New methods for identification of disinfection byproducts of toxicological relevance: Progress and future directions

Wawryk, Nicholas J.P.; Craven, Caley B.; Blackstock, Lindsay K. Jmaiff; Li, Xing‐Fang

doi:10.1016/j.jes.2020.06.020

Cited by 45 publications

(16 citation statements)

References 82 publications

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“…Single liquid–liquid extraction (LLE) is frequently used in chemical and biological analyses of DBPs. , Recent studies have demonstrated that multiple LLE increased the extraction recoveries of various halo-DBPs in disinfected waters compared with the commonly used single LLE , and solid-phase extraction . Thus, the extraction efficiency of multiple LLE with methyl tert -butyl ether (MtBE) was evaluated using a 0.5 h chlorinated water sample as a representative.…”

Section: Materials and Methodsmentioning

confidence: 99%

“…Tremendous efforts have been made to uncover unknown halo-DBPs, especially the toxicologically important ones. ,,, In recent years, by connecting ultraperformance liquid chromatography to electrospray ionization-triple quadrupole mass spectrometry (UPLC/ESI-tqMS), approximately 100 new halo-DBPs have been identified. Most of these newly identified halo-DBPs are aromatics, including halophenols, halohydroquinones, halohydroxybenzaldehydes, halohydroxybenzoic acids, and halosalicylic acids. ,− Li and co-workers have identified another group of previously unknown halo-DBPs, halobenzoquinones, , which are usually in equilibrium with halohydroquinones in water .…”

Section: Introductionmentioning

confidence: 99%

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How Much of the Total Organic Halogen and Developmental Toxicity of Chlorinated Drinking Water Might Be Attributed to Aromatic Halogenated DBPs?

Han

Zhang

Jiang

et al. 2021

Environ. Sci. Technol.

169

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Although >700 disinfection byproducts (DBPs) have been identified, >50% of the total organic halogen (TOX) in drinking water chlorination is unknown, and the DBPs responsible for the chlorination-associated health risks remain largely unclear. Recent studies have revealed numerous aromatic halo-DBPs, which generally present substantially higher developmental toxicity than aliphatic halo-DBPs. This raises a fascinating and important question: how much of the TOX and developmental toxicity of chlorinated drinking water can be attributed to aromatic halo-DBPs? In this study, an effective approach with ultraperformance liquid chromatography was developed to separate the DBP mixture (from chlorination of bromide-rich raw water) into aliphatic and aromatic fractions, which were then characterized for their TOX and developmental toxicity. For chlorine contact times of 0.25−72 h, aromatic fractions accounted for 49−67% of the TOX in the obtained aliphatic and aromatic fractions, which were equivalent to 26−36% of the TOX in the original chlorinated water samples. Aromatic halo-DBP fractions were more developmentally toxic than the corresponding aliphatic fractions, and the overall developmental toxicity of chlorinated water samples was dominated by aromatic halo-DBP fractions. This might be explained by the considerably higher potentials of aromatic halo-DBPs to bioconcentrate and then generate reactive oxygen species in the organism.

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Section: Materials and Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

How Much of the Total Organic Halogen and Developmental Toxicity of Chlorinated Drinking Water Might Be Attributed to Aromatic Halogenated DBPs?

Han

Zhang

Jiang

et al. 2021

Environ. Sci. Technol.

169

View full text Add to dashboard Cite

show abstract

“…Currently, all options for connecting gas and liquid chromatographs with mass spectrometers are widely used to study the processes that occur in the disinfection of drinking water and pool water. In particular, Wawryk et al [ 34 ] considered the currently available mass-spectrometric approaches to the detection of new toxicologically significant DBPs.…”

Section: Introductionmentioning

confidence: 99%

Transformation of Organic Compounds during Water Chlorination/Bromination: Formation Pathways for Disinfection By-Products (A Review)

