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Perfluorononanoic acid

Manufactured by Merck Group
Sourced in United States

Perfluorononanoic acid is a chemical compound with the formula C9F19COOH. It is a fluorocarbon carboxylic acid. The compound serves as a starting material for the synthesis of other perfluorinated compounds.

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9 protocols using perfluorononanoic 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

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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3

Characterization of PFCA compounds

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Four perfluorocarboxylic acid (PFCA) compounds including perfluorobutanoic acid (PFBA, 95%), perfluoropentanoic acid (PFPeA, 97%), perfluoheptanoic acid (PFHpA, 99%), perfluorononanoic acid (PFNA, 97%), and perfluorooctane sulfonate (PFOS, ∼40% in H2O) were acquired from Sigma-Aldrich and they were used as reference materials. Additional descriptions of all chemical reagents and the sample preparation protocol were summarized in Supplementary Table S1.
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4

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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5

Fluorescent Probes for Cellular Assays

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Perfluorononanoic acid (PFNA, 97%), 3-Isobutyl-1-methylxanthine (IBMX, ≥ 99%) and 2′,7′-dichlorofluorescin diacetate (DCFH-DA, ≥ 97%) were obtained from Sigma-Aldrich (St. Louis, MO, USA). JC-1 Mitochondrial Membrane Potential Detection Kit and MitoView™ Green were purchased from Biotium (Hayward, CA, USA). Mouse monoclonal anti-α-Tubulin-FITC antibody and anti-phospho-Histone H2A.X (Ser139) antibody, clone JBW301 were purchased from Sigma-Aldrich (St. Louis, MO, USA). Anti-phospho-p44/42 MAPK (Erk1/2) antibody was purchased from Cell Signaling Technologies. Alexa Fluor 488-conjugated goat anti-mouse IgG (H + L) and Alexa Fluor 594-conjugated goat anti-rabbit IgG (H + L) secondary antibodies were obtained from Molecular Probes.
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6

Quantification of Perfluorinated Compounds

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PFCAs (>98% purity) were purchased from Sigma-Aldrich Inc. and included perfluorobutanoic acid (PFBA), perfluoropentanoic acid (PFPeA), perfluorohexanoic acid (PFHxA), perfluoroheptanoic acid (PFHpA), perfluorooctanoic acid (PFOA), and perfluorononanoic acid (PFNA). A precursor of PFOA, perfluorooctane sulfonamide (PFOSA, 98%) was also obtained from Sigma-Aldrich Inc. Dicyclohexylcarbodiimide (DCC) and 3, 4-dichloroaniline (DCA) were purchased from J&K Scientific Ltd (Beijing, China). SPE silica-gel columns (Cleanert Pesticarb-SPE cartridge) were provided by Bonna-Agela Technologies Inc (Tianjin, China). Ultrapure water (18.2 MΩ/cm, Hitech, China) was used for aqueous sample preparation. Possible contamination was avoided by verifying all solids and solvents with procedural blanks in advance.
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7

Profiling Cellular Responses to Chemical Exposure

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The 21 chemicals [sodium (meta) arsenite, cadmium chloride, copper (II) chloride, lead (II) acetate trihydrate, mercury (II) chloride, phenanthrene, p,p′-DDE (dichlorodiphenyldichloroethylene), thiram, 1,4-dichlorobenzene, 2,5-dichlorophenol, methylparaben, propylparaben, perfluorodecanoic acid (PFDA), perfluorononanoic acid (PFNA), perfluorooctanoic acid (PFOA), perfluorooctanesulfonic acid (PFOS), polychlorinated biphenyl 153 (PCB153), polychlorinated biphenyl 187 (PCB187), bisphenol A, bisphenol F, bisphenol S] were purchased from Sigma-Aldrich and Cayman Chemicals (Table S1). The chemicals were weighed and dissolved in dimethyl sulfoxide (DMSO) (for most) and in sterile water (for some) at a concentration of 5mg/mL and stored at 20°C for long-term storage. For dosing, we prepared an intermediate stock concentration of 5 mM for each of the chemicals, which was further diluted into final concentrations for dosing the MCF10A cells: 25μM , 2.5μM , 0.25μM , and 0.025μM . These final concentrations were prepared fresh in MCF10A media for each experiment. For chemicals dissolved in DMSO, the final DMSO concentration was 0.5%, as were the vehicle controls. For chemicals dissolved in water, an equivalent amount of water was included in the vehicle control.
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8

Chemical Characterization of Carbon Additives

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Graphite powder (particle size <20 μm), PFPA, perfluorohexanoic acid (PFHxA), perfluoroheptanoic acid (PFHtA), PFOA, perfluorononanoic acid (PFNA), and perfluorodecanoic acid (PFDA) were purchased from Sigma Aldrich. Teflonized acetylene black was purchased from Denka Co. Ltd polydimethylsiloxane (PDMS) Sylgard 184 was purchased from Dow Corning.
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9

Analytical Method for Emerging Contaminants

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Reagents purchased were HPLC grade and the standards used were of high purity grade (>95%): perfluorooctanoic acid (PFOA), perfluoroheptanoic acid (PFHpA), perfluorononanoic acid (PFNA), perfluorodecanoic acid (PFDA), perfluoroundecanoic acid (PFUnDA), bisphenol A (BPA) and acetaminophen (ACT), caffeine (CAF), diclofenac (DCF), lamivudine (LA), triclosan (TS), phenytoin (PHE), sulfamethoxazole (SMX), carbamazepine (CAR), 2nitrophenol, sulfamethoxazole-d 4 and acetaminophen-d 4 from Sigma Aldrich (South Africa). Individual stock standards and isotopically labelled internal standards were prepared in methanol at a concentration of 1000 mg/L. Stock solutions in methanol were stored at À20 C. Working standard solutions were prepared by appropriate dilution of the stock solutions in methanol stored at 4 C in appropriate storage amber container glassware to prevent light degradation. Working standard solutions were used for preparation of the calibration curves and for spiking samples in the validation study. The cartridges Oasis HLB (6 mL, 200 mg) were obtained by Waters Corporation (Mildford, MA, USA). HPLC grade methanol, acetonitrile and acetone from Sigma Aldrich (South Africa), ultrapure water was purified by Milli-Q system (Millipore, Bedford, MA, USA).
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