A Mechanistic Approach to Modeling Respiratory Sensitization

Chemical Research in Toxicology

Volumn 27, Issue 2, 2014, Pages 219-239

  Mekenyan, Ovanes ^a   Patlewicz, Grace ^b   Kuseva, Chanita ^a   Popova, Ioanna ^a   Mehmed, Aycel ^a   Kotov, Stefan ^a   Zhechev, Teodor ^a   Pavlov, Todor ^a   Temelkov, Stanislav ^a   Roberts, David W ^c  

^a ASSEN ZLATAROV UNIVERSITY   (Bulgaria)

^b DUPONT COMPANY   (United States)

^c LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AIR POLLUTANTS, OCCUPATIONAL; ALLERGENS; ANIMALS; BIOLOGICAL AVAILABILITY; CYSTEINE; DERMATITIS, ALLERGIC CONTACT; HUMANS; LIVER; LUNG; LYSINE; MODELS, BIOLOGICAL; PEPTIDES; PROTEIN BINDING; RESPIRATORY HYPERSENSITIVITY; RISK ASSESSMENT; SKIN; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84894239507     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx400345b     Document Type: Article

References (76)

1. Kimber, I., Agius, R., Basketter, D. A., Corsini, A., Cullinan, P., Dearman, R. J., Gimenez-Arnau, E., Greenwell, L., Hartung, T., Kuper, F., Maestrelli, P., Roggen, E., and Rovida, C. (2007) Chemical respiratory allergy: opportunities for hazard identification and characterization. The report and recommendations of ECVAM workshop 60 Altern. Lab. Anim. 35, 243-265
2. Isola, D., Kimber, I., Sarlo, K., Lalko, J., and Sipes, I. G. (2008) Chemical respiratory allergy and occupational asthma: what are the key areas of uncertainty? J. Appl. Toxicol. 28, 249-253
3. ECHA (2008) Guidance on Information Requirements and Chemical Safety Assessment, Chapter R.7a, European Chemicals Agency, Helsinki, Finland.
4. Basketter, D. A. and Kimber, I. (2011) Assessing the potency of respiratory allergens: Uncertainties and challenges Regul. Toxicol. Pharmacol. 61, 365-372
5. Dearman, R. J., Basketter, D. A., and Kimber, I. (2011) Inter-relationships between different classes of chemical allergens J. Appl. Toxicol. 33, 558-565
6. Goutet, M., Pepin, E., Langonne, I., Huguet, N., and Ban, M. (2012) Identification of contact and respiratory sensitizers according to IL-4 receptor alpha expression and IL-2 production Toxicol. Appl. Pharmacol. 260, 95-104
7. Agius, R. M., Nee, J., McGovern, B., and Robertson, A. (1991) Structure activity hypotheses in occupational asthma caused by low molecular weight substances Ann. Occup. Hyg. 35, 129-137
8. Agius, R. M., Elton, R. A., Sawyer, L., and Taylor, P. (1994) Occupational asthma and the chemical properties of low molecular weight organic substances Occup. Med. 44, 34-36
9. Lhasa Ltd. http://www.lhasalimited.org/products/derek-nexus.htm (accessed 14 Nov, 2013).
10. Graham, C., Rosenkranz, H. S., and Karol, M. H. (1997) Structure activity model of chemicals that cause human respiratory sensitization Regul. Toxicol. Pharmacol. 26, 296-306
11. Jarvis, J., Seed, M. J., Elton, R., Sawyer, L., and Agius, R. (2005) Relationship between chemical structure and the occupational asthma hazard of low molecular weight organic compounds Occup. Environ. Med. 62, 243-250
12. Warne, M. A., Nicholson, J. K., Lindon, J. C., Guiney, P. D., and Gartland, K. P. R. (2009) A QSAR investigation of dermal and respiratory chemical sensitizers based on computational chemistry properties SAR QSAR Environ. Res. 20, 429-451
13. Enoch, S. J., Roberts, D. W., and Cronin, M. T. D. (2009) Electrophilic reaction chemistry of low molecular weight respiratory sensitizers Chem. Res. Toxicol. 22, 1447-1453
14. Enoch, S. J., Roberts, D. W., and Cronin, M. T. D. (2010) Mechanistic category formation for the prediction of respiratory sensitization Chem. Res. Toxicol. 23, 1547-1555
15. Enoch, S. J., Seed, M. J., Roberts, D. W., Cronin, M. T. D., Stocks, S. J., and Agius, R. M. (2012) Development of mechanism-based structural alerts for respiratory sensitization hazard identification Chem. Res. Toxicol. 25, 2490-2498
16. 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
