메뉴 건너뛰기




Volumn 41, Issue 9, 2011, Pages 783-802

A review of the electrophilic reaction chemistry involved in covalent protein binding relevant to toxicity

Author keywords

(Q)SAR Toolbox; Chemical categories; Covalent protein binding; Electrophilic reaction chemistry; Structural alerts

Indexed keywords

ALKENE; ALKYNE; CARBONYL DERIVATIVE; ISOCYANATE; NITROGEN; QUINONE DERIVATIVE; SCHIFF BASE;

EID: 80052959270     PISSN: 10408444     EISSN: 15476898     Source Type: Journal    
DOI: 10.3109/10408444.2011.598141     Document Type: Review
Times cited : (165)

References (109)
  • 1
    • 0026147821 scopus 로고
    • Structure activity hypotheses in occupational asthma caused by low molecular weight substances
    • Agius RM, Nee J, McGovern B, Robertson A. 1991. Structure activity hypotheses in occupational asthma caused by low molecular weight substances. Ann Occup Hyg 35:129-137.
    • (1991) Ann Occup Hyg , vol.35 , pp. 129-137
    • Agius, R.M.1    Nee, J.2    McGovern, B.3    Robertson, A.4
  • 2
    • 0037568064 scopus 로고    scopus 로고
    • 13C-labeled skin sensitizers, 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI)
    • Alvarez-Sánchez R, Basketter D, Pease C, Lepoittevin JP. 2003. Studies of chemical selectivity of hapten, reactivity, and skin sensitization potency. 3. Synthesis and studies on the reactivity toward model nucleophiles of the 13C-labeled skin sensitizers, 5-chloro-2-methylisothiazol-3-one (MCI) and 2-methylisothiazol-3-one (MI). Chem Res Toxicol 16:627-636. (Pubitemid 36613096)
    • (2003) Chemical Research in Toxicology , vol.16 , Issue.5 , pp. 627-636
    • Alvarez-Sanchez, R.1    Basketter, D.2    Pease, C.3    Lepoittevin, J.-P.4
  • 3
    • 70349328528 scopus 로고    scopus 로고
    • Chemical mechanisms for skin sensitization by aromatic compounds with hydroxy and amino groups
    • Aptula AO, Enoch SJ, Roberts DW. 2009. Chemical mechanisms for skin sensitization by aromatic compounds with hydroxy and amino groups. Chem Res Toxicol 22:1541-1547.
    • (2009) Chem Res Toxicol , vol.22 , pp. 1541-1547
    • Aptula, A.O.1    Enoch, S.J.2    Roberts, D.W.3
  • 4
    • 25444520273 scopus 로고    scopus 로고
    • Skin sensitization: Reaction mechanistic applicability domains for structure-activity relationships
    • DOI 10.1021/tx050075m
    • Aptula AO, Patlewicz G, Roberts DW. 2005. Skin sensitization: Reaction mechanistic applicability domains for structure-activity relationships. Chem Res Toxicol 18:1420-1426. (Pubitemid 41361715)
    • (2005) Chemical Research in Toxicology , vol.18 , Issue.9 , pp. 1420-1426
    • Aptula, A.O.1    Patlewicz, G.2    Roberts, D.W.3
  • 5
    • 30644477451 scopus 로고    scopus 로고
    • Non-enzymatic glutathione reactivity and in vitro toxicity: A non-animal approach to skin sensitization
    • DOI 10.1016/j.tiv.2005.07.003, PII S0887233305001542
    • Aptula AO, Patlewicz G, Roberts DW, Schultz TW. 2006. Non-enzymatic glutathione reactivity and in vitro toxicity: A non-animal approach to skin sensitization. Toxicol In Vitro 20:239-247. (Pubitemid 43087707)
    • (2006) Toxicology in Vitro , vol.20 , Issue.2 , pp. 239-247
    • Aptula, A.O.1    Patlewicz, G.2    Roberts, D.W.3    Schultz, T.W.4
  • 6
    • 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 AO, 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. (Pubitemid 44384841)
    • (2006) Chemical Research in Toxicology , vol.19 , Issue.8 , pp. 1097-1105
    • Aptula, A.O.1    Roberts, D.W.2
  • 7
    • 57349172613 scopus 로고    scopus 로고
    • Reactivity assays for non-animal based prediction of skin sensitisation potential
    • Aptula N, Roberts DW, Schultz TW, Pease C. 2007. Reactivity assays for non-animal based prediction of skin sensitisation potential. Toxicology 231:117-118.
    • (2007) Toxicology , vol.231 , pp. 117-118
    • Aptula, N.1    Roberts, D.W.2    Schultz, T.W.3    Pease, C.4
  • 8
    • 0029595333 scopus 로고
    • Structure activity relationships in skin sensitization using the murine local lymph node assay
    • DOI 10.1016/0300-483X(95)03132-Y
    • Ashby J, Basketter DA, Paton D, Kimber I. 1995. Structure activity relationships in skin sensitization using the murine local lymph node assay. Toxicology 103:177-194. (Pubitemid 26008365)
    • (1995) Toxicology , vol.103 , Issue.3 , pp. 177-194
    • Ashby, J.1    Basketter, D.A.2    Paton, D.3    Kimber, I.4
  • 9
    • 79952492543 scopus 로고    scopus 로고
    • Reactivity and aquatic toxicity of aromatic compounds transformable to quinone-type Michael acceptors
    • Bajot F, Cronin MT, Roberts DW, Schultz TW. 2011. Reactivity and aquatic toxicity of aromatic compounds transformable to quinone-type Michael acceptors. SAR QSAR Environ Res 22:51-65.
