155
Views
17
CrossRef citations to date
0
Altmetric
Original Articles

Quantitative structure-activity relationship modelling of the carcinogenic risk of nitroso compounds using regression analysis and the TOPS-MODE approach

, , &
Pages 277-304 | Received 03 Oct 2009, Accepted 25 Feb 2010, Published online: 08 Jun 2010

References

  • Helguera , AM , Gonzalez , MP , Cordeiro , MNDS and Cabrera , MA . 2007 . Quantitative structure carcinogenicity relationship for detecting structural alerts in nitroso-compounds . Toxicol. Appl. Pharmacol. , 221 : 189 – 202 .
  • Helguera , AM , Cordeiro , MNDS , Cabrera , MA , Combes , RD and Gonzalez , MP . 2008 . Quantitative structure carcinogenicity relationship for detecting structural alerts in nitroso-compounds: species: rat; sex: male; route of administration: water . Toxicol. Appl. Pharmacol. , 231 : 197 – 207 .
  • Helguera , AM , Gonzalez , MP , Cordeiro , MNDS and Cabrera , MA . 2008 . Quantitative structure-carcinogenicity relationship for detecting structural alerts in nitroso compounds: species, rat; sex, female; route of administration, gavage . Chem. Res. Toxicol. , 21 : 633 – 642 .
  • Frankish , H . 15 million new cancer cases per year by 2020, says WHO, Lancet 361 (2003), p. 1278
  • Belpomme , D , Irigaray , P , Sasco , AJ , Newby , JA , Howard , V , Clapp , R and Hardell , L . 2007 . The growing incidence of cancer: Role of lifestyle and screening detection . Int. J. Oncol. , 30 : 1037 – 1049 .
  • Jemal , A , Siegel , R , Ward , E , Hao , Y , Xu , J , Murray , T and Thun , MJ . 2008 . Cancer Statistics, 2008 . CA Cancer J. Clin. , 58 : 71 – 96 .
  • Tomatis , L , Huff , J , Hertz-Picciotto , I , Sandler , DP , Bucher , J , Boffetta , P , Axelson , O , Blair , A , Taylor , J , Stayner , L and Barrett , JC . 1997 . Avoided and avoidable risks of cancer . Carcinogenesis , 18 : 97 – 105 .
  • Commission of the European Communities, White Paper on the Strategy for a Future Chemicals Policy, 2001
  • de Vocht , F , Burstyn , I , Straif , K , Vermeulen , R , Jakobsson , K , Nichols , L , Peplonska , B , Taeger , D and Kromhout , H . 2007 . Occupational exposure to NDMA and NMor in the European rubber industry . J. Environ. Monit. , 9 : 253 – 259 .
  • IARC, IARC Monographs on the evaluation of carcinogenic risks to humans, Lyon, France, 2006, available at http://monographs.iarc.fr
  • Jakszyn , P , Bingham , S , Pera , G , Agudo , A , Luben , R , Welch , A , Boeing , H , Giudice , G del , Palli , D , Saieva , C , Krogh , V , Sacerdote , C , Tumino , R , Panico , S , Berglund , G , Siman , H , Hallmans , G , Sanchez , MJ , Larranaga , N , Barricarte , A , Chirlaque , MD , Quiros , JR , Key , TJ , Allen , N , Lund , E , Carneiro , F , Linseisen , J , Nagel , G , Overvad , K , Tjonneland , A , Olsen , A , Bueno-de-Mesquita , HB , Ocke , MO , Peeters , PHM , Numans , ME , Clavel-Chapelon , F , Trichopoulou , A , Fenger , C , Stenling , R , Ferrari , P , Jenab , M , Norat , T , Riboli , E and Gonzalez , CA . Endogenous versus exogenous exposure to N-nitroso compounds and gastric cancer risk in the European Prospective Investigation into Cancer and Nutrition (EPIC-EURGAST) study, Carcinogenesis 27 (2006), pp. 1497–1501
  • Straif , K , Keil , U , Taeger , D , Holthenrich , D , Sun , Y , Bungers , M and Weiland , SK . 2000 . Exposure to nitrosamines, carbon black, asbestos, and talc and mortality from stomach, lung, and laryngeal cancer in a cohort of rubber workers . Am. J. Epidemiol. , 152 : 297 – 306 .
  • Benigni , R . 2005 . Structure-activity relationship studies of chemical mutagens and carcinogens: mechanistic investigations and prediction approaches . Chem. Rev. , 105 : 1767 – 800 .
  • Loeppky , RN , Ye , Q , Goelzer , P and Chen , Y . 2002 . DNA adducts from N-nitrosodiethanolamine and related α-oxidized nitrosamines in vivo: 32P-Postlabeling methods for glyoxal- and O6 hydroxyethyldeoxyguanosine adducts . Chem. Res. Toxicol. , 15 : 470 – 482 .
