Skin sensitization prediction using quantum chemical calculations: A theoretical model for the SNAr domain

Chemical Research in Toxicology

Volumn 27, Issue 1, 2014, Pages 51-60

  Promkatkaew, Malinee ^a   Gleeson, Duangkamol ^b   Hannongbua, Supa ^a   Gleeson, M Paul ^a  

^a KASETSART UNIVERSITY   (Thailand)

^b KING MONGKUT'S INSTITUTE OF TECHNOLOGY LADKRABANG   (Thailand)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL COMPOUND; NUCLEOPHILE; ORGANIC COMPOUND;

ACCURACY; AROMATIC NUCLEOPHILIC SUBSTITUTION; ARTICLE; CALCULATION; CONTROLLED STUDY; DENSITY FUNCTIONAL THEORY; ENERGY; KINETICS; MEASUREMENT; PREDICTION; QUANTITATIVE ANALYSIS; QUANTUM CHEMISTRY; SKIN SENSITIZATION; SUBSTITUTION REACTION; THEORETICAL MODEL; THERMODYNAMICS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; QUANTUM THEORY; SKIN; TOXICITY TESTING;

KINETICS; MODELS, MOLECULAR; ORGANIC CHEMICALS; QUANTUM THEORY; SKIN; SKIN IRRITANCY TESTS; THERMODYNAMICS;

EID: 84892893751     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx400323e     Document Type: Article

References (35)

