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Dimethyl fumarate

Manufactured by Merck Group
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Dimethyl fumarate is a laboratory compound used in various research applications. It is a white crystalline solid with the chemical formula C6H8O4. The compound serves as a precursor and intermediate in organic synthesis.

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Lab products found in correlation

Dimethyl succinate, by Merck Group (6 mentions) Succinate, by Merck Group (5 mentions) Sulforaphane, by Merck Group (3 mentions) Dimethyl alpha ketoglutarate, by Merck Group (3 mentions) Propidium iodide, by Merck Group (3 mentions) Dimethyl 2 oxoglutarate, by Merck Group (3 mentions) Dimethyl sulfoxide (dmso), by Merck Group (3 mentions) Polytetrafluoroethylene ptfe, by Merck Group (2 mentions) Strat m, by Merck Group (2 mentions) Polysorbate 80, by Merck Group (2 mentions) Glutamine, by Thermo Fisher Scientific (2 mentions) Ml385, by Merck Group (2 mentions) Antimycin a, by Merck Group (2 mentions) Diethyl fumarate, by Merck Group (2 mentions) Monoethyl fumarate, by Merck Group (2 mentions) Monoethyl succinate, by Merck Group (2 mentions) Cycloheximide (chx), by Merck Group (2 mentions) Rpmi 1640 medium, by Lonza (2 mentions) Fetal bovine serum (fbs), by Thermo Fisher Scientific (2 mentions) Methanol, by Thermo Fisher Scientific (2 mentions)

Close spelling variants of this product

Dimethyl fumarate (DMF) (18 citations)

42 protocols using dimethyl fumarate

1

Preparation and Characterization of DMF Formulations

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Dimethyl fumarate (dimethyl (E)-but-2-enedioate, DMF), polysorbate 80 (polyoxyethylene sorbitan monooleate, tween 80, T80), and xanthan gum (x-gum) were purchased from Merck Life Science S.r.l. (Milan, Italy). The soybean lecithin (PC) (90% phosphatidylcholine) was Epikuron 200 from Lucas Meyer (Hamburg, Germany). Polytetrafluoroethylene (PTFE, Whatman®) (pore size 200 nm, thickness 155.6 μm), and Strat-M® (thickness 316.9 μm) [40 (link)] membranes were purchased from Merck Life Science S.r.l. (Milan, Italy). Solvents were of HPLC grade, and all other chemicals were of analytical grade.
Ferrara F., Benedusi M., Cervellati F., Sguizzato M., Montesi L., Bondi A., Drechsler M., Pula W., Valacchi G, & Esposito E. (2022). Dimethyl Fumarate-Loaded Transethosomes: A Formulative Study and Preliminary Ex Vivo and In Vivo Evaluation. International Journal of Molecular Sciences, 23(15), 8756.
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2

Preparation of Dimethyl Fumarate Formulation

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Dimethyl fumarate (dimethyl (E)-but-2-enedioate, DMF), poloxamer 407 (p-407), xanthan gum (x-gum), blue Coomassie, and deuterated water (D2O) were purchased from Merck Life Science S.r.l. (Milan, Italy). The soybean lecithin (PC) (90% phosphatidylcholine) was Epikuron 200 from Lucas Meyer (Hamburg, Germany). Polytetrafluoroethylene (PTFE, Whatman®) (pore size 200 nm), and STRAT-M® membranes were purchased from Merck Life Science S.r.l. (Milan, Italy). Solvents were of HPLC grade, and all other chemicals were of analytical grade.
Sicurella M., Pula W., Musiał K., Cieślik-Boczula K., Sguizzato M., Bondi A., Drechsler M., Montesi L., Esposito E, & Marconi P. (2023). Ethosomal Gel for Topical Administration of Dimethyl Fumarate in the Treatment of HSV-1 Infections. International Journal of Molecular Sciences, 24(4), 4133.
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3

