Linoleic acid

Manufactured by Cayman Chemical

Sourced in United States, United Kingdom

Linoleic acid is a polyunsaturated fatty acid that serves as a core component in various laboratory applications. It is a naturally occurring compound found in many plant and animal oils.

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Lab products found in correlation

29 protocols using linoleic acid

Fatty Acid and RNAi Regulation Study

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DHA, arachidonic acid (AA; 20:4n-6), and linoleic acid (LA; 18:2n-6) were obtained from Cayman Chemicals and prepared as 100 mM stocks in ethanol. ON-TARGETplus siRNAs were purchased from Dharmacon. RNAiMAX was purchased from Invitrogen. The 5-aminoimidazole-4-carboxamide ribonucleotide (AICAR), collagenase (C6885), and type B bovine gelatin were purchased from Sigma-Aldrich (St. Louis, MO). GW501516 (GW1516) was purchased from R&D Systems (Minneapolis, MN). Dispase I was purchased from Wako Pure Chemicals and complete protease inhibitor cocktail was from Roche Applied Science.

Valentine W.J., Tokuoka S.M., Hishikawa D., Kita Y., Shindou H, & Shimizu T. (2017). LPAAT3 incorporates docosahexaenoic acid into skeletal muscle cell membranes and is upregulated by PPARδ activation. Journal of Lipid Research, 59(2), 184-194.

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Formulation of Basal Cell Culture Media

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For basal media, Dulbecco's modified Eagle's medium (DMEM) with HEPES, and Coon's modified Ham's F-12 with HEPES (F12) were obtained from Sigma-Aldrich. DMEM without calcium chloride was obtained from Life Technologies (Carlsbad, CA). KBM-Gold™ (keratinocyte basal medium, calcium ion-free) from Lonza (Walkersville, MD).
Unless otherwise stated, the following reagents were used as purchased from Sigma-Aldrich: Alanyl-glutamine, bovine serum albumin, calcium chloride, cholesterol, ethanolamine, fructose, fucose, ga lactose, glucose, glucosamine, gluconic acid, glucuronic acid, glutathione (reduced), heparin, hydrocortisone, hypoxanthine, lactose, LONG®R³ IGF-1, manganese (II) chloride, non-essential amino acids, oxalacetic acid, progesterone (soluble), putrescine, retinyl acetate (soluble), sodium pyruvate, sodium selenite, TAPSO (N-[Tris(hydroxymethyl)methyl]-3-amino-2-hydroxypropanesulfonic acid), taurine, thioglycerol, partially saturated human transferrin, triiodothyronine (T3), uridine, and vitamin E acetate. Other reagents and sources were as follows: Ascorbic acid phosphate, Mg salt (Wako Chemicals, Richmond, VA); ammonium molybdate (Fisher Scientific, Suwanee, GA); bovine calf serum (CS; Lonza); carnitine tartrate (LKT Laboratories, St. Paul, MN); linoleic acid (Cayman Chemical, Ann Arbor, MI); thiamine and thymidine (Santa Cruz Biotechnology, Dallas, TX).

Pfeffer B.A., Xu L., Porter N.A., Rao S.R, & Fliesler S.J. (2016). Differential Cytotoxic Effects of 7-Dehydrocholesterol-derived Oxysterols on Cultured Retina-derived Cells: Dependence on Sterol Structure, Cell Type, and Density. Experimental eye research, 145, 297-316.

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Fatty Acid Effects on E. coli Growth

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Escherichia coli MG1655, purchased from ATCC, was used for all experiments. Overnight cultures grown in Luria broth were pelleted, washed with PBS, and transferred to M9 minimal medium [0.4% glucose supplemented with 150 mM NaCl] for initiation of most experiments. All experiments were performed at 37 °C. Fatty acids used in this study were purchased from Cayman Chemicals [linoleic acid (18:2), α-linolenic acid (18:3α), γ-linolenic acid (18:3γ), dihomo-γ-linolenic acid (20:3), arachidonic acid (20:4), eicosapentaenoic acid (20:5), and docosahexaenoic acid (22:6)].

Herndon J.L., Peters R.E., Hofer R.N., Simmons T.B., Symes S.J, & Giles D.K. (2020). Exogenous polyunsaturated fatty acids (PUFAs) promote changes in growth, phospholipid composition, membrane permeability and virulence phenotypes in Escherichia coli. BMC Microbiology, 20, 305.

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Antioxidant and Cytotoxicity Evaluation

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All chemicals, reagents and kits that were used in this study were purchased according to the following description: Fluorescent probe 2,7-dichlorofluorescein diacetate (DCF-DA), 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium (MTT), Triton X-100, FBS and rhodamine-123, 1,1-diphenyl-2-picryl-hydrazyl (DPPH), β-carotene, doxorubicin and caspase-3 detection kit from Sigma, Aldrich (St Louis, MO, USA); DMEM-F12 from Gibco (Gibco, Grand Island, NY, USA); super oxide dismutase assay kit from Cayman; gallic acid, linoleic acid, sodium carbonate, ferrous chloride, dimethyl sulfoxide (DMSO), chloroform, EDTA, Tween® 40, Folin-Ciocalteu’s phenol reagent, butylatedhydroxyltoluene (BHT), LiChroprep® RP-18 (15-25 µm) from Merck; ascorbic acid from VWR; ferrozine iron reagent from Acros; organics and all the solvents used for extraction and fractionation from Scharlau (Sentmenate, Spain).

