Demonstration of the first-pass metabolism in the skin of the hair dye, 4-amino-2-hydroxytoluene, using the Chip2 skin-liver microphysiological model

J Appl Toxicol. 2021 Oct;41(10):1553-1567. doi: 10.1002/jat.4146. Epub 2021 Feb 17.

Abstract

We used TissUse's HUMIMIC Chip2 microfluidic model, incorporating reconstructed skin models and liver spheroids, to investigate the impact of consumer-relevant application scenarios on the metabolic fate of the hair dye, 4-amino-2-hydroxytoluene (AHT). After a single topical or systemic application of AHT to Chip2 models, medium was analysed for parent and metabolites over 5 days. The metabolic profile of a high dose (resulting in a circuit concentration of 100 μM based on 100% bioavailability) of AHT was the same after systemic and topical application to 96-well EpiDerm™ models. Additional experiments indicated that metabolic capacity of EpiDerm™ models were saturated at this dose. At 2.5 μM, concentrations of AHT and several of its metabolites differed between application routes. Topical application resulted in a higher Cmax and a 327% higher area under the curve (AUC) of N-acetyl-AHT, indicating a first-pass effect in the EpiDerm™ models. In accordance with in vivo observations, there was a concomitant decrease in the Cmax and AUC of AHT-O-sulphate after topical, compared with systemic application. A similar alteration in metabolite ratios was observed using a 24-well full-thickness skin model, EpiDermFT™, indicating that a first-pass effect was also possible to detect in a more complex model. In addition, washing the EpiDermFT™ after 30 min, thus reflecting consumer use, decreased the systemic exposure to AHT and its metabolites. In conclusion, the skin-liver Chip2 model can be used to (a) recapitulate the first-pass effect of the skin and alterations in the metabolite profile of AHT observed in vivo and (b) provide consumer-relevant data regarding leave-on/rinse-off products.

Keywords: 4-amino-2-hydroxytoluene; Chip2; EpiDerm; EpiDermFT; cosmetics; first-pass metabolism; microphysiological systems; skin.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / metabolism*
  • Aniline Compounds / toxicity*
  • Cells, Cultured / drug effects
  • Cells, Cultured / metabolism
  • Cresols / metabolism*
  • Cresols / toxicity*
  • Hair Dyes / metabolism*
  • Hair Dyes / toxicity*
  • Humans
  • Liver / drug effects
  • Liver / metabolism*
  • Organ Culture Techniques
  • Skin / drug effects
  • Skin / metabolism*

Substances

  • Aniline Compounds
  • Cresols
  • Hair Dyes