Tissue Accumulation and Biotransformation of 6PPD-Quinone in Adult Zebrafish and Its Effects on the Intestinal Microbial Community DOI
Xiao-Liang Liao, Zhifeng Chen,

Qian-Yi Liu

et al.

Environmental Science & Technology, Journal Year: 2024, Volume and Issue: 58(23), P. 10275 - 10286

Published: June 3, 2024

The pronounced lethality of N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine quinone (6PPD-quinone or 6PPDQ) toward specific salmonids, while sparing other fish species, has received considerable attention. However, the underlying cause this species-specific toxicity remains unresolved. This study explored 6PPDQ toxicokinetics and intestinal microbiota composition in adult zebrafish during a 14-day exposure to environmentally realistic concentrations, followed by 7-day recovery phase. Predominant accumulation occurred brain, intestine, eyes, with lowest levels liver. Six metabolites were found undergo hydroxylation, two additionally undergoing O-sulfonation. Semiquantitative analyses revealed that predominant metabolite featured hydroxy group situated on phenyl ring adjacent quinone. was further validated assessing enzyme activity determining silico binding interactions. Notably, affinity between phase I II enzymes exceeded corresponding coho salmon 1.04–1.53 times, suggesting higher potential for detoxification tolerant species. Whole-genome sequencing significant increases genera Nocardioides Rhodococcus after 6PPDQ. Functional annotation pathway enrichment predicted these would be responsible biodegradation metabolism xenobiotics. These findings offer crucial data comprehending 6PPDQ-induced toxicity.

Language: Английский

First Report on the Occurrence of N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD) and 6PPD-Quinone as Pervasive Pollutants in Human Urine from South China DOI
Bibai Du, Bowen Liang, Yi Li

et al.

Environmental Science & Technology Letters, Journal Year: 2022, Volume and Issue: 9(12), P. 1056 - 1062

Published: Nov. 21, 2022

N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD) and its quinone derivative, 6PPD-quinone (6PPD-Q), have been found to be prevalent in the environment, but there are currently no data on their presence humans. Herein, we conducted first human biomonitoring study of 6PPD 6PPD-Q by measuring 150 urine samples collected from three different populations (general adults, children, pregnant women) South China. Both were detected samples, with detection frequencies between 60% 100%. Urinary concentrations significantly higher than those correlated well (p < 0.01), indicating coexposure In vitro metabolic experiments demonstrated rapid depletion liver microsomes, which should responsible for lower urine. Additionally, women exhibited apparently (median 0.068 2.91 ng/mL, respectively) did adults (0.018 0.40 ng/mL) children (0.015 0.076 ng/mL). The high daily urinary excretion was estimated 273 (ng/kg bw)/day. Considering that a lethal toxicant multiple aquatic species, potential health risks posed long-term exposure require urgent attention.

Language: Английский

Citations

122
Widespread Occurrence and Transport of p-Phenylenediamines and Their Quinones in Sediments across Urban Rivers, Estuaries, Coasts, and Deep-Sea Regions DOI
Lixi Zeng, Yi Li, Yuxin Sun

et al.

Environmental Science & Technology, Journal Year: 2023, Volume and Issue: 57(6), P. 2393 - 2403

Published: Jan. 31, 2023

p-Phenylenediamines (PPDs) are widely used as antioxidants in tire rubber, and their derived quinone transformation products (PPD-Qs) may pose a threat to marine ecosystems. A compelling example is N-(1,3-dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD)-derived quinone, called 6PPD-Q, the causal toxicant for stormwater-linked acute mortality toward coho salmon. However, knowledge of co-occurrences PPDs PPD-Qs transport from freshwater oceanic waterbodies on large geographical scale remains unknown. Herein, we performed first large-scale survey these chemicals sediments across urban rivers, estuaries, coasts, deep-sea regions. Our results demonstrated that seven four ubiquitously present riverine, estuarine, coastal sediments, most them also occur sediments. The dominant concern were identified 6PPD 6PPD-Q. Total sedimentary concentrations presented clear spatial trend with decreasing levels rivers (medians: 39.7 15.2 ng/g) estuaries (14.0 5.85 then coasts (9.47 2.97 regions (5.24 3.96 ng/g). Interestingly, variation ratios 6PPD-Q (R6PPD/6PPD-Q) trend. field measurements implied riverine outflows be an important route rubber-derived open oceans.

Language: Английский

Citations

104
Analysis, environmental occurrence, fate and potential toxicity of tire wear compounds 6PPD and 6PPD-quinone DOI
Xiaoli Chen, Tao He, Xinlu Yang

et al.

Journal of Hazardous Materials, Journal Year: 2023, Volume and Issue: 452, P. 131245 - 131245

Published: March 21, 2023

Language: Английский

Citations

99
Transformation Products of Tire Rubber Antioxidant 6PPD in Heterogeneous Gas-Phase Ozonation: Identification and Environmental Occurrence DOI
Haoqi Zhao, Ximin Hu, Zhenyu Tian

et al.

