메뉴 건너뛰기




Volumn 21, Issue 3, 2008, Pages 643-658

Decabromobiphenyl (PBB-209) activates the aryl hydrocarbon receptor while decachlorobiphenyl (PCB-209) is inactive: Experimental evidence and computational rationalization of the different behavior of some halogenated biphenyls

Author keywords

[No Author keywords available]

Indexed keywords

3,3',4,4',5 PENTACHLOROBIPHENYL; AROMATIC HYDROCARBON RECEPTOR; BIPHENYL DERIVATIVE; DECABROMOBIPHENYL; DECACHLOROBIPHENYL; UNCLASSIFIED DRUG;

EID: 84962338779     PISSN: 0893228X     EISSN: None     Source Type: Journal    
DOI: 10.1021/tx700362u     Document Type: Article
Times cited : (17)

References (139)
  • 1
    • 0020010617 scopus 로고
    • 2,3,7,8 Tetrachlorodibenzo -p-dioxin and related halogenated aromatic hydrocarbons: Examination of the mechanism of toxicity
    • Poland, A., and Knutson, J. C. (1982) 2,3,7,8 Tetrachlorodibenzo -p-dioxin and related halogenated aromatic hydrocarbons: Examination of the mechanism of toxicity. Annu. Rev. Pharmacol. Toxicol. 22, 517-554.
    • (1982) Annu. Rev. Pharmacol. Toxicol , vol.22 , pp. 517-554
    • Poland, A.1    Knutson, J.C.2
  • 2
    • 2042506296 scopus 로고    scopus 로고
    • In vitro metabolism of polychlorinated biphenyl congeners by beluga whale (Dephinanterus leucas) and pilot whale (Globicephala melas) and relationship to cytochrome P450 expression
    • White, R. D., Shea, D., Schlezinger, J. J., Hahn, M. E., and Stegeman, J. J. (2000) In vitro metabolism of polychlorinated biphenyl congeners by beluga whale (Dephinanterus leucas) and pilot whale (Globicephala melas) and relationship to cytochrome P450 expression. Comp. Biochem. Physiol. 126C, 267-284.
    • (2000) Comp. Biochem. Physiol , vol.126 C , pp. 267-284
    • White, R.D.1    Shea, D.2    Schlezinger, J.J.3    Hahn, M.E.4    Stegeman, J.J.5
  • 3
    • 0036223696 scopus 로고    scopus 로고
    • Sulfhydryl binding and topoisomerase inhibition by PCB metabolites
    • Srinivasan, A., Robertson, L. W., and Ludewig, G. (2002) Sulfhydryl binding and topoisomerase inhibition by PCB metabolites. Chem. Res. Toxicol. 15, 497-505.
    • (2002) Chem. Res. Toxicol , vol.15 , pp. 497-505
    • Srinivasan, A.1    Robertson, L.W.2    Ludewig, G.3
  • 4
    • 33749388483 scopus 로고    scopus 로고
    • Polychlorinated biphenyls and hydroxylated polychlorinated biphenyls in plasma of bottlenose dolphins (Tursiops truncatus) from the Western Atlantic and the Gulf of Mexico
    • Houde, M., Pacepavicius, G., Wells, R. S., Fair, P. A., Letcher, R. J., Alaee, M., Bossart, G. D., Hohn, A. A., Sweeney, J., Solomon, K. R., and Muir, D. C. (2006) Polychlorinated biphenyls and hydroxylated polychlorinated biphenyls in plasma of bottlenose dolphins (Tursiops truncatus) from the Western Atlantic and the Gulf of Mexico. Environ. Sci. Technol. 40, 5860-5866.
    • (2006) Environ. Sci. Technol , vol.40 , pp. 5860-5866
    • Houde, M.1    Pacepavicius, G.2    Wells, R.S.3    Fair, P.A.4    Letcher, R.J.5    Alaee, M.6    Bossart, G.D.7    Hohn, A.A.8    Sweeney, J.9    Solomon, K.R.10    Muir, D.C.11
  • 5
    • 27644570731 scopus 로고    scopus 로고
    • Levels and trends of polychlorinated dibenzo-p-dioxins/furans (PCDD/Fs) and dioxin-like polychlorinated biphenyls (PCBs) in Spanish commercial fish and shellfish products, 1995-2003
    • Gomara, B., Bordajandi, L. R., Fernandez, M. A., Herrero, L., Abad, E., Abalos, M., Rivera, J., and Gonzalez, M. J. (2005) Levels and trends of polychlorinated dibenzo-p-dioxins/furans (PCDD/Fs) and dioxin-like polychlorinated biphenyls (PCBs) in Spanish commercial fish and shellfish products, 1995-2003. J. Agric. Food Chem. 53, 8406-8413.
    • (2005) J. Agric. Food Chem , vol.53 , pp. 8406-8413
    • Gomara, B.1    Bordajandi, L.R.2    Fernandez, M.A.3    Herrero, L.4    Abad, E.5    Abalos, M.6    Rivera, J.7    Gonzalez, M.J.8
  • 6
    • 25144445380 scopus 로고    scopus 로고
    • Brominated frame retardants and other organobromines in Norwegian predatory bird eggs
    • Herzke, D., Berger, U., Kallenborn, R., Nygard, T., and Vetter, W. (2005) Brominated frame retardants and other organobromines in Norwegian predatory bird eggs. Chemosphere 61, 441-449.
    • (2005) Chemosphere , vol.61 , pp. 441-449
    • Herzke, D.1    Berger, U.2    Kallenborn, R.3    Nygard, T.4    Vetter, W.5
  • 8
    • 33645938310 scopus 로고    scopus 로고
    • Polychlorinated biphenyls (PCBs): Routes of exposure and effects on human health
    • Carpenter, D. O. (2006) Polychlorinated biphenyls (PCBs): Routes of exposure and effects on human health. Rev. Environ. Health. 21, 1-23.
    • (2006) Rev. Environ. Health , vol.21 , pp. 1-23
    • Carpenter, D.O.1
  • 9
    • 0032522907 scopus 로고    scopus 로고
    • Impact of dioxin-type induction of drug-metabolizing enzymes on the metabolism of endo- and xenobiotics
    • Schrenk, D. (1998) Impact of dioxin-type induction of drug-metabolizing enzymes on the metabolism of endo- and xenobiotics. Biochem. Pharmacol. 55, 1155-1162.
    • (1998) Biochem. Pharmacol , vol.55 , pp. 1155-1162
    • Schrenk, D.1
  • 10
    • 84907112511 scopus 로고
    • Carcinogenicity of polyhalogenated biphenyls: PCBs and PBBs
    • Silberhorn, E. M., Glauert, H. P., and Robertson, L. W. (1990) Carcinogenicity of polyhalogenated biphenyls: PCBs and PBBs. Crit. Rev. Toxicol. 20, 440-496.
    • (1990) Crit. Rev. Toxicol , vol.20 , pp. 440-496
    • Silberhorn, E.M.1    Glauert, H.P.2    Robertson, L.W.3
  • 11
    • 84962366940 scopus 로고    scopus 로고
    • ATSDR (2000) U.S. Department of Health and Human Services, Public Health Service, Agency for Toxic Substances and Disease Registry, Toxicological Profile for Polychlorinated Biphenyls.
    • ATSDR (2000) U.S. Department of Health and Human Services, Public Health Service, Agency for Toxic Substances and Disease Registry, Toxicological Profile for Polychlorinated Biphenyls.
  • 12
    • 0036223196 scopus 로고    scopus 로고
    • An overview of brominated flame retardants in the environment
    • de Wit, C. A. (2002) An overview of brominated flame retardants in the environment. Chemosphere 46, 583-624.
    • (2002) Chemosphere , vol.46 , pp. 583-624
    • de Wit, C.A.1
  • 13
    • 0242319568 scopus 로고    scopus 로고
    • An overview of commercially used brominated flame retardants their applications, their use patterns in different countries/regions and possible modes of release
    • Alaee, M., Arias, P., Sjodinc, A., and Bergmand, A. (2003) An overview of commercially used brominated flame retardants their applications, their use patterns in different countries/regions and possible modes of release. Environ. Int. 29, 683-689.
    • (2003) Environ. Int , vol.29 , pp. 683-689
    • Alaee, M.1    Arias, P.2    Sjodinc, A.3    Bergmand, A.4
  • 15
    • 84962343866 scopus 로고    scopus 로고
    • Directive 76/769/EEC. Council directive of 27 July 1976 on the approximation of the laws, regulations and administrative provisions of the Member States relating to restrictions on the marketing and use of certain dangerous substances and preparations.
