Structure confirmation, reactivity, bacterial mutagenicity and quantification of 2,2,4-tribromo-5-hydroxycyclopent-4-ene-1,3-dione in drinking water

Autor: Davide Ciccarelli, Ben M. J. Lancaster, D. Christopher Braddock, Matteo Calvaresi, Miroslav Mišík, Siegfried Knasmüller, Edoardo Jun Mattioli, Francesco Zerbetto, Andrew J. P. White, Tim Marczylo, Timothy W. Gant, Leon P. Barron
Jazyk: angličtina
Rok vydání: 2024
Předmět:
Zdroj: Communications Chemistry, Vol 7, Iss 1, Pp 1-11 (2024)
Druh dokumentu: article
ISSN: 2399-3669
DOI: 10.1038/s42004-024-01356-3
Popis: Abstract 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.
Databáze: Directory of Open Access Journals
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