    • (2011) SAR QSAR Environ Res , vol.22 , pp. 51-65
    • Bajot, F.1    Cronin, M.T.2    Roberts, D.W.3    Schultz, T.W.4
  • 10
    • 0041806645 scopus 로고    scopus 로고
    • Mutagenicity and DNA damage studies of N-acyloxy-N-alkoxyamides - The role of electrophilic nitrogen
    • Banks TM, Bonin AM, Glover SA, Prakash AS. 2003. Mutagenicity and DNA damage studies of N-acyloxy-N-alkoxyamides-the role of electrophilic nitrogen. Org Biomol Chem 1:2238-2246.
    • (2003) Org Biomol Chem , vol.1 , pp. 2238-2246
    • Banks, T.M.1    Bonin, A.M.2    Glover, S.A.3    Prakash, A.S.4
  • 11
    • 0030266185 scopus 로고    scopus 로고
    • The local lymph node assay: A viable alternative to currently accepted skin sensitization tests
    • DOI 10.1016/S0278-6915(96)00059-2, PII 0278691596000592
    • Basketter DA, Gerberick G F, Kimber I, Loveless SE. 1996. Te local lymph node assay: A viable alternative to currently accepted skin sensitization tests. Food Chem Toxicol 34:985-997. (Pubitemid 27036781)
    • (1996) Food and Chemical Toxicology , vol.34 , Issue.10 , pp. 985-997
    • Basketter, D.A.1    Gerberick, G.F.2    Kimber, I.3    Loveless, S.E.4
  • 15
    • 79954550877 scopus 로고    scopus 로고
    • Mechanisms of chemical carcinogenicity and mutagenicity: A review with implications for predictive toxicology
    • Benigni R, Bossa C. (2011). Mechanisms of chemical carcinogenicity and mutagenicity: A review with implications for predictive toxicology. Chem Rev 111:2507-2536.
    • (2011) Chem Rev , vol.111 , pp. 2507-2536
    • Benigni, R.1    Bossa, C.2
  • 17
    • 34547672814 scopus 로고    scopus 로고
    • N-dealkylation of arylpiperazine derivatives: Disposition and metabolism of the 1-aryl-piperazines formed
    • DOI 10.2174/138920007781368908
    • Caccia S. (2007). N-dealkylation of arylpiperazine derivatives: Disposition and metabolism of the 1-aryl-piperazines formed. Curr Drug Metab, 8, 612-622. (Pubitemid 47209098)
    • (2007) Current Drug Metabolism , vol.8 , Issue.6 , pp. 612-622
    • Caccia, S.1
  • 18
    • 34548496649 scopus 로고    scopus 로고
    • Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway
    • DOI 10.1021/tx700139g
    • Chipinda I, Hettick JM, Simoyi RH, Siegel PD. (2007). Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway. Chem Res Toxicol 20:1084-1092. (Pubitemid 47372986)
    • (2007) Chemical Research in Toxicology , vol.20 , Issue.8 , pp. 1084-1092
    • Chipinda, I.1    Hettick, J.M.2    Simoyi, R.H.3    Siegel, P.D.4
  • 20
    • 80052949001 scopus 로고    scopus 로고
    • Formation of mechanistic categories and local models to facilitate the prediction of toxicity
    • Cronin MTD, Enoch SJ, Hewitt M, Madden JC. 2010. Formation of mechanistic categories and local models to facilitate the prediction of toxicity. ALTEX 27:127-131.
    • (2010) ALTEX , vol.27 , pp. 127-131
    • Mtd, C.1    Enoch, S.J.2    Hewitt, M.3    Madden, J.C.4
  • 21
    • 58349104593 scopus 로고    scopus 로고
    • Repair of DNA damage induced by anthanthrene, a polycyclic aromatic hydrocarbon (PAH) without bay or fjord regions
    • Desler C, Johannessen C, Rasmussen LJ. (2009). Repair of DNA damage induced by anthanthrene, a polycyclic aromatic hydrocarbon (PAH) without bay or fjord regions. Chem Biol Interact 177:212-217.
    • (2009) Chem Biol Interact , vol.177 , pp. 212-217
    • Desler, C.1    Johannessen, C.2    Rasmussen, L.J.3
  • 22
    • 74949107201 scopus 로고    scopus 로고
    • Formaldehyde-releasers in cosmetics: Relationship to formaldehyde contact allergy. Part 1. Characterization, frequency and relevance of sensitization, and frequency of use in cosmetics
    • de Groot AC, White IR, Flyvholm MA, Lensen G, Coenraads PJ. (2010). Formaldehyde-releasers in cosmetics: Relationship to formaldehyde contact allergy. Part 1. Characterization, frequency and relevance of sensitization, and frequency of use in cosmetics. Contact Derm 62:2-17.
    • (2010) Contact Derm , vol.62 , pp. 2-17
    • De Groot, A.C.1    White, I.R.2    Flyvholm, M.A.3    Lensen, G.4    Coenraads, P.J.5
  • 23
    • 69249135513 scopus 로고    scopus 로고
    • Formaldehyde-releasers: Relationship to formaldehyde contact allergy. Contact allergy to formaldehyde and inventory of formaldehyde-releasers
    • de Groot AC, Flyvholm MA, Lensen G, Menné T, Coenraads PJ. (2009). Formaldehyde-releasers: Relationship to formaldehyde contact allergy. Contact allergy to formaldehyde and inventory of formaldehyde-releasers. Contact Derm, 61:63-85.
