophobicity as determinants of mutagenicity by nitroaromatic compounds in . S. typhimurium. Environ. Mol. Mutagen. , 15 : 44 – 55 .
   PubMed Web of Science ®Google Scholar
• Debnath , A. K. , Lopez de Compadre , R. L. , Debnath , G. , Shusterman , A. J. and Hansch , C. 1991 . Structure-activity relationships of mutagenic aromatic heteroaromatic nitro compounds. Correlation with molecular orbital energies and hydrophobicity. . J. Med. Chem. , 34 : 786 – 797 .
   PubMed Web of Science ®Google Scholar
• Debnath , A. K. , Lopez de Compadre , R. L. , Shusterman , A. J. and Hansch , C. 1992 . Quantitative structure-activity relationships investigation of the role of hydrophobicity in regulating mutagenicity in the Ames test: 2. Mutagenicity of aromatic and heteroaromatic nitro compound in Salmonella typhimurium TA100. . Environ. Mol. Mutagen. , 19 : 53 – 70 .
   PubMed Web of Science ®Google Scholar
• Debnath , A. K. , Shusterman , A. J. , Lopez de Compadre , R. L. and Hansch , C. 1994 . The importance of the hydrophobic interactions in the mutagenicity of organic compounds. . Mutat. Res. , 305 : 63 – 72 .
   PubMed Web of Science ®Google Scholar
• Hansch , C. and Leo , A. 1995 . “ QSAR of mutagenesis, carcinogenesis, and antitumor drugs. ” . In Exploring QSAR. Fundamentals and Applications in Chemistry and Biology , Washington, D.C. : ACS .
   Google Scholar
• Hansch , C. , Leo , A. and Hoekman , D. 1995 . Exploring QSAR. Hydrophobic, Electronic, and Steric Constants , 219 – 304 . Washington, D.C. : ACS .
   Google Scholar
• Fu , P. P. , Chou , M. W. , Miller , D. W. , White , G. L. , Heflich , R. H. and Beland , F. A. 1985 . The orientation of the nitro substituent predicts the direct-acting bacterial mutagenicity of nitrated polycyclic aromatic hydrocarbons. . Mutat. Res. , 143 : 173 – 181 .
   PubMed Web of Science ®Google Scholar
• Fu , P. P. , Heflich , R. H. , Unruh , L. E. , Shaikh , A. U. , Wu , Y. , Lai , C. C. and Lai , J. S. 1988 . Relationships among direct-acting mutagenicity, nitro group orientation and polarographic reduction potential of 6-nitrobenzo[a]pyrene, 7-nitrobenz[a]anthracene and their derivatives. . Mutat. Res. , 209 : 115 – 122 .
   PubMed Web of Science ®Google Scholar
• Jung , H. A. , Shaikh , A. U. , Heflich , R. H. and Fu , P. P. 1991 . Nitro group orientation, reduction potential and direct-acting mutagenicity of nitro-polycyclic aromatic hydrocarbons. . Environ. Mol. Mutag. , 17 : 169 – 180 .
   PubMed Web of Science ®Google Scholar
• Yu , S. , Herreno-Saenz , D. , Miller , D. W. , Kadlubar , F. F. and Fu , P. 1992 . Mutagenicity of nitro-polycyclic aromatic hydrocarbons with the nitro substituent situated at the longest molecular axis. . Mutat. Res. , 283 : 45 – 52 .
   PubMed Web of Science ®Google Scholar
• Sams , R. L. , Compadre , R. L. , Castleberry , A. , Samokyszyn , V. M. , Ronis , M. and Compadre , C. M. 1995 . “ Quantitation of physico-chemical properties affecting the mutagenicity and rates of reduction of nitroaromatics. In, QSAR and Molecular Modeling '94: Concepts ” . In Computational Tools and Biological Applications , Edited by: Sanz , F. , Giraldo , J. and Manuat , F. 484 – 487 . Barcelona, , Spain : Prous Science Publishers .
   Google Scholar
• Compadre , R. L. , Byrd , C. and Compadre , C. M. 1998 . “ Comparative QSAR and 3-D-QSAR of the mutagenicity of nitroaromatic compounds. ” . In Comparative QSAR , Edited by: Devillers , J. 111 – 136 . Washington, D.C. : Taylor and Francis .
   Google Scholar
• “ SYBYL 6.3, Tripos Inc. ” . 1699 St. Louis, , Missouri, USA : South Hanley Road . 63144–2913
   Google Scholar
• Dewar , M. J. S. , Zoebisch , E. G. , Healy , E. F. and Stewart , J. J. P. AMI: A new general-purpose quantum mechanical molecular model. . J. Am Chem. Soc. , 107 3902 – 3909 .
   Google Scholar
• 1985 . “ MOPAC 6.0, Quantum Chemistry Program Exchange ” . Bloomington, , IN, USA : Indiana University, 840 State Highway 46 Bypass . 47405
   Google Scholar
• Clark , T. 1985 . “ A Handbook of Computational Chemistry. ” . In A Practical Guide to Chemical Structure and Energy Calculations , 158 New York : John Wiley and Sons .
   Google Scholar
• Cramer , R. D. III , Patterson , D. E. and Brunce , J. D. Recent advances in comparative molecular field analysis (CoMFA). . Prog. Clin. Biol. Res. , 291 161 – 165 .
   PubMedGoogle Scholar
• 1989 . “ CLOGP is a tool to predict lipophilicity and molar refractivity with access to the Pomona database. ” . Irvine, , CA, U.S.A. : DAYLIGHT Chemical Information System, Inc., 18500 Von Karmen Av. . Suite 450, 92715
   Google Scholar
• Goodford , P. J. A computational procedure for defining energetically favorable binding sites of biologically important macromolecules. . J. Med. Chem. , 28 849 – 857 . Also see Molecular Discovery Ltd. West Way House, Elms Parade, Oxford OX2 9LL, England 1985
   PubMedGoogle Scholar
• Debnath , A. K. , Hansch , C. , Kim , K. H. and Martin , Y. C. 1993 . Mechanistic interpretation of the genotoxicity of nitrofurans (antibacterial agents) using quantitative structure-activity relationships and comparative molecular field analysis. . J. Med. Chem. , 36 : 1007 – 1016 .
   PubMed Web of Science ®Google Scholar
• Hansch , C. , Gao , H. and Hoekman , D. 1998 . “ A generalized approach to comparative QSAR. ” . In Comparative QSAR , Edited by: Devillers , J. 285 – 368 . Washington, D.C. : Taylor and Francis .
   Google Scholar
• Zhang , L. , Sannes , K. , Shusterman , J. A. and Hansch , C. 1992 . The structure-activity relationships of skin carcinogenicity of aromatic hydrocarbons and heterocycles . Chem.-Biol.-Interactions , 81 : 149 – 180 .
   PubMed Web of Science ®Google Scholar