    • Directive 76/769/EEC. Council directive of 27 July 1976 on the approximation of the laws, regulations and administrative provisions of the Member States relating to restrictions on the marketing and use of certain dangerous substances and preparations.
  • 16
    • 84962477079 scopus 로고    scopus 로고
    • Directive 2002/95/EC of the European Parliament and of the Council of 27 January 2003 on the restriction of the use of certain hazardous substance in electrical and electric equipment. Off. J. Eur. Union, 13.2.2003.
    • Directive 2002/95/EC of the European Parliament and of the Council of 27 January 2003 on the restriction of the use of certain hazardous substance in electrical and electric equipment. Off. J. Eur. Union, 13.2.2003.
  • 17
    • 84962477075 scopus 로고    scopus 로고
    • ATSDR (2004) U.S. Department of Health and Human Services, Public Health Service, Agency for Toxic Substances and Disease Registry, Toxicological Profile for Polybrominated Biphenyls and Polybrominated Diphenyl Ethers.
    • ATSDR (2004) U.S. Department of Health and Human Services, Public Health Service, Agency for Toxic Substances and Disease Registry, Toxicological Profile for Polybrominated Biphenyls and Polybrominated Diphenyl Ethers.
  • 18
    • 0024997614 scopus 로고
    • Polychlorinated biphenyls dibenzo-p-dioxins, dibenzofurans and related compounds: Environmental and mechanistic considerations which support the development of toxic equivalency factors (TEF)
    • Safe, S. (1990) Polychlorinated biphenyls dibenzo-p-dioxins, dibenzofurans and related compounds: Environmental and mechanistic considerations which support the development of toxic equivalency factors (TEF). Crit. Rev. Toxicol. 21, 1-88.
    • (1990) Crit. Rev. Toxicol , vol.21 , pp. 1-88
    • Safe, S.1
  • 19
    • 0028985279 scopus 로고
    • Increased [3H]phorbol ester binding in rat cerebellar granule cells by polychlorinated biphenyl mixtures and congeners: Structure-activity relationships
    • Kodavanti, P. R. S., Ward, T. R., McKinney, J. D., and Tilson, H. A. (1995) Increased [3H]phorbol ester binding in rat cerebellar granule cells by polychlorinated biphenyl mixtures and congeners: Structure-activity relationships. Toxicol. Appl. Pharmacol. 130, 140-148.
    • (1995) Toxicol. Appl. Pharmacol , vol.130 , pp. 140-148
    • Kodavanti, P.R.S.1    Ward, T.R.2    McKinney, J.D.3    Tilson, H.A.4
  • 20
    • 0142074373 scopus 로고    scopus 로고
    • Potential human cancer risks from exposure to PCBs: A tale of two evaluations
    • Golden, R., Doull, J., Waddell, W., and Mandel, J. (2003) Potential human cancer risks from exposure to PCBs: A tale of two evaluations. Crit. Rev. Toxicol. 33, 543-580.
    • (2003) Crit. Rev. Toxicol , vol.33 , pp. 543-580
    • Golden, R.1    Doull, J.2    Waddell, W.3    Mandel, J.4
  • 21
    • 33745612970 scopus 로고    scopus 로고
    • Cellular and molecular mechanisms mediating the effect of polychlorinated biphenyls on oocyte in vitro maturation
    • Pocar, P., Brevini, T. A. L., Antonini, S., and Gandolfi, F. (2006) Cellular and molecular mechanisms mediating the effect of polychlorinated biphenyls on oocyte in vitro maturation. Reprod. Toxicol. 22, 242-249.
    • (2006) Reprod. Toxicol , vol.22 , pp. 242-249
    • Pocar, P.1    Brevini, T.A.L.2    Antonini, S.3    Gandolfi, F.4
  • 22
    • 29144470328 scopus 로고    scopus 로고
    • Environmental xenobiotics and nuclear receptors - Interactions effects and in vitro assessment
    • Janosek, J., Hilscherova, K., Blaha, L., and Holoubek, I. (2006) Environmental xenobiotics and nuclear receptors - Interactions effects and in vitro assessment. Toxicol. in Vitro 20, 18-37.
    • (2006) Toxicol. in Vitro , vol.20 , pp. 18-37
    • Janosek, J.1    Hilscherova, K.2    Blaha, L.3    Holoubek, I.4
  • 23
    • 0022916441 scopus 로고
    • Structurally specific binding of halogenated biphenyls to thyroxine transport protein
    • Rickenbacher, U., McKinney, J. D., Oatley, S. J., and Blake, C. C. F. (1986) Structurally specific binding of halogenated biphenyls to thyroxine transport protein. J. Med. Chem. 29, 641-648.
    • (1986) J. Med. Chem , vol.29 , pp. 641-648
    • Rickenbacher, U.1    McKinney, J.D.2    Oatley, S.J.3    Blake, C.C.F.4
  • 24
    • 17144447462 scopus 로고    scopus 로고
    • Effect of highly bioaccumulated polychlorinated biphenyl congeners on estrogen and androgen receptor activity
    • Bonefeld-Jørgensen, E. C., Andersen, H. R., Rasmussen, T. H., and Vinggaard, A. M. (2001) Effect of highly bioaccumulated polychlorinated biphenyl congeners on estrogen and androgen receptor activity. Toxicology 158, 141-153.
    • (2001) Toxicology , vol.158 , pp. 141-153
    • Bonefeld-Jørgensen, E.C.1    Andersen, H.R.2    Rasmussen, T.H.3    Vinggaard, A.M.4
  • 25
    • 0036167913 scopus 로고    scopus 로고
    • A molecular motif required for the activation of rat neutrophil phospholipase A2 by organochlorine compounds
    • Olivero, J., Bezdecny, S. A., and Ganey, P. E. (2002) A molecular motif required for the activation of rat neutrophil phospholipase A2 by organochlorine compounds. Chem. Res. Toxicol. 15, 153-159.
    • (2002) Chem. Res. Toxicol , vol.15 , pp. 153-159
    • Olivero, J.1    Bezdecny, S.A.2    Ganey, P.E.3
  • 26
    • 33745624266 scopus 로고    scopus 로고
    • c-Src is the primary signaling mediator of polychlorinated biphenyl-induced interleukin-8 expression in a human microvascular endothelial cell line
    • Eum, S. Y., Rha, G. B., Hennig, B., and Toborek, M. (2006) c-Src is the primary signaling mediator of polychlorinated biphenyl-induced interleukin-8 expression in a human microvascular endothelial cell line. Toxicol. Sci. 92, 311-320.
    • (2006) Toxicol. Sci , vol.92 , pp. 311-320
    • Eum, S.Y.1    Rha, G.B.2    Hennig, B.3    Toborek, M.4
  • 28
    • 0027458138 scopus 로고
    • The Ah-receptor - Genetics structure and function
    • Swanson, H. I., and Bradfield, C. A. (1993) The Ah-receptor - Genetics structure and function. Pharmacogenetics 3, 213-230.
    • (1993) Pharmacogenetics , vol.3 , pp. 213-230
    • Swanson, H.I.1    Bradfield, C.A.2
  • 29
    • 0028987872 scopus 로고
    • The Aryl-hydrocarbon receptor complex
    • Hankinson, O. (1995) The Aryl-hydrocarbon receptor complex. Annu. Rev. Pharmacol. Toxicol. 35, 307-340.
    • (1995) Annu. Rev. Pharmacol. Toxicol , vol.35 , pp. 307-340
    • Hankinson, O.1
  • 30
    • 0034087885 scopus 로고    scopus 로고
    • Mechanistic aspects the dioxin (aryl hydrocarbon) receptor
    • Poellinger, L. (2000) Mechanistic aspects the dioxin (aryl hydrocarbon) receptor. Food Addit. Contam. 17, 261-266.
    • (2000) Food Addit. Contam , vol.17 , pp. 261-266
    • Poellinger, L.1
  • 31
    • 34447511096 scopus 로고    scopus 로고
    • The aryl hydrocarbon receptor more than a xenobiotic-interacting protein
    • Barouki, R., Coumoul, X., and Fernandez-Salguero, P. M. (2007) The aryl hydrocarbon receptor more than a xenobiotic-interacting protein. FEBS Lett. 581, 3608-3615.
    • (2007) FEBS Lett , vol.581 , pp. 3608-3615
    • Barouki, R.1    Coumoul, X.2    Fernandez-Salguero, P.M.3
  • 32
    • 34447530842 scopus 로고    scopus 로고
    • An aryl hydrocarbon receptor odyssey to the shores of toxicology
    • Okey, A. B. (2007) An aryl hydrocarbon receptor odyssey to the shores of toxicology. Toxicol. Sci. 98, 5-38.