    • (2009) Contact Derm , vol.61 , pp. 63-85
    • De Groot, A.C.1    Flyvholm, M.A.2    Lensen, G.3    Menné, T.4    Coenraads, P.J.5
  • 26
    • 80052934651 scopus 로고    scopus 로고
    • 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
    • EC. Commission of the European Communities. 2003 Union L 66/26-L 33/35 of 11.3.2003
    • EC. 2003. 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. Of J Eur Union L 66/26-L 33/35 of 11.3.2003
    • (2003) Of J Eur
  • 28
    • 80052944950 scopus 로고    scopus 로고
    • 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. Of J Eur Union L 396/1 of 30.12.2006
    • 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. Of J Eur Union L 396/1 of 30.12.2006
    • (1999)
  • 32
    • 77952638113 scopus 로고    scopus 로고
    • Using in silico tools in a weight of evidence approach to aid toxicological assessment
    • Ellison CM, Madden JC, Judson PN, Cronin MTD. 2010. Using in silico tools in a weight of evidence approach to aid toxicological assessment. Molecular Informatics 29:97-110.
    • (2010) Molecular Informatics , vol.29 , pp. 97-110
    • Ellison, C.M.1    Madden, J.C.2    Judson, P.N.3    Mtd, C.4
  • 34
    • 79958004706 scopus 로고    scopus 로고
    • Chemical category formation and read-across for the prediction of toxicity
    • In Puzyn T, Leszczynski J, Cronin MTD. (Eds.) Springer
    • Enoch SJ. 2010. Chemical category formation and read-across for the prediction of toxicity. In Puzyn T, Leszczynski J, Cronin MTD. (Eds.) Recent advances in QSAR studies: Methods and applications. Springer.
    • (2010) Recent Advances in QSAR Studies: Methods and Applications
    • Enoch, S.J.1
  • 35
    • 77955902675 scopus 로고    scopus 로고
    • A review of the electrophilic reaction chemistry involved in covalent DNA binding
    • Enoch SJ, Cronin MT. (2010). A review of the electrophilic reaction chemistry involved in covalent DNA binding. Crit Rev Toxicol 40:728-748.
    • (2010) Crit Rev Toxicol , vol.40 , pp. 728-748
    • Enoch, S.J.1    Cronin, M.T.2
  • 36
    • 79957998067 scopus 로고    scopus 로고
    • Te use of a chemistry-based profler for covalent DNA binding in the development of chemical categories for read-across for genotoxicity
    • Enoch SJ, Cronin MT, Ellison CM. (2011). Te use of a chemistry-based profler for covalent DNA binding in the development of chemical categories for read-across for genotoxicity. Altern Lab Anim 39:131-145.
    • (2011) Altern Lab Anim , vol.39 , pp. 131-145
    • Enoch, S.J.1    Cronin, M.T.2    Ellison, C.M.3
  • 37
    • 67949118899 scopus 로고    scopus 로고
    • Formation of structural categories to allow for read-across for teratogenicity
    • Enoch SJ, Cronin MTD, Madden JC, Hewitt M. 2009a. Formation of structural categories to allow for read-across for teratogenicity. QSAR & Combinatorial Science 28:696-708.
    • (2009) QSAR & Combinatorial Science , vol.28 , pp. 696-708
    • Enoch, S.J.1    Mtd, C.2    Madden, J.C.3    Hewitt, M.4
  • 38
    • 41649114183 scopus 로고    scopus 로고
    • Quantitative and mechanistic read across for predicting the skin sensitization potential of alkenes acting via Michael addition
    • Enoch SJ, Cronin MT, Schultz TW, Madden JC. (2008a). Quantitative and mechanistic read across for predicting the skin sensitization potential of alkenes acting via Michael addition. Chem Res Toxicol 21:513-520.
    • (2008) Chem Res Toxicol , vol.21 , pp. 513-520
    • Enoch, S.J.1    Cronin, M.T.2    Schultz, T.W.3    Madden, J.C.4
  • 39
    • 53849113018 scopus 로고    scopus 로고
    • Identifcation of mechanisms of toxic action for skin sensitisation using a SMARTS pattern based approach
    • Enoch SJ, Madden JC, Cronin MT. (2008b). Identifcation of mechanisms of toxic action for skin sensitisation using a SMARTS pattern based approach. SAR QSAR Environ Res 19:555-578.
    • (2008) SAR QSAR Environ Res , vol.19 , pp. 555-578
    • Enoch, S.J.1    Madden, J.C.2    Cronin, M.T.3
  • 40
    • 68949143008 scopus 로고    scopus 로고
    • Electrophilic reaction chemistry of low molecular weight respiratory sensitizers
    • Enoch SJ, Roberts DW, Cronin MT. (2009b). Electrophilic reaction chemistry of low molecular weight respiratory sensitizers. Chem Res Toxicol 22:1447-1453.
    • (2009) Chem Res Toxicol , vol.22 , pp. 1447-1453
    • Enoch, S.J.1    Roberts, D.W.2    Cronin, M.T.3
  • 41
    • 77958099452 scopus 로고    scopus 로고
    • Mechanistic category formation for the prediction of respiratory sensitisation
    • Enoch SJ, Roberts DW, Cronin MTD. 2010. Mechanistic category formation for the prediction of respiratory sensitisation. Chemical Research in Toxicology 23:1547-1555.
