메뉴 건너뛰기




Volumn 6, Issue , 2016, Pages

Peptide Reactivity of Isothiocyanates-Implications for Skin Allergy

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; HAPTEN; ISOTHIOCYANIC ACID DERIVATIVE; PEPTIDE; THIOL DERIVATIVE;

EID: 84958568160     PISSN: None     EISSN: 20452322     Source Type: Journal    
DOI: 10.1038/srep21203     Document Type: Article
Times cited : (23)

References (35)
  • 1
    • 35248880520 scopus 로고    scopus 로고
    • The epidemiology of contact allergy in the general population-prevalence and main findings
    • Thyssen, J. P., Linneberg, A., Menne, T., Johansen, J. D. The epidemiology of contact allergy in the general population-prevalence and main findings. Contact dermatitis 57, 287-299, doi: 10.1111/j.1600-0536.2007.01220.x (2007).
    • (2007) Contact Dermatitis , vol.57 , pp. 287-299
    • Thyssen, J.P.1    Linneberg, A.2    Menne, T.3    Johansen, J.D.4
  • 2
    • 38949130710 scopus 로고    scopus 로고
    • Allergic contact dermatitis-formation, structural requirements, and reactivity of skin sensitizers
    • Karlberg, A. T., Bergstrom, M. A., Borje, A., Luthman, K., Nilsson, J. L. Allergic contact dermatitis-formation, structural requirements, and reactivity of skin sensitizers. Chemical research in toxicology 21, 53-69, doi: 10.1021/tx7002239 (2008).
    • (2008) Chemical Research in Toxicology , vol.21 , pp. 53-69
    • Karlberg, A.T.1    Bergstrom, M.A.2    Borje, A.3    Luthman, K.4    Nilsson, J.L.5
  • 3
    • 34447547764 scopus 로고    scopus 로고
    • Quantification of chemical peptide reactivity for screening contact allergens: A classification tree model approach
    • Gerberick, G. F. et al. Quantification of chemical peptide reactivity for screening contact allergens: a classification tree model approach. Toxicological sciences: an official journal of the Society of Toxicology 97, 417-427, doi: 10.1093/toxsci/kfm064 (2007).
    • (2007) Toxicological Sciences: An Official Journal of the Society of Toxicology , vol.97 , pp. 417-427
    • Gerberick, G.F.1
  • 4
    • 84870876983 scopus 로고    scopus 로고
    • Reactivity of chemical respiratory allergens in the Peroxidase Peptide Reactivity Assay
    • Lalko, J. F. et al. Reactivity of chemical respiratory allergens in the Peroxidase Peptide Reactivity Assay. Toxicology in vitro: an international journal published in association with BIBRA 27, 651-661, doi: 10.1016/j.tiv.2012.10.016 (2013).
    • (2013) Toxicology in Vitro: An International Journal Published in Association with BIBRA , vol.27 , pp. 651-661
    • Lalko, J.F.1
  • 6
    • 84922906856 scopus 로고    scopus 로고
    • Investigation of diethylthiourea and ethyl isothiocyanate as potent skin allergens in chloroprene rubber
    • Ramzy, A. G., Hagvall, L., Pei, M. N., Samuelsson, K., Nilsson, U. Investigation of diethylthiourea and ethyl isothiocyanate as potent skin allergens in chloroprene rubber. Contact dermatitis 72, 139-146, doi: 10.1111/cod.12318 (2015).
    • (2015) Contact Dermatitis , vol.72 , pp. 139-146
    • Ramzy, A.G.1    Hagvall, L.2    Pei, M.N.3    Samuelsson, K.4    Nilsson, U.5
  • 7
    • 14344251179 scopus 로고    scopus 로고
    • Evaluation of the skin sensitizing potency of chemicals by using the existing methods and considerations of relevance for elicitation
    • Basketter, D. A. et al. Evaluation of the skin sensitizing potency of chemicals by using the existing methods and considerations of relevance for elicitation. Contact dermatitis 52, 39-43, doi: 10.1111/j.0105-1873.2005.00490.x (2005).
    • (2005) Contact Dermatitis , vol.52 , pp. 39-43
    • Basketter, D.A.1
  • 8
    • 13844292704 scopus 로고    scopus 로고
    • A conjugated diene identified as a prohapten: Contact allergenic activity and chemical reactivity of proposed epoxide metabolites
    • Nilsson, A. M., Bergstrom, M. A., Luthman, K., Nilsson, J. L., Karlberg, A. T. A conjugated diene identified as a prohapten: contact allergenic activity and chemical reactivity of proposed epoxide metabolites. Chemical research in toxicology 18, 308-316, doi: 10.1021/tx049758c (2005).
