Structure–activity relationships for selected fragrance allergens
Fragrance substances represent a very diverse group of chemicals, a proportion of them providing not only desirable aroma characteristics, but also being associated with adverse effects, notably the ability to cause allergic reactions in the skin. However, efforts to find substitute materials are ha...
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Gespeichert in:
| Autor*in: |
Patlewicz, G. Y. [verfasserIn] Wright, Z. M. [verfasserIn] Basketter, D. A. [verfasserIn] |
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| Format: |
E-Artikel |
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| Erschienen: |
Oxford, UK: Munksgaard International Publishers ; 2002 |
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Online-Ressource |
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2002 ; Blackwell Publishing Journal Backfiles 1879-2005 |
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In: Contact dermatitis - Oxford [u.a.] : Wiley-Blackwell, 1975, 47(2002), 4, Seite 0 |
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volume:47 ; year:2002 ; number:4 ; pages:0 |
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| DOI / URN: |
10.1034/j.1600-0536.2002.470406.x |
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| 520 | |a Fragrance substances represent a very diverse group of chemicals, a proportion of them providing not only desirable aroma characteristics, but also being associated with adverse effects, notably the ability to cause allergic reactions in the skin. However, efforts to find substitute materials are hampered by the need to undertake animal testing to evaluate both the presence and the degree of skin sensitization hazard. One potential route to avoid such testing is to understand the relationships between chemical structure and skin sensitization. In the present work we have evaluated two groups of fragrance chemicals, saturated aldehydes (aryl substituted and aliphatic aldehydes) and α,β-unsaturated aldehydes. Data on their skin sensitization potency defined using the local lymph node assay has been evaluated in relation to their physicochemical properties. The initial outcome has been consistent with the concept that α,β-unsaturated aldehydes react largely via Michael addition, whilst the group of saturated aldehydes form Schiff bases with proteins. Simple models of chemical reactivity based on these mechanisms suggest that it may be possible to predict allergenic potency. Accordingly, the evaluation of an additional group of similar aldehydes is now underway to assess the robustness of these models, with some emphasis being based on ensuring a wider spread of chemical reactivity. | ||
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10.1034/j.1600-0536.2002.470406.x doi (DE-627)NLEJ242533612 DE-627 ger DE-627 rakwb Patlewicz, G. Y. verfasserin aut Structure–activity relationships for selected fragrance allergens Oxford, UK Munksgaard International Publishers 2002 Online-Ressource nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Fragrance substances represent a very diverse group of chemicals, a proportion of them providing not only desirable aroma characteristics, but also being associated with adverse effects, notably the ability to cause allergic reactions in the skin. However, efforts to find substitute materials are hampered by the need to undertake animal testing to evaluate both the presence and the degree of skin sensitization hazard. One potential route to avoid such testing is to understand the relationships between chemical structure and skin sensitization. In the present work we have evaluated two groups of fragrance chemicals, saturated aldehydes (aryl substituted and aliphatic aldehydes) and α,β-unsaturated aldehydes. Data on their skin sensitization potency defined using the local lymph node assay has been evaluated in relation to their physicochemical properties. The initial outcome has been consistent with the concept that α,β-unsaturated aldehydes react largely via Michael addition, whilst the group of saturated aldehydes form Schiff bases with proteins. Simple models of chemical reactivity based on these mechanisms suggest that it may be possible to predict allergenic potency. Accordingly, the evaluation of an additional group of similar aldehydes is now underway to assess the robustness of these models, with some emphasis being based on ensuring a wider spread of chemical reactivity. 2002 Blackwell Publishing Journal Backfiles 1879-2005 |2002|||||||||| aldehydes Wright, Z. M. verfasserin aut Basketter, D. A. verfasserin aut Pease, C. K. oth Lepoittevin, J.-P. oth Giménez arnau, E. oth In Contact dermatitis Oxford [u.a.] : Wiley-Blackwell, 1975 47(2002), 4, Seite 0 Online-Ressource (DE-627)NLEJ243927118 (DE-600)2027120-7 1600-0536 nnns volume:47 year:2002 number:4 pages:0 http://dx.doi.org/10.1034/j.1600-0536.2002.470406.x text/html Verlag Deutschlandweit zugänglich Volltext GBV_USEFLAG_U ZDB-1-DJB GBV_NL_ARTICLE AR 47 2002 4 0 |
