Experimental verification of structural alerts for the protein binding of cyclic compounds acting as Michael acceptors

SAR and QSAR in Environmental Research

Volumn 24, Issue 11, 2013, Pages 963-977

  Rodriguez Sanchez, N ^a   Schultz, T W ^b   Cronin, M T D ^a   Enoch, S J ^a  

^a LIVERPOOL JOHN MOORES UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF TENNESSEE   (United States)

Author keywords

applicability domain; category formation; in chemico; Michael addition; OECD QSAR Toolbox; structural alerts

Indexed keywords

ADDITION REACTIONS; BIOCHEMISTRY; COMPUTATIONAL CHEMISTRY; INTERNATIONAL COOPERATION; TOXICITY;

APPLICABILITY DOMAIN; CATEGORY FORMATION; CYCLIC COMPOUNDS; EXPERIMENTAL VERIFICATION; IN CHEMICO; MICHAEL ADDITIONS; OECD QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP TOOLBOX; PROTEIN-BINDING; QUANTITATIVE STRUCTURE ACTIVITY RELATIONSHIP; STRUCTURAL ALERT; OECD QUANTITATIVE STRUCTURE–ACTIVITY RELATIONSHIP TOOLBOX;

PROTEINS;

ALKANE; ALKENE; GLUTATHIONE; HETEROCYCLIC COMPOUND; KETONE; ORGANIC COMPOUND;

ARTICLE; BINDING SITE; CHEMICAL STRUCTURE; CHEMISTRY; CYCLIZATION; DRUG EFFECT; DRUG LEGISLATION; EUROPEAN UNION; PROTEIN BINDING; QUANTITATIVE STRUCTURE ACTIVITY RELATION; TETRAHYMENA PYRIFORMIS; TOXICITY TESTING; TOXICOLOGY;

ALKANES; ALKENES; BINDING SITES; CYCLIZATION; EUROPEAN UNION; GLUTATHIONE; HETEROCYCLIC COMPOUNDS; KETONES; LEGISLATION, DRUG; MOLECULAR STRUCTURE; ORGANIC CHEMICALS; PROTEIN BINDING; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; TETRAHYMENA PYRIFORMIS; TOXICITY TESTS; TOXICOLOGY;

EID: 84889584123     PISSN: 1062936X     EISSN: 1029046X     Source Type: Journal    
DOI: 10.1080/1062936X.2013.820793     Document Type: Article

References (25)