    • (2010) Chemical Research in Toxicology , vol.23 , pp. 1547-1555
    • Enoch, S.J.1    Roberts, D.W.2    Mtd, C.3
  • 42
    • 33749857464 scopus 로고    scopus 로고
    • A category approach for reproductive effects of phthalates
    • DOI 10.1080/10408440600894914, PII G03047055044R66X
    • Fabjan E, Hulzebos E, Mennes W, Piersma AH. (2006). A category approach for reproductive efects of phthalates. Crit Rev Toxicol 36:695-726. (Pubitemid 44564844)
    • (2006) Critical Reviews in Toxicology , vol.36 , Issue.9 , pp. 695-726
    • Fabjan, E.1    Hulzebos, E.2    Mennes, W.3    Piersma, A.H.4
  • 44
    • 12344304313 scopus 로고    scopus 로고
    • 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
    • Gerner I, Barratt MD, Zinke S, Schlegel K, 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. Altern Lab Anim 32:487-509. (Pubitemid 40128844)
    • (2004) ATLA Alternatives to Laboratory Animals , vol.32 , Issue.5 , pp. 487-509
    • Gerner, I.1    Barratt, M.D.2    Zinke, S.3    Schlegel, K.4    Schlede, E.5
  • 45
    • 77954853108 scopus 로고    scopus 로고
    • Hepatotoxicity and hepatic metabolism of available drugs: Current problems and possible solutions in preclinical stages
    • Giri S, Nieber K, Bader A. (2010). Hepatotoxicity and hepatic metabolism of available drugs: Current problems and possible solutions in preclinical stages. Expert Opin Drug Metab Toxicol, 6:895-917.
    • (2010) Expert Opin Drug Metab Toxicol , vol.6 , pp. 895-917
    • Giri, S.1    Nieber, K.2    Bader, A.3
  • 47
    • 0021262832 scopus 로고
    • Chlorination of endogenous amines by isolated neutrophils. Ammonia-dependent bactericidal, cytotoxic, and cytolytic activities of the chloramines
    • Grisham MB, Jeferson MM, Melton DF, Tomas EL. (1984). Chlorination of endogenous amines by isolated neutrophils. Ammonia-dependent bactericidal, cytotoxic, and cytolytic activities of the chloramines. J Biol Chem 259:10404-10413. (Pubitemid 14065348)
    • (1984) Journal of Biological Chemistry , vol.259 , Issue.16 , pp. 10404-10413
    • Grisham, M.B.1    Jefferson, M.M.2    Melton, D.F.3    Thomas, E.L.4
  • 48
    • 84856583073 scopus 로고    scopus 로고
    • Nickel compounds - A category approach for metals in EU Legislation
    • Hart J. 2007. Nickel compounds-a category approach for metals in EU Legislation. A report to the Danish Environmental Protection Agency. http://cms.mim.dk/NR/rdonlyres/07DB028E-134E-4796-BF6D-97B9AD5F9E82/0/Nikkel. pdf.
    • (2007) A Report to the Danish Environmental Protection Agency
    • Hart, J.1
  • 49
    • 0025003750 scopus 로고
    • Electrophiles and acute toxicity to fsh
    • Hermens JL. (1990). Electrophiles and acute toxicity to fsh. Environ Health Perspect 87:219-225.
    • (1990) Environ Health Perspect , vol.87 , pp. 219-225
    • Hermens, J.L.1
  • 50
    • 77954088460 scopus 로고    scopus 로고
    • Integrating (Q)SAR models, expert systems and read-across approaches for the prediction of developmental toxicity
    • Hewitt M, Ellison CM, Enoch SJ, Madden JC, Cronin MT. (2010). Integrating (Q)SAR models, expert systems and read-across approaches for the prediction of developmental toxicity. Reprod Toxicol 30:147-160.
    • (2010) Reprod Toxicol , vol.30 , pp. 147-160
    • Hewitt, M.1    Ellison, C.M.2    Enoch, S.J.3    Madden, J.C.4    Cronin, M.T.5
  • 52
    • 18344395176 scopus 로고    scopus 로고
    • Use of structural alerts to develop rules for identifying chemical substances with skin irritation or skin corrosion potential
    • DOI 10.1002/qsar.200430905
    • Hulzebos E, Walker JD, Gerner I, Schlegel K. 2005. Use of structural alerts to develop rules for identifying chemical substances with skin irritation or skin corrosion potential. QSAR & Combinatorial Science 24:332-342. (Pubitemid 40637935)
    • (2005) QSAR and Combinatorial Science , vol.24 , Issue.3 , pp. 332-342
    • Hulzebos, E.1    Walker, J.D.2    Gerner, I.3    Schlegel, K.4
  • 53
    • 0038682208 scopus 로고    scopus 로고
    • Verification of literature-derived SARs for skin irritation and corrosion
    • Hulzebos EM, Maslankiewicz L, Walker JD. 2003. Verifcation of literature-derived SARs for skin irritation and corrosion. QSAR & Combinatorial Science 22:351-363. (Pubitemid 36733490)
    • (2003) QSAR and Combinatorial Science , vol.22 , Issue.3 , pp. 351-363
    • Hulzebos, E.M.1    Maslankiewicz, L.2    Walker, J.D.3
  • 54
    • 67650272430 scopus 로고    scopus 로고
    • Skin sensitization and possible groupings for 'read across' for rosin based substances
    • Illing HP, Malmfors T, Rodenburg L. (2009). Skin sensitization and possible groupings for 'read across' for rosin based substances. Regul Toxicol Pharmacol 54:234-241.
