Chiral perspective evaluations: Enantioselective hydrolysis of 6PPD and 6PPD-quinone in water and enantioselective toxicity to Gobiocypris rarus and Oncorhynchus mykiss

Di, Shanshan; Liu, Zhenzhen; Zhao, Huiyu; Liu, Ying; Qi, Peipei; Wang, Zhiwei; Hao, X. Q.; Jin, Yuanxiang; Wang, Xinquan

doi:10.1016/j.envint.2022.107374

Cited by 54 publications

(47 citation statements)

References 21 publications

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“…9 The transformation product, 6PPD-quinone (6PPD-Q), is generated by the reaction of 6PPD with atmospheric ozone and has been found worldwide from stormwater runoff, 9−14 road dust, 15−17 and atmospheric particles. 18,19 6PPD-Q can cause lethality in coho salmon at a 24 h median lethal concentration (LC 50 ) as low as 0.095 μg/L 20 and is also highly toxic to other salmonid species, as demonstrated by a recent study: 21,22 rainbow trout (Oncorhynchus mykiss) and brook trout (Salvelinus fontinalis) with 24 h LC 50 values of <2 μg/L.…”

Section: ■ Introductionmentioning

confidence: 97%

“…In contrast to the extremely high toxicity to some salmonid species, 6PPD-Q does not exhibit acute lethality to other fish species at environmentally relevant concentrations (i.e., <12 μg/L), including zebrafish ( Danio rerio ), Japanese medaka ( Oryzias latipes ), white sturgeon ( Acipenser transmontanus ), and Chinese rare minnow ( Gobiocypris rarus ). − Surprisingly, the insensitive species include salmonid species: arctic char ( Salvelinus alpinus ), Atlantic salmon ( Salmo salar ), and brown trout ( Salmo trutta ) . Chum ( Oncorhynchus keta ) and sockeye salmon ( Oncorhynchus nerka ) are also likely tolerant of 6PPD-Q at environmentally relevant concentrations, whereas Chinook salmon ( Oncorhynchus tshawytscha ) has intermediate sensitivity. , These large differences in sensitivity to 6PPD-Q among salmonids require further investigation for more species, which is expected to improve our understanding of the toxic mechanisms of 6PPD-Q.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, acute mortality of coho salmon ( Oncorhynchus kisutch ) following exposure to urban stormwater runoff was demonstrated to be caused by a transformation product of tire rubber antioxidant N -(1,3-dimethylbutyl)- N ′-phenyl- p -phenylenediamine (6PPD) . The transformation product, 6PPD-quinone (6PPD-Q), is generated by the reaction of 6PPD with atmospheric ozone and has been found worldwide from stormwater runoff, − road dust, − and atmospheric particles. , 6PPD-Q can cause lethality in coho salmon at a 24 h median lethal concentration (LC 50 ) as low as 0.095 μg/L and is also highly toxic to other salmonid species, as demonstrated by a recent study: , rainbow trout ( Oncorhynchus mykiss ) and brook trout ( Salvelinus fontinalis ) with 24 h LC 50 values of <2 μg/L.…”

Section: Introductionmentioning

confidence: 99%

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The Tire-Derived Chemical 6PPD-quinone Is Lethally Toxic to the White-Spotted Char Salvelinus leucomaenis pluvius but Not to Two Other Salmonid Species

Hiki

Yamamoto

2022

Environ. Sci. Technol. Lett.

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-N′-phenyl-p-phenylenediamine-quinone, also known as 6PPD-quinone (6PPD-Q), was recently identified as the toxic chemical that causes acute mortality in coho salmon following exposure to urban road runoff. Subsequent studies found that there were large differences in sensitivity to 6PPD-Q (>100-fold) even among salmonid species.Here we performed 96 h acute toxicity tests of 6PPD-Q with three salmonid species (Salvelinus leucomaenis pluvius, Salvelinus curilus, and Oncorhynchus masou masou) and found that 6PPD-Q was lethally toxic to S. leucomaenis pluvius with a 24 h median lethal concentration (LC 50 ) of 0.51 μg/L but not to the other two species at environmentally relevant concentrations (<3.8 μg/L). In addition, we measured the concentrations of 6PPD-Q and the suspected monohydroxylated metabolite in brain and gill tissues for the three species. The median internal lethal concentrations (ILC 50 ) of 6PPD-Q were estimated to be 4.0 μg/kg of wet weight in brain and 6.2 μg/kg of wet weight in gill for S. leucomaenis pluvius, while the tissue concentrations of 6PPD-Q in the other two surviving species exceeded the ILC 50 values for S. leucomaenis pluvius. These results suggest that species sensitivity differences might be affected by toxicodynamic factors as well as toxicokinetics.

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Section: ■ Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The Tire-Derived Chemical 6PPD-quinone Is Lethally Toxic to the White-Spotted Char Salvelinus leucomaenis pluvius but Not to Two Other Salmonid Species

Hiki

Yamamoto

2022

Environ. Sci. Technol. Lett.

