A QSAR investigation of dermal and respiratory chemical sensitizers based on computational chemistry properties

References

• EC, Annex VI of Commission Directive 93/21/EEC, the 18th Adaptation to Technical Progress of the Council Directive 67/548/EEC on Dangerous Substances, 1993
   Google Scholar
• EC, Annex V of Council Directive 67/548/EEC on Dangerous Substances, Off. J. Eur. Comm. 196 (1967), p. 1
   Google Scholar
• EC, Technical Guidance Document in support of Commission Directive 93/67/EEC on Risk Assessment for New Notified Substances and Commission Regulation (EC) No. 1488/94 on Risk Assessment for Existing Substances, 1993
   Google Scholar
• EC, Off. J. Eur. Comm. 35 (1993), L154
   Google Scholar
• Magnusson , B and Kligman , AM . 1970 . “ Allergic contact dermatitis in the guinea pig ” . In Identification of Contact Allergens , 102 – 123 . Springfield, IL : Charles C. Thomas .
   Google Scholar
• Buehler , EV . 1965 . Delayed contact hypersensitivity in the guinea pig . Arch. Dermatol. , 91 : 171 – 176 .
   PubMed Web of Science ®Google Scholar
• EC, Off. J. Eur. Comm. 35 (1993), L383
   Google Scholar
• OECD, Guideline 406 Skin Sensitization, 1992
   Google Scholar
• EC, Council Directive 88/379/EC on Dangerous Preparations, 1988
   Google Scholar
• EPA, Health Effects Test Guidelines OPPTS 870.2600 [Skin Sensitization], 2003
   Google Scholar
• Basketter , DA , Dearman , RJ , Ryan , CA , Gerberick , FG , Fielder , RJ and Kimber , I . 2004 . The local lymph node assay: Current regulatory status . The Toxicologist , 78 ( 1-S ) : 43
   Google Scholar
• Kimber , I , Agius , R , Basketter , DA , Corsini , E , Cullinan , P , Dearman , RJ , 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 characterisation [The Report and Recommendations of ECVAM Workshop 60] . ATLA , 35 : 243 – 265 .
   Google Scholar
• Cronin , MTD , Jaworska , JS , Walker , JD , Comber , MHI , Watts , DC and Worth , AP . 2003 . Use of QSARs in international decision-making frameworks to predict health effects of chemical substances . Environ. Health Perspec. , 111 : 1391 – 1401 .
   PubMed Web of Science ®Google Scholar
• Jaworska , JS , Comber , M , Auer , C and Van Leeuwen , CJ . 2003 . Summary of the workshop on regulatory acceptance of (Q)SARs . Environ. Health Perspec. , 111 ( 10 ) : 1358 – 1360 .
   PubMed Web of Science ®Google Scholar
• 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)
   Google Scholar
• Gerner , I , Barratt , MD , Zinke , S , Schlegel , K and Schlede , E . 2004 . Development and prevalidation of a list of structure–activity relationship rules to be used in expert systems for prediction of the skin-sensitising properties of chemicals . ATLA , 32 : 487 – 509 .
   Google Scholar
• Rodford , R , Patlewicz , G , Walker , JD and Payne , MP . 2003 . Quantitative structure–activity relationships for predicting skin and respiratory sensitization . Environ. Toxicol. Chem. , 22 : 1855 – 1861 .
   PubMed Web of Science ®Google Scholar
• Smith Pease , CK , Basketter , DA and Patlewicz , GY . 2003 . Contact allergy: the role of skin chemistry and metabolism . Clin. Exp. Dermatol. , 28 : 177 – 183 .
   PubMed Web of Science ®Google Scholar
• Dupuis , G and Benezra , C . 1982 . Contact Dermatitis to Simple Chemicals: A Molecular Approach , New York : Marcel Dekker .
   Google Scholar
• Wass , U and Berlin , L . 1990 . An in vitro method for predicting sensitizing properties of inhaled chemicals . Scand. J. Work Environ. Health , 16 : 208 – 214 .
   PubMed Web of Science ®Google Scholar
• Karol , MH , Graham , C , Gealy , R , Macina , OT , Sussman , N and Rosenkranz , HS . 1996 . Structure–activity relationships and computer-assisted analysis of respiratory sensitization potential . Toxicol. Lett. , 86 : 187 – 191 .