    • (2007) Toxicol. Sci , vol.98 , pp. 5-38
    • Okey, A.B.1
  • 33
    • 0036385626 scopus 로고    scopus 로고
    • Specificity of nuclear protein binding to a CYP1A1 negative regulatory element
    • Nagy, S. R., and Denison, M. S. (2002) Specificity of nuclear protein binding to a CYP1A1 negative regulatory element. Biochem. Biophys. Res. Commun. 296, 799-805.
    • (2002) Biochem. Biophys. Res. Commun , vol.296 , pp. 799-805
    • Nagy, S.R.1    Denison, M.S.2
  • 34
    • 0036961084 scopus 로고    scopus 로고
    • Use of 1-125 4′-iodoflavone as a tool to characterize ligand-dependent differences in Ah receptor behavior
    • Swanson, H. I., Whitelaw, M. L., Petrulis, J. R., and Perdew, G. H. (2002) Use of 1-125 4′-iodoflavone as a tool to characterize ligand-dependent differences in Ah receptor behavior. J. Biochem. Mol. Toxicol. 16, 298-310.
    • (2002) J. Biochem. Mol. Toxicol , vol.16 , pp. 298-310
    • Swanson, H.I.1    Whitelaw, M.L.2    Petrulis, J.R.3    Perdew, G.H.4
  • 36
    • 84892268812 scopus 로고    scopus 로고
    • Induction of cytochrome P450 enzymes
    • 3rd ed, Ortízde Montellano, P, Ed, pp, Kluwer Academic/Plenum Publishers, New York
    • Williams, S. N., Dunham, E., and Bradfield, C. A. (2005) Induction of cytochrome P450 enzymes. In Cytochrome P450. Structure, Mechanism, and Biochemistry, 3rd ed. (Ortízde Montellano, P., Ed.) pp 323-346, Kluwer Academic/Plenum Publishers, New York.
    • (2005) Cytochrome P450. Structure, Mechanism, and Biochemistry , pp. 323-346
    • Williams, S.N.1    Dunham, E.2    Bradfield, C.A.3
  • 37
    • 34547681417 scopus 로고    scopus 로고
    • Cytochrome P450 gene regulation and physiological functions mediated by the aryl hydrocarbon receptor
    • Kawajiri, K., and Fujii-Kuriyama, Y. (2007) Cytochrome P450 gene regulation and physiological functions mediated by the aryl hydrocarbon receptor. Arch. Biochem. Biophys. 464, 207-212.
    • (2007) Arch. Biochem. Biophys , vol.464 , pp. 207-212
    • Kawajiri, K.1    Fujii-Kuriyama, Y.2
  • 38
    • 0028978788 scopus 로고
    • Three dimensional quantitative structure-activity relationships of dioxins and dioxin-like compounds: Model validation and Ah receptor characterization
    • Waller, C. L., and McKinney, J. D. (1995) Three dimensional quantitative structure-activity relationships of dioxins and dioxin-like compounds: Model validation and Ah receptor characterization. Chem. Res. Toxicol. 8, 847-858.
    • (1995) Chem. Res. Toxicol , vol.8 , pp. 847-858
    • Waller, C.L.1    McKinney, J.D.2
  • 39
    • 0027049081 scopus 로고
    • A new structure activity model for Ah receptor-binding-polychlorinated dibenzo-p-dioxins and dibenzofurans
    • Kafafi, S. A., Afeefy, H. Y., Said, H. K., and Hakimi, J. M. (1992) A new structure activity model for Ah receptor-binding-polychlorinated dibenzo-p-dioxins and dibenzofurans. Chem. Res. Toxicol. 5, 856-862.
    • (1992) Chem. Res. Toxicol , vol.5 , pp. 856-862
    • Kafafi, S.A.1    Afeefy, H.Y.2    Said, H.K.3    Hakimi, J.M.4
  • 40
    • 0027299699 scopus 로고
    • Relationship between aryl-hydrocarbon receptor-binding, induction of aryl-hydrocarbon hydroxylase and 7 ethoxyresorufin O-deethylase enzymes, and toxic activities of aromatic xenobiotics in animals. A new model
    • Kafafi, S. A., Afeefy, H. Y., Said, H. K., and Kafafi, A. G. (1993) Relationship between aryl-hydrocarbon receptor-binding, induction of aryl-hydrocarbon hydroxylase and 7 ethoxyresorufin O-deethylase enzymes, and toxic activities of aromatic xenobiotics in animals. A new model. Chem. Res. Toxicol. 6, 328-334.
    • (1993) Chem. Res. Toxicol , vol.6 , pp. 328-334
    • Kafafi, S.A.1    Afeefy, H.Y.2    Said, H.K.3    Kafafi, A.G.4
  • 41
    • 84962448835 scopus 로고    scopus 로고
    • Computational studies on biphenyl derivatives. Analysis of the conformational mobility, molecular electrostatic potential, and dipole moment of chlorinated biphenyl: Searching for the rationalization of the selective toxicity of polychlorinated biphenyls (PCBs)
    • Chana, A., Concejero, M. A., de Frutos, M., Gonzalez, M. J., and Herradon, B. (2002) Computational studies on biphenyl derivatives. Analysis of the conformational mobility, molecular electrostatic potential, and dipole moment of chlorinated biphenyl: Searching for the rationalization of the selective toxicity of polychlorinated biphenyls (PCBs). Chem. Res. Toxicol. 15, 1514-1526.
    • (2002) Chem. Res. Toxicol , vol.15 , pp. 1514-1526
    • Chana, A.1    Concejero, M.A.2    de Frutos, M.3    Gonzalez, M.J.4    Herradon, B.5
  • 42
    • 0038768712 scopus 로고    scopus 로고
    • Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals
    • Denison, M. S., and Nagy, S. R. (2003) Activation of the aryl hydrocarbon receptor by structurally diverse exogenous and endogenous chemicals. Annu. Rev. Pharmacol. Toxicol. 43, 309-334.
    • (2003) Annu. Rev. Pharmacol. Toxicol , vol.43 , pp. 309-334
    • Denison, M.S.1    Nagy, S.R.2
  • 43
    • 0037568105 scopus 로고    scopus 로고
    • Induction of CYPIA by the N-imidazole derivative 1-benzylimidazole
    • Navas, J. M., Chana, A., Herradon, B., and Segner, H. (2003) Induction of CYPIA by the N-imidazole derivative 1-benzylimidazole. Environ. Toxicol. Chem. 22, 830-836.
    • (2003) Environ. Toxicol. Chem , vol.22 , pp. 830-836
    • Navas, J.M.1    Chana, A.2    Herradon, B.3    Segner, H.4
  • 44
    • 9644258952 scopus 로고    scopus 로고
    • Induction of cytochrome P4501A (CYPIA) by clotrimazole a nonplanar aromatic compound. Computational studies on structural features of clotrimazole and related imidazole derivatives
    • Navas, J. M., Chana, A., Herradon, B., and Segner, H. (2004) Induction of cytochrome P4501A (CYPIA) by clotrimazole a nonplanar aromatic compound. Computational studies on structural features of clotrimazole and related imidazole derivatives. Life Sci. 76, 699-714.
    • (2004) Life Sci , vol.76 , pp. 699-714
    • Navas, J.M.1    Chana, A.2    Herradon, B.3    Segner, H.4
  • 45
    • 27644440419 scopus 로고    scopus 로고
    • Cytochrome P4501A induction caused by the imidazole derivative Prochloraz in a rainbow trout cell line
    • Babin, M., Casado, S., Chana, A., Herradon, B., Segner, H., Tarazona, J. V., and Navas, J. M. (2005) Cytochrome P4501A induction caused by the imidazole derivative Prochloraz in a rainbow trout cell line. Toxicol. in Vitro 19, 899-902.
    • (2005) Toxicol. in Vitro , vol.19 , pp. 899-902
    • Babin, M.1    Casado, S.2    Chana, A.3    Herradon, B.4    Segner, H.5    Tarazona, J.V.6    Navas, J.M.7
  • 46
    • 33846206467 scopus 로고    scopus 로고
    • Activation of the aryl hydrocarbon receptor by carbaryl: Computational evidence of the ability of carbaryl to assume a planar conformation
    • Casado, S., Alonso, M., Herradon, B., Tarazona, J. V., and Navas, J. M. (2006) Activation of the aryl hydrocarbon receptor by carbaryl: Computational evidence of the ability of carbaryl to assume a planar conformation. Environ. Toxicol. Chem. 25, 3141-3147.
