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Perfluorooctanoic acid

Manufactured by Merck Group
Sourced in United States, Germany, France

Perfluorooctanoic acid is a synthetic chemical compound used in various industrial and laboratory applications. It is a colorless, odorless, and water-soluble substance. Perfluorooctanoic acid serves as a surfactant and is employed in the manufacturing of fluoropolymers, such as Teflon. Its core function is to improve the wetting and spreading properties of liquids.

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24 protocols using perfluorooctanoic acid

1

Plasma Protein Binding of PFAS Compounds

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The molecular structures of the 14 PFAS evaluated are in Figure S1 and physiochemical properties, such as molecular weight (MW) and logD shown in Table S1. The following fourteen PFAS were either obtained from Accustandard, Inc. (New Haven, CT, USA) or Sigma-Aldrich (St. Louis, MO, USA): Perfluorobutanoic acid (PFBA), perfluoropentanoic acid (PFPA), perfluorohexanoic acid (PFHxA), perfluoroheptanoic acid (PFHpA), perfluorooctanoic acid (PFOA), perfluorononanoic acid (PFNA), perfluorodecanoic acid (PFDA), perfluoroundecanoic acid (PFUDA), perfluorododecanoic acid (PFDoDA), perfluorohexanesulfonic acid (PFHxS), perfluorooctanesulfonamide (PFOSA), 6:2 fluorotelomer sulfonate (6:2 FtS), perfluorobutanesulfonic acid (PFBS), and perfluorooctanesulfonic acid (PFOS). Human, rat (Wistar-Han), and mouse (CD-1; C57BL/6) equal sex pooled (minimum of 3 male and 3 female) plasma was obtained from BioIVT (Hicksville, NY, USA). The equilibrium dialysis device (HTD96) and cellulose membranes with a molecular weight cutoff of 12–14 kDa were obtained from HTDialysis, LLC (Gales Ferry, CT, USA). Human, rat, and mouse albumin, along with all other reagents were obtained from Sigma-Aldrich unless specified otherwise.
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2

Preparation of Ecotoxicological Chemical Mixture

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The following chemicals were purchased from Sigma-Aldrich (Saint-Quentin Fallavier, France): bisphenol-A (BPA purity >99%), triclosan (TCS >97%), benzophenone-3 (BP3_98%), decabromodiphenyl ether (BDE-209 98%), sodium perchlorate (>98%), 4-4′-dichlorodiphenyldichloroethylen (4,4′-DDE 99%), hexachlorobenzene (HCB 99.9%), dibutylphtalate (DBP 99%), diethylhexylphtalate (DEHP 99%), PCB-153, 2-Naphtol (99%), perfluorooctanesulfonic acid (PFOS >98%), perfluorooctanoic acid (PFOA >98%), methyl mercury chloride (>99.9%), lead chloride (98%), dimethyl sulfoxide (DMSO), acetone, 3,3′,5,5′tetraiodo-L-thyronine T4 >98%) and triiodothyronine (T3 99%). NH-3, a thyroid hormone antagonist18 (link) was synthesized by AGV Discovery (France), absence of contamination by benzofurane was verified56 (link). All chemicals were dissolved at 10−1 M in DMSO, with the exception of HCB (10−1 M in acetone) and BDE 209 (10−2 M in DMSO). These solutions were aliquoted and stored at −20 °C until use. T3 was prepared in 30% NaOH, 70% milliQ Water at 10−2 M concentration, aliquoted and stored at −20 °C until use. The chemical mixture was prepared at 105-fold concentration by mixing appropriate volumes of stocks as described in Supplementary Table 1, aliquoted and stored at −20 °C.
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3

Synthesis of Perfluoroalkyl Compounds

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Perfluorooctanoic acid (96%, PFOA), FAs (≥99%, including OA, EA, LA, and ALA), 2,2,2‐trifluoroethanol (TFE), phenylalanine (99%), sodium hydroxide, ammonium hydroxide, methanol, ethanol, and acetonitrile (HPLC grade solvents) were purchased from Sigma‐Aldrich (Saint‐Quentin‐Fallavier, France). Perfluorooctanoyl chloride (97%) was supplied from Fisher Scientific‐Alfa Aesar (Illkirch, France). Deuterated solvents were supplied from Eurisotop (Saint‐Aubin, France).
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4

Perfluorinated Compounds Stock Preparation

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Perfluorooctanoic acid (PFOA, 95% purity) and perfluorononanoic acid (PFNA, 99% purity) were obtained from Sigma-Aldrich (Zwijndrecht, The Netherlands). Perfluorohexane sulfonate (PFHxS, 95% purity) and perfluorooctane sulfonate (PFOS, 97% purity) were obtained from Synquest laboratories (Alachua FL, USA). All stocks were prepared in 100% dimethyl sulfoxide (DMSO HybriMax, Sigma-Aldrich).
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5

Preparation of Chemical Stock Solutions

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Prochloraz (purity 99.1%, CAS 67747-09-5), tributyltin (TBT) chloride (96%, CAS 1461-22-9), tetrabromobisphenol A (TBBPA, 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane) (97%, CAS 79-94-7), perfluorooctanoic acid (PFOA) (96%, CAS 335-67-1), imazalil (99.7%, CAS 35554-44-0), butralin (99.8%, CAS 33629-47-9), clofibrate (CAS 637-07-0), and gemfibrozil (CAS 25812-30-0) were obtained from Sigma-Aldrich (St. Louis, MO). Tetrachlorobisphenol A (TCBPA, 2,2-bis(3,5-dichloro-4-hydroxyphenyl)propane) (95%, CAS 79-95-8) was purchased from TCI America (Portland, OR). All chemicals were dissolved and diluted in DMSO to make 1000× stock solutions.
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6

