메뉴 건너뛰기




Volumn 24, Issue 11, 2011, Pages 2018-2027

Relating skin sensitizing potency to chemical reactivity: Reactive Michael acceptors inhibit NF-κB signaling and are less sensitizing than S NAr- and S N2-reactive chemicals

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL AGENT; I KAPPA B KINASE; IMMUNOGLOBULIN ENHANCER BINDING PROTEIN; MICHAEL ACCEPTOR; UNCLASSIFIED DRUG;

EID: 81755167002     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx2003678     Document Type: Article
Times cited : (41)

References (41)
  • 3
    • 56649085336 scopus 로고    scopus 로고
    • LC-MS-based characterization of the peptide reactivity of chemicals to improve the in vitro prediction of the skin sensitization potential
    • Natsch, A. and Gfeller, H. (2008) LC-MS-based characterization of the peptide reactivity of chemicals to improve the in vitro prediction of the skin sensitization potential Toxicol. Sci. 106, 464-478
    • (2008) Toxicol. Sci. , vol.106 , pp. 464-478
    • Natsch, A.1    Gfeller, H.2
  • 4
    • 35649009496 scopus 로고    scopus 로고
    • Utility and limitations of a peptide reactivity assay to predict fragrance allergens in vitro
    • DOI 10.1016/j.tiv.2007.03.016, PII S0887233307001294, Fourteenth International Workshop on In Vitro Toxicology
    • Natsch, A., Gfeller, H., Rothaupt, M., and Ellis, G. (2007) Utility and limitations of a peptide reactivity assay to predict fragrance allergens in vitro Toxicol. in Vitro 21, 1220-1226 (Pubitemid 350030873)
    • (2007) Toxicology in Vitro , vol.21 , Issue.7 , pp. 1220-1226
    • Natsch, A.1    Gfeller, H.2    Rothaupt, M.3    Ellis, G.4
  • 5
    • 65949100117 scopus 로고    scopus 로고
    • High throughput kinetic profiling approach for covalent binding to peptides: Application to skin sensitization potency of michael acceptor electrophiles
    • Roberts, D. W. and Natsch, A. (2009) High throughput kinetic profiling approach for covalent binding to peptides: Application to skin sensitization potency of michael acceptor electrophiles Chem. Res. Toxicol. 22, 592-603
    • (2009) Chem. Res. Toxicol. , vol.22 , pp. 592-603
    • Roberts, D.W.1    Natsch, A.2
  • 7
    • 34447295889 scopus 로고    scopus 로고
    • The local lymph node assay and the assessment of relative potency: Status of validation
    • Basketter, D. A., Gerberick, F., and Kimber, I. (2007) The local lymph node assay and the assessment of relative potency: Status of validation Contact Dermatitis 57, 70-75
    • (2007) Contact Dermatitis , vol.57 , pp. 70-75
    • Basketter, D.A.1    Gerberick, F.2    Kimber, I.3
  • 8
    • 33748640373 scopus 로고    scopus 로고
    • Mechanistic applicability domains for nonanimal-based prediction of toxicological end points: General principles and application to reactive toxicity
    • DOI 10.1021/tx0601004
    • 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 (Pubitemid 44384841)
    • (2006) Chemical Research in Toxicology , vol.19 , Issue.8 , pp. 1097-1105
    • Aptula, A.O.1    Roberts, D.W.2
  • 9
    • 44349084840 scopus 로고    scopus 로고
    • Chemical reactivity indices and mechanism-based read-across for non-animal based assessment of skin sensitisation potential
    • DOI 10.1002/jat.1293
    • Roberts, D. W., Aptula, A. O., Patlewicz, G., and Pease, C. (2008) Chemical reactivity indices and mechanism-based read-across for non-animal based assessment of skin sensitisation potential J. Appl. Toxicol. 28, 443-454 (Pubitemid 351727978)
    • (2008) Journal of Applied Toxicology , vol.28 , Issue.4 , pp. 443-454