Mojarrab M., Nasseri S., Hosseinzadeh L, & Farahani F. (2016). Evaluation of antioxidant and cytoprotective activities of Artemisia ciniformis extracts on PC12 cells. Iranian Journal of Basic Medical Sciences, 19(4), 430-438.

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Fatty Acids Modulation of Neuronal Activity

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All chemical compounds were purchased from Wako unless otherwise stated. DHA (cis-4,7,10,13,16,19-docosahexaenoic acid: DHA), DHA-Me, ARA, EPA (cis-5,8,11,14,17-eicosapentaenoic acid), DHK, indomethacin, and Triton X-100 were purchased from Sigma. DHA-CoA and CoA were purchased from Avanti. Oleic acid, linOleic acid, ALA, cis-11,14-eicosadienoic acid, cis-11,14,17-eicosatrienoic acid, cis-13,16,19-docosatrienoic acid (DTriA), cis-7,10,13,16-docosatetraenoic acid (DTetA), cis-7,10,13,16,19-docosapentaenoic acid (DPA), and N-(2-hydroxyethyl)-4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenamide (DHA-EA) were purchased from Cayman Chemical. L-Glu stock solution (20 mM) in purified water (DIRECT-Q; Millipore) was diluted to the required final concentration with ND96 just before application. Stock solutions of fatty acids (100 mM) in ethanol was diluted to the required final concentration with ND96 on demand and used within 2 h to avoid precipitation. We confirmed that the vehicle had no effect prior to each experiment.

Takahashi K., Chen L., Sayama M., Wu M., Hayashi M.K., Irie T., Ohwada T, & Sato K. (2022). Leucine 434 is essential for docosahexaenoic acid–induced augmentation of L-glutamate transporter current. The Journal of Biological Chemistry, 299(1), 102793.

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Lipid Metabolism in HepG2 Hepatocellular Carcinoma

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Human liver hepatocellular carcinoma cell line (HepG2 cells) was
purchased from the American Type Culture Collection (ATCC; Manassas, VA). Cells
were cultured in EMEM (ATCC) supplemented with 10% fetal bovine serum
(Life Technologies; Carlsbad, CA) in 25 cm² polystyrene flasks placed
in a Hera Cell 5% CO₂ 37°C incubator (ThermoFisher
Scientific; Waltham, MA). Routine passage was carried out every 2 or 3 days.
About 2 × 10⁵ HepG2 cells were seeded per 6-cm plate
and serum-starved for 24 h before the following treatments: 50, 100 or 200
μg/ml human LDL-cholesterol (LDL-C) (Kalen Biomedical; Montgomery Vlg,
MD); 10, 30 or 90 μM simvastatin (Sigma; St Louis, MO); 100 nM insulin
(Sigma); 30 nM glucose (Sigma); 5 μM Bay-11 (Cayman; Ann Arbor, MI); 200
μM fatty acids conjugated with 0.2% BSA (30 mM) in 1%
ethanol. We treated HepG2 cells for 24 h with palmitic acid (Sigma), palmitoleic
acid, stearic acid, oleic acid, linoleic acid, linolenic acid, and
eicosapentaenoic acid (Cayman).

Alvarez M.L., Khosroheidari M., Eddy E, & Done S.C. (2015). MicroRNA-27a decreases the level and efficiency of the LDL receptor and contributes to the dysregulation of cholesterol homeostasis. Atherosclerosis, 242(2), 595-604.

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Fatty Acid Metabolism in Klebsiella pneumoniae

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Klebsiella pneumoniae ATCC13883 was used in this study. CM9 and G56 minimal media (0.4% Glucose, 0.4% casamino acids (Fisher BioReagents), supplemented with 150 mmol/L NaCl) were used for growth of bacteria in experiments, except for sole carbon source experiments which were performed in M9 minimal media lacking glucose. All experiments were performed at 37°C. Fatty acids used in this study were purchased from Cayman Chemicals [linoleic acid (18:2), α‐linolenic acid (18:3α), γ‐linolenic acid (18:3γ), dihomo‐γ‐linolenic acid (20:3), arachidonic acid (20:4), eicosapentaenoic acid (20:5), and docosahexaenoic acid (22:6)] and administered at a concentration of 300 μmol/L for each experiment, except for sole carbon source where they were administered at 1 mmol/L.

Hobby C.R., Herndon J.L., Morrow C.A., Peters R.E., Symes S.J, & Giles D.K. (2018). Exogenous fatty acids alter phospholipid composition, membrane permeability, capacity for biofilm formation, and antimicrobial peptide susceptibility in Klebsiella pneumoniae. MicrobiologyOpen, 8(2), e00635.