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10.1034/j.1600-0536.2002.470406.x doi (DE-627)NLEJ242533612 DE-627 ger DE-627 rakwb Patlewicz, G. Y. verfasserin aut Structure–activity relationships for selected fragrance allergens Oxford, UK Munksgaard International Publishers 2002 Online-Ressource nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Fragrance substances represent a very diverse group of chemicals, a proportion of them providing not only desirable aroma characteristics, but also being associated with adverse effects, notably the ability to cause allergic reactions in the skin. However, efforts to find substitute materials are hampered by the need to undertake animal testing to evaluate both the presence and the degree of skin sensitization hazard. One potential route to avoid such testing is to understand the relationships between chemical structure and skin sensitization. In the present work we have evaluated two groups of fragrance chemicals, saturated aldehydes (aryl substituted and aliphatic aldehydes) and α,β-unsaturated aldehydes. Data on their skin sensitization potency defined using the local lymph node assay has been evaluated in relation to their physicochemical properties. The initial outcome has been consistent with the concept that α,β-unsaturated aldehydes react largely via Michael addition, whilst the group of saturated aldehydes form Schiff bases with proteins. Simple models of chemical reactivity based on these mechanisms suggest that it may be possible to predict allergenic potency. Accordingly, the evaluation of an additional group of similar aldehydes is now underway to assess the robustness of these models, with some emphasis being based on ensuring a wider spread of chemical reactivity. 2002 Blackwell Publishing Journal Backfiles 1879-2005 |2002|||||||||| aldehydes Wright, Z. M. verfasserin aut Basketter, D. A. verfasserin aut Pease, C. K. oth Lepoittevin, J.-P. oth Giménez arnau, E. oth In Contact dermatitis Oxford [u.a.] : Wiley-Blackwell, 1975 47(2002), 4, Seite 0 Online-Ressource (DE-627)NLEJ243927118 (DE-600)2027120-7 1600-0536 nnns volume:47 year:2002 number:4 pages:0 http://dx.doi.org/10.1034/j.1600-0536.2002.470406.x text/html Verlag Deutschlandweit zugänglich Volltext GBV_USEFLAG_U ZDB-1-DJB GBV_NL_ARTICLE AR 47 2002 4 0 |
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10.1034/j.1600-0536.2002.470406.x doi (DE-627)NLEJ242533612 DE-627 ger DE-627 rakwb Patlewicz, G. Y. verfasserin aut Structure–activity relationships for selected fragrance allergens Oxford, UK Munksgaard International Publishers 2002 Online-Ressource nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Fragrance substances represent a very diverse group of chemicals, a proportion of them providing not only desirable aroma characteristics, but also being associated with adverse effects, notably the ability to cause allergic reactions in the skin. However, efforts to find substitute materials are hampered by the need to undertake animal testing to evaluate both the presence and the degree of skin sensitization hazard. One potential route to avoid such testing is to understand the relationships between chemical structure and skin sensitization. In the present work we have evaluated two groups of fragrance chemicals, saturated aldehydes (aryl substituted and aliphatic aldehydes) and α,β-unsaturated aldehydes. Data on their skin sensitization potency defined using the local lymph node assay has been evaluated in relation to their physicochemical properties. The initial outcome has been consistent with the concept that α,β-unsaturated aldehydes react largely via Michael addition, whilst the group of saturated aldehydes form Schiff bases with proteins. Simple models of chemical reactivity based on these mechanisms suggest that it may be possible to predict allergenic potency. Accordingly, the evaluation of an additional group of similar aldehydes is now underway to assess the robustness of these models, with some emphasis being based on ensuring a wider spread of chemical reactivity. 2002 Blackwell Publishing Journal Backfiles 1879-2005 |2002|||||||||| aldehydes Wright, Z. M. verfasserin aut Basketter, D. A. verfasserin aut Pease, C. K. oth Lepoittevin, J.-P. oth Giménez arnau, E. oth In Contact dermatitis Oxford [u.a.] : Wiley-Blackwell, 1975 47(2002), 4, Seite 0 Online-Ressource (DE-627)NLEJ243927118 (DE-600)2027120-7 1600-0536 nnns volume:47 year:2002 number:4 pages:0 http://dx.doi.org/10.1034/j.1600-0536.2002.470406.x text/html Verlag Deutschlandweit zugänglich Volltext GBV_USEFLAG_U ZDB-1-DJB GBV_NL_ARTICLE AR 47 2002 4 0 |
