Genotoxic effects of chlorinated disinfection by-products of 1,3-diphenylguanidine (DPG): Cell-based in-vitro testing and formation potential during water disinfection

Santos, Mauricius Marques dos; Cheriaux, Camille; Jia, Shenglan; Thomas, Mikaël; Gallard, Hervé; Croué, Jean-Philippe; Carato, Pascal; Snyder, Shane A.

doi:10.1016/j.jhazmat.2022.129114

Cited by 22 publications

(37 citation statements)

References 51 publications

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“…While previous studies have recently reported the potential for the formation of chlorinated byproducts of DPG during simulated drinking water treatment, , to the best of our knowledge, this is the first reporting of occurrence of such compounds in real drinking water samples. While we had previously shown the reaction of DPG with monochloramine to be close to negligible, observed occurrence of compound CC15 was also most favorably formed during simulated water chlorination experiments . Additionally, CC11 was also shown to have potential genotoxic properties, as revealed by a multi-biomarker approach using next-generation (NGS) RNA sequencing, immunofluorescence assay for phosphorylation of the serine-139 residue of histone H2AX (pH2AX, a sensitive marker of DNA damage and repair, being an early molecular response to DNA double-strand breaks (DSBs)), and qPCR analysis of multiple genes involved in DSB repair …”

Section: Resultsmentioning

confidence: 73%

“…All analytical standards used in this study were of purity >95% and purchased from commercially available sources or synthesized by IHES research group, EBI/CIC INSERM 1402; details on synthesis procedure, characterization, and purity determination were reported previously . A complete list of chemicals used and their sources is available in Supplementary Text 1.…”

Section: Methodsmentioning

confidence: 99%

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Occurrence of Polymer Additives 1,3-Diphenylguanidine (DPG), N-(1,3-Dimethylbutyl)-N′-phenyl-1,4-benzenediamine (6PPD), and Chlorinated Byproducts in Drinking Water: Contribution from Plumbing Polymer Materials

Marques dos Santos,

Snyder

2023

Environ. Sci. Technol. Lett.

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While the occurrence of polymer additives in the environment has gained much attention in recent years, particularly through the emission of tire wear particles (TWPs), evidence of the occurrence of such chemicals in drinking water systems is limited. Even less information is available regarding potential chlorination/chloramination transformation byproducts. In this study, we report the occurrence of N-(1,3-dimethylbutyl)-N′-phenyl-1,4-benzenediamine (6PPD), 1,3-diphenylguanidine (DPG), and three chlorinated byproducts (1,3-bis(2-chlorophenyl)guanidine (CC15), 1-(4-chlorophenyl)-3-(2,4-dichlorophenyl)guanidine (CC05), and 1-(2,4-dichlorophenyl)-3-phenylguanidine) (CC11)) in drinking water samples (n = 20). DPG showed detection frequency of 100%; median 4.3 ng/L (min = 0.25 ng/L; max = 32.6 ng/L), and a chlorinated by product of DPG (CC15) was also detected in 100% of samples; median 1.7 ng/L (min = 0.29 ng/L; max = 11.2 ng/L). CC11 was also found in 10% of samples and was previously reported as potentially genotoxic. While most studies have focused on the tire rubber related origin of DPG and 6PPD in the environment, results show a potential major contribution of other polymer materials used in household devices such as tap water aerators, particularly O-rings and seals. Leaching potential of such materials was demonstrated, and contact with free chlorine and monochloramine induced the formation of different halogenated transformation byproducts.

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Section: Resultsmentioning

confidence: 73%

Section: Methodsmentioning

confidence: 99%

Occurrence of Polymer Additives 1,3-Diphenylguanidine (DPG), N-(1,3-Dimethylbutyl)-N′-phenyl-1,4-benzenediamine (6PPD), and Chlorinated Byproducts in Drinking Water: Contribution from Plumbing Polymer Materials

Marques dos Santos,

Snyder

2023

Environ. Sci. Technol. Lett.

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“…1,3-Diphenylguanidine, a possible genotoxic chemical, shows toxicity across the different in vitro and in vivo bioassays for EC 50 concentration down to 3 μM, especially AR antagonism and Nrf2 (oxidative stress) activity. The antiandrogen pharmaceutical bicalutamide shows not only hormone receptor interaction as expected (known for its antiandrogen activity) but also general oxidative stress detected by Nrf2 activity.…”

Section: Resultsmentioning

confidence: 99%

“…The lack of data is concerning as it can be seen such as (a) for guanyl urea, where the embryogenesis disruption potential in fish was shown before, 48 and (b) for 17α-hydroxypregnenolone, which is a progesterone-related compound and therefore suspected to be endocrine-disruptive in the ng/L range. 49 1,3-Diphenylguanidine, a possible genotoxic chemical, 50 shows toxicity across the different in vitro and in vivo bioassays for EC 50 concentration down to 3 μM, especially AR antagonism and Nrf2 (oxidative stress) activity. The antiandrogen pharmaceutical bicalutamide shows not only hormone receptor interaction as expected (known for its antiandrogen activity 51 ) but also general oxidative stress detected by Nrf2 activity.…”

Section: Toxicity Assessmentmentioning

confidence: 99%

Supercritical Fluid Chromatography Coupled to High-Resolution Mass Spectrometry Reveals Persistent Mobile Organic Compounds with Unknown Toxicity in Wastewater Effluents

Tisler

Savvidou

Jørgensen³

et al. 2023

Environ. Sci. Technol.

