An alpha,beta-unsaturated oxime identified as a strong contact allergen. Indications of antigen formation via several pathways.
The aim of this study was to examine the possible skin sensitizing effect of oximes, employing an alpha,beta-unsaturated oxime as the model compound. Oximes are not frequently used as biologically active compounds. However, they have been shown to possess both anti-inflammatory and anti-allergic activities. Furthermore, in a recent study, a number of oximes and oxime-ethers of hydroxylated benzaldehydes and acetophenones were found to be powerful antioxidants suggested to be used in consumer products such as cosmetics and food. Although there are only few reports on the sensitizing effect of oximes, their ability to be hydrolyzed to the corresponding ketones or aldehydes makes them potential contact allergens. The oxime investigated in this study was demonstrated to be a strong contact allergen in both mice and guinea pigs, capable of sensitize the control animals after only one dermal exposure. In order to elucidate the mechanisms for the formation of the complete antigen, a variety of analogues with different reactivity were tested. The results indicate that alpha,beta-unsaturated oximes can react with proteins via several different pathways. Most likely, a metabolic transformation is involved. Due to the strong allergenic effect of the oxime investigated, we strongly advise against the use of such oximes in consumer products until a better understanding of their interactions with biological macromolecules has been obtained.
Department of Chemistry, Dermatochemistry and Skin Allergy, Göteborg University, SE-412 96 Göteborg, Sweden. amnil@chem.gu.se
Anna-Malin
AM
Nilsson
Moa Andresen
MA
Bergström
Kristina
K
Luthman
J Lars G
JL
Nilsson
Ann-Therese
AT
Karlberg
D000485:Allergens / Q000737:chemistry / Q000633:toxicity*; D000818:Animals; D003429:Cross Reactions; D003877:Dermatitis, Contact / Q000473:pathology; D005260:Female; D005620:Freund's Adjuvant / Q000633:toxicity; D006168:Guinea Pigs; D007202:Indicators and Reagents; D023441:Local Lymph Node Assay; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D008808:Mice, Inbred CBA; D009584:Nitrogen / Q000737:chemistry; D010091:Oximes / Q000737:chemistry / Q000633:toxicity*; D012882:Skin Tests; D013455:Sulfur / Q000737:chemistry
D000485:Allergens; D007202:Indicators and Reagents; D010091:Oximes; D013455:Sulfur; D005620:Freund's Adjuvant; D009584:Nitrogen