  • Singer , SS . 1985 . Decomposition reactions of (hydroxyalkyl) nitrosoureas and related compounds: possible relationship to carcinogenicity . J. Med. Chem. , 28 : 1088 – 1093 .
  • Zaidi , NH , O'Connor , PJ and Butler , WH . 1993 . N-methyl-N′-nitro-N-nitrosoguanidine-induced carcinogenesis: Differential pattern of upper gastrointestinal tract tumours in Wistar rats after single or chronic oral doses . Carcinogenesis , 14 : 1561 – 1567 .
  • Bellec , G , Goasduff , T , Dreano , Y , Menez , JF and Berthou , F . 1996 . Effect of the length of alkyl chain on the cytochrome P450 dependent metabolism of N-diakylnitrosamines . Cancer Lett. , 100 : 115 – 123 .
  • Lijinsky , W . 1987 . Structure-activity relations in carcinogenesis by N-nitroso compounds . Cancer Metastasis Rev. , 6 : 301 – 356 .
  • Wishnok , JS and Archer , MC . 1976 . Structure-activity relationships in nitrosamine carcinogenesis . Br. J. Cancer , 33 : 307 – 311 .
  • Wishnok , JS , Archer , MC , Edelman , AS and Rand , WM . 1978 . Nitrosamine carcinogenicity: a quantitative Hansch–Taft structure-activity relationship . Chem. Biol. Interact. , 20 : 43 – 54 .
  • Luan , F , Zhang , R , Zhao , C , Yao , X , Liu , M , Hu , Z and Fan , B . 2005 . Classification of the carcinogenicity of N-nitroso compounds based on support vector machines and linear discriminant analysis . Chem. Res. Toxicol. , 18 : 198 – 203 .
  • Dunn , WJ 3rd and Wold , S . 1981 . An assessment of carcinogenicity of N-nitroso compounds by the SIMCA method of pattern recognition . J. Chem. Inf. Comput. Sci. , 21 : 8 – 13 .
  • Gutiérrez , Y and Estrada , E . 2002–2004 . MODESLAB 1.5 (Molecular DEScriptors LABoratory) for Windows , España : Universidad de Santiago de Compostela .
  • Weininger , D . 1988 . SMILES, a chemical language and information system. I. Introduction to methodology and encoding rules . J. Chem. Inf. Comput. Sci. , 28 : 31 – 36 .
  • Gold , LS , Manley , NB , Slone , TH and Rohrbach , L . 1999 . Supplement to the Carcinogenic Potency Database (CPDB): results of animal bioassays published in the general literature in 1993 to 1994 and by the National Toxicology Program in 1995 to 1996 . Environ. Health Perspect. , 107 : 527 – 600 .
  • Gold , L , Manley , NB and Slone , TH . 1997 . Handbook of Carcinogenic Potency and Genotoxicity Databases , Boca Raton, FL : CRC Press .
  • Abraham , MH and Rafols , C . 1995 . Factors that influence tadpole narcosis. An LFER analysis . J. Chem. Soc. Perkin Trans. 2 , : 1843 – 1851 .
  • Platts , JA , Butina , D , Abraham , MH and Hersey , A . 1999 . Estimation of molecular linear free energy relation descriptors using a group contribution approach . J. Chem. Inf. Comput. Sci. , 39 : 835 – 845 .
  • Helguera , AM , Cabrera , MA , Combes , RD and González , MP . The prediction of carcinogenicity from molecular structure, Curr. Comput. Aided Drug. Design 1 (2005), pp. 237–255
  • Todeschini , R , Ballabio , D , Consonni , V , Mauri , A and Pavan , M . Mobydigs Computer Software, TALETE srl, Milano, 2004
  • Leardi , R , Boggia , R and Terrile , M . 1992 . Genetic algorithms as a strategy for feature selection . J. Chemometr. , 6 : 267 – 281 .
  • Garcia-Domenech , R and de Julian-Ortiz , JV . 1998 . Antimicrobial activity characterization in a heterogeneous group of compounds . J. Chem. Inf. Comput. Sci. , 38 : 445 – 449 .
  • Pestana , M and Gageiro , J . Análise de Dados para Ciências Sociais. A Complementaridade do SPSS, Edições Sílabo, Lisboa, 2008
  • Gonzalez , MP , Helguera , AM and Collado , IG . 2006 . A topological substructural molecular design to predict soil sorption coefficients for pesticides . Mol. Divers. , 10 : 109 – 118 .