    • (2009) Regul Toxicol Pharmacol , vol.54 , pp. 234-241
    • Illing, H.P.1    Malmfors, T.2    Rodenburg, L.3
  • 56
    • 34249085274 scopus 로고    scopus 로고
    • How can structural similarity analysis help in category formation?
    • Jaworska J, Nikolova-Jeliazkova N. (2007). How can structural similarity analysis help in category formation? SAR QSAR Environ Res 18:-207.
    • (2007) SAR QSAR Environ Res , vol.18 , pp. 207
    • Jaworska, J.1    Nikolova-Jeliazkova, N.2
  • 57
    • 70350273017 scopus 로고    scopus 로고
    • Structural alerts reactive metabolites, and protein covalent binding: How reliable are these attributes as predictors of drug toxicity?
    • Kalgutkar AS, Didiuk MT. (2009). Structural alerts, reactive metabolites, and protein covalent binding: How reliable are these attributes as predictors of drug toxicity? Chem Biodivers, 6:2115-2137.
    • (2009) Chem Biodivers , vol.6 , pp. 2115-2137
    • Kalgutkar, A.S.1    Didiuk, M.T.2
  • 60
    • 79151478391 scopus 로고    scopus 로고
    • Chemical reactivity measurements: Potential for characterization of respiratory chemical allergens
    • Lalko J F, Kimber I, Dearman RJ, Gerberick GF, Sarlo K, Api AM. (2011). Chemical reactivity measurements: Potential for characterization of respiratory chemical allergens. Toxicol In Vitro 25:433-445.
    • (2011) Toxicol in Vitro , vol.25 , pp. 433-445
    • Lalko, J.F.1    Kimber, I.2    Dearman, R.J.3    Gerberick, G.F.4    Sarlo, K.5    Api, A.M.6
  • 61
    • 67650587754 scopus 로고    scopus 로고
    • Nucleophilic substitution reaction at an sp2 carbon of vinyl halides with an intramolecular thiol moiety: Synthesis of thio-heterocycles
    • Lei M-Y, Xiao Y-J, Liu W-M, Fukamizu K, Chiba S, Ando K, Narasaka K. 2009. Nucleophilic substitution reaction at an sp2 carbon of vinyl halides with an intramolecular thiol moiety: Synthesis of thio-heterocycles. Tetrahedron 65:6888-6902.
    • (2009) Tetrahedron , vol.65 , pp. 6888-6902
    • Lei, M.-Y.1    Xiao, Y.-J.2    Liu, W.-M.3    Fukamizu, K.4    Chiba, S.5    Ando, K.6    Narasaka, K.7
  • 62
    • 0034780122 scopus 로고    scopus 로고
    • Chemical reactions in cottonseed protein cross-linking by formaldehyde, glutaraldehyde, and glyoxal for the formation of protein flms with enhanced mechanical properties
    • Marqui C. 2001. Chemical reactions in cottonseed protein cross-linking by formaldehyde, glutaraldehyde, and glyoxal for the formation of protein flms with enhanced mechanical properties. Journal of Agricultural and Food Chemistry 49:4676-4681.
    • (2001) Journal of Agricultural and Food Chemistry , vol.49 , pp. 4676-4681
    • Marqui, C.1
  • 63
    • 38149020825 scopus 로고    scopus 로고
    • Identifying the structural requirements for chromosomal aberration by incorporating molecular fexibility and metabolic activation of chemicals
    • Mekenyan O, Todorov M, Serafmova R, Stoeva S, Aptula A, Finking R, Jacob E. (2007). Identifying the structural requirements for chromosomal aberration by incorporating molecular fexibility and metabolic activation of chemicals. Chem Res Toxicol 20:1927-1941.
    • (2007) Chem Res Toxicol , vol.20 , pp. 1927-1941
    • Mekenyan, O.1    Todorov, M.2    Serafmova, R.3    Stoeva, S.4    Aptula, A.5    Finking, R.6    Jacob, E.7
  • 64
    • 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, 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
  • 65
    • 0035069685 scopus 로고    scopus 로고
    • Discriminating toxicant classes by mode of action: 2. Physico-chemical descriptors
    • DOI 10.100 2/1521-3838(20 0012)19:6<581::AI D-QSAR581>3.0.CO;2-A
    • Nendza M, Muller M. 2001. Discriminating toxicant classes by mode of action: 2. Physico-chemical descriptors. Quantitative Structure-Activity Relationships 19:581-598. (Pubitemid 32267159)
    • (2001) Quantitative Structure-Activity Relationships , vol.19 , Issue.6 , pp. 581-598
    • Nendza, M.1    Muller, M.2
  • 66
    • 33847008768 scopus 로고    scopus 로고
    • Discriminating toxicant classes by mode of action: 3. Substructure indicators
    • Nendza M, Müller M. (2007). Discriminating toxicant classes by mode of action: 3. Substructure indicators. SAR QSAR Environ Res 18:155-168.
