Identification of mechanisms of toxic action for skin sensitisation using a SMARTS pattern based approach

References

• EC . 2007 . REACH technical guidance Available at http://ecb.jrc.it/reach/rip/
   Google Scholar
• EC, Commission of the European Communities . 2003 . 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, L 66/26 – L 33/35 of 11.3.2003 ,
   Google Scholar
• Combes , R and Balls , M . 2005 . Intelligent testing strategies for chemical testing–A case of more haste, less speed? . ATLA , 33 : 289 – 297 .
   Google Scholar
• Worth , AP . 2004 . “ The tiered approach to toxicity assessment based on the integrated use of alternative (non-animal) tests ” . In Predicting Chemical Toxicity and Fate , Edited by: Cronin , MTD and Livingstone , DJ . 391 – 412 . Boca Raton, FL : CRC Press .
   Google Scholar
• Miller , MD , Yourtee , DM , Glaros , AG , Chappelow , CC , Eick , JD and Holder J. , Andrew . 2005 . Quantum mechanical structure–activity relationship analyses for skin sensitization . J. Chem. Inf. Model. , 45 : 924 – 929 .
   PubMed Web of Science ®Google Scholar
• Cronin , MTD and Basketter , DA . 1993 . “ A QSAR evaluation of an existing contact allergy database ” . In Trends in QSAR and Molecular Modelling 92 , Edited by: Wermuth , CG . 297 – 298 . Leiden : Escom .
   Google Scholar
• Cronin , MTD and Basketter , DA . 1994 . A multivariate QSAR analysis of a skin sensitization database . SAR QSAR Environ. Res. , 2 : 159 – 179 .
   PubMedGoogle Scholar
• Devillers , J . 2000 . A neural network SAR model for allergic contact dermatitis . Toxicol. Meth. , 10 : 181 – 193 .
   Web of Science ®Google Scholar
• Li , Y , Tseng , YJ , Pan , DH , Liu , JZ , Kern , PS , Gerberick , GF and Hopfinger , AJ . 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 .
   PubMed Web of Science ®Google Scholar
• Roberts , DW , Aptula , AO , Cronin , MTD , Hulzebos , E and Patlewicz , G . 2007 . Global (Q)SARs for skin sensitisation – assessment against OECD principles . SAR QSAR Environ. Res. , 18 : 343 – 365 .
   PubMed Web of Science ®Google Scholar
• Cronin , MTD and Schultz , TW . 2003 . Pitfalls in QSAR . J. Mol. Struct.-Theochem. , 622 : 39 – 51 .
   Web of Science ®Google Scholar
• Patlewicz , G , Basketter , DA , Smith , CK , Hotchkiss , SAM and Roberts , DW . 2001 . Skin-sensitization structure–activity relationships for aldehydes . Contact Dermatitis , 44 : 331 – 336 .
   PubMed Web of Science ®Google Scholar
• Patlewicz , G , Wright , ZM , Basketter , DA , Pease , CK , Lepoittevin , JP and Arnau , EG . 2002 . Structure-activity relationships for selected fragrance allergens . Contact Dermatitis , 47 : 219 – 226 .
   PubMed Web of Science ®Google Scholar
• Barratt , MD , Basketter , DA , Chamberlain , M , Admans , GD and Langowski , JJ . 1994 . An expert-system rulebase for identifying contact allergens . Toxicol. in vitro , 8 : 1053 – 1060 .
   PubMed Web of Science ®Google Scholar
• Barratt , MD , Basketter , DA , Chamberlain , M , Payne , MP , Admans , GD and Langowski , JJ . 1994 . Development of an expert-system rulebase for identifying contact allergens . Toxicol. In vitro , 8 : 837 – 839 .
   PubMed Web of Science ®Google Scholar
• Enslein , K , Gomber , VK , Blake , BW , Maibach , HI , Hostynek , JJ , Sigman , CC and Bagheri , D . 1997 . A quantitative structure–toxicity relationships model for the dermal sensitization guinea pig maximization assay . Food Chem. Toxicol. , 35 : 1091 – 1098 .
   PubMed Web of Science ®Google Scholar
• Graham , C , Gealy , R , Macina , OT , Karol , MH and Rosenkranz , HS . 1996 . QSAR for allergic contact dermatitis . Quant. Struct.-Act. Relat. , 15 : 224 – 229 .
   Web of Science ®Google Scholar
• Patlewicz , G , Dimitrov , SD , Low , LK , Kern , PS , Dimitrova , GD , Comber , MIH , Aptula , AO , Phillips , RD , Niemela , J , Madsen , C , Wedebye , EB , Roberts , DW , Bailey , PT and Mekenyan , OG . 2007 . TIMES-SS – A promising tool for the assessment of skin sensitization hazard. A characterization with repect to the OECD validation principles for (Q)SARs and an external evaluation for predictivity . Reg. Toxicol. Pharmacol. , 48 : 225 – 239 .
   PubMed Web of Science ®Google Scholar
• Cronin , MTD , Enoch , SJ and Madden , JC . 2008 . “ Quantitative structure-activity relationships for skin corrosivity and sensitization ” . In Dermal Absorption and Toxicity Assessment , 2 , Edited by: Roberts , MS and Walters , KA . 339 – 357 . New York : Informa Healthcare USA, Inc. .
   Google Scholar
• Patlewicz , G , Aptula , AO , Uriate , E , Roberts , DW , Kern , PS , Gerberick , F , Kimber , I , Dearman , RJ , Ryan , CA and Basketter , DA . 2007 . An evaluation of selected global (Q)SARs/expert systems for the prediction of skin sensitisation potential . SAR QSAR Environ. Res. , 18 : 515 – 541 .
