In vitro interactions of biological nucleophiles with fluorotelomer unsaturated acids and aldehydes: fate and consequences

Environmental Science & Technology
Amy A Rand, Scott A Mabury

Abstract

Fluorotelomer unsaturated aldehydes and acids (FTUALs and FTUCAs) are intermediate metabolites that form from the biotransformation of fluorotelomer-based chemicals. FTUALs and FTUCAs have been previously suggested to contribute to the toxicity associated with human exposure to fluorotelomer compounds by covalently binding to biological nucleophiles. However, the extent of their reactivity has only been assessed with glutathione. The purpose of the present study was to assess the reactivity of these intermediate metabolites with a series of nucleophilic amino acids and model proteins. In vitro experiments were carried out in an aqueous buffer system to determine the reactivity of nucleophilic amino acids with FTUCAs and FTUALs having varying fluorinated chain lengths. Using (19)F NMR spectroscopy to monitor the disappearance of the FTUCAs and FTUAL signals and the production of a fluoride signal, reaction rate constants were determined under pseudo-first-order conditions. The FTUCAs reacted only with cysteine with the following second order rate constants: 3.63 (± 1.37) × 10(-5) min(-1) mM(-1) (4:2 FTUCA), 1.19 (± 0.91) × 10(-5) min(-1) mM(-1) (6:2 FTUCA), and 4.56 (± 0.94) × 10(-5) min(-1) mM(-1) (8:2 FTUCA). The FTUALs were s...Continue Reading

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Citations

Dec 22, 2012·Environmental Science & Technology·Amy A Rand, Scott A Mabury
Nov 22, 2013·Environmental Science & Technology·Lisa A D'Agostino, Scott A Mabury
Sep 29, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Weitao ZhuBo Chen
Feb 18, 2021·Environmental Health Perspectives·Simona Andreea BălanAndré Maurice Algazi

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