    • (2007) SAR QSAR Environ Res , vol.18 , pp. 155-168
    • Nendza, M.1    Müller, M.2
  • 67
    • 33646836776 scopus 로고    scopus 로고
    • Discriminating toxicant classes by mode of action 1. (Eco)toxicity profiles
    • DOI 10.1065/espr2006.01.013
    • Nendza M, Wenzel A. (2006). Discriminating toxicant classes by mode of action. 1. (Eco)toxicity profles. Environ Sci Pollut Res Int 13:192-203. (Pubitemid 43773753)
    • (2006) Environmental Science and Pollution Research , vol.13 , Issue.3 , pp. 192-203
    • Nendza, M.1    Wenzel, A.2
  • 68
    • 33644623520 scopus 로고    scopus 로고
    • Formation and repair of interstrand cross-links in DNA
    • Noll DM, Mason TM, Miller PS. (2006). Formation and repair of interstrand cross-links in DNA. Chem Rev 106:277-301.
    • (2006) Chem Rev , vol.106 , pp. 277-301
    • Noll, D.M.1    Mason, T.M.2    Miller, P.S.3
  • 69
    • 0014480637 scopus 로고
    • Te identifcation of contact allergens by animal assay. Te guinea pig maximization test
    • Magnusson B, Kligman AM. (1969). Te identifcation of contact allergens by animal assay. Te guinea pig maximization test. J Invest Dermatol 52:268-276.
    • (1969) J Invest Dermatol , vol.52 , pp. 268-276
    • Magnusson, B.1    Kligman, A.M.2
  • 70
    • 53549100467 scopus 로고    scopus 로고
    • Can in vitro metabolism-dependent covalent binding data in liver microsomes distinguish hepatotoxic from nonhepatotoxic drugs? An analysis of 18 drugs with consideration of intrinsic clearance and daily dose
    • Obach RS, Kalgutkar AS, Soglia JR, Zhao SX. (2008). Can in vitro metabolism-dependent covalent binding data in liver microsomes distinguish hepatotoxic from nonhepatotoxic drugs? An analysis of 18 drugs with consideration of intrinsic clearance and daily dose. Chem Res Toxicol 21:1814-1822.
    • (2008) Chem Res Toxicol , vol.21 , pp. 1814-1822
    • Obach, R.S.1    Kalgutkar, A.S.2    Soglia, J.R.3    Zhao, S.X.4
  • 71
    • 72149108274 scopus 로고    scopus 로고
    • OECD. (available from
    • OECD. 2007. Guidance on Grouping of Chemicals. (available from: http://www.oecd.org/LongAbstract/0,3425,en-2649-34379-39404999-119829-1-1-37407, 00.html).
    • (2007) Guidance on Grouping of Chemicals
  • 72
    • 84856583085 scopus 로고    scopus 로고
    • OECD. (available from
    • OECD. 2009. Te OECD QSAR Application Toolbox. (available from: http://www.qsartoolbox.org/)
    • (2009) Te OECD QSAR Application Toolbox
  • 73
    • 47349112107 scopus 로고    scopus 로고
    • Toxmatch - A new software tool to aid in the development and evaluation of chemically similar groups
    • DOI 10.1080/10629360802083848, PII 793162730
    • Patlewicz G, Jeliazkova N, Gallegos Saliner A, Worth AP. (2008). Toxmatch-a new software tool to aid in the development and evaluation of chemically similar groups. SAR QSAR Environ Res 19:397-412. (Pubitemid 351998861)
    • (2008) SAR and QSAR in Environmental Research , vol.19 , Issue.3-4 , pp. 397-412
    • Patlewicz, G.1    Jeliazkova, N.2    Gallegos Saliner, A.3    Worth, A.P.4
  • 76
    • 0028167546 scopus 로고
    • Structure-activity relationships for skin sensitization potential: Development of structural alerts for use in knowledge-based toxicity prediction systems
    • Payne MP, Walsh PT. (1994). Structure-activity relationships for skin sensitization potential: Development of structural alerts for use in knowledge-based toxicity prediction systems. J Chem Inf Comput Sci 34:154-161.
    • (1994) J Chem Inf Comput Sci , vol.34 , pp. 154-161
    • Payne, M.P.1    Walsh, P.T.2
  • 77
    • 0035283131 scopus 로고    scopus 로고
    • Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine, and ascorbate
    • DOI 10.1016/S0891-5849(00)00506-2, PII S0891584900005062
    • Peskin AV, Winterbourn CC. (2001). Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine, and ascorbate. Free Radic Biol Med 30:572-579. (Pubitemid 32162964)
    • (2001) Free Radical Biology and Medicine , vol.30 , Issue.5 , pp. 572-579
    • Peskin, A.V.1    Winterbourn, C.C.2
  • 78
    • 14744285303 scopus 로고    scopus 로고
    • Characterization of monochloramine toxicity on PC12 cells and protective effect of tocopherol via antioxidative function
    • DOI 10.1016/j.abb.2005.01.021
    • Piga R, Saito Y, Chen Z, Yoshida Y, Niki E. (2005). Characterization of monochloramine toxicity on PC12 cells and protective efect of tocopherol via antioxidative function. Arch Biochem Biophys 436:101-109. (Pubitemid 40332430)
    • (2005) Archives of Biochemistry and Biophysics , vol.436 , Issue.1 , pp. 101-109
    • Piga, R.1    Saito, Y.2    Chen, Z.3    Yoshida, Y.4    Niki, E.5
  • 79
    • 77953636959 scopus 로고    scopus 로고
    • Reactivity assays: Dealing with substances and samples in an in vitro world - The solution and the real problem
    • Roberts DW, Basketter DA. (2010). Reactivity assays: Dealing with substances and samples in an in vitro world-the solution and the real problem. Contact Derm 63:55-56.