    • (2005) Chemical Research in Toxicology , vol.18 , pp. 308-316
    • Nilsson, A.M.1    Bergstrom, M.A.2    Luthman, K.3    Nilsson, J.L.4    Karlberg, A.T.5
  • 9
    • 67449104863 scopus 로고    scopus 로고
    • Nuclear magnetic resonance studies on covalent modification of amino acids thiol and amino residues by monofunctional aryl 13C-isocyanates, models of skin and respiratory sensitizers: Transformation of thiocarbamates into urea adducts
    • Fleischel, O., Gimenez-Arnau, E., Lepoittevin, J. P. Nuclear magnetic resonance studies on covalent modification of amino acids thiol and amino residues by monofunctional aryl 13C-isocyanates, models of skin and respiratory sensitizers: transformation of thiocarbamates into urea adducts. Chemical research in toxicology 22, 1106-1115, doi: 10.1021/tx9000539 (2009).
    • (2009) Chemical Research in Toxicology , vol.22 , pp. 1106-1115
    • Fleischel, O.1    Gimenez-Arnau, E.2    Lepoittevin, J.P.3
  • 10
    • 65949117445 scopus 로고    scopus 로고
    • Covalent modification of lysine residues by allyl isothiocyanate in physiological conditions: Plausible transformation of isothiocyanate from thiol to amine
    • Nakamura, T., Kawai, Y., Kitamoto, N., Osawa, T., Kato, Y. Covalent modification of lysine residues by allyl isothiocyanate in physiological conditions: plausible transformation of isothiocyanate from thiol to amine. Chemical research in toxicology 22, 536-542, doi: 10.1021/tx8003906 (2009).
    • (2009) Chemical Research in Toxicology , vol.22 , pp. 536-542
    • Nakamura, T.1    Kawai, Y.2    Kitamoto, N.3    Osawa, T.4    Kato, Y.5
  • 11
    • 84937562080 scopus 로고    scopus 로고
    • Stable isotope labeling method for the investigation of protein haptenation by electrophilic skin sensitizers
    • Parkinson, E. et al. Stable isotope labeling method for the investigation of protein haptenation by electrophilic skin sensitizers. Toxicological sciences: an official journal of the Society of Toxicology 142, 239-249, doi: 10.1093/toxsci/kfu168 (2014).
    • (2014) Toxicological Sciences: An Official Journal of the Society of Toxicology , vol.142 , pp. 239-249
    • Parkinson, E.1
  • 12
    • 34248573312 scopus 로고    scopus 로고
    • Nucleophilicities of primary and secondary amines in water
    • Brotzel, F., Chu, Y. C., Mayr, H. Nucleophilicities of primary and secondary amines in water. The Journal of organic chemistry 72, 3679-3688, doi: 10.1021/jo062586z (2007).
    • (2007) The Journal of Organic Chemistry , vol.72 , pp. 3679-3688
    • Brotzel, F.1    Chu, Y.C.2    Mayr, H.3
  • 13
    • 33746238128 scopus 로고    scopus 로고
    • Towards a general scale of nucleophilicity?
    • Phan, T. B., Breugst, M., Mayr, H. Towards a general scale of nucleophilicity? Angew Chem Int Ed Engl 45, 3869-3874, doi: 10.1002/anie.200600542 (2006).
    • (2006) Angew Chem Int Ed Engl , vol.45 , pp. 3869-3874
    • Phan, T.B.1    Breugst, M.2    Mayr, H.3
  • 14
    • 75249099695 scopus 로고    scopus 로고
    • The Nrf2-Keap1-ARE toxicity pathway as a cellular sensor for skin sensitizers-functional relevance and a hypothesis on innate reactions to skin sensitizers
    • Natsch, A. The Nrf2-Keap1-ARE toxicity pathway as a cellular sensor for skin sensitizers-functional relevance and a hypothesis on innate reactions to skin sensitizers. Toxicological sciences: an official journal of the Society of Toxicology 113, 284-292, doi: 10.1093/toxsci/kfp228 (2010).
    • (2010) Toxicological Sciences: An Official Journal of the Society of Toxicology , vol.113 , pp. 284-292
    • Natsch, A.1
  • 15
    • 77952950728 scopus 로고    scopus 로고
    • Performance of a novel keratinocyte-based reporter cell line to screen skin sensitizers in vitro
    • Emter, R., Ellis, G., Natsch, A. Performance of a novel keratinocyte-based reporter cell line to screen skin sensitizers in vitro. Toxicology and applied pharmacology 245, 281-290, doi: 10.1016/j.taap.2010.03.009 (2010).