17. Holsapple, M. P., Jones, D., Kawabata, T. T., Kimber, I., Sarlo, K., Selgrade, M. K., Shah, J., and Woolhiser, M. R. (2006) Assessing the potential to induce respiratory hypersensitivity Toxicol. Sci. 91, 4-13
18. Lalko, J. F., Kimber, I., Dearman, R. J., Gerberick, F. G., Sarlo, K., and Api, A. M. (2011) Chemical reactivity measurements: Potential for characterization of respiratory chemical allergens Toxicol. in Vitro 25, 433-445
19. Gerberick, G. F., Vassallo, J. D., Bailey, R. E., Chaney, J. G., Morrall, S. W., and Lepoittevin, J. P. (2004) Development of a peptide reactivity assay for screening contact allergens Toxicol. Sci. 81, 332-343
20. Gerberick, G. F., Vassallo, J. D., Foertsch, L. M., Price, B. B., Chaney, J. G., and Lepoittevin, J. P. (2007) Quantification of chemical peptide reactivity for screening contact allergens: a classification tree model approach Toxicol. Sci. 97, 417-427
21. Lalko, J. F, Dearman, R. J., Gerberick, G. F., Troutman, J. A., Api, A. M., and Kimber, I. (2013) Reactivity of chemical respiratory allergens in the peroxidase peptide reactivity assay Toxicol. in Vitro 27, 651-661
22. Lalko, J. F., Kimber, I., Geberick, G. F., Foertsch, L. M., Api, A. M., and Dearman, R. J. (2012) The direct peptide reactivity assay: selectivity of chemical respiratory allergens Toxicol. Sci. 129, 421-431
23. Lalko, J. F., Kimber, I., Dearman, R. J., Api, A. M., and Gerberick, G. F. (2013) The selective peptide reactivity of chemical respiratory allergens under competitive and non-competitive conditions J. Immunotoxicol. 10, 292-301
24. OECD (2012) The Adverse Outcome Pathway for Skin Sensitisation Initiated by Covalent Binding to Proteins Part 1: Scientific Evidence, Series on Testing and Assessment No. 168 ENV/JM/MONO(2012)10/PART1, OECD, Paris, France.
25. Patlewicz, G., Dimitrov, S., Low, L. K., Kern, P. S., Dimitrova, G. D., Comber, M. I., Aptula, A. O., Phillips, R. D., Niemelä, J., Madsen, C., Wedebye, E. B., Roberts, D. W., Bailey, P. T., and Mekenyan, O. G. (2007) TIMES-SS-A promising tool for the assessment of skin sensitization hazard. A characterization with respect to the OECD validation principles for (Q)SARs and an external evaluation for predictivity Reg. Toxicol. Pharmacol 48, 225-239
26. Wass, U. and Bellin, L. (1990) An in vitro method for predicting sensitizing properties of inhaled chemicals Scand. J. Work. Environ. Health 16, 208-214
27. Karol, M. H., Graham, C., Gealy, R., Macina, O. T., Sussman, N., and Rosenkranz, H. S. (1996) Structure-activity relationships and computer-assisted analysis of respiratory sensitization potential Toxicol. Lett. 86, 187-191
28. Rodford, R. A., Patlewicz, G., Walker, J. D., and Payne, M. P. (2003) Quantitative structure activity relationships (QSARs) for predicting skin and respiratory sensitization Environ. Toxicol. Chem. 22, 1855-1861
29. Sarlo, K. and Clark, E. D. (1992) A tiered approach for evaluating the respiratory allergenicity of low molecular weight chemicals Fundam. Appl. Toxicol. 18, 107-114
30. EC (1993) Annex VI of Commission Directive 93/21/EEC, the 18th Adaptation to Technical Progress of the Council Directive 67/548/EEC on Dangerous Substances, Official Journal of the European Communities, Brussels, Belgium.
31. EC (2003) Technical Guidance Document (TGD) on Risk Assessment in Support of Commission Directive 93/67/EEC on Risk Assessment for New Notified Substances, Commission Regulation (EC) No 1488/94 on Risk Assessment for Existing Substances, Directive 98/8/EC of the European Parliament and of the Council Concerning the Placing of Biocidal Products on the Market Part I, 257-258, EUR 20418 EN/1, European Communities, Ispra, Italy.
32. Seed, M. J., Cullinan, P., and Agius, R. M. (2008) Methods for the prediction of low-molecular-weight occupational respiratory sensitisers Curr. Opin. Allergy Clin. Immunol. 8, 103-109
33. Sastre, J., Vandenplas, O., and Park, H. S. (2003) Pathogenesis of occupational asthma Eur. Respir. J. 22, 364-373
34. Mekenyan, O. G., Dimitrov, S. D., Pavlov, T. S., and Veith, G. D. (2004) A systems approach to simulating metabolism in computational toxicology. I. The TIMES heuristic modelling framework Curr. Pharm. Des 10, 1273-1293