    • (2006) Environ. Toxicol. Chem , vol.25 , pp. 3141-3147
    • Casado, S.1    Alonso, M.2    Herradon, B.3    Tarazona, J.V.4    Navas, J.M.5
  • 47
    • 0037376089 scopus 로고    scopus 로고
    • Mutational analysis of the mouse aryl hydrocarbon receptor tyrosine residues necessary for recognition of dioxin response elements
    • Minsavage, G. D., Vorojeikina, D. P., and Gasiewicz, T. A. (2003) Mutational analysis of the mouse aryl hydrocarbon receptor tyrosine residues necessary for recognition of dioxin response elements. Arch. Biochem. Biophys. 412, 95-105.
    • (2003) Arch. Biochem. Biophys , vol.412 , pp. 95-105
    • Minsavage, G.D.1    Vorojeikina, D.P.2    Gasiewicz, T.A.3
  • 48
    • 8444245911 scopus 로고    scopus 로고
    • A critical role for MAP kinases in the control of Ah receptor complex activity
    • Tan, Z., Hunag, M., Puga, A., and Xia, Y. (2004) A critical role for MAP kinases in the control of Ah receptor complex activity. Toxicol. Sci. 80-87.
    • (2004) Toxicol. Sci , pp. 80-87
    • Tan, Z.1    Hunag, M.2    Puga, A.3    Xia, Y.4
  • 49
    • 15744366369 scopus 로고    scopus 로고
    • ERK kinase inhibition stabilizes the aryl hydrocarbon receptor. Implications for transcriptional activation and protein degradation
    • Chen, S., Operaña, T., Bonzo, J., Nguyen, N., and Tukey, R. H. (2005) ERK kinase inhibition stabilizes the aryl hydrocarbon receptor. Implications for transcriptional activation and protein degradation. J. Biol. Chem. 280, 4350-4359.
    • (2005) J. Biol. Chem , vol.280 , pp. 4350-4359
    • Chen, S.1    Operaña, T.2    Bonzo, J.3    Nguyen, N.4    Tukey, R.H.5
  • 50
    • 24044496560 scopus 로고    scopus 로고
    • The role of protein kinase C in regulation of TCDD-mediated CYP1A1 gene expression
    • Machemer, D. E., and Tukey, R. H. (2005) The role of protein kinase C in regulation of TCDD-mediated CYP1A1 gene expression. Toxicol. Sci. 87, 27-37.
    • (2005) Toxicol. Sci , vol.87 , pp. 27-37
    • Machemer, D.E.1    Tukey, R.H.2
  • 51
    • 0032522907 scopus 로고    scopus 로고
    • Impact of dioxin-type induction of drug-metabolizing enzymes on the metabolism of endo- and xenobiotics
    • Schrenk, D. (1998) Impact of dioxin-type induction of drug-metabolizing enzymes on the metabolism of endo- and xenobiotics. Biochem. Pharmacol. 55, 1155-1162.
    • (1998) Biochem. Pharmacol , vol.55 , pp. 1155-1162
    • Schrenk, D.1
  • 53
    • 26844556661 scopus 로고    scopus 로고
    • Chemical-activated luciferase gene expression (CALUX): A novel in vitro bioassay for Ah receptor active compounds in sediments and pore water
    • Murk, A. J., Legler, J., Denison, M. S., Giesy, J. P., van de Guchte, C., and Brouwer, A. (1996) Chemical-activated luciferase gene expression (CALUX): A novel in vitro bioassay for Ah receptor active compounds in sediments and pore water. Fundam. Appl. Toxicol. 33, 149-160.
    • (1996) Fundam. Appl. Toxicol , vol.33 , pp. 149-160
    • Murk, A.J.1    Legler, J.2    Denison, M.S.3    Giesy, J.P.4    van de Guchte, C.5    Brouwer, A.6
  • 54
    • 26844566935 scopus 로고    scopus 로고
    • Species-specific recombinant cell lines as bioassay systems for the detection of 2,3,7,8 tetrachlorodibenzo-p-dioxin-like chemicals
    • Garrison, P. M., Tullis, K., Aarts, J., Brouwer, A., Giesy, J. P., and Denison, M. S. (1996) Species-specific recombinant cell lines as bioassay systems for the detection of 2,3,7,8 tetrachlorodibenzo-p-dioxin-like chemicals. Fundam. Appl. Toxicol. 30, 194-203.
    • (1996) Fundam. Appl. Toxicol , vol.30 , pp. 194-203
    • Garrison, P.M.1    Tullis, K.2    Aarts, J.3    Brouwer, A.4    Giesy, J.P.5    Denison, M.S.6
  • 55
  • 56
    • 0032832442 scopus 로고    scopus 로고
    • Ability of polycyclic aromatic hydrocarbons to induce 7-ethoxyresorufin-O-deethylase activity in a trout liver cell line
    • Bols, N. C., Schirmer, K., Joyce, E. M., Dixon, D. G., Greenberg, B. M., and Whyte, J. J. (1999) Ability of polycyclic aromatic hydrocarbons to induce 7-ethoxyresorufin-O-deethylase activity in a trout liver cell line. Ecotoxicol. Environ. Saf. 44, 118-128.
    • (1999) Ecotoxicol. Environ. Saf , vol.44 , pp. 118-128
    • Bols, N.C.1    Schirmer, K.2    Joyce, E.M.3    Dixon, D.G.4    Greenberg, B.M.5    Whyte, J.J.6
  • 57
    • 84962359880 scopus 로고    scopus 로고
    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A, Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keith, T, Al-La
    • Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Jr., Vreven, T., Kudin, K. N., Burant, J. C., Millam, J. M., Iyengar, S. S., Tomasi, J., Barone, V., Mennucci, B., Cossi, M., Scalmani, G., Rega, N., Petersson, G. A., Nakatsuji, H., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Klene, M., Li, X., Knox, J. E., Hratchian, H. P., Cross, J. B., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R. E., Yazyev, O., Austin, A. J., Cammi, R., Pomelli, C., Ochterski, J. W., Ayala, P. Y., Morokuma, K., Voth, G. A., Salvador, P., Dannenberg, J. J., Zakrzewski, V. G., Dapprich, S., Daniels, A. D., Strain, M. C., Farkas, O., Malick, D. K., Rabuck, A. D., Raghavachari, K., Foresman, J. B., Ortiz, J. V., Cui, Q., Baboul, A. G., Clifford, S., Cioslowski, J., Stefanov, B. B., Liu, G., Liashenko, A., Piskorz, P., Komaromi, I., Martin, R. L., Fox, D. J., Keith, T., Al-Laham, M. A., Peng, C. Y., Nanayakkara, A., Challacombe, M., Gill, P. M. W., Johnson, B., Chen, W., Wong, M. W., Gonzalez, C., and Pople, J. A. (2003) Gaussian 03, revision B.04, Gaussian, Inc., Pittsburgh, PA.
  • 59
    • 0345491105 scopus 로고
    • Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density
    • Lee, C. T., Yang, W. T., and Parr, R. G. (1988) Development of the Colle-Salvetti correlation-energy formula into a functional of the electron-density. Phys. Rev. B 37, 785-789.
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.T.1    Yang, W.T.2    Parr, R.G.3
  • 60
    • 4243553426 scopus 로고
    • Density-functional exchange-energy approximation with correct asymptotic behavior
    • Becke, A. D. (1988) Density-functional exchange-energy approximation with correct asymptotic behavior. Phys. Rev. A 38, 3098-3100.
    • (1988) Phys. Rev. A , vol.38 , pp. 3098-3100
    • Becke, A.D.1
  • 61
    • 34250817103 scopus 로고
    • A new mixing of Hartree-Fock and local density-functional theories
    • Becke, A. D. (1993) A new mixing of Hartree-Fock and local density-functional theories. J. Chem. Phys. 98, 1372-1377.
    • (1993) J. Chem. Phys , vol.98 , pp. 1372-1377
    • Becke, A.D.1
  • 62
    • 0037034646 scopus 로고    scopus 로고
    • Structures, potential energy curves, and torsional barrier heights for selected polychlorinated biphenyls: A density functional theory study
    • Arulmozhiraja, S., Selvin, P. C., and Fujii, T. (2002) Structures, potential energy curves, and torsional barrier heights for selected polychlorinated biphenyls: A density functional theory study. J. Phys. Chem. A 106, 1765-1769.
