Mutagenic By-Products from Chlorination of Humic Acid

Meier, John R.; Ringhand, H. P.; Coleman, W. Emile; Schenck, Kathleen M.; Munch, Jean W.; Streicher, Robert P.; Kaylor, William H.; Kopfler, Frederick C.

doi:10.2307/3430377

Cited by 15 publications

(19 citation statements)

References 3 publications

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“…The most known halogenated 292 furanone formed by chlorination of drinking water is the highly mutagenic MX and its analogues 293 (Hemming et al, 1986;Kronberg and Vartiaine, 1988;Meier et al, 1986). In a previous study on 294 chlorination of phenolic compounds, resorcinol was found to produce MX, but in low concentration at 295 acidic pH (i.e., 0.01 mmol/mol, pH 2) (Långvik et al, 1991).…”

Section: Hydroxy-2-pyridone With Four Chlorine Atoms (Text S3) 271mentioning

confidence: 99%

Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds

Nihemaiti

Roux

Hoppe‐Jones

et al. 2016

Environ. Sci. Technol.

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18The potential formation of nitrogenous disinfection by-products (N-DBPs) was investigated from the 19 chloramination of nitrogenous and non-nitrogenous aromatic compounds. All molecules led to the 20 formation of known N-DBPs (e.g., dichloroacetonitrile, dichloroacetamide) with various production 21 yields. Resorcinol, a major precursor of chloroform, also formed di-/tri-chloroacetonitrile, di-/tri-22 chloroacetamide, and haloacetic acids, indicating that it is a precursor of both N-DBPs and 23carbonaceous DBPs (C-DBPs) upon chloramination. More detailed experiments were conducted on 24 resorcinol to understand N-DBPs formation mechanisms and to identify reaction intermediates. Based 25 on the accurate mass from high resolution Quadrupole Time-of-Flight GC-MS (GC-QTOF) and 26 fragmentation patterns from electronic impact and positive chemical ionization modes, several 27 products were tentatively identified as nitrogenous heterocyclic compounds (e.g., 3-chloro-5-hydroxy-28 1H-pyrrole-2-one with dichloromethyl group, 3-chloro-2,5-pyrroledione). These products were 29 structurally similar to the heterocyclic compounds formed during chlorination, such as the highly 30 mutagenic MX (3-chloro-4-(dichloromethyl)-5-hydroxy-2(5H)-furanone) or halogenated pyrroles. To 31 our knowledge, this is the first time that the formation of halogenated nitrogenous heterocyclic 32 compounds is reported from chloramination process. The formation of these nitrogenous by-products 33 during chloramination might be of concern considering their potential toxicity. 34 ABSTRACT ART35 36 37 INTRODUCTION 38

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Section: Hydroxy-2-pyridone With Four Chlorine Atoms (Text S3) 271mentioning

confidence: 99%

Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds

Nihemaiti

Roux

Hoppe‐Jones

et al. 2016

Environ. Sci. Technol.

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“…A number of organochlorine by-products (OBPs) have been shown to be non-genotoxic carcinogens in laboratory animals [5,6]. These compounds are also able to induce mutagenic effects in some biological systems such as bacteria [7], polychaete [8], teleost fish [9,10], mouse cells [11] and human B-lymphoblastoid cells [12]. Long-term studies in rats treated with the disinfectant sodium hypochlorite (NaClO) in drinking water showed an increase in leukaemia in female rats [13].…”

Section: Introductionmentioning

confidence: 99%

Perturbation of cytochrome P450, generation of oxidative stress and induction of DNA damage in Cyprinus carpio exposed in situ to potable surface water