    • (2010) Contact Derm , vol.63 , pp. 55-56
    • Roberts, D.W.1    Basketter, D.A.2
  • 80
    • 33749004016 scopus 로고    scopus 로고
    • Mechanistic applicability domains for non-animal based prediction of toxicological endpoints. QSAR analysis of the Schiff base applicability domain for skin sensitization
    • DOI 10.1021/tx060102o
    • Roberts DW, Aptula AO, Patlewicz G. (2006). Mechanistic applicability domains for non-animal based prediction of toxicological endpoints. QSAR analysis of the schif base applicability domain for skin sensitization. Chem Res Toxicol 19:1228-1233. (Pubitemid 44454040)
    • (2006) Chemical Research in Toxicology , vol.19 , Issue.9 , pp. 1228-1233
    • Roberts, D.W.1    Aptula, A.O.2    Patlewicz, G.3
  • 81
    • 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 DW, Aptula AO, Patlewicz G. (2007a). Electrophilic chemistry related to skin sensitization. Reaction mechanistic applicability domain classifcation 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
  • 85
    • 57349146797 scopus 로고    scopus 로고
    • Category analysis of the substituted anilines studied in a 28-day repeat-dose toxicity test conducted on rats: Correlation between toxicity and chemical structure
    • Sakuratani Y, Sato S, Nishikawa S, Yamada J, Maekawa A, Hayashi M. (2008). Category analysis of the substituted anilines studied in a 28-day repeat-dose toxicity test conducted on rats: Correlation between toxicity and chemical structure. SAR QSAR Environ Res 19:681-696.
    • (2008) SAR QSAR Environ Res , vol.19 , pp. 681-696
    • Sakuratani, Y.1    Sato, S.2    Nishikawa, S.3    Yamada, J.4    Maekawa, A.5    Hayashi, M.6
  • 88
    • 78649797207 scopus 로고    scopus 로고
    • Reactivity-based toxicity modelling of fve-membered heterocyclic compounds: Application to Tetrahymena pyriformis
    • Schultz TW, Sparfkin CL, Aptula AO. (2010). Reactivity-based toxicity modelling of fve-membered heterocyclic compounds: Application to Tetrahymena pyriformis. SAR QSAR Environ Res 21:681-691.
    • (2010) SAR QSAR Environ Res , vol.21 , pp. 681-691
    • Schultz, T.W.1    Sparfkin, C.L.2    Aptula, A.O.3
  • 90
    • 13844294282 scopus 로고    scopus 로고
    • Structure-toxicity relationships for the effects to Tetrahymena pyriformis of aliphatic, carbonyl-containing, α,β-unsaturated chemicals
    • DOI 10.1021/tx049833j
    • Schultz TW, Netzeva TI, Roberts DW, Cronin MT. (2005a). Structure-toxicity relationships for the efects to Tetrahymena pyriformis of aliphatic, carbonyl-containing, alpha,beta-unsaturated chemicals. Chem Res Toxicol 18:330-341. (Pubitemid 40256254)
    • (2005) Chemical Research in Toxicology , vol.18 , Issue.2 , pp. 330-341
    • Schultz, T.W.1    Netzeva, T.I.2    Roberts, D.W.3    Cronin, M.T.D.4
  • 91
    • 33847041550 scopus 로고    scopus 로고
    • Structure-activity relationships for abiotic thiol reactivity and aquatic toxicity of halo-substituted carbonyl compounds
    • Schultz TW, Ralston KE, Roberts DW, Veith GD, Aptula AO. (2007a). Structure-activity relationships for abiotic thiol reactivity and aquatic toxicity of halo-substituted carbonyl compounds. SAR QSAR Environ Res 18:21-29.
    • (2007) SAR QSAR Environ Res , vol.18 , pp. 21-29
    • Schultz, T.W.1    Ralston, K.E.2    Roberts, D.W.3    Veith, G.D.4    Aptula, A.O.5
  • 92
    • 58149293575 scopus 로고    scopus 로고
    • Read-across to rank skin sensitization potential: Subcategories for the Michael acceptor domain
    • Schultz TW, Rogers K, Aptula AO. (2009). Read-across to rank skin sensitization potential: Subcategories for the Michael acceptor domain. Contact Derm 60:21-31.
    • (2009) Contact Derm , vol.60 , pp. 21-31
    • Schultz, T.W.1    Rogers, K.2    Aptula, A.O.3
  • 94
    • 1642289985 scopus 로고    scopus 로고
    • Trends in structure-toxicity relationships for carbonyl-containing α,β-unsaturated compounds
    • DOI 10.1080/10629360410001665839
    • Schultz TW, Yarbrough JW. (2004). Trends in structure-toxicity relationships for carbonyl-containing alpha,beta-unsaturated compounds. SAR QSAR Environ Res 15:139-146. (Pubitemid 38390852)
    • (2004) SAR and QSAR in Environmental Research , vol.15 , Issue.2 , pp. 139-146
    • Schultz, T.W.1    Yarbrough, J.W.2
  • 96
    • 24644446845 scopus 로고    scopus 로고
    • Structure-activity relationships for reactivity of carbonyl-containing compounds with glutathione
    • DOI 10.1080/10659360500204152
    • Schultz TW, Yarbrough JW, Johnson EL. (2005b). Structure-activity relationships for reactivity of carbonyl-containing compounds with glutathione. SAR QSAR Environ Res 16:313-322. (Pubitemid 41283776)
    • (2005) SAR and QSAR in Environmental Research , vol.16 , Issue.4 , pp. 313-322
    • Schultz, T.W.1    Yarbrough, J.W.2    Johnson, E.L.3
  • 98
    • 0028905042 scopus 로고
    • Sulfur mustard: Its continuing threat as a chemical warfare agent, the cutaneous lesions induced, progress in understanding its mechanism of action, its long-term health efects, and new developments for protection and therapy
    • Smith KJ, Hurst CG, Moeller RB, Skelton HG, Sidell FR. (1995). Sulfur mustard: Its continuing threat as a chemical warfare agent, the cutaneous lesions induced, progress in understanding its mechanism of action, its long-term health efects, and new developments for protection and therapy. J Am Acad Dermatol 32:765-776.