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10.1034/j.1600-0536.2002.470406.x doi (DE-627)NLEJ242533612 DE-627 ger DE-627 rakwb Patlewicz, G. Y. verfasserin aut Structure–activity relationships for selected fragrance allergens Oxford, UK Munksgaard International Publishers 2002 Online-Ressource nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Fragrance substances represent a very diverse group of chemicals, a proportion of them providing not only desirable aroma characteristics, but also being associated with adverse effects, notably the ability to cause allergic reactions in the skin. However, efforts to find substitute materials are hampered by the need to undertake animal testing to evaluate both the presence and the degree of skin sensitization hazard. One potential route to avoid such testing is to understand the relationships between chemical structure and skin sensitization. In the present work we have evaluated two groups of fragrance chemicals, saturated aldehydes (aryl substituted and aliphatic aldehydes) and α,β-unsaturated aldehydes. Data on their skin sensitization potency defined using the local lymph node assay has been evaluated in relation to their physicochemical properties. The initial outcome has been consistent with the concept that α,β-unsaturated aldehydes react largely via Michael addition, whilst the group of saturated aldehydes form Schiff bases with proteins. Simple models of chemical reactivity based on these mechanisms suggest that it may be possible to predict allergenic potency. Accordingly, the evaluation of an additional group of similar aldehydes is now underway to assess the robustness of these models, with some emphasis being based on ensuring a wider spread of chemical reactivity. 2002 Blackwell Publishing Journal Backfiles 1879-2005 |2002|||||||||| aldehydes Wright, Z. M. verfasserin aut Basketter, D. A. verfasserin aut Pease, C. K. oth Lepoittevin, J.-P. oth Giménez arnau, E. oth In Contact dermatitis Oxford [u.a.] : Wiley-Blackwell, 1975 47(2002), 4, Seite 0 Online-Ressource (DE-627)NLEJ243927118 (DE-600)2027120-7 1600-0536 nnns volume:47 year:2002 number:4 pages:0 http://dx.doi.org/10.1034/j.1600-0536.2002.470406.x text/html Verlag Deutschlandweit zugänglich Volltext GBV_USEFLAG_U ZDB-1-DJB GBV_NL_ARTICLE AR 47 2002 4 0 |
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10.1034/j.1600-0536.2002.470406.x doi (DE-627)NLEJ242533612 DE-627 ger DE-627 rakwb Patlewicz, G. Y. verfasserin aut Structure–activity relationships for selected fragrance allergens Oxford, UK Munksgaard International Publishers 2002 Online-Ressource nicht spezifiziert zzz rdacontent nicht spezifiziert z rdamedia nicht spezifiziert zu rdacarrier Fragrance substances represent a very diverse group of chemicals, a proportion of them providing not only desirable aroma characteristics, but also being associated with adverse effects, notably the ability to cause allergic reactions in the skin. However, efforts to find substitute materials are hampered by the need to undertake animal testing to evaluate both the presence and the degree of skin sensitization hazard. One potential route to avoid such testing is to understand the relationships between chemical structure and skin sensitization. In the present work we have evaluated two groups of fragrance chemicals, saturated aldehydes (aryl substituted and aliphatic aldehydes) and α,β-unsaturated aldehydes. Data on their skin sensitization potency defined using the local lymph node assay has been evaluated in relation to their physicochemical properties. The initial outcome has been consistent with the concept that α,β-unsaturated aldehydes react largely via Michael addition, whilst the group of saturated aldehydes form Schiff bases with proteins. Simple models of chemical reactivity based on these mechanisms suggest that it may be possible to predict allergenic potency. Accordingly, the evaluation of an additional group of similar aldehydes is now underway to assess the robustness of these models, with some emphasis being based on ensuring a wider spread of chemical reactivity. 2002 Blackwell Publishing Journal Backfiles 1879-2005 |2002|||||||||| aldehydes Wright, Z. M. verfasserin aut Basketter, D. A. verfasserin aut Pease, C. K. oth Lepoittevin, J.-P. oth Giménez arnau, E. oth In Contact dermatitis Oxford [u.a.] : Wiley-Blackwell, 1975 47(2002), 4, Seite 0 Online-Ressource (DE-627)NLEJ243927118 (DE-600)2027120-7 1600-0536 nnns volume:47 year:2002 number:4 pages:0 http://dx.doi.org/10.1034/j.1600-0536.2002.470406.x text/html Verlag Deutschlandweit zugänglich Volltext GBV_USEFLAG_U ZDB-1-DJB GBV_NL_ARTICLE AR 47 2002 4 0 |