   PubMed Web of Science ®Google Scholar
• Barratt , MD and Basketter , DA . 1992 . Possible origin of the skin sensitization potential of eugenol and related compounds . Cont. Derm. , 27 : 98 – 104 .
   PubMed Web of Science ®Google Scholar
• Barratt , MD . 1995 . Quantitative structure activity relationships for skin permeability . Toxicol. Vitro , 9 : 27 – 37 .
   PubMed Web of Science ®Google Scholar
• Barratt , MD , Basketter , DA and Roberts , DW . 1997 . “ Structure–activity relationships for contact hypersensitivity ” . In Allergic Contact Dermatitis, the Molecular Basis , Edited by: Lipoittevin , J-P , Basketter , DA , Goossens , A and Karlberg , A-T . 129 – 154 . Heidelberg : Springer .
   Google Scholar
• Graham , C , Rosenkranz , HS and Karol , MH . 1997 . Structure–activity model of chemicals that cause human respiratory sensitization . Regul. Toxicol. Pharmacol. , 26 : 296 – 306 .
   PubMed Web of Science ®Google Scholar
• Roberts , DW and Aptula , AO . 2008 . Determinants of skin sensitization potential . J. Appl. Toxicol. , 28 : 377 – 387 .
   PubMed Web of Science ®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
• 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: Contact Atopic Occup. Drug: Off. J. Am. Contact Derm. Soc. , 16 ( 4 ) : 157 – 202 .
   PubMed Web of Science ®Google Scholar
• Dearman , RJ , Warbrick , EV , Humphreys , IR and Kimber , I . 2000 . Characterisation in mice of the immunological properties of five allergenic acid anhydrides . J. Appl. Toxicol. , 20 : 221 – 230 .
   PubMed Web of Science ®Google Scholar
• Hilton , J , Dearman , RJ , Basketter , DA and Kimber , I . 1995 . Identification of chemical respiratory allergens: dose–response relationships in the mouse IgE test . Toxicol. Methods , 5 : 51 – 60 .
   Web of Science ®Google Scholar
• Dewar , MJS , Zoebisch , EG , Healy , EF and Stewart , JJP . 1985 . A new general purpose quantum mechanical molecular model . J. Amer. Chem. Assoc. , 107 : 3902 – 3909 .
   Web of Science ®Google Scholar
• SPARTAN version 5.0. Wavefunction Inc., 18401 Von Karman Avenue, Suite 370, Irvine CA 92612, U.S.A
   Google Scholar
• Wavefunction Inc., 18401 Von Karman Avenue, Suite 370, Irvine, CA 92612, USA
   Google Scholar
• Oxford Molecular, Medawar Centre, Oxford Science Park, Oxford OX4 4GA, UK
   Google Scholar
• Alkorta , I and Villar , HO . 1992 . Quantum mechanical parametrization of a conformationally dependent hydrophobicity index . Int. J. Quant. Chem. , 44 : 203 – 218 .
   Web of Science ®Google Scholar
• Klamt , A and Schuurman , G . 1993 . COSMO: a new approach to dielectric screening in solvents with explicit expressions for the screening energy and its gradient . J. Chem. Soc. Perkin Trans. II , : 799
   Google Scholar
• Ghose , AK , Pritchett , A and Crippen , GM . 1988 . Atomic physicochemical parameters for three-dimensional structure-directed quantitative structure–activity relationships . J. Comput. Chem. , 9 : 80 – 90 .
   Web of Science ®Google Scholar
• Kier , LB and Hall , LH . 1986 . Molecular Connectivity in Structure–Activity Analysis , New York : J. Wiley & Sons .
   Google Scholar
• Fukui , K , Yonezawa , T and Nagata , C . 1954 . Theory of substitution in conjugated molecules . Bull. Chem. Soc. Japan. , 27 : 423 – 427 .
   Google Scholar
• SAS Institute Inc., Campus Drive, Cary, NC 27513, USA.
   Google Scholar
• Gartland , KPR , Beddell , CR , Lindon , JC and Nicholson , JK . 1991 . The application of pattern recognition methods to the analysis and classification of toxicological data derived from proton NMR spectroscopy of urine . Mol. Pharm. , 39 : 629 – 642 .