    • (1995) J Am Acad Dermatol , vol.32 , pp. 765-776
    • Smith, K.J.1    Hurst, C.G.2    Moeller, R.B.3    Skelton, H.G.4    Sidell, F.R.5
  • 99
    • 15144351089 scopus 로고
    • Te reaction mechanism of azodicarbonamide in dough
    • Tsen CC. 1963. Te reaction mechanism of azodicarbonamide in dough. Cereal Chemistry 40:638-647.
    • (1963) Cereal Chemistry , vol.40 , pp. 638-647
    • Tsen, C.C.1
  • 101
    • 77955854810 scopus 로고    scopus 로고
    • US EPA.
    • US EPA. 2009. Chemical categories report (http://www.epa.gov/opptintr/ newchems/pubs/chemcat.htm).
    • (2009) Chemical Categories Report
  • 104
    • 0026785215 scopus 로고
    • Classifying environmental pollutants. 1: Structure-activity relationships for prediction of aquatic toxicity
    • Verhaar HJM, Van Leeuwen CJ, Hermens JLM. 1992.) Classifying environmental pollutants. 1: Structure-activity relationships for prediction of aquatic toxicity. Chemosphere 25:471-491.
    • (1992) Chemosphere , vol.25 , pp. 471-491
    • Hjm, V.1    Van Leeuwen, C.J.2    Hermens, J.L.M.3
  • 105
    • 15344344378 scopus 로고    scopus 로고
    • Structural alerts - A new classification model to discriminate excess toxicity from narcotic effect levels of organic compounds in the acute daphnid assay
    • DOI 10.1021/tx0497954
    • von der Ohe PC, Kühne R, Ebert RU, Altenburger R, Liess M, Schüürmann G. (2005). Structural alerts-a new classifcation model to discriminate excess toxicity from narcotic efect levels of organic compounds in the acute daphnid assay. Chem Res Toxicol 18:536-555. (Pubitemid 40393175)
    • (2005) Chemical Research in Toxicology , vol.18 , Issue.3 , pp. 536-555
    • Von Der Ohe, P.C.1    Kuhne, R.2    Ebert, R.-U.3    Altenburger, R.4    Liess, M.5    Schuurmann, G.6
  • 106
    • 54949104386 scopus 로고    scopus 로고
    • Structure-activity relationships for aldehyde categories
    • Walker JD, Printup H. 2008. Structure-activity relationships for aldehyde categories. QSAR and Combinatorial Science 27:475-482.
    • (2008) QSAR and Combinatorial Science , vol.27 , pp. 475-482
    • Walker, J.D.1    Printup, H.2
  • 107
    • 75549092069 scopus 로고    scopus 로고
    • A framework for using structural, reactivity, metabolic and physicochemical similarity to evaluate the suitability of analogs for SAR-based toxicological assessments
    • Wu S, Blackburn K, Amburgey J, Jaworska J, Federle T. (2010). A framework for using structural, reactivity, metabolic and physicochemical similarity to evaluate the suitability of analogs for SAR-based toxicological assessments. Regul Toxicol Pharmacol 56:67-81.
    • (2010) Regul Toxicol Pharmacol , vol.56 , pp. 67-81
    • Wu, S.1    Blackburn, K.2    Amburgey, J.3    Jaworska, J.4    Federle, T.5
  • 108
    • 20444412643 scopus 로고    scopus 로고
    • Metabolic activation of polycyclic and heterocyclic aromatic hydrocarbons and DNA damage: A review
    • DOI 10.1016/j.taap.2004.11.006, PII S0041008X04005149
    • Xue W, Warshawsky D. (2005). Metabolic activation of polycyclic and heterocyclic aromatic hydrocarbons and DNA damage: A review. Toxicol Appl Pharmacol 206:73-93. (Pubitemid 40800430)
    • (2005) Toxicology and Applied Pharmacology , vol.206 , Issue.1 , pp. 73-93
    • Xue, W.1    Warshawsky, D.2
  • 109
    • 0036323878 scopus 로고    scopus 로고
    • Evaluation of a rule base for identifying contact allergens by using a regulatory database: Comparison of data on chemicals notified in the European Union with "structural alerts" used in the DEREK expert system
    • Zinke S, Gerner I, Schlede E. (2002). Evaluation of a rule base for identifying contact allergens by using a regulatory database: Comparison of data on chemicals notifed in the European Union with "structural alerts" used in the DEREK expert system. Altern Lab Anim 30:285-298. (Pubitemid 34815271)
    • (2002) ATLA Alternatives to Laboratory Animals , vol.30 , Issue.3 , pp. 285-298
    • Zinke, S.1    Gerner, I.2    Schlede, E.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.