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Fragrance substances represent a very diverse group of chemicals, a proportion of them providing not only desirable aroma characteristics, but also being associated with adverse effects, notably the ability to cause allergic reactions in the skin. However, efforts to find substitute materials are hampered by the need to undertake animal testing to evaluate both the presence and the degree of skin sensitization hazard. One potential route to avoid such testing is to understand the relationships between chemical structure and skin sensitization. In the present work we have evaluated two groups of fragrance chemicals, saturated aldehydes (aryl substituted and aliphatic aldehydes) and α,β-unsaturated aldehydes. Data on their skin sensitization potency defined using the local lymph node assay has been evaluated in relation to their physicochemical properties. The initial outcome has been consistent with the concept that α,β-unsaturated aldehydes react largely via Michael addition, whilst the group of saturated aldehydes form Schiff bases with proteins. Simple models of chemical reactivity based on these mechanisms suggest that it may be possible to predict allergenic potency. Accordingly, the evaluation of an additional group of similar aldehydes is now underway to assess the robustness of these models, with some emphasis being based on ensuring a wider spread of chemical reactivity. |
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Fragrance substances represent a very diverse group of chemicals, a proportion of them providing not only desirable aroma characteristics, but also being associated with adverse effects, notably the ability to cause allergic reactions in the skin. However, efforts to find substitute materials are hampered by the need to undertake animal testing to evaluate both the presence and the degree of skin sensitization hazard. One potential route to avoid such testing is to understand the relationships between chemical structure and skin sensitization. In the present work we have evaluated two groups of fragrance chemicals, saturated aldehydes (aryl substituted and aliphatic aldehydes) and α,β-unsaturated aldehydes. Data on their skin sensitization potency defined using the local lymph node assay has been evaluated in relation to their physicochemical properties. The initial outcome has been consistent with the concept that α,β-unsaturated aldehydes react largely via Michael addition, whilst the group of saturated aldehydes form Schiff bases with proteins. Simple models of chemical reactivity based on these mechanisms suggest that it may be possible to predict allergenic potency. Accordingly, the evaluation of an additional group of similar aldehydes is now underway to assess the robustness of these models, with some emphasis being based on ensuring a wider spread of chemical reactivity. |
| abstract_unstemmed |
Fragrance substances represent a very diverse group of chemicals, a proportion of them providing not only desirable aroma characteristics, but also being associated with adverse effects, notably the ability to cause allergic reactions in the skin. However, efforts to find substitute materials are hampered by the need to undertake animal testing to evaluate both the presence and the degree of skin sensitization hazard. One potential route to avoid such testing is to understand the relationships between chemical structure and skin sensitization. In the present work we have evaluated two groups of fragrance chemicals, saturated aldehydes (aryl substituted and aliphatic aldehydes) and α,β-unsaturated aldehydes. Data on their skin sensitization potency defined using the local lymph node assay has been evaluated in relation to their physicochemical properties. The initial outcome has been consistent with the concept that α,β-unsaturated aldehydes react largely via Michael addition, whilst the group of saturated aldehydes form Schiff bases with proteins. Simple models of chemical reactivity based on these mechanisms suggest that it may be possible to predict allergenic potency. Accordingly, the evaluation of an additional group of similar aldehydes is now underway to assess the robustness of these models, with some emphasis being based on ensuring a wider spread of chemical reactivity. |
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Structure–activity relationships for selected fragrance allergens |
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Wright, Z. M. Basketter, D. A. Pease, C. K. Lepoittevin, J.-P. Giménez arnau, E. |
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Wright, Z. M. Basketter, D. A. Pease, C. K. Lepoittevin, J.-P. Giménez arnau, E. |
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10.1034/j.1600-0536.2002.470406.x |
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