    • (2002) J. Phys. Chem. A , vol.106 , pp. 1765-1769
    • Arulmozhiraja, S.1    Selvin, P.C.2    Fujii, T.3
  • 63
    • 33646178990 scopus 로고    scopus 로고
    • Molecular and electronic structures as well as vibrational spectra assignment of biphenyl, 2,2′- and 4,4′-dichlorobiphenyl from density functional calculations
    • Zhang, X., Xi, R., Liu, J., Jiang, J., Wang, G., and Zeng, Q. (2006) Molecular and electronic structures as well as vibrational spectra assignment of biphenyl, 2,2′- and 4,4′-dichlorobiphenyl from density functional calculations. J. Mol. Struct. (Theochem) 763, 67-73.
    • (2006) J. Mol. Struct. (Theochem) , vol.763 , pp. 67-73
    • Zhang, X.1    Xi, R.2    Liu, J.3    Jiang, J.4    Wang, G.5    Zeng, Q.6
  • 64
    • 0141867585 scopus 로고    scopus 로고
    • Density functional theory study of conformations, barriers to internal rotations and torsional potentials of polychlorinated biphenyls
    • Dorofeeva, O. V., Novikov, V. P., Moiseeva, N. F., and Yungman, V. S. (2003) Density functional theory study of conformations, barriers to internal rotations and torsional potentials of polychlorinated biphenyls. J. Mol. Struct. (Theochem) 637, 137-153.
    • (2003) J. Mol. Struct. (Theochem) , vol.637 , pp. 137-153
    • Dorofeeva, O.V.1    Novikov, V.P.2    Moiseeva, N.F.3    Yungman, V.S.4
  • 65
    • 0026590397 scopus 로고
    • A graphics program for the analysis and display of molecular dynamics trajectories
    • Laaksonen, L. (1992) A graphics program for the analysis and display of molecular dynamics trajectories. J. Mol. Graph. 10, 33-34.
    • (1992) J. Mol. Graph , vol.10 , pp. 33-34
    • Laaksonen, L.1
  • 66
    • 0031251820 scopus 로고    scopus 로고
    • Visualization of solvation structures in liquid mixtures
    • Bergman, D. L., Laaksonen, L., and Laaksonen, A. (1997) Visualization of solvation structures in liquid mixtures. J. Mol. Graph. 15, 301-306.
    • (1997) J. Mol. Graph , vol.15 , pp. 301-306
    • Bergman, D.L.1    Laaksonen, L.2    Laaksonen, A.3
  • 67
    • 0011190497 scopus 로고    scopus 로고
    • Nucleus-independent chemical shifts: A simple and efficient aromaticity probe
    • Schleyer, P. v. R., Maerker, C, Dransfeld, A., Jiao, H. J., and Hommes, N. (1996) Nucleus-independent chemical shifts: A simple and efficient aromaticity probe. J. Am. Chem. Soc. 118, 6317-6318.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 6317-6318
    • Schleyer, P.V.R.1    Maerker, C.2    Dransfeld, A.3    Jiao, H.J.4    Hommes, N.5
  • 68
    • 27744530363 scopus 로고    scopus 로고
    • Nucleus-independent chemical shifts (NICS) as an aromaticity criterion
    • Chen, Z., Wannere, C. S., Corminboeuf, C., Puchta, R., and Schleyer, P. v. R. (2005) Nucleus-independent chemical shifts (NICS) as an aromaticity criterion. Chem. Rev. 105, 3842-3888.
    • (2005) Chem. Rev , vol.105 , pp. 3842-3888
    • Chen, Z.1    Wannere, C.S.2    Corminboeuf, C.3    Puchta, R.4    Schleyer, P.V.R.5
  • 69
    • 11744305193 scopus 로고
    • Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations
    • Wolinski, K., Hinton, J. F., and Pulay, P. (1990) Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. J. Am. Chem. Soc. 112, 8251-8260.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 8251-8260
    • Wolinski, K.1    Hinton, J.F.2    Pulay, P.3
  • 70
    • 0000662399 scopus 로고    scopus 로고
    • An evaluation of the aromaticity of inorganic rings: Refined evidence from magnetic properties
    • Schleyer, P. v. R., Jiao, H. J., Hommes, N., Malkin, V. G., and Malkina, O. L. (1997) An evaluation of the aromaticity of inorganic rings: Refined evidence from magnetic properties. J. Am. Chem. Soc. 119, 12669-12670.
    • (1997) J. Am. Chem. Soc , vol.119 , pp. 12669-12670
    • Schleyer, P.V.R.1    Jiao, H.J.2    Hommes, N.3    Malkin, V.G.4    Malkina, O.L.5
  • 71
    • 0000867708 scopus 로고
    • Definition of aromaticity basing on harmonic oscillator model
    • Kruszewski, J., and Krygowski, T. (1972) Definition of aromaticity basing on harmonic oscillator model. Tetrahedron Lett. 13, 3839-3842.
    • (1972) Tetrahedron Lett , vol.13 , pp. 3839-3842
    • Kruszewski, J.1    Krygowski, T.2
  • 72
    • 34250473173 scopus 로고
    • Theoretical investigations on the solvation process. I. A simple model for the dimeric water associate
    • Bonaccorsi, R., Petrongolo, C., Scrocco, E., and Tomasi, J. (1971) Theoretical investigations on the solvation process. I. A simple model for the dimeric water associate. Theor. Chim. Acta 20, 331-342.
    • (1971) Theor. Chim. Acta , vol.20 , pp. 331-342
    • Bonaccorsi, R.1    Petrongolo, C.2    Scrocco, E.3    Tomasi, J.4
  • 74
    • 84962338941 scopus 로고    scopus 로고
    • Molecular electrostatic potentials from density functional theory
    • Murray, J. S, and Sen, K, Eds, pp, Elsevier, Amsterdam
    • Köster, A. M., Leboeuf, M., and Salahub, D. R. (1996) Molecular electrostatic potentials from density functional theory. In Molecular Electrostatic Potentials. Concepts and Applications (Murray, J. S., and Sen, K., Eds.) pp 105-142, Elsevier, Amsterdam.
    • (1996) Molecular Electrostatic Potentials. Concepts and Applications , pp. 105-142
    • Köster, A.M.1    Leboeuf, M.2    Salahub, D.R.3
  • 75
    • 0035354583 scopus 로고    scopus 로고
    • Chemical applications of X-ray charge-density analysis
    • Koritsánszky, T. S., and Coppens, P. (2001) Chemical applications of X-ray charge-density analysis. Chem. Rev. 101, 1583-1627.
    • (2001) Chem. Rev , vol.101 , pp. 1583-1627
    • Koritsánszky, T.S.1    Coppens, P.2
  • 76
    • 0002252623 scopus 로고
    • Statistically-based interaction indexes derived from molecular-surface electrostatic potentials. A general interaction properties function (GIPF)
    • Murray, J. S., Brinck, T., Lane, P., Paulsen, K., and Politzer, P. (1994) Statistically-based interaction indexes derived from molecular-surface electrostatic potentials. A general interaction properties function (GIPF). J. Mol. Struct. (Theochem) 113, 55-64.
    • (1994) J. Mol. Struct. (Theochem) , vol.113 , pp. 55-64
    • Murray, J.S.1    Brinck, T.2    Lane, P.3    Paulsen, K.4    Politzer, P.5
  • 77
    • 84962374317 scopus 로고
    • Permanent and induced molecular moments and long-range intermolecular forces
    • Buckingham, A. D. (1967) Permanent and induced molecular moments and long-range intermolecular forces. Adv. Chem. Phys. 12, 107-166.
    • (1967) Adv. Chem. Phys , vol.12 , pp. 107-166
    • Buckingham, A.D.1
  • 79
    • 0347291894 scopus 로고
    • Absolute hardness: Companion parameter to absolute electronegativity
    • Parr, R. G., and Pearson, R. G. (1983) Absolute hardness: Companion parameter to absolute electronegativity. J. Am. Chem. Soc. 105, 7512-7516.
    • (1983) J. Am. Chem. Soc , vol.105 , pp. 7512-7516
    • Parr, R.G.1    Pearson, R.G.2
  • 82
    • 0001335057 scopus 로고
    • The polarizability of planar aromatic systems. An application to polychlorinated biphenyls (PCBs), dioxins and polyaromatic hydrocarbons
    • McKinney, J. D., Gottschalk, K. E., and Pedersen, L. (1983) The polarizability of planar aromatic systems. An application to polychlorinated biphenyls (PCBs), dioxins and polyaromatic hydrocarbons. J. Mol. Struct. (Theochem) 105, 427-438.
