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BibTex format

@article{Ciccarelli:2024:10.1038/s42004-024-01356-3,
author = {Ciccarelli, D and Lancaster, BMJ and Braddock, DC and Calvaresi, M and Miík, M and Knasmüller, S and Mattioli, EJ and Zerbetto, F and White, AJP and Marczylo, T and Gant, TW and Barron, LP},
doi = {10.1038/s42004-024-01356-3},
journal = {Communications Chemistry},
title = {Structure confirmation, reactivity, bacterial mutagenicity and quantification of 2,2,4-tribromo-5-hydroxycyclopent-4-ene-1,3-dione in drinking water},
url = {http://dx.doi.org/10.1038/s42004-024-01356-3},
volume = {7},
year = {2024}
}
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TY  - JOUR
AB  - The presence of two new disinfectant by-product (DBP) groups in the UK was recently shown using non-target analysis, halogenated-hydroxycyclopentenediones and halogenated-methanesulfonic acids. In this work, we confirmed the structure of 2,2,4-tribromo-5-hydroxycyclopent-4-ene-1,3-dione (TBHCD), and quantified it together with dibromomethanesulfonic acid at 122 ± 34 and 326 ± 157 ng L−1 on average in London’s drinking water, respectively (n = 21). We found TBHCD to be photolabile and unstable in tap water and at alkaline pH. Furthermore, spectral and computational data for TBHCD and three other halogenated-hydroxycyclopentenediones indicated they could act as a source of radicals in water and in the body. Importantly, TBHCD was calculated to have a 14.5 kcal mol−1 lower C-Br bond dissociation enthalpy than the N-Br bond of N-bromosuccinimide, a common radical substitution reagent used in organic synthesis. TBHCD was mutagenic in Salmonella/microsome assays using strains TA98, TA100 and TA102. This work reveals the unique features, activity and toxicity of trihalogenated hydroxycyclopent-4-ene-1,3-diones, prompting a need to more comprehensively assess their risks.
AU  - Ciccarelli,D
AU  - Lancaster,BMJ
AU  - Braddock,DC
AU  - Calvaresi,M
AU  - Miík,M
AU  - Knasmüller,S
AU  - Mattioli,EJ
AU  - Zerbetto,F
AU  - White,AJP
AU  - Marczylo,T
AU  - Gant,TW
AU  - Barron,LP
DO  - 10.1038/s42004-024-01356-3
PY  - 2024///
SN  - 2399-3669
TI  - Structure confirmation, reactivity, bacterial mutagenicity and quantification of 2,2,4-tribromo-5-hydroxycyclopent-4-ene-1,3-dione in drinking water
T2  - Communications Chemistry
UR  - http://dx.doi.org/10.1038/s42004-024-01356-3
UR  - https://www.nature.com/articles/s42004-024-01356-3
UR  - http://hdl.handle.net/10044/1/116384
VL  - 7
ER  -
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