1. European Commission, Corrigendum to Regulation (EC) No 1907/2006 of the European Parliament and of the Council of 18 December 2006 concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH), establishing a European Chemicals Agency, amending Directive 1999/45/EC and repealing Council Regulation (EEC) No 793/93 and Commission Regulation (EC) No 1488/94 as well as Council Directive 76/769/EEC and Commission Directives 91/155/EEC, 93/67/EEC, 93/105/EC and 2000/21/EC. Off. J. Eur. Union L136 (2007) pp. 3-280.
2. European Commission, Regulation (EC) No 1907/2006 of the European Parliament and of the Council of 18 December 2006 concerning the Registration, Evaluation, Authorisation and Restriction of Chemicals (REACH), establishing a European Chemicals Agency, amending Directive 1999/45/EC and repealing Council Regulation (EEC) No 793/93 and Commission Regulation (EC) No 1488/94 as well as Council Directive 76/769/EEC and Commission Directives 91/155/EEC, 93/67/EEC, 93/105/EC and 2000/21/EC. Off. J. Eur. Union L396 (2006) pp. 1-849.
3. European Parliament and European Council, Directive 2003/15/EC of the European Parliament and of the Council of 27 February 2003 amending Council Directive 76/768/EEc on the approximation of the laws of the Member States relating to cosmetic products, Off. J. Eur. Union, L66 (2003), pp. 26-35.
4. S. Adler, D. Basketter, S. Creton, O. Pelkonen, J. Benthem, V. Zuang, K.E. Andersen, A. Angers-Loustau, A. Aptula, A. Bal-Price, E. Benfenati, U. Bernauer, J. Bessems, F.Y. Bois, A. Boobis, E. Brandon, S. Bremer, T. Broschard, S. Casati, S. Coecke, R. Corvi, M. Cronin, G. Daston, W. Dekant, S. Felter, E. Grignard, U. Gundert-Remy, T. Heinonen, I. Kimber, J. Kleinjans, H. Komulainen, R. Kreiling, J. Kreysa, S.B. Leite, G. Loizou, G. Maxwell, P. Mazzatorta, S. Munn, S. Pfuhler, P. Phrakonkham, A. Piersma, A. Poth, P. Prieto, G. Repetto, V. Rogiers, G. Schoeters, M. Schwarz, R. Serafimova, H. Tähti, E. Testai, J. Delft, H. Loveren, M. Vinken and A. Worth, J-M Zaldivar, Alternative (non-animal) methods for cosmetics testing: current status and future prospects-2010, Arch. Toxicol. 85, (2011), 367-485.
5. T.W. Schultz, Adverse outcome pathways: a way of linking chemical structure to in vivo toxicological hazards, in In Silico Toxicology: Principles and Applications, M.T.D. Cronin and J.C. Madden, eds., Royal Society of ChemistryCambridge, 2010, pp. 346-371.
6. Organisation for Economic Co-operation and Development (OECD), Report of the workshop on using mechanistic information in forming chemical categories, OECD Environment Health and Safety Publications Series on Testing and Assesment No. 138, OECD, Paris, 2011.
7. European Chemicals Agency, Guidance on information requirements and chemical safety assessment. Chapter R.6: QSARs and grouping of chemicals, in Guidance for the implementation of REACH 2008, European Chemicals Agency, Helsinki; 2008. Available at: http://echa.europa.eu/guidance-documents/guidance-on-information-requirements-and-chemical-safety-assessment.
8. European Chemicals Agency, Practical guide 6: how to report read-across and categories, European Chemicals AgencyHelsinki, 2009.
9. S.J. Enoch, M.T.D. Cronin, T.W. Schultz and J.C. Madden, Quantitative and mechanistic read-across for predicting skin sensitization potential of alkenes acting via Michael addition, Chem. Res. Toxicol. 21, (2008), 513-520.
10. T.W. Schultz, K. Rogers and A.O. Aptula, Read-across to rank skin sensitization potential: Subcategories for the Michael acceptor domain, Contact Dermatitis 60, (2009), 21-31.
11. S.J. Enoch, Chemical category formation and read-across for the prediction of toxicity, in Recent Advances in QSAR Studies: Methods and Applications, T. Puzyn, J. Leszczynski and M.T.D. Cronin, eds., Springer, Dordrecht, HeidelbergLondon and New York, 2010, pp. 209-219.
12. A.O. Aptula and D.W. Roberts, Mechanistic applicability domains for nonanimal-based prediction of toxicological end points: General principles and application to reactive toxicity, Chem. Res. Toxicol. 19, (2006), 1097-1105.
13. J.A.H. Schwöbel, Y.K. Koleva, F. Bajot, S. Enoch, M. Hewitt, J.C. Madden, D.W. Roberts, T.W. Schultz, and M.T.D Cronin, Measurement and estimation of electrophilic reactivity for predictive toxicology, Chem. Rev. 111 (2011), pp. 2562-2596.
14. T.W. Schultz, J.W. Yarbrough and E.L. Johnson, Structure-activity relationships for the reactivity of carbonyl-containing with glutathione, SAR QSAR Environ. Res. 16, (2005), 313-322.
15. D.W. Roberts, A.O. Aptula, G. Patlewicz and C.J. Pease, Chemical reactivity indices and mechanism-based read-across for non-animal based assessment of skin sensitisation potential, J. Appl. Toxicol. 28, (2008), 443-454.
16. OECD QSAR Toolbox V3.1; software available at www.qsartoolbox.org
17. T.W. Schultz, J.W. Yarbrough, R.S. Hunter and A.O. Aptula, Verification of the structural alerts for Michael acceptors, Chem. Res. Toxicol. 20, (2007), 1359-1363.
18. S.J. Enoch, M.T.D. Cronin, T.W. Schultz and J.C. Madden, Quantitative and mechanistic read across for predicting the skin sensitisation potential of alkenes acting via Michael addition, Chem. Res. Toxicol. 21, (2008), 513-520.
19. S.J. Enoch, C.M. Ellison, T.W. Schultz and M.T.D. Cronin, A review of the electrophilic reaction chemistry involved in covalent protein binding relevant to toxicity, Crit. Rev. Toxicol. 41, (2011), 783-802.
20. J.W. Yarbrough and T.W. Schultz, Abiotic sulfhydryl reactivity: A predictor of aquatic toxicity for carbonyl-containing α,β-unsaturated compounds, Chem. Res. Toxicol. 20, (2007), 558-562.
21. M.D. Nelms, M.T.D Cronin, T.W. Schultz, and S.J. Enoch, Experimental verification of and domain definition of structural alerts for protein binding: epoxides, lactones, nitroso, nitros, aldehydes and ketones, SAR QSAR Environ. Res., DOI: 10.1080/1062936X.2013.792874
22. T.W. Schultz, TERATOX: T. pyriformis population growth impairment endpoint - A surrogate for fish lethality, Toxicol. Methods 7, (1997), 289-309.
23. A.O. Aptula, G. Patlewicz, D.W. Roberts and T.W. Schultz, Non-enzymatic glutathione reactivity and in vitro toxicity: A non-animal appraoch to skin sensitisation, Toxicol. In Vitro 20, (2006), 239-247.
24. C.M. Ellison, M.T.D. Cronin, J.C. Madden and T.W. Schultz, Definition of the structural domain of the baseline non-polar narcosis model for T. pyriformis, SAR QSAR Environ. Res. 19, (2008), 751-783.
25. S.J. Enoch and D.W. Roberts, Predicting skin sensitisation potency for Michael acceptors in the LLNA using quantum mechanics calculations, Chem. Res. Toxicol. 26, (2013), 767-774.