    • (1983) J. Mol. Struct. (Theochem) , vol.105 , pp. 427-438
    • McKinney, J.D.1    Gottschalk, K.E.2    Pedersen, L.3
  • 83
    • 0000815488 scopus 로고    scopus 로고
    • Molecular polarizability as a tool for understanding the binding properties of polychlorinated dibenzo-p-dioxins: Definition of a reliable computational procedure
    • Fraschini, E., Bonati, L., and Pitea, D. (1996) Molecular polarizability as a tool for understanding the binding properties of polychlorinated dibenzo-p-dioxins: Definition of a reliable computational procedure. J. Phys. Chem. 100, 10564-10569.
    • (1996) J. Phys. Chem , vol.100 , pp. 10564-10569
    • Fraschini, E.1    Bonati, L.2    Pitea, D.3
  • 84
    • 0035438390 scopus 로고    scopus 로고
    • Polarizability fields for use in three-dimensional quantitative structure-activity relationships (3D-QSAR)
    • Bradley, M., and Waller, C. L. (2001) Polarizability fields for use in three-dimensional quantitative structure-activity relationships (3D-QSAR). J. Chem. Inf. Comput. Sci. 41, 1301-1307.
    • (2001) J. Chem. Inf. Comput. Sci , vol.41 , pp. 1301-1307
    • Bradley, M.1    Waller, C.L.2
  • 86
  • 87
    • 0030180540 scopus 로고    scopus 로고
    • Measurements of octanol/air partition coefficients for polychlorinated biphenyls
    • Harner, T., and Bidleman, T. F. (1996) Measurements of octanol/air partition coefficients for polychlorinated biphenyls. J. Chem. Eng. Data 41, 895-899.
    • (1996) J. Chem. Eng. Data , vol.41 , pp. 895-899
    • Harner, T.1    Bidleman, T.F.2
  • 88
    • 0034321189 scopus 로고    scopus 로고
    • Henry's law constants of polychlorinated biphenyl congeners and their variation with temperature
    • Bamford, H. A., Poster, D. L., and Baker, J. E. (2000) Henry's law constants of polychlorinated biphenyl congeners and their variation with temperature. J. Chem. Eng. Data 45, 1069-1074.
    • (2000) J. Chem. Eng. Data , vol.45 , pp. 1069-1074
    • Bamford, H.A.1    Poster, D.L.2    Baker, J.E.3
  • 90
    • 0000300024 scopus 로고
    • The crystal and molecular structure of biphenyl
    • Trotter, J. (1961) The crystal and molecular structure of biphenyl. Acta Crystallogr. 14, 1135-1140.
    • (1961) Acta Crystallogr , vol.14 , pp. 1135-1140
    • Trotter, J.1
  • 91
    • 0002305877 scopus 로고
    • Structure and barrier of internal rotation of biphenyl derivatives in the gaseous state: Part 1. The molecular structure and normal coordinate analysis of normal biphenyl and perdeuterated biphenyl
    • Almenningen, A., Bastiansen, O., Fernholt, L., Cyvin, B. N., Cyvin, S. J., and Samdal, S. (1985) Structure and barrier of internal rotation of biphenyl derivatives in the gaseous state: Part 1. The molecular structure and normal coordinate analysis of normal biphenyl and perdeuterated biphenyl. J. Mol. Struct. 128, 59-76.
    • (1985) J. Mol. Struct , vol.128 , pp. 59-76
    • Almenningen, A.1    Bastiansen, O.2    Fernholt, L.3    Cyvin, B.N.4    Cyvin, S.J.5    Samdal, S.6
  • 92
    • 0035894316 scopus 로고    scopus 로고
    • Torsional barrier, ionization potential, and electron affinity of biphenyl - A theoretical study
    • Arulmozhiraja, S., and Fujii, T. (2001) Torsional barrier, ionization potential, and electron affinity of biphenyl - A theoretical study. J. Chem. Phys. 115, 10589-10594.
    • (2001) J. Chem. Phys , vol.115 , pp. 10589-10594
    • Arulmozhiraja, S.1    Fujii, T.2
  • 93
    • 0031956728 scopus 로고    scopus 로고
    • Stepping backward to improve assessment of PCB congener toxicities
    • Hansen, L. G. (1998) Stepping backward to improve assessment of PCB congener toxicities. Environ. Health Perspect. 106, 171-189.
    • (1998) Environ. Health Perspect , vol.106 , pp. 171-189
    • Hansen, L.G.1
  • 96
    • 34250324176 scopus 로고    scopus 로고
    • Neural networks as a tool to classify compounds according to aromaticity criteria
    • Alonso, M., and Herradon, B. (2007) Neural networks as a tool to classify compounds according to aromaticity criteria. Chem. Eur. J. 13, 3913-3923.
    • (2007) Chem. Eur. J , vol.13 , pp. 3913-3923
    • Alonso, M.1    Herradon, B.2
  • 97
    • 27744578989 scopus 로고    scopus 로고
    • Energetic aspects of cyclic π-electron derealization: Evaluation of the methods of estimating aromatic stabilization energies
    • Cyranski, M. K. (2005) Energetic aspects of cyclic π-electron derealization: Evaluation of the methods of estimating aromatic stabilization energies. Chem. Rev. 105, 3773-3811.
    • (2005) Chem. Rev , vol.105 , pp. 3773-3811
    • Cyranski, M.K.1
  • 98
    • 33947315480 scopus 로고
    • Diamagnetic susceptibility exaltation as a criterion of aromaticity
    • Dauben, H. J., Wilson, J. D., and Laity, J. L. (1968) Diamagnetic susceptibility exaltation as a criterion of aromaticity. J. Am. Chem. Soc. 90, 811-813.
    • (1968) J. Am. Chem. Soc , vol.90 , pp. 811-813
    • Dauben, H.J.1    Wilson, J.D.2    Laity, J.L.3
  • 99
    • 0031189711 scopus 로고    scopus 로고
    • Molecular recognition of protein-ligand complexes. Applications to drug design
    • Babine, R. E., and Bender, S. L. (1997) Molecular recognition of protein-ligand complexes. Applications to drug design. Chem. Rev. 97, 1359-1472.
    • (1997) Chem. Rev , vol.97 , pp. 1359-1472
    • Babine, R.E.1    Bender, S.L.2
  • 101
    • 0036100338 scopus 로고    scopus 로고
    • An improved hydrogen bond potential: Impact on medium resolution protein structures
    • Fabiola, F., Bertram, R., Korostelev, A., and Chapman, M. S. (2002) An improved hydrogen bond potential: Impact on medium resolution protein structures. Protein Sci. 11, 1415-1423.
    • (2002) Protein Sci , vol.11 , pp. 1415-1423
    • Fabiola, F.1    Bertram, R.2    Korostelev, A.3    Chapman, M.S.4
  • 102
    • 0003686055 scopus 로고    scopus 로고
    • The molecular electrostatic potential: A tool for understanding and predicting molecular interactions
    • Sapse, A. M, Ed, pp, Oxford University Press, New York
    • Murray, J. S., and Politzer, P. (1998) The molecular electrostatic potential: A tool for understanding and predicting molecular interactions. In Molecular Orbital Calculations for Biological Systems (Sapse, A. M., Ed.), pp 49-84, Oxford University Press, New York.
    • (1998) Molecular Orbital Calculations for Biological Systems , pp. 49-84
    • Murray, J.S.1    Politzer, P.2
  • 103
    • 4243468938 scopus 로고    scopus 로고
    • The cation-pi interaction
    • Ma, J. C., and Dougherty, D. A. (1997) The cation-pi interaction. Chem. Rev. 97, 1303-1324.
    • (1997) Chem. Rev , vol.97 , pp. 1303-1324
    • Ma, J.C.1    Dougherty, D.A.2
  • 105
    • 2342538389 scopus 로고    scopus 로고
    • Studies on aromatic compounds: Inhibition of calpain I by biphenyl derivatives and peptide-biphenyl hybrids
    • Montero, A., Alonso, M., Benito, E., Chana, A., Mann, E., Navas, J. M., and Herradon, B. (2004) Studies on aromatic compounds: Inhibition of calpain I by biphenyl derivatives and peptide-biphenyl hybrids. Bioorg. Med. Chem. Lett. 14, 2753-2757.
    • (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 2753-2757
    • Montero, A.1    Alonso, M.2    Benito, E.3    Chana, A.4    Mann, E.5    Navas, J.M.6    Herradon, B.7
  • 106
    • 11144293432 scopus 로고    scopus 로고
    • Crystallization-induced dynamic resolution and analysis of the noncovalent interactions in the crystal packing of peptide-biphenyl hybrids
    • Herradon, B., Montero, A., Mann, E., and Maestro, M. A. (2004) Crystallization-induced dynamic resolution and analysis of the noncovalent interactions in the crystal packing of peptide-biphenyl hybrids. CrystEngComm 6, 512-521.