    • Roberts, D.W.1    Aptula, A.O.2    Patlewicz, G.3    Pease, C.4
  • 11
    • 75249099695 scopus 로고    scopus 로고
    • The Nrf2-Keap1-ARE toxicity pathway as a cellular sensor for skin sensitizers: Functional relevance and a hypothesis on innate reactions to skin sensitizers
    • Natsch, A. (2010) The Nrf2-Keap1-ARE toxicity pathway as a cellular sensor for skin sensitizers: Functional relevance and a hypothesis on innate reactions to skin sensitizers Toxicol. Sci. 113, 284-292
    • (2010) Toxicol. Sci. , vol.113 , pp. 284-292
    • Natsch, A.1
  • 12
    • 34447547764 scopus 로고    scopus 로고
    • Quantification of chemical peptide reactivity for screening contact allergens: A classification tree model approach
    • DOI 10.1093/toxsci/kfm064
    • 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 (Pubitemid 47073857)
    • (2007) Toxicological Sciences , vol.97 , Issue.2 , pp. 417-427
    • Gerberick, G.F.1    Vassallo, J.D.2    Foertsch, L.M.3    Price, B.B.4    Chaney, J.G.5    Lepoittevin, J.-P.6
  • 13
    • 58049202229 scopus 로고    scopus 로고
    • Filling the concept with data: Integrating data from different in vitro and in silico assays on skin sensitizers to explore the battery approach for animal-free skin sensitization testing
    • Natsch, A., Emter, R., and Ellis, G. (2009) Filling the concept with data: Integrating data from different in vitro and in silico assays on skin sensitizers to explore the battery approach for animal-free skin sensitization testing Toxicol. Sci. 107, 106-121
    • (2009) Toxicol. Sci. , vol.107 , pp. 106-121
    • Natsch, A.1    Emter, R.2    Ellis, G.3
  • 14
    • 77958586769 scopus 로고    scopus 로고
    • In vitro and in vivo analysis of pro- and anti-inflammatory effects of weak and strong contact allergens
    • Lass, C., Merfort, I., and Martin, S. F. (2010) In vitro and in vivo analysis of pro- and anti-inflammatory effects of weak and strong contact allergens Exp. Dermatol. 19, 1007-1013
    • (2010) Exp. Dermatol. , vol.19 , pp. 1007-1013
    • Lass, C.1    Merfort, I.2    Martin, S.F.3
  • 16
    • 54949147176 scopus 로고    scopus 로고
    • New regulators of NF-κB in inflammation
    • Ghosh, S. and Hayden, M. S. (2008) New regulators of NF-κB in inflammation Nature Rev. Immunol. 8, 837-848
    • (2008) Nature Rev. Immunol. , vol.8 , pp. 837-848
    • Ghosh, S.1    Hayden, M.S.2
  • 17
    • 0034610759 scopus 로고    scopus 로고
    • Anti-inflammatory cyclopentenone prostaglandins are direct inhibitors of IB kinase
    • DOI 10.1038/47520
    • Rossi, A., Kapahi, P., Natoli, G., Takahashi, T., Chen, Y., Karin, M., and Santoro, M. G. (2000) Anti-inflammatory cyclopentenone prostaglandins are direct inhibitors of IkappaB kinase Nature 403, 103-108 (Pubitemid 30038530)
    • (2000) Nature , vol.403 , Issue.6765 , pp. 103-108
    • Rossi, A.1    Kapahi, P.2    Natoli, G.3    Takahashi, T.4    Chen, Y.5    Karin, M.6    Santoro, M.G.7
  • 18
    • 0035947678 scopus 로고    scopus 로고
    • IkappaB kinase, a molecular target for inhibition by 4-hydroxy-2-nonenal
    • Ji, C., Kozak, K. R., and Marnett, L. J. (2001) IkappaB kinase, a molecular target for inhibition by 4-hydroxy-2-nonenal J. Biol. Chem. 276, 18223-18228
    • (2001) J. Biol. Chem. , vol.276 , pp. 18223-18228
    • Ji, C.1    Kozak, K.R.2    Marnett, L.J.3
  • 19
    • 0034879173 scopus 로고    scopus 로고
    • The anti-inflammatory natural product parthenolide from the medicinal herb Feverfew directly binds to and inhibits IB kinase
    • DOI 10.1016/S1074-5521(01)00049-7, PII S1074552101000497
