2,2',6-Tribromobisphenol A

2,2',6-Tribromobisphenol A (Tri-BBPA) is a degradation product of the flame retardant tetrabromobisphenol A and an environmental contaminant.¹ It is an inhibitor of 12-lipoxygenase (12-LO) and 15-LO (IC₅₀s = 7 and 5 µM, respectively, for the human enzymes).² Tri-BBPA (60 µM) induces apoptosis and cell cycle arrest at the G₀/G₁ phase in primary human embryonic stem cells (ESCs).³ It decreases serum levels of total protein, albumin, γ-glutamyl transpeptidase (GGT), lactate dehydrogenase (LDH), creatine kinase (CK), and urea, increases serum levels of acetylcholinesterase (AChE), and disrupts hepatic metabolism of tryptophan in mice when administered at a dose of 200 mg/kg per day for 14 days.⁴ Tri-BBPA has been found in industrial soil samples and human breast milk.^1,5

References:
[1]. Liu, A., Shi, J., Qu, G., et al.Identification of emerging brominated chemicals as the transformation products of tetrabromobisphenol A (TBBPA) derivatives in soilEnviron. Sci. Technol.51(10)5434-5444(2017).
[2]. Segraves, E.N., Shah, R.R., Segraves, N.L., et al.Probing the activity differences of simple and complex brominated aryl compounds against 15-soybean, 15-human, and 12-human lipoxygenaseJ. Med. Chem.47(16)4060-4065(2004).
[3]. Yang, Y., He, S., Qi, Z., et al.Proliferation toxicity and mechanism of novel mixed bromine/chlorine transformation products of tetrabromobisphenol A on human embryonic stem cellJ. Hazard. Mater.449131050(2023).
[4]. Kuang, H.X., Dong, C.Y., Yan, L., et al.Exposure to synthesized tribromobisphenol A and critical effects: Metabolic pathways, disease signature, and benchmark dose derivationSci. Total Environ.932173117(2024).
[5]. Nakao, T.A., Akiyama, E., Kakutani, H., et al.Levels of tetrabromobisphenol A, tribromobisphenol A, dibromobisphenol A, monobromobisphenol A, and bisphenol a in Japanese breast milkChem. Res. Toxicol.28(4)722-728(2015).