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在基于鱼类和哺乳动物的试验中,常见轮胎防腐剂6PPD及其降解产物6PPD-醌的生物活性。

Bioactivity of the ubiquitous tire preservative 6PPD and degradant, 6PPD-quinone in fish- and mammalian-based assays.

作者信息

Jankowski Mark D, Carpenter Amy F, Harrill Joshua A, Harris Felix R, Hill Bridgett, Labiosa Rochelle, Makarov Sergei S, Martinović-Weigelt Dalma, Nyffeler Jo, Padilla Stephanie, Shafer Timothy J, Smeltz Marci G, Villeneuve Daniel L

机构信息

U.S. EPA, Region 10, Laboratory Services and Applied Science Division, Seattle, WA 98101, United States.

Oak Ridge Associated Universities, Oak Ridge, TN 37830, United States.

出版信息

Toxicol Sci. 2025 Apr 1;204(2):198-217. doi: 10.1093/toxsci/kfaf008.

Abstract

6PPD-quinone (N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine quinone), a transformation product of the antiozonant 6PPD (N-(1,3-dimethylbutyl)-N'-phenyl-p-phenylenediamine) is a likely causative agent of coho salmon (Oncorhynchus kisutch) pre-spawn mortality. Stormwater runoff transports 6PPD-quinone into freshwater streams, rapidly leading to neurobehavioral, respiratory distress, and rapid mortality in laboratory-exposed coho salmon, but causing no mortality in many laboratory-tested species. Given this identified hazard, and potential for environmental exposure, we evaluated a set of U.S. Environmental Protection Agency's high-throughput assays for their capability to detect the large potency difference between 6PPD and 6PPD-quinone observed in coho salmon and screen for bioactivities of concern. Assays included transcriptomics in larval fathead minnow (FHM), developmental and behavioral toxicity in larval zebrafish, phenotypic profiling in a rainbow trout gill cell line, acute and developmental neurotoxicity in mammalian cells, and reporter transcription factor activity in HepG2 cells. 6PPD was more consistently bioactive across assays, with distinct activity in the developmental neurotoxicity assay (mean 50th centile activity concentration = 0.91 µM). Although 6PPD-quinone was less potent in FHM and zebrafish, and displayed minimal neurotoxic activity in mammalian cells, it was highly potent in altering organelle morphology in RTgill-W1 cells (phenotype-altering concentration = 0.024 µM compared with 0.96 µM for 6PPD). Although in vitro sensitivity of RTgill-W1 cells may not be as sensitive as intact Coho salmon, the assay may be a promising approach to test chemicals for 6PPD-quinone-like activities. The other assays each identified unique bioactivities of 6PPD, with neurobehavioral and developmental neurotoxicity being most affected, indicating a need for further assessment of this chemical. Our results demonstrate that the common tire additive, 6PPD, is bioactive in a broader set of assays than the environmental transformation product 6PPD-quinone and that it may be a developmental neurotoxicant in mammals, whereas 6PPD-quinone was much more potent than 6PPD in altering the intracellular phenotype of rainbow trout gill cells. Application of the set of high-throughput and high-content bioassays to test the bioactivity of this emerging pollutant has provided data to inform both ecological and human health assessments.

摘要

6PPD-醌(N-(1,3-二甲基丁基)-N'-苯基-对苯二胺醌)是抗臭氧剂6PPD(N-(1,3-二甲基丁基)-N'-苯基-对苯二胺)的转化产物,它可能是银大麻哈鱼(Oncorhynchus kisutch)产卵前死亡的致病因子。雨水径流将6PPD-醌输送到淡水溪流中,在实验室暴露的银大麻哈鱼中会迅速导致神经行为异常、呼吸窘迫和快速死亡,但在许多实验室测试的物种中不会导致死亡。鉴于鉴于这种已确定的危害以及环境暴露的可能性,我们评估了美国环境保护局的一组高通量检测方法,以检测它们检测银大麻哈鱼中6PPD和6PPD-醌之间巨大效力差异的能力,并筛选出相关生物活性。检测方法包括黑头呆鱼(FHM)幼体的转录组学、斑马鱼幼体的发育和行为毒性、虹鳟鱼鳃细胞系的表型分析、哺乳动物细胞的急性和发育神经毒性以及HepG2细胞中的报告转录因子活性。6PPD在各种检测中表现出更一致的生物活性,在发育神经毒性检测中具有明显活性(平均第50百分位数活性浓度 = 0.91 μM)。虽然6PPD-醌在FHM和斑马鱼中效力较低,在哺乳动物细胞中显示出最小的神经毒性活性,但它在改变RTgill-W1细胞的细胞器形态方面具有高效力(表型改变浓度 = 0.024 μM,而6PPD为0.96 μM)。虽然RTgill-W1细胞的体外敏感性可能不如完整的银大麻哈鱼,但该检测方法可能是测试化学品是否具有6PPD-醌样活性的一种有前途的方法。其他检测方法各自确定了6PPD独特的生物活性,其中神经行为和发育神经毒性受影响最大,这表明需要对这种化学物质进行进一步评估。我们的结果表明,常见的轮胎添加剂6PPD在比环境转化产物6PPD-醌更广泛的一组检测中具有生物活性,并且它可能是哺乳动物中的一种发育神经毒物,而6PPD-醌在改变虹鳟鱼鳃细胞的细胞内表型方面比6PPD效力更强。应用这组高通量和高内涵生物检测方法来测试这种新兴污染物的生物活性,为生态和人类健康评估提供了数据。

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本文引用的文献

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Synthesis and Toxicity Evaluation of -Phenylenediamine-Quinones.对苯二胺醌的合成与毒性评估
Environ Sci Technol. 2025 Apr 22;59(15):7485-7494. doi: 10.1021/acs.est.4c12220. Epub 2025 Apr 8.

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