    • Kwok, B. H., Koh, B., Ndubuisi, M. I., Elofsson, M., and Crews, C. M. (2001) The anti-inflammatory natural product parthenolide from the medicinal herb Feverfew directly binds to and inhibits IkappaB kinase Chem. Biol. 8, 759-766 (Pubitemid 32752455)
    • (2001) Chemistry and Biology , vol.8 , Issue.8 , pp. 759-766
    • Kwok, B.H.B.1    Koh, B.2    Ndubuisi, M.I.3    Elofsson, M.4    Crews, C.M.5
  • 20
    • 0035955729 scopus 로고    scopus 로고
    • Cysteine 38 in p65/NF-κB plays a crucial role in DNA binding inhibition by sesquiterpene lactones
    • Garcia-Pineres, A. J., Castro, V., Mora, G., Schmidt, T. J., Strunck, E., Pahl, H. L., and Merfort, I. (2001) Cysteine 38 in p65/NF-κB plays a crucial role in DNA binding inhibition by sesquiterpene lactones J. Biol. Chem. 276, 39713-39720
    • (2001) J. Biol. Chem. , vol.276 , pp. 39713-39720
    • Garcia-Pineres, A.J.1    Castro, V.2    Mora, G.3    Schmidt, T.J.4    Strunck, E.5    Pahl, H.L.6    Merfort, I.7
  • 21
    • 0001112989 scopus 로고    scopus 로고
    • The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-B by directly targeting p65
    • DOI 10.1074/jbc.273.50.33508
    • Lyss, G., Knorre, A., Schmidt, T. J., Pahl, H. L., and Merfort, I. (1998) The anti-inflammatory sesquiterpene lactone helenalin inhibits the transcription factor NF-κB by directly targeting p65 J. Biol. Chem. 273, 33508-33516 (Pubitemid 29005734)
    • (1998) Journal of Biological Chemistry , vol.273 , Issue.50 , pp. 33508-33516
    • Ly, G.1    Knorre, A.2    Schmidt, T.J.3    Pahl, H.L.4    Merfort, I.5
  • 22
    • 39149086011 scopus 로고    scopus 로고
    • Skin sensitizers induce antioxidant response element dependent genes: Application to the in vitro testing of the sensitization potential of chemicals
    • DOI 10.1093/toxsci/kfm259
    • Natsch, A. and Emter, R. (2008) Skin sensitizers induce antioxidant response element dependent genes: Application to the in vitro testing of the sensitization potential of chemicals Toxicol. Sci. 102, 110-119 (Pubitemid 351250473)
    • (2008) Toxicological Sciences , vol.102 , Issue.1 , pp. 110-119
    • Natsch, A.1    Emter, R.2
  • 23
    • 1842833425 scopus 로고    scopus 로고
    • Reproducible prediction of contact allergenic potency using the local lymph node assay
    • DOI 10.1111/j.0105-1873.2004.00278.x
    • Basketter, D. A. and Cadby, P. (2004) Reproducible prediction of contact allergenic potency using the local lymph node assay Contact Dermatitis 50, 15-17 (Pubitemid 38491337)
    • (2004) Contact Dermatitis , vol.50 , Issue.1 , pp. 15-17
    • Basketter, D.A.1    Cadby, P.2
  • 24
    • 68949144888 scopus 로고    scopus 로고
    • Updating the skin sensitization in vitro data assessment paradigm in 2009
    • Basketter, D. A. and Kimber, I. (2009) Updating the skin sensitization in vitro data assessment paradigm in 2009 J. Appl. Toxicol. 29, 545-550
    • (2009) J. Appl. Toxicol. , vol.29 , pp. 545-550
    • Basketter, D.A.1    Kimber, I.2
  • 25
    • 85025403160 scopus 로고
    • Studies on the sensitization of animals with simple chemical compounds
    • Landsteiner, K. and Jacobs, J. (1936) Studies on the sensitization of animals with simple chemical compounds J. Exp. Med 64, 625-639
    • (1936) J. Exp. Med , vol.64 , pp. 625-639
    • Landsteiner, K.1    Jacobs, J.2
  • 26
    • 33846889946 scopus 로고    scopus 로고
    • 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
    • DOI 10.1021/tx060121y
    • 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 (Pubitemid 46220154)