Sapone¹,

Gustavino²,

Monfrinotti³

et al. 2007

Mutation Research/Genetic Toxicology and Environmental Mutagene

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Epidemiological evidence suggests a link between consumption of chlorinated drinking water and various cancers. Chlorination of water rich in organic chemicals produces carcinogenic organochlorine by-products (OBPs) such as trihalomethanes and haloacetic acids. Since the discovery of the first OBP in the 1970s, there have been several investigations designed to determine the biological effects of single chemicals or small artificial OBP combinations. However, there is still insufficient information regarding the general biological response to these compounds, and further studies are still needed to evaluate their potential genotoxic effects. In the current study, we evaluated the effect of three drinking water disinfectants on the activity of cytochrome P450 (CYP)-linked metabolizing enzymes and on the generation of oxidative stress in the livers of male and female Cyprinus carpio fish (carp). The fish were exposed in situ for up 20 days to surface water obtained from the Trasmene lake in Italy. The water was treated with 1-2 mg/L of either sodium hypochlorite (NaClO) or chlorine dioxide (ClO 2 ) as traditional disinfectants or with a relatively new disinfectant product, peracetic acid (PAA). Micronucleus (MN) frequencies in circulating erythrocytes from the fish were also analysed as a biomarker of genotoxic effect. In the CYP-linked enzyme assays, a significant induction (up to a 57-fold increase in the deethylation of ethoxyresorufin with PAA treatment) and a notable inactivation (up to almost a 90% loss in hydroxylation of p-nitrophenol with all disinfectants, and of testosterone 2␤-hydroxylation with NaClO) was observed in subcellular liver preparations from exposed fish. Using the electron paramagnetic resonance (EPR) spectroscopy radical-probe technique, we also observed that CYP-modulation was associated with the production of reactive oxygen species (ROS). In addition, we found a significant increase in MN frequency in circulating erythrocytes after 10 days of exposure of fish to water treated with ClO 2 , while a non-significant six-fold increase in MN frequency was observed with NaClO, but not with PAA. Our data suggest that the use of ClO 2 and NaClO to disinfect drinking water could generate harmful OBP mixtures that are able to perturb CYP-mediated reactions, generate oxidative stress and induce Abbreviations: NaClO, sodium hypochlorite; ClO 2 , chlorine dioxide; PAA, peracetic acid; CYP, cytochrome P450; MN, micronuclei; OBPs, organochlorine by-products; ROS, reactive oxygen species * Corresponding author. . Sapone et al. / Mutation Research 626 (2007) 143-154 genetic damage. These data may provide a mechanistic explanation for epidemiological studies linking consumption of chlorinated drinking water to increased risk of urinary, gastrointestinal and bladder cancers.

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“…These organic halogenated compounds induce genotoxic/mutagenic effects [4][5][6][7][8]. Humic acids (HA) constitute the major portion of organic material present in surface waters, deriving from living or decaying vegetation or microbial decomposition processes [5]; they are usually quantified in terms of total organic carbon (TOC).…”

Section: Introductionmentioning

confidence: 99%

“…Since humic acids are the main organic component of surface fresh waters and because their interaction with chlorinated disinfectants generates genotoxic byproducts [4][5][6][7][8], our attention in the present work is focused on the role of these disinfectants in the induction of genotoxic or mutagenic effects in specific physiological conditions of animals and in a controlled experimental environment.…”

Section: Introductionmentioning

confidence: 99%

“…In view of the possible relevance of the results in relation to drinking-water consumption, we tested the disinfectants at low concentrations: the highest concentration employed (0.2 ppm) corresponds to the maximum free disinfectant residue adopted in surface water disinfection experiments [18,22]. The humic acids concentration (0.1 ppm) was chosen to obtain a 1:0.32 molar-ratio C:Cl for the highest NaClO concentration and a 1:0.08 molar-ratio for the lowest concentration (0.05 ppm), so as to achieve almost complete reaction of chlorine with organic carbon, according to carcinogenicity/mutagenicity studies [4,52,53].…”

Section: Introductionmentioning

confidence: 99%

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Modulating effects of humic acids on genotoxicity induced by water disinfectants in Cyprinus carpio

Gustavino

Buschini

Monfrinotti

et al. 2005

Mutation Research/Genetic Toxicology and Environmental Mutagene

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The use of chlorinated disinfectants during drinking-water production has been shown to generate halogenated compounds as a result of interactions of humic acids with chlorine. Such chlorinated by-products have been shown to induce genotoxic effects and consumption of chlorinated drinking-water has been correlated with increased risk for cancer induction in human populations. The aim of this work was to test the potential genotoxic effects on circulating erythrocytes of the fish Cyprinus carpio exposed in vivo to well-waters disinfected with sodium hypochlorite (NaClO), chlorine dioxide (ClO 2 ) or peracetic acid (CH 3 COO 2 H, PAA), in the absence or presence of standard humic acids (HA). The effects were measured by use of the micronucleus (MN) and the single-cell gel electrophoresis (Comet) assays at different sampling times after a 3-day exposure period. The exposure to chlorine disinfectants without the addition of HA produced a clear toxic effect. Significant cytogenetic damage (i.e. MN induction) was detected in fish populations exposed to both NaClO and ClO 2 with humic acids. In the Comet assay, a significant decrease of DNA migration was observed in erythrocytes of specimens after exposure to NaClO-disinfected water without HA. No effects were observed in any other experimental condition.

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Mutagenic By-Products from Chlorination of Humic Acid

Cited by 15 publications

References 3 publications

Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds

Formation of Haloacetonitriles, Haloacetamides, and Nitrogenous Heterocyclic Byproducts by Chloramination of Phenolic Compounds

Perturbation of cytochrome P450, generation of oxidative stress and induction of DNA damage in Cyprinus carpio exposed in situ to potable surface water

Modulating effects of humic acids on genotoxicity induced by water disinfectants in Cyprinus carpio

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