Introduction of a methoxymethyl side chain into p-phenylenediamine attenuates its sensitizing potency and reduces the risk of allergy induction

Toxicology and Applied Pharmacology
Carsten GoebelBrunhilde Blömeke

Abstract

The strong sensitizing potencies of the most important primary intermediates of oxidative hair dyes, p-phenylenediamine (PPD) and p-toluylenediamine (PTD, i.e. 2-methyl-PPD) are well established. They are considered as the key sensitizers in hair dye allergic contact dermatitis. While modification of their molecular structure is expected to alter their sensitizing properties, it may also impair their color performance. With introduction of a methoxymethyl side chain we found the primary intermediate 2-methoxymethyl-p-phenylenediamine (ME-PPD) with excellent hair coloring performance but significantly reduced sensitizing properties compared to PPD and PTD: In vitro, ME-PPD showed an attenuated innate immune response when analyzed for its protein reactivity and dendritic cell activation potential. In vivo, the effective concentration of ME-PPD necessary to induce an immune response 3-fold above vehicle control (EC3 value) in the local lymph node assay (LLNA) was 4.3%, indicating a moderate skin sensitizing potency compared to values of 0.1 and 0.17% for PPD and PTD, respectively. Finally, assessing the skin sensitizing potency of ME-PPD under consumer hair dye usage conditions through a quantitative risk assessment (QRA) indicate...Continue Reading

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Citations

Mar 31, 2016·Contact Dermatitis·David A BasketterJohn P McFadden
Jul 18, 2015·Toxicological Sciences : an Official Journal of the Society of Toxicology·Nora L KrutzBrunhilde Blömeke
Oct 29, 2014·Contact Dermatitis·Stefan F Martin
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May 22, 2016·The British Journal of Dermatology·K PongpairojD A Basketter
Jan 23, 2015·Current Opinion in Allergy and Clinical Immunology·Stefan F Martin
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Aug 3, 2017·Contact Dermatitis·Jennifer Hennen, Brunhilde Blömeke
May 21, 2016·Contact Dermatitis·Marie-Louise A SchuttelaarFrancesca Larese Filon
Dec 2, 2020·Journal of Hazardous Materials·Gopalakrishnan VenkatesanGiorgia Pastorin

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