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“…Furthermore, using 6PPD-quinone solutions, Brinkmann et al (2022) showed 6PPD-quinone toxicity in brook trout (Salvelinus fontinalis) and rainbow trout. The 6PPD-quinone toxicity in rainbow trout has also been confirmed by Di et al (2022). Lack of response to 6PPD-quinone at environmentally relevant concentrations has also been documented in Artic char (Salvelinus alpinus) and white sturgeon (Acipenser transmontanus; Brinkmann et al, 2022), zebrafish (Danio rerio) larvae (Hiki et al, 2021;Varshney et al, 2022), Japanese medaka (Oryzias latipes; Hiki et al, 2021) and a cyprinid fish endemic to China (Gobiocypris rarus; Di et al, 2022).…”

Section: Introductionmentioning

confidence: 89%

Acute Toxicity Testing of the Tire Rubber–Derived Chemical 6PPD‐quinone on Atlantic Salmon (Salmo salar) and Brown Trout (Salmo trutta)

Foldvik

Kryuchkov

Sandodden

et al. 2022

Enviro Toxic and Chemistry

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Recent identification of 6PPD-quinone as the chemical causing acute toxicity in coho salmon has led to substantial concern regarding the toxicity of this contaminant for other aquatic species. Environmental occurrence of 6PPD-quinone is probably high, because it is an oxidation product of a common tire rubber additive. Research on 6PPD-quinone toxicity in fish has revealed a rather unusual pattern, with closely related species exhibiting responses ranging from extreme sensitivity to no effect. Of 11 previously studied fish species, 6PPD-quinone was toxic to four. The species-specific toxicity of 6PPDquinone complicates urgently needed environmental risk assessment. We investigated the acute toxicity of 6PPD-quinone in Atlantic salmon and brown trout alevins (sac fry). These species have previously not been tested for sensitivity to 6PPDquinone. The fish were exposed in static conditions in eight treatments with initial concentrations ranging from 0.095 to 12.16 µg/L. Fish were observed for 48 h, and changes in concentrations of 6PPD-quinone were monitored throughout the experiment. No mortalities or substantial changes in behavior were recorded in either Atlantic salmon or brown trout. This provides an important first step in assessing effects of 6PPD-quinone on these economically and culturally highly important species.

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“…A prominent example is a tire rubber additive N -(1,3-dimethylbutyl)- N ′-phenyl- p -phenylenediamine (6PPD), which upon deploying its protective antioxidative function, yields hazardous transformation products including 6PPD-quinone, a chemical that is now known to be highly toxic to many aquatic species (Section S6.3). − …”

Section: Chemicals In Plastics Inevitably Influence the Effectiveness...mentioning

confidence: 99%

Integrating a Chemicals Perspective into the Global Plastic Treaty

Wang

Praetorius

2022

Environ. Sci. Technol. Lett.

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Driven by the growing concern about plastic pollution, countries have agreed to establish a global plastic treaty addressing the full life cycle of plastics. However, while plastics are complex materials consisting of mixtures of chemicals such as additives, processing aids, and nonintentionally added substances, it is at risk that the chemical aspects of plastics may be overlooked in the forthcoming treaty. This is highly concerning because a large variety of over 10,000 chemical substances may have been used in plastic production, and many of them are known to be hazardous to human health and the environment. In this Global Perspective, we further highlight an additional, generally overlooked, but critical aspect that many chemicals in plastics hamper the technological solutions envisioned to solve some of the major plastic issues: mechanical recycling, waste-to-energy, chemical recycling, biobased plastics, biodegradable plastics, and durable plastics. Building on existing success stories, we outline three concrete recommendations on how the chemical aspects can be integrated into the global plastic treaty to ensure its effectiveness: (1) reducing the complexity of chemicals in plastics, (2) ensuring the transparency of chemicals in plastics, and (3) aligning the right incentives for a systematic transition.

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Chiral perspective evaluations: Enantioselective hydrolysis of 6PPD and 6PPD-quinone in water and enantioselective toxicity to Gobiocypris rarus and Oncorhynchus mykiss

Cited by 54 publications

References 21 publications

The Tire-Derived Chemical 6PPD-quinone Is Lethally Toxic to the White-Spotted Char Salvelinus leucomaenis pluvius but Not to Two Other Salmonid Species

The Tire-Derived Chemical 6PPD-quinone Is Lethally Toxic to the White-Spotted Char Salvelinus leucomaenis pluvius but Not to Two Other Salmonid Species

Acute Toxicity Testing of the Tire Rubber–Derived Chemical 6PPD‐quinone on Atlantic Salmon (Salmo salar) and Brown Trout (Salmo trutta)

Integrating a Chemicals Perspective into the Global Plastic Treaty

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