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Fatty Acid Modulation of Dendritic Cells

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Fatty acids (FAs) were purchased from Cayman and diluted in ethanol for all FAs [Palmitic acid (PA, C16:0), stearic acid(C18:0), palmit oleic acid (C16:1), oleic acid (OA, C18:1n-9), linoleic acid (LA, C18:2n6c), cis-8,11,14-eicosatrienoic acid (C20:3n6), cis-11,14,17- eicosatrienoic acid (C20:3n3), erucic acid (C22:1n9), eicosapentaenoic acid (EPA, C20:5n3), nervonic acid (C24:1n9), docosahexenoic acid (DHA, C22:6n3) and arachidonic acid (AA, C20:4n-6)] . The FAs-free medium was contained RPMI-1640 basic medium, 1×ITS medium supplement (Sigma) and 20 ng/ml GM-CSF without FAs supplement. Before addition to the culture medium, all FAs were conjugated to bovine serum albumin (BSA, fatty acid-free, Sigma) at the indicated concentration with FAs-free medium containing 1% BSA. The fatty acids were incubated with 1% BSA for 2 h before adding to DC. The concentration of saturated, monounsaturated, and polyunsaturated fatty acids in ITS medium was 20 µM. Half of the medium was discarded and replaced with fresh DC medium every other day. On day 6, DC were infected with the virus for 24 h and then analyzed by FACS.

Zhao C., Zhou J., Meng Y., Shi N., Wang X., Zhou M., Li G, & Yang Y. (2020). DHA Sensor GPR120 in Host Defense Exhibits the Dual Characteristics of Regulating Dendritic Cell Function and Skewing the Balance of Th17/Tregs. International Journal of Biological Sciences, 16(3), 374-387.

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Ferroptosis Induction and Inhibition Assays

Cited 2 times

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The following compounds were obtained from Sigma-Aldrich: ML210 (SML0521, purity ≥ 98%, used at wide concentration range), 1S, 3R-RSL3 (RSL3, SML2234, purity ≥ 98%, used at wide concentration range), ferrostatin-1 (Fer-1, SML0583, purity ≥ 95%, used at 5 μM), erastin (E7781, purity ≥ 98%, used at wide concentration range) and L-buthionine-[S,R]-sulfoximine (BSO, B2515, purity ≥ 97%, used at wide concentration range). Free fatty acids, including oleic acid (OA, C18:1), linoleic acid (LA, C18:2), a-linolenic acid (ALA, C18:3), arachidonic acid (AA, C20:4), eicosapentaenoic acid (EPA, C20:5), docosapentaenoic acid (DPA, C22:5), and docosahexaenoic acid (DHA, C22:6) were purchased from Cayman Chemicals and conjugated with fatty-acid free BSA (Sigma-Aldrich) using previously described protocols⁵¹, and treated cells at 20 μM for 3 days in the viability assays. The following compounds were prepared according to known literature procedures: FINO2^{36 (link)} and FIN56^{34 (link)}. Alkyne analogs of ML210 and RSL3 (ML210-yne and RSL3-yne, respectively) were synthesized as previously described^{15 (link)}.

Zou Y., Li H., Graham E.T., Deik A.A., Eaton J.K., Wang W., Sandoval-Gomez G., Clish C.B., Doench J.G, & Schreiber S.L. (2020). Cytochrome P450 oxidoreductase contributes to phospholipid peroxidation in ferroptosis. Nature chemical biology, 16(3), 302-309.

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Expansion and Stimulation of ILC2s from Murine Models

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Wt and Pla2g5-null mice received four doses of 25ug of Alternaria in 20ul of PBS i.n. on day 0, 3, 6 and 9 and euthanized 18h later in order to expand ILC2s prior to FACs sorting. Sorting of ILC2s (CD45⁺ Lin− (CD3, CD19, Ly6g, CD11c, CD11b, Nk1.1, FcεR1⁻), Thy1.2⁺) was performed using a FACSDiva 8.0.1 cell sorter (BD Bioscience). Purified CD45⁺ lin-Thy1.2⁺ cells (>98%) were rested for 40h with 10ng/mL rIL-2 and rIL-7 (R&D Systems, Minneapolis, MN) in 96 well around bottom plates (20000 cells per well). Prior to stimulation, the medium was changed to fresh medium. ILC2s were cultured with 30ng/mL rIL-33 (R&D Systems), 200 μM Lin Oleic Acid (Cayman Chemical) or 200 μM Oleic Acid (Cayman Chemical)^{22 (link)} or all together for 8h. For intracellular cytokine staining, 1 μl/mL of Golgi Plug (BD Bioscience) was added to ILC2s 6h before collection for FACs analysis.

Yamaguchi M., Samuchiwal S.K., Quehenberger O., Boyce J.A, & Balestrieri B. (2017). Macrophages regulate lung ILC2 activation via Pla2g5-dependent mechanisms. Mucosal immunology, 11(3), 615-626.

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