    • (2007) Chemical Research in Toxicology , vol.20 , Issue.1 , pp. 44-60
    • Roberts, D.W.1    Aptula, A.O.2    Patlewicz, G.3
  • 27
  • 30
    • 34548590870 scopus 로고    scopus 로고
    • Comparative analysis of skin sensitization potency of acrylates (methyl acrylate, ethyl acrylate, butyl acrylate, and ethylhexyl acrylate) using the local lymph node assay
    • DOI 10.1111/j.1600-0536.2007.01215.x
    • Dearman, R. J., Betts, C. J., Farr, C., McLaughlin, J., Berdasco, N., Wiench, K., and Kimber, I. (2007) Comparative analysis of skin sensitization potency of acrylates (methyl acrylate, ethyl acrylate, butyl acrylate, and ethylhexyl acrylate) using the local lymph node assay Contact Dermatitis 57, 242-247 (Pubitemid 47397798)
    • (2007) Contact Dermatitis , vol.57 , Issue.4 , pp. 242-247
    • Dearman, R.J.1    Betts, C.J.2    Farr, C.3    McLaughlin, J.4    Berdasco, N.5    Wiench, K.6    Kimber, I.7
  • 32
    • 3042844427 scopus 로고    scopus 로고
    • A chemical dataset for evaluation of alternative approaches to skin-sensitization testing
    • DOI 10.1111/j.0105-1873.2004.00290.x
    • Gerberick, G. F., Ryan, C. A., Kern, P. S., Dearman, R. J., Kimber, I., Patlewicz, G. Y., and Basketter, D. A. (2004) A chemical dataset for evaluation of alternative approaches to skin-sensitization testing Contact Dermatitis 50, 274-288 (Pubitemid 38869902)
    • (2004) Contact Dermatitis , vol.50 , Issue.5 , pp. 274-288
    • Gerberick, G.F.1    Ryan, C.A.2    Kern, P.S.3    Dearman, R.J.4    Kimber, I.5    Patlewicz, G.Y.6    Basketter, D.A.7
  • 33
    • 0031058234 scopus 로고    scopus 로고
    • Dinitrohalobenzenes: Evaluation of relative skin sensitization potential using the local lymph node assay
    • DOI 10.1111/j.1600-0536.1997.tb00421.x
    • Basketter, D. A., Dearman, R. J., Hilton, J., and Kimber, I. (1997) Dinitrohalobenzenes: evaluation of relative skin sensitization potential using the local lymph node assay Contact Dermatitis 36, 97-100 (Pubitemid 27095634)
    • (1997) Contact Dermatitis , vol.36 , Issue.2 , pp. 97-100
    • Basketter, D.A.1    Dearman, R.J.2    Hilton, J.3    Kimber, I.4
  • 34
    • 0030040330 scopus 로고    scopus 로고
    • Dichloronitrobenzene: A reappraisal of its skin sensitization potential
    • DOI 10.1111/j.1600-0536.1996.tb02113.x
    • Basketter, D. A., Scholes, E. W., Fielding, I., Dearman, R. J., Hilton, J., and Kimber, I. (1996) Dichloronitrobenzene: a reappraisal of its skin sensitization potential Contact Dermatitis 34, 55-58 (Pubitemid 26019829)
    • (1996) Contact Dermatitis , vol.34 , Issue.1 , pp. 55-58
    • Basketter, D.A.1    Scholes, E.W.2    Fielding, I.3    Dearman, R.J.4    Hilton, J.5    Kimber, I.6
  • 35
    • 0036050212 scopus 로고    scopus 로고
    • Examination of a vehicle for use with water soluble materials in the murine local lymph node assay
    • Ryan, C. A., Cruse, L. W., Skinner, R. A., Dearman, R. J., Kimber, I., and Gerberick, G. F. (2002) Examination of a vehicle for use with water soluble materials in the murine local lymph node assay Food Chem. Toxicol. 40, 1719-1725
    • (2002) Food Chem. Toxicol. , vol.40 , pp. 1719-1725
    • Ryan, C.A.1    Cruse, L.W.2    Skinner, R.A.3    Dearman, R.J.4    Kimber, I.5    Gerberick, G.F.6
  • 36
    • 81755177206 scopus 로고    scopus 로고
    • Allergic contact dermatitis - chemical and metabolic mechanisms. Taylor & Francis, UK
    • Smith, C. K. and Hotchkiss, S. A. M. (2010) Allergic contact dermatitis - chemical and metabolic mechanisms. Taylor & Francis, UK.