  • Perez-Garrido , A , Helguera , AM , Cordeiro , MNDS and Escudero , AG . 2009 . QSPR modelling with the topological substructural molecular design approach: Beta-cyclodextrin complexation . J. Pharm. Sci. , 98 : 2
  • Randić , M . 1991 . Correlation of enthalphy of octanes with orthogonal connectivity indices . J. Mol. Struct. (Teochem) , 233 : 45 – 59 .
  • Bhatia , MS , Ingale , KB , Choudhari , PB , Bhatia , NM and Sawant , RL . 2009 . Application quantum and physico chemical molecular descriptors utilizing principal components to study mode of anticoagulant activity of pyridyl chromen-2-one derivatives . Bioorg. Med. Chem. 17 , : 1654 – 1662 .
  • Todeschini , R and Consonni , V . 2000 . Handbook of Molecular Descriptors , Weinheim, Germany : Wiley VCH .
  • Eriksson , L , Jaworska , J , Worth , AP , Cronin , MTD , McDowell , RM 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 .
  • Papa , E , Villa , F and Gramatica , P . 2005 . Statistically validated QSARs, based on theoretical descriptors, for modeling aquatic toxicity of organic chemicals in Pimephales promelas (fathead minnow) . J. Chem. Inf. Model. , 45 : 1256 – 1266 .
  • Ramos de Armas , R , Gonzalez Diaz , H , Molina , R , González , MP and Uriarte , E . 2004 . Stochastic-based descriptors studying peptides biological properties: modeling the bitter tasting threshold of dipeptides . Bioorg. Med. Chem. , 12 : 4815 – 4822 .
  • González , MP , Helguera , AM , Molina , R and García , JR . 2004 . A topological sub-structural approach of the mutagenic activity in dental monomers. 1. Aromatic epoxides . Polymer , 45 : 2773 – 2779 .
  • González , MP and Helguera , AM . 2003 . TOPS-MODE versus DRAGON descriptors to predict permeability coefficients through low-density polyethylene . J. Comput. Aided Mol. Design , 17 : 665 – 672 .
  • Gottmann , E , Kramer , S , Pfahringer , B and Helma , C . 2001 . Data quality in predictive toxicology: reproducibility of rodent carcinogenicity experiments . Environ. Health Perspect. , 109 : 509 – 514 .
  • Environment Directorate OECD, Guidance Document on the Validation of (Quantitative) Structure-Activity Relationships [(Q)SAR] Models, OECD Environmental Health and Safety Publications, Series on Testing and Assessment, Paris, France, 2007
  • Lijinsky , W . 1992 . Chemistry and Biology of N-Nitroso Compounds , Cambridge : Cambridge University Press .
  • Gnewuch , CT and Sosnovsky , G . 1997 . A critical appraisal of the evolution of N-nitrosoureas as anticancer drugs . Chem. Rev. , 97 : 829 – 1013 .
  • Shibuya , T and Morimoto , K . 1993 . A review of the genotoxicity of 1-ethyl-1-nitrosourea . Mutat. Res. , 297 : 3 – 38 .
  • Yano , K , Sonoda , M and Sakagishi , Y . 1987 . Reactions of N-nitrosoureas with cell membranes . IARC Sci. Publ. , 84 : 202 – 205 .
  • Brubaker , WF Jr , Zhao , HP and Prusoff , WH . 1986 . Measurement of carbamoylating activity of nitrosoureas and isocyanates by a novel high-pressure liquid chromatography assay . Biochem. Pharmacol. , 35 : 2359 – 2365 .
  • Zhang , F , Bartels , MJ , Pottenger , LH and Gollapudi , BB . 2005 . Differential adduction of proteins vs. deoxynucleosides by methyl methanesulfonate and 1-methyl-1-nitrosourea in vitro . Rapid Commun. Mass Spectrom. , 19 : 438 – 448 .
  • Babson , JR , Reed , DJ and Sinkey , MA . 1977 . Active site specific inactivation of chymotrypsin by cyclohexyl isocyanate formed during degradation of the carcinostatic 1-(2-chloroethyl)-3-cyclohexyl-1-nitrosourea . Biochemistry , 16 : 1584 – 1589 .
  • Babson , JR and Reed , DJ . 1978 . Inactivation of glutathione reductase by 2-chloroethyl nitrosourea-derived isocyanates . Biochem. Biophys. Res. Commun. , 83 : 754 – 762 .
  • Jump , DB , Sudhakar , S , Tew , KD and Smulson , M . 1980 . Probes to study the effect of methyl nitrosourea on ADP-ribosylation and chromatin structure at the subunit level . Chem. Biol. Interact. , 30 : 35 – 51 .