   PubMed Web of Science ®Google Scholar
• Aptula , AO and Roberts , DW . 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 .
   PubMed Web of Science ®Google Scholar
• Aptula , AO , Patlewicz , G and Roberts , DW . 2005 . Skin sensitization: Reaction mechanistic applicability domains for structure–activity relationships . Chem. Res. Toxicol. , 18 : 1420 – 1426 .
   PubMed Web of Science ®Google Scholar
• Roberts , DW , Aptula , AO 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 .
   PubMed Web of Science ®Google Scholar
• Roberts , DW , Aptula , AO 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 .
   PubMed Web of Science ®Google Scholar
• Roberts , DW , Patlewicz , G , Kern , PS , Gerberick , F , Kimber , I , Dearman , RJ , Ryan , CA , Basketter , DA and Aptula , AO . 2007 . Mechanistic applicability domain classification of a local lymph node assay dataset for skin sensitization . Chem. Res. Toxicol. , 20 : 1019 – 1030 .
   PubMed Web of Science ®Google Scholar
• Gerberick , F , Aleksic , M , Basketter , D , Casati , S , Karlberg , A-T , Kern , P , Kimber , I , Lepoittevin , JP , Natsch , A , Ovigne , JM , Rovida , C , Sakaguchi , H and Schultz , T . 2008 . Chemical reactivity measurement and the predictive identification of skin sensitisers . ATLA , 36 : 215 – 242 .
   Google Scholar
• Barratt , MD . 2003 . QSAR, read-across and REACH . ATLA , 31 : 463 – 465 .
   Google Scholar
• Enoch , SJ , Cronin , MTD , Schultz , TW and Madden , JC . 2008 . Quantitative and mechanistic read-across for predicting the skin sensitization potential of alkenes acting via Michael addition . Chem. Res. Toxicol. , 21 : 513 – 520 .
   PubMed Web of Science ®Google Scholar
• OECD . 2004 . The report from the Expert Group on (quantitative) structure–activity relationship ([Q]SARs) on the principles for the validation of (Q)SARs . OECD Series on Testing and Assessment No. 49. ENV/JM/MONO(2004)/24 ,
   Google Scholar
• Gerberick , GF , Ryan , CA , Kern , PS , Schlatter , H , Dearman , RJ , Kimber , I , Patlewicz , GY and Basketter , DA . 2005 . Compilation of historical local lymph node data for evaluation of skin sensitization alternative methods . Dermatitis , 16 : 157 – 202 .
   PubMed Web of Science ®Google Scholar
• Roberts , DW , Patlewicz , G , Dimitrov , SD , Low , LK , Aptula , AO , Kern , PS , Dimitrova , GD , Comber , MIH , Phillips , RD , Niemela , J , Madsen , C , Wedebye , EB , Bailey , PT and Mekenyan , OG . 2007 . TIMES-SS–A mechanistic evaluation of an external validation study using reaction chemistry principles . Chem. Res. Toxicol. , 20 : 1321 – 1330 .
   PubMed Web of Science ®Google Scholar
• OECD . 2002 . Guideline no. 429. Skin sensitisation: The local lymph node assay. Organisation for Economic Co-operation and Development
   Google Scholar
• Frisch , MJ , Trucks , GW , Schlegel , HB , Scuseria , GE , Robb , MA , Cheeseman , JR , Zakrzewski , VG , Montgomery , JA Jr , Stratmann , RE , Dapprich , JC , Millam , JM , Daniels , AD , Kudin , KN , Strain , MC , Farkas , O , Tomasi , J , Barone , V , Cossi , M , Cammi , R , Mennucci , B , Pomelli , C , Adamo , C , Clifford , S , Ochterski , J , Petersson , GA , Ayala , PY , Cui , O , Morokuma , K , Malick , DK , Rabuck , AD , Raghavachari , K , Foresman , JB , Cioslowski , J , Ortiz , JV , Stefanov , BB , Liu , G , Liaschenko , A , Piskorz , P , Komaromi , I , Gomperts , R , Martin , RL , Fox , DJ , Keith , T , Al-Laham , MA , Peng , CY , Nanayakkara , A , Gonzalez , C , Challacombe , M , Gill , WPM , Johnson , B , Chen , W , Wong , MW , Andres , JL , Gonzalez , C , Head-Gordon , M , Replogle , ES and Pople , JA . 2003 . Gaussian 03 Revision-B.04 , XX
   Google Scholar
• EC . 2006 . 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, L 396/1 of 30.12.2006. ,
   Google Scholar
• Taubman , MA and Atassi , MZ . 1968 . Reaction of β-propiolactone with amino acids and its specificity for methionine . Biochem. J. , 106 : 829 – 834 .
   PubMed Web of Science ®Google Scholar
• Bach , RD , Coddens , BA and Wolber , GJ . 1986 . Origin of the reactivity of allyl chloride and α-chloroacetaldehyde in SN2 nucleophilic substitution reactions: A theoretical comparison . J. Org. Chem. , 51 : 1030 – 1033 .
   Google Scholar
• Smith , CK and Hotchkiss , SAM . 2001 . Allergic Contact Dermatitis: Chemical and Metabolic Mechanisms , London : Taylor & Francis .
   Google Scholar
• Grindon , C , Combes , R , Cronin , MTD , Roberts , DW and Garrod , JF . 2007 . Integrated decision-tree testing strategies for skin corrosion and irritation with respect to the requirements of the EU REACH legislation . ATLA , 35 : 673 – 682 .
   Google Scholar
• Grindon , C , Combes , R , Cronin , MTD , Roberts , DW and Garrod , JF . 2007 . An integrated decision-tree testing strategy for skin sensitisation with respect to the requirements of the EU REACH legislation . ATLA , 35 : 683 – 697 .
   Google Scholar