DTPD-Q (Synonyms: 2,5-Bis(o-tolylamino)cyclohexa-2,5-diene-1,4-dione,DTPD-quinone)

DTPD-Q is an oxidized derivative of the antioxidant and methylphenyl substituted p-phenylenediamine DTPD.¹ It is an inhibitor of dynamin 1 (IC₅₀ = 273 µM) and reduces clathrin-mediated endocytosis in serum-starved U2OS cells (IC₅₀ = 120 µM). DTPD-Q is less toxic to the aquatic bacterium V. fischeri than DTPD (EC₅₀ = 1.98 mg/L).² It increases intestinal permeability of, and production of reactive oxygen species (ROS) in, C. elegans when used at concentrations of 1 or 10 µg/ml.³ DTPD-Q has been found in roadway runoff water and roadside soils, indoor dust, as well as consumer products made from recycled tire rubber.^4,5,6

References:
[1].MacGregor, K.A., Abdel-Hamid, M.K., Odell, L.R., et al.Development of quinone analogues as dynamin GTPase inhibitorsEur. J. Med. Chem.85191-206(2014).
[2].Wang, W., Chen, Y., Fang, J., et al.Toxicity of substituted p-phenylenediamine antioxidants and their derived novel quinones on aquatic bacterium: Acute effects and mechanistic insightsJ. Hazard. Mater.469:133900(2024).
[3].Wang, Y., Liang, G., Chao, J., et al.Comparison of intestinal toxicity in enhancing intestinal permeability and in causing ROS production of six PPD quinones in Caenorhabditis elegansSci. Total Environ.927172306(2024).
[4].Cao, G., Wang, W., Zhang, J., et al.New evidence of rubber-derived quinones in water, air, and soilEnviron. Sci. Technol.56(7)4142-4150(2022).
[5].Zhu, J., Guo, R., Jiang, S., et al.Occurrence of p-phenylenediamine antioxidants (PPDs) and PPDs-derived quinones in indoor dustSci. Total Environ.912169325(2024).
[6].Zhao, H.N., Hu, X., Gonzalez, M., et al.Screening p-phenylenediamine antioxidants, their transformation products, and industrial chemical additives in crumb rubber and elastomeric consumer productsEnviron. Sci. Technol.57(7)2779-2791(2023).