The tire-rubber-derived ozonation product of -(1,3-dimethylbutyl)-'-phenyl--phenylenediamine (6PPD), -(1,3-dimethylbutyl)-'-phenyl--phenylenediamine-quinone (6PPD-Q), was recently discovered to cause acute mortality in coho salmon (). -Phenylenediamines (PPDs) with variable side chains distinct from 6PPD have been identified as potential replacement antioxidants, but their toxicities remain unclear under environmentally relevant ozone conditions. We herein tested the multiphase gas-surface ozone reactivity of four select PPDs [6PPD, -isopropyl-'-phenyl--phenylenediamine (IPPD), ,'-diphenyl--phenylenediamine (DPPD), and -phenyl-'-cyclohexyl--phenylenediamine (CPPD)] and evaluated the toxicity of their reaction mixtures in coho salmon, rainbow trout (), and fathead minnow (). 6PPD and IPPD were found to rapidly react with ozone, while no significant multiphase ozone reactivity was observed for DPPD or CPPD. The viability of coho salmon CSE-119 cells was strongly affected by the ozonolysis products of 6PPD but not by those of the other three PPDs. Acute mortality was only observed in juvenile rainbow trout that were exposed to oxidized 6PPD, suggesting a common mechanism of toxic action in the two salmonid fish species. This study reports the structurally selective ozone reactivity of PPDs and the unique toxicity of 6PPD ozonolysis mixtures, which demonstrates that other PPDs are potential alternative antioxidants.
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http://dx.doi.org/10.1021/acs.est.4c04817 | DOI Listing |
Int J Biol Macromol
December 2024
School of Chemistry and Chemical Engineering, Nanchang University, Nanchang 330031, Jiangxi, China. Electronic address:
N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine-quinone (6PPD-Q), an oxidative derivative of tire anti-degradant, has been linked to mortality in coho salmon (Oncorhynchus kisutch) and has exhibited potential human toxicity. Hence, exploring how 6PPD-Q interacts with biomacromolecules like enzymes is indispensable to assess its human toxicity and elucidate its mechanism of action. This investigation aims to explore the impact of 6PPD-Q on lactate dehydrogenase (LDH) through various methods.
View Article and Find Full Text PDFACS ES T Water
December 2024
Applied Environmental Research Laboratories, Chemistry, Vancouver Island University, Nanaimo V9R 5S5, Canada.
6PPDQ is a tire-derived contaminant toxic to coho salmon (LC = 41-95 ng/L) found widely distributed in urban environments. Most monitoring efforts have relied on relatively few discrete samples collected at select locations across rain events. Early work has revealed that 6PPDQ concentrations vary widely over time and space, raising questions about when and where to collect samples.
View Article and Find Full Text PDFFish Shellfish Immunol
December 2024
Departments of Aquatic Animal Health and Analysis and Diagnostics, Norwegian Veterinary Institute, Ås, Norway; Department of Biotechnology, Fisheries and Economy, UiT Arctic University of Norway, Tromsø, Norway. Electronic address:
Piscine orthoreovirus (PRV) infection is common in aquaculture of salmonids. The three known PRV genotypes (PRV-1-3) have host species specificity and cause different diseases, but all infect and replicate in red blood cells (RBCs) in early infection phase. PRV-1 is the causative agent of heart and skeletal muscle inflammation (HSMI) in farmed Atlantic salmon (Salmo salar), PRV-2 causes erythrocytic inclusion body syndrome (EIBS) in coho salmon (Oncorhynchus kisutch), while PRV-3 induces HSMI-like disease in farmed rainbow trout (Oncorhynchus mykiss).
View Article and Find Full Text PDFProteomics
December 2024
Fullerton, Biological Sciences, California State University, Fullterton, California, USA.
Environ Sci Technol
December 2024
Department of Chemistry, University of Toronto, Toronto, Ontario M5S 3H6, Canada.
The tire-rubber-derived ozonation product of -(1,3-dimethylbutyl)-'-phenyl--phenylenediamine (6PPD), -(1,3-dimethylbutyl)-'-phenyl--phenylenediamine-quinone (6PPD-Q), was recently discovered to cause acute mortality in coho salmon (). -Phenylenediamines (PPDs) with variable side chains distinct from 6PPD have been identified as potential replacement antioxidants, but their toxicities remain unclear under environmentally relevant ozone conditions. We herein tested the multiphase gas-surface ozone reactivity of four select PPDs [6PPD, -isopropyl-'-phenyl--phenylenediamine (IPPD), ,'-diphenyl--phenylenediamine (DPPD), and -phenyl-'-cyclohexyl--phenylenediamine (CPPD)] and evaluated the toxicity of their reaction mixtures in coho salmon, rainbow trout (), and fathead minnow ().
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