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Broad screening approaches for monitoring wastewater are normally based on reversed-phase liquid chromatography (LC) coupled to high-resolution mass spectrometry (HRMS). This method is not sufficient for the very polar micropollutants, neglected in the past due to a lack of suitable analytical methods. In this study, we used supercritical fluid chromatography (SFC) to detect very polar and yet-undetected micropollutants in wastewater effluents. We tentatively identified 85 compounds, whereas 18 have only rarely been detected and 11 have not previously been detected in wastewater effluents such as 17α-hydroxypregnenolone, a likely transformation product (TP) of steroids, and 1H-indole-3-carboxamide, a likely TP from new synthetic cannabinoids. Suspect screening of 25 effluent wastewater samples from 8 wastewater treatment plants revealed several distinct potential pollution sources such as a pharmaceutical company and a golf court. The analysis of the same samples with LC−HRMS showed clearly how SFC increases the ionization efficiency for low-molecular-weight micropollutants (m/z < 300 Da) by a factor 2 to 87 times, which significantly improved the mass spectra for identifying very polar compounds. In order to assess which micropollutants might be of environmental concern, literature and toxicological databases were screened. There was a lack of available hazard and bio-activity data for regulatory-relevant in vitro and in vivo assays for >50% of the micropollutants. Especially, 70% of the data were lacking for the whole organism (in vivo) tests.

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“…While DPG can be considered as a persistent and mobile organic chemical (PMOC), , its occurrence is not restricted to the aquatic environment, and it has also been reported in urban air and indoor household dust, with DPG concentrations surpassing the concentrations of other commonly studied chemicals such as PFOA, PFOS, and tetrabromobisphenol A (TBBPA) . While DPG effects on human and environmental health not are fully understood, some reports have suggested potential adverse effects. , Furthermore, recent studies have also shown potential genotoxicity associated with chlorinated transformation products of DPG that could be generated during drinking water treatment …”

Section: Introductionmentioning

confidence: 99%

Polymer Additives to Go? Occurrence of the Rubber Additive 1,3-Diphenylguanidine (DPG) in Bottled Water

Marques dos Santos,

Snyder

2023

Environ. Sci. Technol. Lett.

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The occurrence of polymer additives such as 1,3diphenylguanidine (DPG) has been recently reported in different human samples, including urine and plasma. It has also been widely reported in many sources of drinking water and tap water. Here, we present the first comprehensive assessment of the occurrence of DPG in bottled water samples. A large-volume direct injection LC-MS/MS method was used for the analysis of polymer additives (DPG, DTG, and 6PPD) and six transformation products in different bottled water samples. The use of a 100 μL direct injection LC-MS/MS method enabled detection and quantification limits as low as 0.01 and 0.05 ng/L, respectively, with no interference of potential contaminants from materials commonly used in the laboratory. Out of 63 different samples from 15 different countries, DPG had a detection frequency of 40%, with samples above the limit of quantification having a median concentration of 0.76 ng/L (maximum of 7.4 ng/L). Although the contribution to human exposure from drinking bottled water could explain little of the observed urine concentrations previously reported, the impact from bottled water consumption cannot be neglected and was estimated to be on the same order of magnitude as that of drinking tap water.

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Genotoxic effects of chlorinated disinfection by-products of 1,3-diphenylguanidine (DPG): Cell-based in-vitro testing and formation potential during water disinfection

Cited by 22 publications

References 51 publications

Occurrence of Polymer Additives 1,3-Diphenylguanidine (DPG), N-(1,3-Dimethylbutyl)-N′-phenyl-1,4-benzenediamine (6PPD), and Chlorinated Byproducts in Drinking Water: Contribution from Plumbing Polymer Materials

Occurrence of Polymer Additives 1,3-Diphenylguanidine (DPG), N-(1,3-Dimethylbutyl)-N′-phenyl-1,4-benzenediamine (6PPD), and Chlorinated Byproducts in Drinking Water: Contribution from Plumbing Polymer Materials

Supercritical Fluid Chromatography Coupled to High-Resolution Mass Spectrometry Reveals Persistent Mobile Organic Compounds with Unknown Toxicity in Wastewater Effluents

Polymer Additives to Go? Occurrence of the Rubber Additive 1,3-Diphenylguanidine (DPG) in Bottled Water

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