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Epoxyalcohols: bioactivation and conjugation required for skin sensitization.

Artikel i vetenskaplig tidskrift
Författare Tamara Delaine
David J. Ponting
Ida B Niklasson
Roger Emter
Lina Hagvall
Per-Ola Norrby
Andreas Natsch
Kristina Luthman
Ann-Therese Karlberg
Publicerad i Chemical research in toxicology
Volym 27
Nummer/häfte 10
Sidor 1860-70
ISSN 1520-5010
Publiceringsår 2014
Publicerad vid Institutionen för kliniska vetenskaper, Avdelningen för dermatologi och venereologi
Institutionen för kemi och molekylärbiologi
Sidor 1860-70
Språk en
Länkar dx.doi.org/10.1021/tx500297d
Ämnesord CD14, Thrombosis, Carotid plaques, Macrophages, Lipopolysaccharides, Angiotensin receptor blocker
Ämneskategorier Dermatologi och venereologi

Sammanfattning

Allylic alcohols, such as geraniol 1, are easily oxidized by varying mechanisms, including the formation of both 2,3-epoxides and/or aldehydes. These epoxides, aldehydes, and epoxy-aldehydes can be interconverted to each other, and the reactivity of them all must be considered when considering the sensitization potential of the parent allylic alcohol. An in-depth study of the possible metabolites and autoxidation products of allylic alcohols is described, covering the formation, interconversion, reactivity, and sensitizing potential thereof, using a combination of in vivo, in vitro, in chemico, and in silico methods. This multimodal study, using the integration of diverse techniques to investigate the sensitization potential of a molecule, allows the identification of potential candidate(s) for the true culprit(s) in allergic responses to allylic alcohols. Overall, the sensitization potential of the investigated epoxyalcohols and unsaturated alcohols was found to derive from metabolic oxidation to the more potent aldehyde where possible. Where this is less likely, the compound remains weakly or nonsensitizing. Metabolic activation of a double bond to form a nonconjugated, nonterminal epoxide moiety is not enough to turn a nonsensitizing alcohol into a sensitizer, as such epoxides have low reactivity and low sensitizing potency. In addition, even an allylic 2,3-epoxide moiety is not necessarily a potent sensitizer, as shown for 2, where formation of the epoxide weakens the sensitization potential.

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