    • (2004) CrystEngComm , vol.6 , pp. 512-521
    • Herradon, B.1    Montero, A.2    Mann, E.3    Maestro, M.A.4
  • 107
    • 0000491257 scopus 로고
    • The molecular electric quadrupole moment and solid-state architecture
    • Williams, J. H. (1993) The molecular electric quadrupole moment and solid-state architecture. Acc. Chem. Res. 26, 593-598.
    • (1993) Acc. Chem. Res , vol.26 , pp. 593-598
    • Williams, J.H.1
  • 108
    • 0001227655 scopus 로고
    • The nature of π-π interactions
    • Hunter, C. A., and Sanders, J. K. M. (1990) The nature of π-π interactions. J. Am. Chem. Soc. 112, 5525-5534.
    • (1990) J. Am. Chem. Soc , vol.112 , pp. 5525-5534
    • Hunter, C.A.1    Sanders, J.K.M.2
  • 109
    • 0032560940 scopus 로고    scopus 로고
    • NMR study of intramolecular interactions between aromatic groups: Van der Waals, charge transfer or quadrupolar interactions
    • Heaton, N. J., Bello, P., Herradón, B., del Campo, A., and Jiménez-Barbero, J. (1998) NMR study of intramolecular interactions between aromatic groups: van der Waals, charge transfer or quadrupolar interactions. J. Am. Chem. Soc. 120, 12371-12384.
    • (1998) J. Am. Chem. Soc , vol.120 , pp. 12371-12384
    • Heaton, N.J.1    Bello, P.2    Herradón, B.3    del Campo, A.4    Jiménez-Barbero, J.5
  • 110
  • 111
    • 0034676509 scopus 로고    scopus 로고
    • Is CYP1A1 induction always related to AhR signaling pathway?
    • Delescluse, C., Lemaire, G., De Sousa, G., and Rahmani, R. (2000) Is CYP1A1 induction always related to AhR signaling pathway? Toxicology 153, 73-82.
    • (2000) Toxicology , vol.153 , pp. 73-82
    • Delescluse, C.1    Lemaire, G.2    De Sousa, G.3    Rahmani, R.4
  • 112
    • 0034021184 scopus 로고    scopus 로고
    • Ah receptor-based chemical screening bioassays: Application and limitations for the detection of Ah receptor agonists
    • Seidel, S. D., Li, V., Winter, G. M., Rogers, W. J., Martinez, E. I., and Denison, M. S. (2000) Ah receptor-based chemical screening bioassays: Application and limitations for the detection of Ah receptor agonists. Toxicol. Sci. 55, 107-115.
    • (2000) Toxicol. Sci , vol.55 , pp. 107-115
    • Seidel, S.D.1    Li, V.2    Winter, G.M.3    Rogers, W.J.4    Martinez, E.I.5    Denison, M.S.6
  • 113
    • 0942279537 scopus 로고    scopus 로고
    • Induced magnetic fields in aromatic [n]-annulenesinterpretation of NICS tensor components
    • Corminboeuf, C., Heine, T., Seifert, G., Schleyer, P. v. R., and Weber, J. (2004) Induced magnetic fields in aromatic [n]-annulenesinterpretation of NICS tensor components. Phys. Chem. Chem. Phys. 6, 273-276.
    • (2004) Phys. Chem. Chem. Phys , vol.6 , pp. 273-276
    • Corminboeuf, C.1    Heine, T.2    Seifert, G.3    Schleyer, P.V.R.4    Weber, J.5
  • 114
    • 36749110469 scopus 로고
    • Relationships between atomic chemical-potentials, electrostatic potentials, and covalent radii
    • Politzer, P., Parr, R. G., and Murphy, D. R. (1983) Relationships between atomic chemical-potentials, electrostatic potentials, and covalent radii. J. Chem. Phys. 79, 3859-3861.
    • (1983) J. Chem. Phys , vol.79 , pp. 3859-3861
    • Politzer, P.1    Parr, R.G.2    Murphy, D.R.3
  • 115
    • 0000598053 scopus 로고    scopus 로고
    • Molecular electrostatic potentials as indicators of covalent radii
    • Wiener, J. J. M., Grice, M. E., Murray, J. S., and Politzer, P. (1996) Molecular electrostatic potentials as indicators of covalent radii. J. Chem. Phys. 104, 5109-5111.
    • (1996) J. Chem. Phys , vol.104 , pp. 5109-5111
    • Wiener, J.J.M.1    Grice, M.E.2    Murray, J.S.3    Politzer, P.4
  • 116
    • 2442521208 scopus 로고    scopus 로고
    • Atomic and molecular energies as functionals of the electrostatic potential
    • Politzer, P. (2004) Atomic and molecular energies as functionals of the electrostatic potential. Theor. Chem. Acc. 111, 395-399.
    • (2004) Theor. Chem. Acc , vol.111 , pp. 395-399
    • Politzer, P.1
  • 117
    • 84946893847 scopus 로고
    • Electrostatic interaction of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects
    • Miertus, S., Scrocco, E., and Tomasi, J. (1981) Electrostatic interaction of a solute with a continuum. A direct utilization of ab initio molecular potentials for the prevision of solvent effects. Chem. Phys. 55, 117-129.
    • (1981) Chem. Phys , vol.55 , pp. 117-129
    • Miertus, S.1    Scrocco, E.2    Tomasi, J.3
  • 118
    • 0542382495 scopus 로고
    • Solvent effects. 1. The mediation of electrostatic effects by solvents
    • Wong, M. W., Frisch, M. J., and Wiberg, K. B. (1991) Solvent effects. 1. The mediation of electrostatic effects by solvents. J. Am. Chem. Soc. 113, 4776-4782.
    • (1991) J. Am. Chem. Soc , vol.113 , pp. 4776-4782
    • Wong, M.W.1    Frisch, M.J.2    Wiberg, K.B.3
  • 119
    • 0000592724 scopus 로고    scopus 로고
    • Relationships between dissociation energies and electrostatic potentials of C-NO 2 bonds: Application to impact sensitivities
    • Politzer, P., and Murray, J. S. (1996) Relationships between dissociation energies and electrostatic potentials of C-NO 2 bonds: Application to impact sensitivities. J. Mol. Struct. 376, 419-424.
    • (1996) J. Mol. Struct , vol.376 , pp. 419-424
    • Politzer, P.1    Murray, J.S.2
  • 120
    • 0001308931 scopus 로고    scopus 로고
    • Electronic perturbations of the aromatic nucleus: Hammett constants and electrostatic potential topography
    • Gadre, S. R., and Suresh, C. H. (1997) Electronic perturbations of the aromatic nucleus: Hammett constants and electrostatic potential topography. J. Org. Chem. 62, 2625-2627.
    • (1997) J. Org. Chem , vol.62 , pp. 2625-2627
    • Gadre, S.R.1    Suresh, C.H.2
  • 121
    • 0037066189 scopus 로고    scopus 로고
    • The complementary roles of molecular surface electrostatic potentials and average local ionization energies with respect to electrophilic processes
    • Politzer, P., Murray, J. S., and Concha, M. C. (2002) The complementary roles of molecular surface electrostatic potentials and average local ionization energies with respect to electrophilic processes. Int. J. Quantum Chem. 88, 19-27.
    • (2002) Int. J. Quantum Chem , vol.88 , pp. 19-27
    • Politzer, P.1    Murray, J.S.2    Concha, M.C.3
  • 122
    • 0000902749 scopus 로고    scopus 로고
    • Calculation of structural similarity by the alignment of molecular electrostatic potentials
    • Thorner, D. A., Wild, D. J., Willett, P., and Wright, P. M. (1998) Calculation of structural similarity by the alignment of molecular electrostatic potentials. Perspect. Drug Discovery Des. 9(11), 301-320.
    • (1998) Perspect. Drug Discovery Des , vol.9 , Issue.11 , pp. 301-320
    • Thorner, D.A.1    Wild, D.J.2    Willett, P.3    Wright, P.M.4
  • 123
    • 33751499871 scopus 로고
    • Correlations between the solvent hydrogen-bond-donating parameter α and the calculated molecular surface electrostatic potential
    • Murray, J. S., and Politzer, P. (1991) Correlations between the solvent hydrogen-bond-donating parameter α and the calculated molecular surface electrostatic potential. J. Org. Chem. 56, 6715-6717.
