Impact of a Heteroatom in a Structure-Activity Relationship Study on Analogues of Phenyl Glycidyl Ether (PGE) from Epoxy Resin Systems.

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Fältnamn	Indikatorer	Metadata
000		03383naa a2200313 4500
001		oai:gup.ub.gu.se/140655
003		SwePub
008		240910s2011 \| \|\|\|\|\|\|\|\|\|\|\|000 \|\|eng\|
024	7	a https://gup.ub.gu.se/publication/1406552 URI
024	7	a https://doi.org/10.1021/tx100417r2 DOI
040		a (SwePub)gu
041		a eng
042		9 SwePub
072	7	a ref2 swepub-contenttype
072	7	a art2 swepub-publicationtype
100	1	a Niklasson, Ida B,d 1982u Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry4 aut
245	1 0	a Impact of a Heteroatom in a Structure-Activity Relationship Study on Analogues of Phenyl Glycidyl Ether (PGE) from Epoxy Resin Systems.
264		c 2011-03-29
264	1	b American Chemical Society (ACS),c 2011
520		a Epoxy resins are among the most common causes of occupational contact dermatitis. They are normally used in so-called epoxy resin systems (ERS). These commercial products are combinations of epoxy resins, curing agents, modifiers, and reactive diluents. The most frequently used resins are diglycidyl ethers based on bisphenol A (DGEBA) and bisphenol F (DGEBF). In this study, we have investigated the contact allergenic properties of a series of analogues to the reactive diluent phenyl glycidyl ether (PGE), all with similar basic structures but with varying heteroatoms or with no heteroatom present. The chemical reactivity of the compounds in the test series toward the hexapeptide H-Pro-His-Cys-Lys-Arg-Met-OH was investigated. All epoxides were shown to bind covalently to both cysteine and proline residues. The percent depletion of nonreacted peptide was also studied resulting in ca. 60% depletion when using either PGE, phenyl 2,3-epoxypropyl sulfide (2), or N-(2,3-epoxypropyl)aniline (3), and only 15% when using 1,2-epoxy-4-phenylbutane (4) at the same time point. The skin sensitization potencies of the epoxides using the murine local lymph node assay (LLNA) were evaluated in relation to the observed physicochemical and reactivity properties. To enable determination of statistical significance between structurally closely related compounds, a nonpooled LLNA was performed. It was found that all investigated compounds containing a heteroatom in the α-position to the epoxide were strong sensitizers, congruent with the reactivity data, indicating that the impact of a heteroatom is crucial for the sensitizing capacity for this type of epoxides.
650	7	a NATURVETENSKAPx Kemi0 (SwePub)1042 hsv//swe
650	7	a NATURAL SCIENCESx Chemical Sciences0 (SwePub)1042 hsv//eng
700	1	a Delaine, Tamara,d 1981u Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry4 aut0 (Swepub:gu)xdelta
700	1	a Luthman, Kristina,d 1953u Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry4 aut0 (Swepub:gu)xlutkr
700	1	a Karlberg, Ann-Therese,d 1947u Gothenburg University,Göteborgs universitet,Institutionen för kemi,Department of Chemistry4 aut0 (Swepub:gu)xkaann
710	2	a Göteborgs universitetb Institutionen för kemi4 org
773	0	t Chemical research in toxicologyd : American Chemical Society (ACS)g 24:4, s. 542-8q 24:4<542-8x 1520-5010x 0893-228X
856	4 8	u https://gup.ub.gu.se/publication/140655
856	4 8	u https://doi.org/10.1021/tx100417r

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Av författaren/redakt...: Niklasson, Ida B ...; Delaine, Tamara, ...; Luthman, Kristin ...; Karlberg, Ann-Th ...

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