Antimicrobial Textile Functionalization

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Tris(hydroxymethyl) aminomethane hydrochloride (Tris,≥98.0%) was obtained from Aladdin Chemicals (Shanghai, China). Dopamine hydrochloride (DA, 98%) and perfluorooctanoic acid (denoted as PFOA) was acquired from Sigma-Aldrich. Ammonia solution (25–27 wt %), silver nitrate, methylene blue (MB), and glucose were provided by Sinopharm Chemical Reagent Co., Ltd., China. Sodium borohydride (NaBH4) was obtained from Fisher Scientific. Sodium perfluorooctanoate (denoted PFOA-Na) with a concentration of 1.0 M was fabricated by the reaction of NaOH and PFOA in ethanol. The commercially available textiles made of cellulose were bought from local stores and ultrasonically cleaned with acetone, alcohol, and deionized water for 20 min in sequence before use. All reagents related to E. coli (E. coli) cultures were purchased TaKaRa (Dalian, China).
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7

Evaluating PFOA Toxicity with β-Cyclodextrin

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Perfluorooctanoic acid (PFOA, 96% purity) was purchased from Sigma-Aldrich (St. Louis, MO, USA). β-Cyclodextrin (β-CD, 98% purity) was purchased from Acros Organics (Geel, Belgium). Both chemicals were used without further purification. Stock solutions of PFOA (7.25 mM, i.e., 3000 parts-per-million (ppm)), 1:1 β-CD:PFOA (β-CD: 7.25 mM, PFOA: 7.25 mM), and 2:1 β-CD:PFOA (β-CD: 14.50 mM, PFOA: 7.25 mM) were prepared with deionized water in polypropylene tubes. The solutions were sonicated until dissolution of the solids was achieved. A control solution of deionized water was also stored in a polypropylene tube. Stock solutions were subsequently diluted over a relevant range of concentrations (see below) for assessment of zebrafish embryo toxicity.
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8

Immunofluorescence Staining of Cell Cultures

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Dimethyl sulfoxide (DMSO), paraformaldehyde, 4′,6-diamidino-2-phenylindole dihydrochloride (DAPI), Triton X-100, propidium iodide (PI), DNAse-free RNAse A, perfluorooctanoic acid, cholera toxin (CT), insulin, 3-(4,5-dimethyl-2-yl)2,5-diphenyl-2H-tetrazolium bromide (MTT), epidermal growth factor (EGF), hydrocortisone and sulforaphane were obtained from Sigma-Aldrich (St Louis, MO, USA). Horse serum, penicillin–streptomycin (P/S), Dulbecco’s Phosphate-Buffered Saline (PBS), Dulbecco’s Modified Eagle’s Medium (DMEM), trypsin solution (0.05%) were obtained from Gibco (Invitrogen, Paisley, UK). p53 monoclonal (DO-7), CDK6 monoclonal (75B9), CDK4 monoclonal (DCS-31) and p21 monoclonal (R.229.6) antibodies were obtained from ThermoFisher Scientific (Rockford, IL, USA). P27 Kip1 (D69C12) and cyclin D1 (92G2) antibodies were obtained from Cell Signaling (Danvers, MA, USA). The secondary antibodies Alexa-Fluor 555 goat anti-mouse IgG or 488 goat anti-rabbit IgG, and the blocking agent (normal goat serum) were obtained from Molecular Probes, Invitrogen. Matrigel Basement Membrane Matrix was obtained from Corning (New York, NY, USA). ER α (sc-8002) and ERβ (sc-8974) monoclonal antibodies were obtained from Santa Cruz Biotechnology (Bergheimer, HD, DE). ICI 182,780, GW 6471 was obtained from Tocris Bioscience (Avonmouth, Bristol, UK).
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9

Perfluorinated Chemicals Protocol

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Perfluoroheptanoic acid (PFHpA, 99% purity), perfluorooctanoic acid (PFOA, 95% purity), perfluorononanoic acid (PFNA, 99% purity), perfluorodecanoic acid (PFDA, 98% purity) and perfluorobutane sulfonate (PFBS; 97% purity) were obtained from Sigma-Aldrich (Zwijndrecht, The Netherlands). Perfluorohexane sulfonate (PFHxS, 95% purity) and perfluorooctane sulfonate (PFOS, 97% purity) were obtained from Synquest laboratories (Alachua FL, USA). All stocks were prepared in 100% dimethyl sulfoxide (DMSO HybriMax, Sigma-Aldrich). Final solvent concentrations in studies amounted to 0.1%.
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10

Lipidomic Analysis of Nanoplastic Exposure

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Triclosan (TCS), perfluorooctanoic acid (PFOA), toluene, methyl tert-butyl ether (MTBE), ammonium formate, ammonium acetate, dimethyl sulfoxide (DMSO), and formic acid were purchased from Sigma Aldrich (St. Louis, MO, USA). The lipid internal standards included sphingosine 17:1, sphingomyelin 18:1/17:0, ceramide 18:1/17:0, triacylglycerol (TG) 17:0/17:0/17:0, phosphatidylcholine (PC) 36:1, and phosphatidylethanolamine (PE) 36:1. PC 32:0 and cholesterol d7 were purchased from Avanti Polar Lipids (Alabaster, AL, USA). Nanopolystyrene (50 nm) was purchased from Polysciences (Warrington, PA, USA). LC-MS grade solvents (water, acetonitrile, 2-propanol, and methanol) were purchased from Merck (Darmstadt, Germany).
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