Mazur

Lebedev

2022

J Anal Chem

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The purity of drinking water is an important issue of the human life quality. Water disinfection has saved millions people from the diseases spread with water. However, that procedure has a certain drawback due to formation of toxic organic disinfection products. Establishing the structures of these products and the mechanisms of their formation and diminishing their levels in drinking water represent an important task for chemistry and medicine, while mass spectrometry is the most efficient tool for the corresponding studies. The current review throws light upon natural and anthropogenic sources of the formation of disinfection by-products (DBPs) and the mechanisms of their formation related to the structural peculiarities and the presence of functional groups. In addition to chlorination, bromination is discussed since it is used quite often as an alternative method of disinfection, particularly, for the purification of swimming pool water. The benefits of the contemporary GC/MS and LC/MS methods for the elucidation of DBP structures and study of the mechanisms of their formation are discussed. The reactions characteristic for various functional groups and directions of transformation of certain classes of organic compounds in conditions of aqueous chlorination/bromination are also covered in the review.

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“… PCP is an important chemical in industry and one of widely spread biocides in agriculture, which has been classified as a group I environmental carcinogen in 2016 . Haloquinoid compounds (XQs), which are a newly emerging class of disinfection byproducts (DBPs), have also been widely detected and identified from treated drinking water and recreational water. , In addition, it has been demonstrated that personal care products such as lotions and sunscreens may partly contribute as a human resource to the formation of XQs in swimming pools, which include trichloro-1,4-benzoquinone (TriCBQ), 2,6-dichloro-3-methyl-1,4-benzoquinone (DCMBQ), and tetrabromo-1,4-benzoquinone (TBrBQ) . XQs have been suspected to increase the risk of developing bladder cancer, which is predicted by quantitative structure–toxicity relationship analysis .…”

Section: Introductionmentioning

confidence: 99%

Mechanistic Study on Oxidative DNA Damage and Modifications by Haloquinoid Carcinogenic Intermediates and Disinfection Byproducts

Zhu

Tang

Huang

et al. 2021

Chem. Res. Toxicol.

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Haloquinones (XQs) are a group of carcinogenic intermediates of the haloaromatic environmental pollutants and newly identified chlorination disinfection byproducts (DBPs) in drinking water. The highly reactive hydroxyl radicals/alkoxyl radicals and quinone enoxy/ketoxy radicals were found to arise in XQs and H2O2 or organic hydroperoxides system, independent of transition-metal ions. However, it was not clear whether these haloquinoid carcinogens and hydroperoxides can cause oxidative DNA damage and modifications, and if so, what are the underlying molecular mechanisms. We found that 8-oxodeoxyguanosine (8-oxodG), DNA strand breaks, and three methyl oxidation products could arise when DNA was treated with tetrachloro-1,4-benzoquinone and H2O2 via a metal-independent and intercalation-enhanced oxidation mechanism. Similar effects were observed with other XQs, which are generally more efficient than the typical Fenton system. We further extended our studies from isolated DNA to genomic DNA in living cells. We also found that potent oxidation of DNA to the more mutagenic imidazolone dIz could be induced by XQs and organic hydroperoxides such as t-butylhydroperoxide or the physiologically relevant hydroperoxide 13S-hydroperoxy-9Z,11E-octadecadienoic acid via an unprecedented quinone-enoxy radical-mediated mechanism. These findings should provide new perspectives to explain the potential genotoxicity, mutagenesis, and carcinogenicity for the ubiquitous haloquinoid carcinogenic intermediates and DBPs.

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New methods for identification of disinfection byproducts of toxicological relevance: Progress and future directions

Cited by 45 publications

References 82 publications

How Much of the Total Organic Halogen and Developmental Toxicity of Chlorinated Drinking Water Might Be Attributed to Aromatic Halogenated DBPs?

How Much of the Total Organic Halogen and Developmental Toxicity of Chlorinated Drinking Water Might Be Attributed to Aromatic Halogenated DBPs?

Transformation of Organic Compounds during Water Chlorination/Bromination: Formation Pathways for Disinfection By-Products (A Review)

Mechanistic Study on Oxidative DNA Damage and Modifications by Haloquinoid Carcinogenic Intermediates and Disinfection Byproducts

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