Microbial biodegradation of a novel fluorotelomer alcohol, 1H,1H,2H,2H,8H,8H-perfluorododecanol, yields short fluorinated acids

Arakaki, Atsushi; Ishii, Yuko; Tokuhisa, Takahito; Murata, Shigeo; Sato, Katsuyuki; Sonoi, Takehiro; Tatsu, Haruyoshi; Matsunaga, Tadashi

doi:10.1007/s00253-010-2815-9

Cited by 19 publications

(25 citation statements)

References 24 publications

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“…In contrast, the 7:3 FTCA incubations showed very low biotransformation-only 1.7 mol% depleted after 90 d. The only transformation product observed was the PFHpA. In contrast to the 7:3 FTCA, the 5:3 FTCA was rapidly degraded in the [29]. Adapted from Arakaki et al [29].…”

Section: Fluorotelomer Carboxylatesmentioning

confidence: 99%

“…In contrast to the 7:3 FTCA, the 5:3 FTCA was rapidly degraded in the [29]. Adapted from Arakaki et al [29]. See Table 1 for definition of abbreviations.…”

Section: Fluorotelomer Carboxylatesmentioning

confidence: 99%

“…Biotransformation pathway of the 1H,1H,2H,2H,8H,8H‐perfluorofluorododecanol (DTFA) as proposed by Arakaki et al . Adapted from Arakaki et al . See Table for definition of abbreviations.…”

Section: Microbialmentioning

confidence: 99%

“…Arakaki et al investigated the biodegradation of the 1H,1H,2H,2H,8H,8H‐perfluorododecanol (referred to as “degradable telomer fluoroalcohol” [DTFA]) in activated sludge under closed‐bottle and aerated, flow‐through conditions for 20 d. In addition, a long‐term study (70 d) was performed under aerated conditions. The DTFA is similar to the 10:2 FTOH, with the exception that the CF 2 group at the 8‐carbon is replaced with a CH 2 group.…”

Section: Microbialmentioning

confidence: 99%

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Biotransformation pathways of fluorotelomer‐based polyfluoroalkyl substances: A review

Butt

Muir

Mabury

2013

Enviro Toxic and Chemistry

258

178

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Abstract:The study reviews the current state of knowledge regarding the biotransformation of fluorotelomer-based compounds, with a focus on compounds that ultimately degrade to form perfluoroalkyl carboxylates (PFCAs). Most metabolism studies have been performed with either microbial systems or rats and mice, and comparatively few studies have used fish models. Furthermore, biotransformation studies thus far have predominately used the 8:2 fluorotelomer alcohol (FTOH) as the substrate. However, there have been an increasing number of studies investigating 6:2 FTOH biotransformation as a result of industry's transition to shorter-chain fluorotelomer chemistry. Studies with the 8:2 FTOH metabolism universally show the formation of perfluorooctanoate (PFOA) and, to a smaller fraction, perfluorononanoate (PFNA) and lower-chain-length PFCAs. In general, the overall yield of PFOA is low, presumably because of the multiple branches in the biotransformation pathways, including conjugation reactions in animal systems. There have been a few studies of non-FTOH biotransformation, which include polyfluoroalkyl phosphates (PAPs), 8:2 fluorotelomer acrylate (8:2 FTAC), and fluorotelomer carboxylates (FTCAs, FTUCAs). The PAPs compounds and 8:2 FTAC were shown to be direct precursors to FTOHs and thus follow similar degradation pathways. Environ Toxicol Chem 2014;33:243-267. # 2013 SETAC

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Section: Fluorotelomer Carboxylatesmentioning

confidence: 99%

“…In contrast to the 7:3 FTCA, the 5:3 FTCA was rapidly degraded in the [29]. Adapted from Arakaki et al [29]. See Table 1 for definition of abbreviations.…”

Section: Fluorotelomer Carboxylatesmentioning

confidence: 99%

“…Biotransformation pathway of the 1H,1H,2H,2H,8H,8H‐perfluorofluorododecanol (DTFA) as proposed by Arakaki et al . Adapted from Arakaki et al . See Table for definition of abbreviations.…”

