Structure‐activity relationships in allergic contact dermatitis induced by methacrylates

Abstract

Some methacrylates are known to be strong contact sensitizers. To determine the effect of side-chain length on sensitizing potential, we examined 11 derivatives with linear side chains from C1 to C18 in an experimental sensitization test in guinea pigs. The results showed an increase in the sensitizing potential with increasing length of the alkyl side chain from C1 to C12. The C12 derivative, lauryl methacrylate, showed the strongest sensitizing potential. Further elongation of the alkyl side chain of methacrylates resulted in a decrease in the potential. With respect to the side-chain-length-dependent sensitizing potential, the present results correspond well with the findings obtained with other compounds like primin, catechols, phenols, hydroquinones, and gallates.

An epidemic of occupational contact dermatitis from an acrylic glue

“…Experiments on guinea pigs have shown that the allergizing potential of methacrylates grows with increasing length of the alkyl side chain from C 1 to C 12 , the C 12 derivative showing the strongest sensitizing potential. Further elongation of the alkyl side chain of methacrylates resulted in a decrease in the potential (15). Our results confirm the opinion that long‐chain acrylates also show a strong sensitizing potential.…”

Allergic contact dermatitis following airborne exposure to methacrylates used in the manufacture of artificial skin

“…The 2 commonest (meth)acrylate sensitizers are ethylene glycol dimethacrylate and 2‐HEMA (1). Kanazawa et al (2) demonstrated that the sensitizing potential increases as the alkyl side‐chain lengthens from C1 to C12. Fortunately, airborne sensitization problems for dental patients are rarely seen, presumably due to limited exposure: there is only 1 reported dental case of airborne allergic contact dermatitis from (meth)acrylates and, in this instance, the patient was already sensitized (3).…”

Final Report of the Cosmetic Ingredient Review Expert Panel Safety Assessment of Polymethyl Methacrylate (PMMA), Methyl Methacrylate Crosspolymer, and Methyl Methacrylate/Glycol Dimethacrylate Crosspolymer

“…80 The minimum induction concentration in a guinea pig maximization test was 1 mol/L (100 and 120 ppm). 81 In a local lymph node assay, MMA had an EC3 (stimulation index [SI] of 3 relative to concurrent vehicle-treated controls) of 60% w/ v in acetone and 90% w/v in olive oil. Methyl methacrylate was rated as a weak contact allergen.…”