    • (1991) J. Org. Chem , vol.56 , pp. 6715-6717
    • Murray, J.S.1    Politzer, P.2
  • 124
    • 0029966107 scopus 로고    scopus 로고
    • Hydrogen bonds: First quantitative agreement between electrostatic potential calculations from experimental X-(X + N) and theoretical ab Initio SCF models
    • Espinosa, E., Lecomte, C., Ghermani, N. E., Devémy, J., Rohmer, M. M., Bérnard, M., and Molins, E. (1996) Hydrogen bonds: First quantitative agreement between electrostatic potential calculations from experimental X-(X + N) and theoretical ab Initio SCF models. J. Am. Chem. Soc. 118, 2501-2502.
    • (1996) J. Am. Chem. Soc , vol.118 , pp. 2501-2502
    • Espinosa, E.1    Lecomte, C.2    Ghermani, N.E.3    Devémy, J.4    Rohmer, M.M.5    Bérnard, M.6    Molins, E.7
  • 125
    • 0034833367 scopus 로고    scopus 로고
    • Alkali metal cation-π interactions observed by using a lariat ether model system
    • Meadows, E. S., De Wall, S. L., Barbour, L. J., and Gokel, G. W. (2001) Alkali metal cation-π interactions observed by using a lariat ether model system. J. Am. Chem. Soc. 123, 3092-3107.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 3092-3107
    • Meadows, E.S.1    De Wall, S.L.2    Barbour, L.J.3    Gokel, G.W.4
  • 126
    • 0035955230 scopus 로고    scopus 로고
    • The magnitude of [C-H⋯O] hydrogen bonding in molecular and supramolecular assemblies
    • Raymo, F. M., Bartberger, M. D., Houk, K. N., and Stoddart, J. F. (2001) The magnitude of [C-H⋯O] hydrogen bonding in molecular and supramolecular assemblies. J. Am. Chem. Soc. 123, 9264-9267.
    • (2001) J. Am. Chem. Soc , vol.123 , pp. 9264-9267
    • Raymo, F.M.1    Bartberger, M.D.2    Houk, K.N.3    Stoddart, J.F.4
  • 127
    • 0021372291 scopus 로고
    • Effects of amino and nitro substituents upon the electrostatic potential of an aromatic ring
    • Politzer, P., Abrahmsen, L., and Sjoberg, P. (1984) Effects of amino and nitro substituents upon the electrostatic potential of an aromatic ring. J. Am. Chem. Soc. 106, 855-860.
    • (1984) J. Am. Chem. Soc , vol.106 , pp. 855-860
    • Politzer, P.1    Abrahmsen, L.2    Sjoberg, P.3
  • 128
    • 84961974221 scopus 로고    scopus 로고
    • A priori prediction of substituent and solvent effects in the basicity of nitriles
    • Colominas, C., Orozco, M., Luque, F. J., Borrell, J. I., and Teixidó, J. (1998) A priori prediction of substituent and solvent effects in the basicity of nitriles. J. Org. Chem. 63, 4947-4953.
    • (1998) J. Org. Chem , vol.63 , pp. 4947-4953
    • Colominas, C.1    Orozco, M.2    Luque, F.J.3    Borrell, J.I.4    Teixidó, J.5
  • 129
    • 0037072311 scopus 로고    scopus 로고
    • Cation-π interactions in ligand recognition by serotonergic (5-HT 3A) and nicotinic acetylcholine receptors: The anomalous binding properties of nicotine
    • Beene, D. L., Brandt, G. S., Zhong, W., Zacharias, N. M., Lester, H. A., and Dougherty, D. A. (2002) Cation-π interactions in ligand recognition by serotonergic (5-HT 3A) and nicotinic acetylcholine receptors: The anomalous binding properties of nicotine. Biochemistry 41, 10262-10269.
    • (2002) Biochemistry , vol.41 , pp. 10262-10269
    • Beene, D.L.1    Brandt, G.S.2    Zhong, W.3    Zacharias, N.M.4    Lester, H.A.5    Dougherty, D.A.6
  • 130
    • 84990647637 scopus 로고
    • A comparative analysis of the electrostatic potential of some structural analogues of 2,3,7,8 tetrachlorodibenzo-p-dioxin and of related aromatic systems
    • Murray, J. S., Evans, P., and Politzer, P. (1990) A comparative analysis of the electrostatic potential of some structural analogues of 2,3,7,8 tetrachlorodibenzo-p-dioxin and of related aromatic systems. Int. J. Quantum Chem. 37, 271-289.
    • (1990) Int. J. Quantum Chem , vol.37 , pp. 271-289
    • Murray, J.S.1    Evans, P.2    Politzer, P.3
  • 131
    • 0002058784 scopus 로고
    • A hypothesis on the Mechanism of PCDD biological-activity based on molecular electrostatic potential modeling. 2
    • Bonati, L., Fraschini, E., Lasagni, M., Modoni, E. P., and Pitea, D. (1995) A hypothesis on the Mechanism of PCDD biological-activity based on molecular electrostatic potential modeling. 2. J. Mol. Struct. (Theochem) 340, 83-95.
    • (1995) J. Mol. Struct. (Theochem) , vol.340 , pp. 83-95
    • Bonati, L.1    Fraschini, E.2    Lasagni, M.3    Modoni, E.P.4    Pitea, D.5
  • 133
    • 0039924760 scopus 로고    scopus 로고
    • Relationships of molecular surface electrostatic potentials to some macroscopic properties
    • Murray, J. S., Brinck, T., and Politzer, P. (1996) Relationships of molecular surface electrostatic potentials to some macroscopic properties. Chem. Phys. 204, 289-299.
    • (1996) Chem. Phys , vol.204 , pp. 289-299
    • Murray, J.S.1    Brinck, T.2    Politzer, P.3
  • 134
    • 0141941537 scopus 로고    scopus 로고
    • Segmental analysis of molecular surface electrostatic potentials: Application to enzyme inhibition
    • Brinck, T., Jin, P., Ma, Y. G., Murray, J. S., and Politzer, P. (2003) Segmental analysis of molecular surface electrostatic potentials: Application to enzyme inhibition. J. Mol. Model. 9, 77-83.
    • (2003) J. Mol. Model , vol.9 , pp. 77-83
    • Brinck, T.1    Jin, P.2    Ma, Y.G.3    Murray, J.S.4    Politzer, P.5
  • 135
    • 0037045252 scopus 로고    scopus 로고
    • Understanding the congener-specific toxicity in polychlorinated dibenzo-p-dioxins: Chlorination pattern and molecular quadrupole moment
    • Mhin, B. J., Lee, J. E., and Choi, W. Y. (2002) Understanding the congener-specific toxicity in polychlorinated dibenzo-p-dioxins: Chlorination pattern and molecular quadrupole moment. J. Am. Chem. Soc. 124, 144-148.
    • (2002) J. Am. Chem. Soc , vol.124 , pp. 144-148
    • Mhin, B.J.1    Lee, J.E.2    Choi, W.Y.3
  • 136
    • 13844289457 scopus 로고    scopus 로고
    • Chlorine substitution pattern, molecular electronic properties, and the nature of the ligand-receptor interaction: Quantitative property-activity relationships of polychlorinated dibenzofurans
    • Hirokawa, S., and Imasaka, T. (2005) Chlorine substitution pattern, molecular electronic properties, and the nature of the ligand-receptor interaction: Quantitative property-activity relationships of polychlorinated dibenzofurans. Chem. Res. Toxicol. 18, 232-238.
    • (2005) Chem. Res. Toxicol , vol.18 , pp. 232-238
    • Hirokawa, S.1    Imasaka, T.2
  • 137
    • 0037138914 scopus 로고    scopus 로고
    • Density functional theory-based reactivity descriptors for dioxins
    • Arulmozhiraja, S., Fujii, T., and Sato, G. (2002) Density functional theory-based reactivity descriptors for dioxins. Mol. Phys. 100, 423-431.
    • (2002) Mol. Phys , vol.100 , pp. 423-431
    • Arulmozhiraja, S.1    Fujii, T.2    Sato, G.3
  • 139
    • 0030784375 scopus 로고    scopus 로고
    • Energetics of the homolytic C-H bond cleavages in polychlorobenzenes: The role of electronic and steric effects
    • Cioslowski, J., Liu, G., and Moncrieff, D. (1997) Energetics of the homolytic C-H bond cleavages in polychlorobenzenes: The role of electronic and steric effects. J. Phys. Chem. A 101, 957-960.
    • (1997) J. Phys. Chem. A , vol.101 , pp. 957-960
    • Cioslowski, J.1    Liu, G.2    Moncrieff, D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.