    • (2010) Toxicology and Applied Pharmacology , vol.245 , pp. 281-290
    • Emter, R.1    Ellis, G.2    Natsch, A.3
  • 16
    • 0006090720 scopus 로고
    • On the reversible reaction of cyanate with sulfhydryl groups and the determination of Nh2-Terminal cysteine and cystine in proteins
    • Stark, G. R. On the Reversible Reaction of Cyanate with Sulfhydryl Groups and the Determination of Nh2-Terminal Cysteine and Cystine in Proteins. The Journal of biological chemistry 239, 1411-1414 (1964).
    • (1964) The Journal of Biological Chemistry , vol.239 , pp. 1411-1414
    • Stark, G.R.1
  • 17
    • 37049112593 scopus 로고
    • The e1cb mechanism for thiocarbamate ester Hydrolysis-Equilibrium and Kinetic-Studies
    • Bourne, N., Williams, A., Douglas, K. T., Penkava, T. R. The E1cb Mechanism for Thiocarbamate Ester Hydrolysis-Equilibrium and Kinetic-Studies. J Chem Soc Perk T 2, 1827-1832, doi: Doi 10.1039/P29840001827 (1984).
    • (1984) J Chem Soc Perk T , vol.2 , pp. 1827-1832
    • Bourne, N.1    Williams, A.2    Douglas, K.T.3    Penkava, T.R.4
  • 18
    • 84876572438 scopus 로고    scopus 로고
    • Skin pH: From basic science to basic skin care
    • Ali, S. M., Yosipovitch, G. Skin pH: from basic science to basic skin care. Acta dermato-venereologica 93, 261-267, doi: 10.2340/00015555-1531 (2013).
    • (2013) Acta Dermato-venereologica , vol.93 , pp. 261-267
    • Ali, S.M.1    Yosipovitch, G.2
  • 20
    • 69249131759 scopus 로고    scopus 로고
    • Accumulation of FITC near stratum corneum-visualizing epidermal distribution of a strong sensitizer using two-photon microscopy
    • Samuelsson, K. et al. Accumulation of FITC near stratum corneum-visualizing epidermal distribution of a strong sensitizer using two-photon microscopy. Contact dermatitis 61, 91-100, doi: 10.1111/j.1600-0536.2009.01591.x (2009).
    • (2009) Contact Dermatitis , vol.61 , pp. 91-100
    • Samuelsson, K.1
  • 21
    • 33845195281 scopus 로고    scopus 로고
    • Local lymph node assay (LLNA) for detection of sensitization capacity of chemicals
    • Gerberick, G. F., Ryan, C. A., Dearman, R. J., Kimber, I. Local lymph node assay (LLNA) for detection of sensitization capacity of chemicals. Methods 41, 54-60, doi: 10.1016/j.ymeth.2006.07.006 (2007).
    • (2007) Methods , vol.41 , pp. 54-60
    • Gerberick, G.F.1    Ryan, C.A.2    Dearman, R.J.3    Kimber, I.4
  • 22
    • 0032776406 scopus 로고    scopus 로고
    • A comparison of statistical approaches to the derivation of EC3 values from local lymph node assay dose responses
    • Basketter, D. et al. A comparison of statistical approaches to the derivation of EC3 values from local lymph node assay dose responses. J. Appl. Toxicol. 19, 261-266 (1999).
    • (1999) J. Appl. Toxicol. , vol.19 , pp. 261-266
    • Basketter, D.1
  • 23
    • 36849115659 scopus 로고
    • Self-Consistent Molecular-Orbital methods IX: An extended Gaussian-type Basis for Molecular-Orbital studies of organic molecules
    • Ditchfield, R., Hehre, W. J., Pople, J. A. Self-Consistent Molecular-Orbital Methods IX: An Extended Gaussian-type Basis for Molecular-Orbital Studies of Organic Molecules. Journal of Chemical Physics 54, 724-728 (1971).
    • (1971) Journal of Chemical Physics , vol.54 , pp. 724-728
    • Ditchfield, R.1    Hehre, W.J.2    Pople, J.A.3
  • 24
    • 0347170005 scopus 로고
    • Self-Consistent Molecular-Orbital Methods XII: Further extensions of gaussian-type basis sets for use in molecular orbital studies of organic molecules
    • Hehre, W. J., Ditchfield, R., Pople, J. A. Self-Consistent Molecular-Orbital Methods XII: Further Extensions of Gaussian-type Basis sets for use in Molecular Orbital Studies of Organic Molecules. Journal of Chemical Physics 56, 2257-2261 (1972).