1. Kimber, I., Basketter, D. A., Gerberick, G. F., and Dearman, R. J. (2002) Allergic contact dermatitis Int. Immunopharmacol. 2, 201-211
2. Kimber, I. and Weisenberger, C. (1989) A murine local lymph node assay for the identification of contact allergens. Assay development and results of an initial validation study Arch. Toxicol. 63, 274-282
3. Anderson, S. E., Siegel, P. D., and Meade, B. J. (2011) The LLNA: a brief review of recent advances and limitations. J. Allergy 2011, doi: 10.1155/2011/424203.
4. Gerberick, F., Aleksic, M., Basketter, D., Casati, S., Karlberg, A. T., Kern, P., Kimber, I., Lepoittevin, J. P., Natsch, A., Ovigne, J., Rovida, C., Sakaguchi, H., and Schultz, T. (2008) Chemical reactivity measurement and the predictive identification of skin sensitisers Altern. Lab. Anim. 36, 215-242
5. Roberts, D. W., Schultz, T. W., Wolf, E. M., and Aptula, A. O. (2009) Experimental reactivity parameters for toxicity modeling: application to the acute aquatic toxicity of SN2 electrophiles to Tetrahymena pyriformis Chem. Res. Toxicol. 23, 228-234
6. Patlewicz, G., Chen, M. W., and Bellin, C. A. (2011) Non-testing approaches under REACH-help or hindrance? Perspectives from a practitioner within industry SAR QSAR Environ. Res. 22, 67-88
7. Schaafsma, G., Kroese, E. D., Tielemans, E. L. J. P., Van de Sandt, J. J. M., and Van Leeuwen, C. J. (2009) REACH, non-testing approaches and the urgent need for a change in mind set Regul. Toxicol. Pharmacol. 53, 70-80
8. Aptula, A. O. and Roberts, D. W. (2006) Mechanistic applicability domains for nonanimal-based prediction of toxicological end points: general principles and application to reactive toxicity Chem. Res. Toxicol. 19, 1097-1105
9. Aptula, A. O., Patlewicz, G., and Roberts, D. W. (2005) Skin sensitization: reaction mechanistic applicability domains for structure-activity relationships Chem. Res. Toxicol. 18, 1420-1426
10. Stepan, A. F., Walker, D. P., Bauman, J., Price, D. A., Baillie, T. A., Kalgutkar, A. S., and Aleo, M. D. (2011) Structural alert/reactive metabolite concept as applied in medicinal chemistry to mitigate the risk of idiosyncratic drug toxicity: a perspective based on the critical examination of trends in the top 200 drugs marketed in the United States Chem. Res. Toxicol. 24, 1345-1410
11. Park, B. K., Boobis, A., Clarke, S., Goldring, C. E. P., Jones, D., Kenna, J. G., Lambert, C., Laverty, H. G., Naisbitt, D. J., Nelson, S., Nicoll-Griffith, D. A., Obach, R. S., Routledge, P., Smith, D. A., Tweedie, D. J., Vermeulen, N., Williams, D. P., Wilson, I. D., and Baillie, T. A. (2011) Managing the challenge of chemically reactive metabolites in drug development Nat. Rev. Drug Discovery 10, 292-306
12. Roberts, D. W., Fraginals, R., Lepoittevin, J. P., and Benezra, C. (1991) Refinement of the relative alkylation index (RAI) model for skin sensitization and application to mouse and guinea-pig test data for alkyl alkanesulphonates Arch. Dermatol. Res. 286, 387-394
13. Li, Y., Tseng, Y. J., Pan, D., Liu, J., Kern, P. S., Gerberick, G. F., and Hopfinger, A. J. (2007) 4D-Fingerprint categorical QSAR models for skin sensitization based on the classification of local lymph node assay measures Chem. Res. Toxicol. 20, 114-128
14. Miller, M. D., Yourtee, D. M., Glaros, A. G., Chappelow, C. C., Eick, J. D., and Holder, A. J. (2005) Quantum mechanical structure-activity relationship analyses for skin sensitization J. Chem. Inf. Model. 45, 924-929
15. Roberts, D. W., Patlewicz, G., Kern, P. S., Gerberick, F., Kimber, I., Dearman, R. J., Ryan, C. A., Basketter, D. A., and Aptula, A. O. (2007) Mechanistic applicability domain classification of a local lymph node assay dataset for skin sensitization Chem. Res. Toxicol. 20, 1019-1030
16. Hansch, C. and Fujita, T. (1964) p-σ-π analysis. A method for the correlation of biological activity and chemical structure J. Am. Chem. Soc. 86, 1616-1626
17. Roberts, D. W., Aptula, A. O., and Patlewicz, G. (2006) Mechanistic applicability domains for non-animal based prediction of toxicological endpoints. QSAR analysis of the Schiff base applicability domain for skin sensitization Chem. Res. Toxicol. 19, 1228-1233
18. Roberts, D. W., Aptula, A. O., and Patlewicz, G. (2007) Electrophilic chemistry related to skin sensitization. reaction mechanistic applicability domain classification for a published data set of 106 chemicals tested in the mouse local lymph node assay Chem. Res. Toxicol. 20, 44-60
19. Enoch, S. J. and Roberts, D. W. (2013) Predicting skin sensitization potency for michael acceptors in the LLNA using quantum mechanics calculations Chem. Res. Toxicol. 26, 767-774
20. Hammond, G. S. (1955) A correlation of reaction rates J. Am. Chem. Soc. 77, 334-338
21. Roberts, D. W., Aptula, A. O., and Patlewicz, G. Y. (2011) Chemistry-based risk assessment for skin sensitization: quantitative mechanistic modeling for the S(N)Ar domain Chem. Res. Toxicol. 24, 1003-1011
22. ChEMBL https://www.ebi.ac.uk/chembl/ (last accessed Nov 14, 2013).
23. ICCVAM, LLNA database, http://iccvam.niehs.nih.gov/methods/immunotox/ rLLNA.htm (last accessed Nov 14, 2013).
24. Kern, P. S., Gerberick, F., Ryan, C. A., Kimber, I., Aptula, A., and Basketter, D. (2010) Local lymph node data for the evaluation of skin sensitization alternatives: a second compilation Dermatitis 21, 8-32
25. Enoch, S. J., Madden, J. C., and Cronin, M. T. (2008) Identification of mechanisms of toxic action for skin sensitisation using a SMARTS pattern based approach SAR QSAR Environ. Res. 19, 555-578
26. Pipeline Pilot www.accelrys.com (last accessed Nov 14, 2013).
27. Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. J. A., Vreven, 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., Bakken, V., 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. (2004) Gaussian 03, revision C.02, Gaussian, Inc., Wallingford, CT.
28. Zhao, Y. and Truhlar, D. G. (2011) Applications and validations of the Minnesota density functionals Chem. Phys. Lett. 502, 1-13
29. Zhao, Y. and Thuhlar, D. G. (2008) Exploring the limit of accuracy of the global hybrid meta density functional for main-group thermochemistry, kinetics, and noncovalent interactions J. Chem. Theory Comput. 4, 1849-1868
30. Zhao, Y. and Truhlar, D. G. (2008) The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals Theor. Chem. Acc. 120, 215-241
31. ChemAxon JChem, http://www.chemaxon.com/jchem/ (last accessed Nov 14, 2013).
32. Kalgutkar, A. S. and Soglia, J. R. (2005) Minimising the potential for metabolic activation in drug discovery Expert Opin. Drug. Metab. Toxicol. 1, 91-142
33. Stumpf, W. E. (2006) The dose makes the medicine Drug Discovery Today 11, 550-555
34. Weaver, S. and Gleeson, M. P. (2008) The importance of the domain of applicability in QSAR modeling J. Mol. Graphics Modell. 26, 1315-1326
35. Schwöbel, J. A. H., Koleva, Y. K., Enoch, S. J., Bajot, F., Hewitt, M., Madden, J. C., Roberts, D. W., Schultz, T. W., and Cronin, M. T. D. (2011) Measurement and estimation of electrophilic reactivity for predictive toxicology Chem. Rev. 111, 2562-2596