Section: Microbialmentioning

confidence: 99%

Section: Microbialmentioning

confidence: 99%

See 2 more Smart Citations

Biotransformation pathways of fluorotelomer‐based polyfluoroalkyl substances: A review

Butt

Muir

Mabury

2013

Enviro Toxic and Chemistry

258

178

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“…The livers of all rats euthanized were analyzed for metabolites of diFESOS. Analysis of the livers of the rats that received (Arakaki et al, 2010;Butt et al, 2014). The product of thioether oxidation of FESCA to produce 2H 3:2 polyfluorinated ether carboxylic acid (2H 3:2 PFECA) was not observed.…”

Section: Analysis Of Metabolites In Rat Urine and Liversmentioning

confidence: 99%

In Vivo Transformation of a Novel Polyfluoroether Surfactant

Folkerson

Joudan

Mabury

et al. 2021

Enviro Toxic and Chemistry

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Per‐ and polyfluoroalkyl substances are a class of fluorochemicals that can degrade into perfluoroalkyl acids, which are well known to be persistent in the environment. It is thus important that novel fluorinated surfactants be designed to degrade into small, nonbioaccumulative products. We report the biotransformation and elimination kinetics of one such novel polyfluorinated surfactant, di(polyfluoroether thioether(S)‐oate) sulfonate (diFESOS), and its metabolites. Biotransformation was investigated in vitro using S9 liver fractions and in vivo in Sprague–Dawley rats. Rats dosed by oral gavage with diFESOS were found to have relatively fast elimination kinetics, with half‐lives on the order of hours, compared with legacy fluorinated surfactants such as the disubstituted polyfluoroalkyl phosphates that have half‐lives on the order of days. To interrogate degradation of the polyfluorinated chain, rats were then dosed with a polyfluoroether thioether alcohol (a suspected product of carboxylate cleavage of diFESOS) either orally or intravenously, and the novel metabolite 2H‐3:2 polyfluoroether sulfonic acid (2H‐3:2 PFESA) was identified. Perfluoropropionic acid was detected in rat urine and is likely a terminal product. The blood of orally dosed rats contained higher levels of metabolites than the blood of intravenously dosed rats, suggesting the importance of metabolism in the gut and liver. Elimination kinetics of all the novel metabolites were faster than their fully fluorinated counterparts. Environ Toxicol Chem 2021;40:3328–3336. © 2021 SETAC

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Biology of Fluoro-Organic Compounds

Zhang

Lai

Kong

2011

Topics in Current Chemistry

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Investigations on diverse aspects of fluoro-organic compounds have rapidly increased during the past decades. Because natural sources of fluoro-organic compounds are extremely rare, the industrial synthesis of fluorinated organic compounds and production of fluorinated natural product derivatives have greatly expanded in recent years because of their increasing importance in the agrochemical and pharmaceutical industries. Due to structural complexity or instability, synthetic modification is often not possible, and various biofluorination strategies have been developed in recent years for applications in the anti-cancer, anti-viral and anti-infection fields. Despite the industrial importance of fluorinated compounds, there have been serious concerns worldwide over the levels and synthetic routes of certain fluorinated organic compounds, in particular perfluorinated chemicals (PFCs). PFCs are emerging and recalcitrant pollutants which are widely distributed in the environment and have been detected in humans and wildlife globally. PFCs have been demonstrated to be potentially carcinogenic, adversely affect the neuroendocrine and immune systems, and produce neurotoxicity, heptatotoxicity and endocrine disrupting effects in vertebrate animals. Here, we provide an overview of recent advances in our understanding of the biology of various fluoro-organic compounds and perspectives for new enzymes and metabolic pathways for bioremediation of these chemicals.

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Microbial biodegradation of a novel fluorotelomer alcohol, 1H,1H,2H,2H,8H,8H-perfluorododecanol, yields short fluorinated acids

Cited by 19 publications

References 24 publications

Biotransformation pathways of fluorotelomer‐based polyfluoroalkyl substances: A review

Biotransformation pathways of fluorotelomer‐based polyfluoroalkyl substances: A review

In Vivo Transformation of a Novel Polyfluoroether Surfactant

Biology of Fluoro-Organic Compounds

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