    • (1972) Journal of Chemical Physics , vol.56 , pp. 2257-2261
    • Hehre, W.J.1    Ditchfield, R.2    Pople, J.A.3
  • 25
    • 36849109128 scopus 로고
    • Self-Consistent Molecular-Orbital Methods XIII: An extended Gaussian-type basis for boron
    • Hehre, W. J., Pople, J. A. Self-Consistent Molecular-Orbital Methods XIII: An Extended Gaussian-type Basis for Boron. Journal of Chemical Physics 56, 4233 (1972).
    • (1972) Journal of Chemical Physics , vol.56 , pp. 4233
    • Hehre, W.J.1    Pople, J.A.2
  • 26
    • 33748545144 scopus 로고
    • The influence of polarization functions on molecular orbital hydrogenation energies
    • Hariharan, P. C., Pople, J. A. The influence of polarization functions on molecular orbital hydrogenation energies. Theoretica Chimica Acta 28, 213-222 (1973).
    • (1973) Theoretica Chimica Acta , vol.28 , pp. 213-222
    • Hariharan, P.C.1    Pople, J.A.2
  • 27
    • 36749111501 scopus 로고
    • Self-Consistent molecular orbital methods XIX: Split-Valence Gaussian-type basis sets for beryllium
    • Binkley, J. S., Pople, J. A. Self-Consistent Molecular Orbital Methods XIX: Split-Valence Gaussian-type Basis Sets for Beryllium. Journal of Chemical Physics 66, 879-880 (1977).
    • (1977) Journal of Chemical Physics , vol.66 , pp. 879-880
    • Binkley, J.S.1    Pople, J.A.2
  • 29
    • 4243553426 scopus 로고
    • Density-Functional Exchange-Energy approximation with correct asymptotic behaviour
    • Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behaviour. Physical Review A 38, 3098-3100 (1988).
    • (1988) Physical Review A , vol.38 , pp. 3098-3100
    • Becke, A.D.1
  • 30
    • 23244460838 scopus 로고
    • Atoms, molecules, solids, and surfaces: Applications of the generalized gradient approximation for exchange and correlation
    • Perdew, J. P. et al. Atoms, molecules, solids, and surfaces: Applications of the generalized gradient approximation for exchange and correlation. Physical Review B 46, 6671-6687 (1992).
    • (1992) Physical Review B , vol.46 , pp. 6671-6687
    • Perdew, J.P.1
  • 31
    • 0000189651 scopus 로고
    • Density functional thermochemistry III: The role of exact exchange
    • Becke, A. D. Density Functional Thermochemistry III: The Role of Exact Exchange. Journal of Chemical Physics 98, 5648-5652 (1993).
    • (1993) Journal of Chemical Physics , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 32
    • 34250817103 scopus 로고
    • A new mixing of Hartree-Fock and Local Density-Functional theories
    • Becke, A. D. A New Mixing of Hartree-Fock and Local Density-Functional Theories. Journal of Chemical Physics 98, 1372-1377 (1993).
    • (1993) Journal of Chemical Physics , vol.98 , pp. 1372-1377
    • Becke, A.D.1
  • 33
    • 33751157732 scopus 로고
    • Ab initio calculation of vibrational absorption and circular dichroism spectra using density functional force fields
    • Stephens, P. J., Devlin, F. J., Chabalowski, C. F., Frisch, M. J. Ab Initio Calculation of Vibrational Absorption and Circular Dichroism Spectra using Density Functional Force Fields. Journal of Physical Chemistry 98, 11623-11627 (1994).
    • (1994) Journal of Physical Chemistry , vol.98 , pp. 11623-11627
    • Stephens, P.J.1    Devlin, F.J.2    Chabalowski, C.F.3    Frisch, M.J.4
  • 34
    • 77951680464 scopus 로고    scopus 로고
    • A consistent and accurate ab inition parametrization of density functional dispersion correlation (DFT-D) for the 94 Elements H-Pu
    • Grimme, S., Antony, J., Ehrlich, S., Krieg, H. A Consistent and Accurate ab inition Parametrization of Density Functional Dispersion Correlation (DFT-D) for the 94 Elements H-Pu. Journal of Chemical Physics 132, 154104 (2010).
    • (2010) Journal of Chemical Physics , vol.132 , pp. 154104
    • Grimme, S.1    Antony, J.2    Ehrlich, S.3    Krieg, H.4
  • 35
    • 79952981826 scopus 로고    scopus 로고
    • A thorough benchmark of density functional methods for general main group thermochemistry kinetics, and non-covalent interactions
    • Goerigk, L., Grimme, S. A Thorough Benchmark of Density Functional Methods for General Main Group Thermochemistry, Kinetics, and Non-Covalent Interactions. Phys. Chem. Chem. Phys. 13, 6670-6688 (2011).
    • (2011) Phys. Chem. Chem. Phys. , vol.13 , pp. 6670-6688
    • Goerigk, L.1    Grimme, S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.