35. Dimitrov, S., Pavlov, T., Veith, G., and Mekenyan, O. (2011) Simulation of chemical metabolism for fate and hazard assessment. I. Approach for simulating metabolism SAR QSAR Environ. Res. 22, 699-718
36. Mekenyan, O., Dimitrov, S., Pavlov, T., Dimitrova, G., Todorov, M., Petkov, P., and Kotov, S. (2012) Simulation of chemical metabolism for fate and hazard assessment. V. Mammalian hazard assessment SAR QSAR Environ. Res. 23, 553-606
37. Patel, J. M., Wood, J. C., and Leibman, K. C. (1980) The biotransformation of allyl alcohol and acrolein in rat liver and lung preparations Drug Metab. Dispos. 8, 305-308
38. Park, M. (2006) Risk Assessment for Scented Products: A Pre-study, RIVM report 320105002, RIVM, Bilthoven, The Netherlands.
39. Levine, W. G. (1991) Metabolism of azo dyes: Implications for detoxification and activation Drug Metab. Dispos. 23, 253-309
40. Cohen, G. M. (1990) Pulmonary metabolism of foreign compounds: its role in metabolic activation Environ. Health Perspect. 85, 31-41
41. Litterst, C. L., Mimnaugh, E. G., Reagan, R. L., and Gram, T. E. (1975) Comparison of in vitro drug metabolism by lung, liver and kidney of several common laboratory species Drug Metab. Dispos. 3, 259-265
42. McCracken, N. W., Blain, P. G., and Williams, F. M. (1993) Nature and role of xenobiotic metabolizing esterases in rat liver, lung, skin and blood Biochem. Pharmacol. 45, 31-36
43. Mekenyan, O., Petkov, P., Kotov, S., Stoeva, S., Kamenska, V., Dimitrov, S., Honma, M., Hayashi, M., Benigni, R., Donner, E. M., and Patlewicz, G. (2012) Investigating the relationship between in vitro-in vivo genotoxicity: derivation of mechanistic QSAR models for in vivo liver genotoxicity and in vivo bone marrow micronucleus formation which encompass metabolism Chem. Res. Toxicol. 25, 277-296
44. Aptula, A. O., Roberts, D. W., and Pease, C. K. (2007) Haptens, prohaptens and prehaptens, or electrophiles and proelectrophiles Contact Dermatitis 56, 54-56
45. 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 Chem. Res. Toxicol. 20, 44-60
46. Basketter, D. A., Gerberick, G. F., Kimber, I., and Loveless, S. E. (1996) The local lymph node assay: a viable alternative to currently accepted skin sensitization tests Food Chem. Toxicol. 34, 985-997
47. Lepoittevin, J. P. (2006) Metabolism versus chemical transformation or pro-versus prehaptens? Contact Dermatitis 54, 73-74
48. Pearson, R. G. (1963) Hard and soft acids and bases J. Am. Chem. Soc. 85, 3533-3539
49. Pearson, R. G. (1968) Hard and soft acids and bases, HSAB, part 1: Fundamental principles J. Chem. Educ. 45, 581-586
50. Pearson, R. G. and Songstad, J. (1967) Application of the principle of hard and soft acids and. bases to organic chemistry J. Am. Chem. Soc. 89, 1827-1836
51. Pearson, R. G. (1966) Acids and bases Science 151, 172-177
52. Dimitrov, S., Low, L., Patlewicz, G., Kern, P. S., Dimitrova, G. D., Comber, M. H., Phillips, R. D., Niemela, J., Bailey, P. T., and Mekenyan, O. G. (2005) Skin sensitization: modelling based on skin metabolism simulation Int. J. Toxicol. 24, 189-204
53. Gerberick, G. F., Troutman, J. A., Foertsch, L. M., Vassallo, J. D., Quijano, M., Dobson, R. L., Goebel, C., and Lepoittevin, J. P. (2009) Investigation of peptide reactivity of pro-hapten skin sensitizers using a peroxidase-peroxide oxidation system Toxicol. Sci. 112, 164-174
54. Roberts, D. W., Patlewicz, G. Y., Kern, P. S., Gerberick, G. 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
55. Roberts, D. W. and Patlewicz, G. (2013) Integrated testing and assessment approaches for skin sensitization: a commentary J. Appl. Toxicol. 33, 1-5
56. Roberts, D. W. and Lepoittevin, J.-P. (1997) Hapten-Protein Interactions, in Allergic Contact Dermatitis. The Molecular Basis (Lepoittevin, J.-P., Basketter, D. A., Goossens, A., Karlberg, A.-T., and Rycroft, R. J. G., Eds.) pp 81-111, Springer, Heidelberg, Germany.
