US EPA

3859260 

Journal Article 

Covalent binding of fluorotelomer unsaturated aldehydes (FTUALs) and carboxylic acids (FTUCAs) to proteins 

Rand, AA; Mabury, SA 

2013 

1 

Environmental Science & Technology
ISSN: 0013-936X
EISSN: 1520-5851 

AMER CHEMICAL SOC 

WASHINGTON 

47 

3 

1655-1663 

English 

23256684 

10.1021/es303760u 

WOS:000314675500061 

Fluorotelomer unsaturated carboxylic acids and aldehydes (FTUCAs and FTUALs) are intermediate compounds that form from the biotransformation of fluorotelomer-based compounds. Previous evidence that FTUCAs and FTUALs bind to biological nucleophiles has indicated that protein binding might give rise to toxicity resulting from protein function disruption. The current study assesses the reactivity of FTUALs and FTUCAs by probing the covalent interactions of FTUALs and FTUCAs with proteins present in rat liver microsomes and bovine blood plasma. The FTUALs exhibited significant levels of protein covalent binding, with binding levels ranging from 20.1 (±2.8)% to 71.3 (±19.5)% in microsomes and 24.0 (±1.5)% to 82.5 (±14.0)% in blood plasma. By contrast, the FTUCAs did not exhibit any apparent covalent binding. Bovine serum albumin (BSA) was extracted and isolated from the plasma after incubation of 8:2 FTUAL (5-100 μM). Electrospray ionization mass spectrometry (ESI-MS) was used to investigate the stoichiometry of 8:2 FTUAL covalently bound to BSA; three measurable FTUAL adducts were formed with BSA. To compare the percent binding results from the FTUAL microsome incubation experiments, 8:2 FTOH was incubated in microsomes to determine the protein binding associated with the biotransformation of 8:2 FTOH. Results from this study showed that the biotransformation of 8:2 FTOH yielded 26.1 (±3.0)% binding, and was statistically similar to the percent binding associated with 8:2 FTUAL exposure (p > 0.05), indicating that the binding of 8:2 FTUAL to proteins might be a primary fate in the biotransformation of 8:2 FTOH.