  • Rostkowska , K , Zwierz , K , Różański , A , Moniuszko-Jakoniuk , J and Roszczenko , A . 1998 . Formation and metabolism of N-nitrosamines . Polish J. Environ. Stud. , 7 : 321 – 325 .
  • Li-Jiao , Z , Ru-Gang , Z , Yan , Z and Qian-Huan , D . 2005 . “ Research on the Quantitative Structure-Carcinogenic Activity Relationship of N-Nitroso Compounds ” . In Engineering in Medicine and Biology 27th Annual Conference Shanghai, , China
  • Loeppky , RN and Goelzer , P . 2002 . Microsome-mediated oxidation of N-nitrosodiethanolamine (NDELA), a bident carcinogen . Chem. Res. Toxicol. , 15 : 457 – 469 .
  • Lethco , EJ , Wallace , WC and Brouwer , E . 1982 . The fate of N-nitrosodiethanolamine after oral and topical administration to rats . Food Chem. Toxicol. , 20 : 401 – 406 .
  • Preussmann , R , Wuertele , G , Eisenbrand , G and Spiegelhalder , B . 1978 . Urinary excretion of N-nitrosodiethanolamine administered orally to rats . Cancer Lett. , 4 : 207 – 209 .
  • Spiegelhalder , B , Eisenbrand , G and Preussmann , R . 1982 . Urinary excretion of N-nitrosamines in rats and humans . IARC Sci. Publ. , 41 : 443 – 449 .
  • Goodall , CM , Lijinsky , W , Tomatis , L and Wenyon , CE . 1970 . Toxicity and oncogenicity of nitrosomethylaniline and nitrosomethylcyclohexylamine . Toxicol. Appl. Pharmacol. , 17 : 426 – 432 .
  • Kroeger-Koepke , MB and Michejda , CJ . 1979 . Evidence for several demethylase enzymes in the oxidation of dimethylnitrosamine and phenylmethylnitrosamine by rat liver fractions . Cancer Res. , 39 : 1587 – 1591 .
  • Gold , B , Farber , J and Rogan , E . 1987 . An investigation of the metabolism of N-nitroso-N-methylaniline by phenobarbital- and pyrazole-induced Sprague-Dawley rat liver and esophagus derived S-9 . Chem. Biol. Interact. , 61 : 215 – 228 .
  • Golbraikh , A and Tropsha , A . 2002 . Beware of q2! . J. Mol. Graph. Model. , 20 : 269 – 276 .
  • Hawkins , DM , Basak , SC and Mills , D . 2003 . Assessing model fit by cross-validation . J. Chem. Inf. Comput. Sci. , 43 : 579 – 586 .
  • Hawkins , DM . 2004 . The problem of overfitting . J. Chem. Inf. Comput. Sci. , 44 : 1 – 12 .
  • Mugford , CA and Kedderis , GL . 1998 . Sex-dependent metabolism of xenobiotics . Drug Metab. Rev. , 30 : 441 – 498 .
  • Pampori , NA and Shapiro , BH . 1999 . Gender differences in the responsiveness of the sex-dependent isoforms of hepatic P450 to the feminine plasma growth hormone profile . Endocrinology , 140 : 1245 – 1254 .
  • Meibohm , B , Beierle , I and Derendorf , H . 2002 . How important are gender differences in pharmacokinetics? . Clin. Pharmacokinet. , 41 : 329 – 342 .
  • Streeter , AJ , Nims , RW , Hrabie , JA , Heur , YH and Keefer , HK . 1989 . Sex differences in the single-dose toxicokinetics of N-nitrosomethyl(2-hydroxyethyl)amine in the rat . Cancer Res. , 49 : 1783 – 1789 .
  • Mori , M , Naito , M , Watanabe , H , Takeichi , N , Dohi , K and Ito , A . 1990 . Effects of sex difference, gonadectomy, and estrogen on N-methyl-N-nitrosourea induced rat thyroid tumors . Cancer Res. , 50 : 7662 – 7667 .
  • Benigni , R , Bossa , C , Jeliazkova , N , Netzeva , T and Worth , A (eds.) . The Benigni/Bossa rulebase for mutagenicity and carcinogenicity – a module of Toxtree (EUR 23241 EN), Office for the Official Publications of the European Communities, EUR – Scientific and Technical Research Series, Luxembourg 2008, available at http://ecb.jrc.ec.europa.eu/documents/QSAR/EUR_23241_EN.pdf
  • Benigni , R , Bossa , C , Netzeva , T , Rodomonte , A and Tsakovska , I . 2007 . Mechanistic QSAR of aromatic amines: New models for discriminating between homocyclic mutagens and nonmutagens, and validation of models for carcinogens . Environ. Mol. Mutagen. , 48 : 754 – 771 .

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.