57. Lepoittevin, J.-P. and Berl, V. (2004) Molecular Basis of Allergic Contact Dermatitis, in Dermatotoxicology (Zhai, H. and Maibach, M. I., Eds.) 6 th ed., pp 265-283, CRC Press, Boca Raton, FL.
58. Menger, F. M. (1968) Michaelis-Menten kinetics in the catalyzed solvolysis of tetrachlorophthalic anhydride J. Am. Chem. Soc. 90, 4387-4389
59. Borak, J., Fields, C., Andrews, L. S., and Pemberton, M. A. (2010) Methyl methacrylae and respiratory sensitization: a critical review Crit. Rev. Toxicol. 41, 230-268
60. Spracklin, D. K., Hankins, D. C., Fisher, J. M., Thummel, K. E., and Kharasch, E. D. (1997) Cytochrome P450 2E1 is the principal catalyst of human oxidative halothane metabolism in vitro J. Pharmacol. Exp. Ther. 281, 400-411
61. Guibas, G. V., Makris, M., Spandou, E., and Priftis, K. N. (2012) Exposure of immunologically naive laboratory rodents to antigen via the airways. Where does tolerance stop and sensitization begin? Clin. Exp. Allergy 42, 1552-1565
62. OECD (2004) OECD Principles for the Validation, for Regulatory Purposes, of (Quantitative) Structure-Activity Relationship Models. http://www.oecd.org/ chemicalsafety/risk-assessment/37849783.pdf (accessed 14 Nov, 2013).
63. Netzeva, T. I., Worth, A. P., Aldenberg, T., Benigni, R., Cronin, M. T. D, Gramatica, P., Jaworska, J. S., Kahn, S., Klopman, G., Marchant, C. A., Myatt, G., Nikolova-Jeliazkova, N., Patlewicz, G. Y., Perkins, R., Roberts, D. W., Schultz, T. W., Stanton, D. T., van de Sandt, J. J. M., Tong, W., Veith, G., and Yang, C. (2005) Current status of methods for defining the applicability domain of (quantitative) structure-activity relationships. the report and recommendations of ECVAM workshop 52 Altern. Lab. Anim. 33, 155-173
64. Dimitrov, S., Dimitrova, G., Pavlov, T., Dimitrova, N., Patlewicz, G., Niemala, J., and Mekenyan, O. (2005) A stepwise approach for defining the applicability domain of SAR and QSAR models J. Chem. Inf. Comput. Sci. 45, 839-849
65. Patel, J. M., Wood, J. C., and Leibman, K. C. (1980) The biotransformation of allyl alcohol and acrolein in rat liver and lung preparations Drug Metab. Dispos. 8, 305-308
66. Autrup, H. and Warwick, G. P. (1975) Some characteristics of two azoreductase systems in rat liver. Relevance to the activity of 2-[4′-di(2″-bromopropyl)-aminophenylazo]benzoic acid (CB10-252), a compound possessing latent cytotoxic activity Chem.-Biol. Interact. 11, 329-342
67. Bodin, A., Linnerborg, M., Nilsson, J. L. G., and Karlberg, A.-T. (2002) Novel hydroperoxides as primary autoxidation products of a model ethoxylated surfactant J. Surfactants Deterg. 5, 107-110
68. Musso, H. (1963) Phenol oxidation reactions Angew. Chem., Int. Ed. 2, 723-735
69. Bastow, T. P., van Aarssen, B. G. K., Herman, R., Alexander, R., and Kagi, R. I. (2003) The effect of oxidation on the distribution of alkylphenols in crude oils Org. Geochem. 34, 1103-1111
70. Wada, E., Kisaki, T., and Saito, K. (1959) Autoxidation of nicotine Arch. Biochem. Biophys. 79, 124-130
71. Aptula, A. O., Enoch, S., and Roberts, D. W. (2009) Chemical mechanisms for skin sensitization by aromatic compounds with hydroxy and amino groups Chem. Res. Toxicol. 22, 1541-1547
72. Herlinger, E., Jameson, R. F., and Linert, W. (1995) Spontaneous autoxidation of dopamine J. Chem. Soc. Perkin Trans. 2 259-263
73. Roberts, A., Lacy, S., Pilon, D., Turner, M., and Rickert, D. (1989) Metabolism of acrilonitrile to 2-cyanoethylene oxide in F-344 rat liver microsomes, lung microsomes, and lung cells Drug Metab. Dispos. 17, 481-486
74. Carlson, G. and Olson, R. (1995) Comparison of the metabolism of alcohols by rat hepatic and pulmonary alcohol dehydrogenase Biochem. Mol. Biol. Int. 37, 65-71
75. Manautou, J. and Carlson, G. (1992) Comparison of rat pulmonary and hepatic cytosolic alcohol dehydrogenase activities J. Toxicol. Environ. Health 35, 7-18
76. Blitt, C., Gandolfi, A., Soltis, J., and Brown, B. (1981) Extrahepatic biotransformation of halothane and enflurane Anesth. Analg. (Hagerstown, MD, U.S.) 60, 129-132