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Updated: May 25, 2026

Elucidating the Metabolism of 2,4-Dibromophenol in Plants
Published on: February 10, 2023
Hormonal activities of new brominated flame retardants
M Ezechiáš1, K Svobodová, T Cajthaml
1Laboratory of Environmental Biotechnology, Institute of Microbiology ASCR, v.v.i., Vídeňská 1083, 142 20 Prague, Czech Republic.
Abstract:
After the phase-out of two commercial mixtures of brominated flame retardants, an increasing number of alternative flame retardants have been introduced in commercial applications. None of them, however, has been thoroughly tested for its hormonal activity. We used two yeast reporter-gene assays to determine the potential of eleven compounds to interfere with estrogenic and androgenic pathways. Our data demonstrate the ability of 2,4,6-tribromophenol to lower the transcriptional activity of human estrogen and androgen receptors. A nominal IC(50) value of 14.1 μM for anti-estrogenic and 3.9 μM for anti-androgenic activity was obtained using the luciferase reporter. An IC(50) value of 9.2 μM was calculated for the anti-estrogenic activity measured by the β-galactosidase assay. Of the tested chemicals, this study highlights the endocrine disrupting effects of 2,4,6-tribromophenol whose occurrence in the environment should be monitored.
Insights
Alternative flame retardants were tested for hormonal activity. 2,4,6-tribromophenol showed anti-estrogenic and anti-androgenic effects, indicating potential endocrine disruption that warrants environmental monitoring.
Area of Science:
- Environmental Chemistry
- Toxicology
- Endocrinology
Background:
- Commercial brominated flame retardants are being phased out.
- Numerous alternative flame retardants lack thorough hormonal activity testing.
- Assessing endocrine disruption potential of new chemicals is crucial.
Purpose of the Study:
- To evaluate the endocrine-disrupting potential of eleven alternative flame retardants.
- To investigate interference with estrogenic and androgenic pathways.
- To identify specific compounds with significant hormonal activity.
Main Methods:
- Utilized two distinct yeast reporter-gene assays.
- Assessed the impact of eleven compounds on human estrogen and androgen receptors.
- Quantified anti-estrogenic and anti-androgenic activity using luciferase and β-galactosidase reporters.
Main Results:
- 2,4,6-tribromophenol demonstrated significant anti-estrogenic and anti-androgenic activity.
- Nominal IC(50) values for anti-estrogenic activity were 14.1 μM (luciferase) and 9.2 μM (β-galactosidase).
- A nominal IC(50) value of 3.9 μM for anti-androgenic activity was observed.
Conclusions:
- 2,4,6-tribromophenol exhibits endocrine-disrupting effects.
- This compound interferes with the transcriptional activity of estrogen and androgen receptors.
- Environmental monitoring of 2,4,6-tribromophenol is recommended due to its endocrine activity.
Related Concept Videos
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Radical Halogenation: Thermodynamics
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene
Radical Substitution: Allylic Bromination
Electrophilic Aromatic Substitution: Chlorination and Bromination of Benzene
Reactions at the Benzylic Position: Halogenation