Environmental Science & Technology, Journal Year: 2023, Volume and Issue: 57(14), P. 5621 - 5632

Published: March 30, 2023

6PPD, a tire rubber antioxidant, poses substantial ecological risks because it can form highly toxic quinone transformation product (TP), 6PPD-quinone (6PPDQ), during exposure to gas-phase ozone. Important data gaps exist regarding the structures, reaction mechanisms, and environmental occurrence of TPs from 6PPD ozonation. To address these gaps, ozonation was conducted over 24–168 h were characterized using high-resolution mass spectrometry. The probable structures proposed for 23 with 5 subsequently standard-verified. Consistent prior findings, 6PPDQ (C18H22N2O2) one major in (∼1 19% yield). Notably, not observed 6QDI (N-(1,3-dimethylbutyl)-N′-phenyl-p-quinonediimine), indicating that formation does proceed through or associated TPs. Other included multiple C18H22N2O C18H22N2O2 isomers, presumptive N-oxide, N,N′-dioxide, orthoquinone structures. Standard-verified quantified roadway-impacted samples, total concentrations 130 ± 3.2 μg/g methanol extracts tread wear particles (TWPs), 34 4 μg/g-TWP aqueous TWP leachates, 2700 1500 ng/L roadway runoff, 1900 1200 creeks. These demonstrate are likely an important ubiquitous class contaminants environments.

Language: Английский

Citations

71
Environmental Occurrence and Toxicity of 6PPD Quinone, an Emerging Tire Rubber-Derived Chemical: A Review DOI
Khaled Zoroufchi Benis, Ali Behnami, Shahab Minaei

et al.

Environmental Science & Technology Letters, Journal Year: 2023, Volume and Issue: 10(10), P. 815 - 823

Published: Sept. 1, 2023

N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine (6PPD) is a chemical added to tires prevent their oxidative degradation. 6PPD highly reactive with ozone and oxygen, leading the formation of transformation products such as quinone (6PPDQ) on tire surfaces and, subsequently, in road wear particles. 6PPDQ toxicant that has been found roadway runoff receiving water systems. Its presence municipal stormwater led acute mortality coho salmon during migration urban creeks reproduce, generating global interest studying its occurrence toxicity environment. This review aims provide critical overview current state knowledge 6PPDQ, assisting researchers policymakers understanding potential impacts this emerging environment human health. As there are many unanswered questions surrounding further research needed. highlights importance including regulations for 6PPD, well all synthetic chemicals concern.

Language: Английский

Citations

57
Urine Excretion, Organ Distribution, and Placental Transfer of 6PPD and 6PPD-Quinone in Mice and Potential Developmental Toxicity through Nuclear Receptor Pathways DOI
Haoqi Zhao, Sydney P. Thomas, Mark J. Zylka

et al.

Environmental Science & Technology, Journal Year: 2023, Volume and Issue: 57(36), P. 13429 - 13438

Published: Aug. 29, 2023

The rubber antioxidant 6PPD has gained significant attention due to its highly toxic transformation product, 6PPD-quinone (6PPDQ). Despite their detection in urines of pregnant women, the placental transfer and developmental toxicity 6PPDQ are unknown. Here, we treated C57Bl/6 mice with 4 mg/kg or investigate urine excretion transfer. Female male exhibited sex difference profiles 6PPDQ. Urine concentrations were one order magnitude lower than those 6PPD, suggesting higher bioaccumulation In from embryonic day 11.5 15.5, showed ∼1.5–8 times placenta, embryo body, brain, Using vitro dual-luciferase reporter assays, revealed that activated human retinoic acid receptor α (RARα) retinoid X (RXRα) at as low 0.3 μM, which was ∼10-fold detected urines. RXRα 1.2 μM. These results demonstrate exposure risks during pregnancy emphasize need for further toxicological epidemiological investigations.

Language: Английский

Citations

50
First insights into 6PPD-quinone formation from 6PPD photodegradation in water environment DOI
Chenguang Li, Yanlei Zhang,

Shiqi Yin

et al.

Journal of Hazardous Materials, Journal Year: 2023, Volume and Issue: 459, P. 132127 - 132127

Published: July 23, 2023

Language: Английский

Citations

49
Occurrence and Fate of Substituted p-Phenylenediamine-Derived Quinones in Hong Kong Wastewater Treatment Plants DOI Creative Commons
Guodong Cao, Wei Wang, Jing Zhang

et al.

Environmental Science & Technology, Journal Year: 2023, Volume and Issue: 57(41), P. 15635 - 15643

Published: Oct. 5, 2023

-Phenylenediamine quinones (PPD-Qs) are a newly discovered class of transformation products derived from

Language: Английский

Citations

49
A new toxicity mechanism of N-(1,3-Dimethylbutyl)-N′-phenyl-p-phenylenediamine quinone: Formation of DNA adducts in mammalian cells and aqueous organisms DOI
Jiabin Wu, Guodong Cao, Feng Zhang

et al.

The Science of The Total Environment, Journal Year: 2023, Volume and Issue: 866, P. 161373 - 161373

Published: Jan. 5, 2023

Language: Английский

Citations

48
Chemical characteristics, leaching, and stability of the ubiquitous tire rubber-derived toxicant 6PPD-quinone DOI
Ximin Hu, Haoqi Zhao, Zhenyu Tian

et al.

Environmental Science Processes & Impacts, Journal Year: 2023, Volume and Issue: 25(5), P. 901 - 911

Published: Jan. 1, 2023

We here report chemical characteristics relevant to the fate and transport of recently discovered environmental toxicant 6PPD-quinone (2-((4-methylpentan-2-yl)amino)-5-(phenylamino)cyclohexa-2,5-diene-1,4-dione or “6PPDQ”).

Language: Английский

Citations

45