    • (2010)
    • Smith, C.K.1    Hotchkiss, S.A.M.2
  • 37
    • 84859776911 scopus 로고    scopus 로고
    • Background on skin sensitization hazard identification: Aspects in the development of in-vitro based alternatives for sensitization testing, LRI workshop, Brussels, 02.02.2010
    • Peiser, M. (2010) Background on skin sensitization hazard identification: Aspects in the development of in-vitro based alternatives for sensitization testing, LRI workshop, Brussels, 02.02.2010, http://www.cefic-lri.org/uploads/ Events%202010/LRI-LLNA-Workshop-100202-Peiser.pdf.
    • (2010)
    • Peiser, M.1
  • 38
    • 30144443263 scopus 로고    scopus 로고
    • Compilation of historical local lymph node data for evaluation of skin sensitization alternative methods
    • Gerberick, G. F., Ryan, C. A., Kern, P. S., Schlatter, H., Dearman, R. J., Kimber, I., Patlewicz, G. Y., and Basketter, D. A. (2005) Compilation of historical local lymph node data for evaluation of skin sensitization alternative methods Dermatitis 16, 157-202 (Pubitemid 43053764)
    • (2005) Dermatitis , vol.16 , Issue.4 , pp. 157-202
    • Gerberick, G.F.1    Ryan, C.A.2    Kern, P.S.3    Schlatter, H.4    Dearman, R.J.5    Kimber, I.6    Patlewicz, G.Y.7    Basketter, D.A.8
  • 40
    • 0030956189 scopus 로고    scopus 로고
    • A re-appraisal of the skin-sensitizing activity of 2,4- dinitrothiocyanobenzene
    • DOI 10.1016/S0278-6915(96)00113-5, PII S0278691596001135
    • Dearman, R. J., Cumberbatch, M., Hilton, J., Fielding, I., Basketter, D. A., and Kimber, I. (1997) A re-appraisal of the skin-sensitizing activity of 2,4-dinitrothiocyanobenzene Food Chem. Toxicol. 35, 261-269 (Pubitemid 27187460)
    • (1997) Food and Chemical Toxicology , vol.35 , Issue.2 , pp. 261-269
    • Dearman, R.J.1    Cumberbatch, M.2    Hilton, J.3    Fielding, I.4    Basketter, D.A.5    Kimber, I.6
  • 41
    • 0033834138 scopus 로고    scopus 로고
    • Sensitizing potential of chlorothalonil in the guinea pig and the mouse
    • Boman, A., Montelius, J., Rissanen, R. L., and Liden, C. (2000) Sensitizing potential of chlorothalonil in the guinea pig and the mouse Contact Dermatitis 43, 273-279
    • (2000) Contact Dermatitis , vol.43 , pp. 273-279
    • Boman, A.1    Montelius, J.2    Rissanen, R.L.3    Liden, C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.