   PubMed Web of Science ®Google Scholar
• Infometrix Inc., PO Box 1528, Woodinville, WA 98072-1528, USA.
   Google Scholar
• Livingstone , D . 1995 . Data Analysis for Chemists: Applications to QSAR and Chemical Product Design , Oxford : Oxford University Press .
   Google Scholar
• Cronin , MTD and Dearden , JC . 1997 . Correspondence analysis of the skin sensitization potential of organic chemicals . Quant. Struct.–Act. Relat. , 16 : 33 – 37 .
   Web of Science ®Google Scholar
• Patlewicz , G , Roberts , DW and Walker , JD . 2003 . QSARs for the skin sensitization potential of aldehydes and related compounds . QSAR Comb. Sci. , 22 : 196 – 203 .
   Google Scholar
• Patlewicz , GY , Basketter , DA , Pease , C , Smith , K , Wilson , K , Wright , ZM , Roberts , DW , Bernard , G , Arnau , EG and Lepoittevin , J-P . 2004 . Further evaluation of quantitative structure–activity relationship models for the prediction of the skin sensitization potency of selected fragrance allergens . Cont. Derm. , 50 : 91 – 97 .
   PubMed Web of Science ®Google Scholar
• Fedorowicz , A , Afshari , H , Zheng , L , Singh , H and Demchuk , E . 8–11 September 2002 . “ Development of new QSAR approaches in occupational contact dermatitis ” . In Proceedings of the International Conference on Occupational and Environmental Exposures of Skin to Chemicals: Science and Policy 8–11 September , Crystal City, VA
   Google Scholar
• Sosted , H , Basketter , DA , Estrada , E , Johansen , JD and Patlewicz , GY . 2004 . Ranking of hair dye substances according to predicted sensitization potency: quantitative structure–activity relationships . Cont. Derm. , 51 : 241
   PubMed Web of Science ®Google Scholar
• Karol , MH , Macina , OT and Cunningham , A . 2001 . Cell and molecular biology of chemical allergy . Ann. Aller. Asth. Immunol. , 87 : 28 – 32 .
   PubMed Web of Science ®Google Scholar
• Klink , KJ and Meade , BJ . 2003 . Dermal exposure to 3-amino-5-mercapto-1,2,4-triazole (AMT) induces sensitization and airway hyperreactivity in BALB/c mice . Toxicol. Sci. , 75 : 89 – 98 .
   PubMed Web of Science ®Google Scholar
• Vanoirbeek , JAJ , Mandervelt , C , Cunningham , AR , Hoet , PHM , Xu , H , Vanhooren , HM and Nemery , B . 2003 . Validity of methods to predict the respiratory sensitizing potential of chemicals: a study with a piperidinyl chlorotriazine derivative that caused an outbreak of occupational asthma . Toxicol. Sci. , 76 : 338 – 346 .
   PubMed Web of Science ®Google Scholar
• Cunningham , R , Cunningham , SL , Consoer , DM , Moss , ST and Karol , MH . 2005 . Development of an information-intensive structure–activity relationship model and its application to human respiratory chemical sensitizers . SAR QSAR Environ. Res. , 16 : 273 – 285 .
   PubMed Web of Science ®Google Scholar
• Warne , MA and Nicholson , JK . 2000 . Quantitative structure–activity relationships (QSARs) in environmental research. Part II. Molecular orbital approaches to property calculation . Prog. Environ. Sci. , 2 : 31 – 52 .
   Google Scholar
• EC, Commission Directive 97/69/EC of 5th December 1997 adapting to technical progress for the 23rd time Council Directive 67/548/EEC on Dangerous Substances, 1997
   Google Scholar
• Barratt , MD . 1995 . The role of structure–activity relationships and expert systems in alternative strategies for the determination of skin sensitization, skin corrosivity and eye irritation . ATLA , 23 : 111 – 122 .
   Google Scholar
• Kirchner , LA , Moody , RP , Doyle , E , Bose , R , Jeffery , J and Chu , I . 1997 . The prediction of skin permeability by using physicochemical data . ATLA , 25 : 359 – 370 .
   Google Scholar