Wound Healing Assay with Poly I:C

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At confluence, scrape damage was applied using a P200 yellow pipette tip to produce a single wound 0.8 mm wide. Cell layers were washed and covered with 250 µl fresh warm medium containing 1-20 µg/ml poly I:C (Sigma) [14, 15] , in the absence and presence of 1 µM WAY 170523 (Tocris Bioscience) [16, 17] , 1-50 µM dimethyl fumarate (Sigma) [18] or 0.01-1 µM bosentan (Sigma) [19] , at the concentrations indicated in the legends and on the
Howell C., Smith J.R, & Shute J.K. (2018). Targeting matrix metalloproteinase-13 in bronchial epithelial repair. Clinical and experimental allergy : journal of the British Society for Allergy and Clinical Immunology, 48(9).
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4

Dimethyl Fumarate and Cell Signaling

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Dimethyl fumarate was obtained from Sigma-Aldrich company (#50744, Sigma-Aldrich, St. Louis, USA). Tween-20 (#P1379), LPS from Escherichia coli 0111:B4 (#L2690), Nrf-2 agonist Sulforaphane (#S6317) and ROS inhibitor NAC (#1009005) were also from Sigma.
Zhou K., Xie M., Yi S., Tang Y., Luo H., Xiao Q., Xiao J, & Li Y. (2021). Dimethyl fumarate ameliorates endotoxin-induced acute kidney injury against macrophage oxidative stress. Renal Failure, 43(1), 1229-1239.
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5

Dimethyl Fumarate Administration in Animals

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Beginning on the 3 rd DPI, the animals received dimethyl fumarate (Sigma-Aldrich), twice a day at a dose of 15 mg/kg, intragastrically using a gauge-pointed needle, up to the day of animal euthanasia. DMF was suspended in 200 µl of vehicle (0.8% methylcellulose, Sigma-Aldrich). The control animals received the vehicle alone.
Kasarełło K., Jesion A., Tyszkowska K., Matusik K., Czarzasta K., Wrzesień R, & Cudnoch-Jedrzejewska A. (2017). Effect of dimethyl fumarate on heme oxygenase-1 expression in experimental allergic encephalomyelitis in rats. Folia neuropathologica, 55(4).
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6

Intrasplenically Injected PLC8024 Cells in Nude Mice

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PLC8024 derivative cells (PDSS2‐Del2 or vector control, 2 × 106) were injected intrasplenically into nude mice as described above. Dimethyl fumarate and methyl cellulose were purchased from Sigma‐Aldrich. At 12 days post surgery, mice from each group were randomized into either vehicle control or DMF groups. Mice were gavaged daily with vehicle (0.8% methyl cellulose) or DMF (30 mg/kg suspended in 0.8% methyl cellulose) [15]. At the end of the experiments, the animals were euthanized and experiments were performed as described above.
Zeng T., Tang Z., Liang L., Suo D., Li L., Li J., Yuan Y., Guan X, & Li Y. (2020). PDSS2‐Del2, a new variant of PDSS2, promotes tumor cell metastasis and angiogenesis in hepatocellular carcinoma via activating NF‐κB. Molecular Oncology, 14(12), 3184-3197.
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7

Rescue Metabolites Enhance Cell Survival

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Cells were seeded in 384-well plates at concentration of 1000–2000 cells/well and allowed to adhere overnight. The next morning growth medium was replaced by fresh growth medium (RPMI-1640+ 10% HI-FBS) containing the following rescue intermediates: nicotinamide mononucleotide (NMN, 25 μM), nicotinic acid (NA, 25 μM), adenine (100 μM, Sigma-Aldrich), uridine (100 μM, Sigma-Aldrich), nucleoside mix (1x, EmbryoMax Nucleosides), dimethyl-alpha-ketoglutarate (50 μM, Sigma-Aldrich), alpha-ketoglutarate (50 μM, Sigma-Aldrich), dimethyl-succinate (50 μM, Sigma-Aldrich), succinate (50 μM, Sigma-Aldrich), dimethyl-fumarate (50 μM, Sigma-Aldrich), fumarate (50 μM, Sigma-Aldrich), dimethyl-malate (50 μM, Sigma-Aldrich), malate (50 μM, Sigma-Aldrich), glutamine (2mM, Gibco) and sodium pyruvate (1mM, Gibco), 3-phosphoglyceric acid (50 μM, 3-PGA, Sigma-Aldrich), N-acetylcysteine (10mM, NAC, Sigma-Aldrich). After replacing the medium with fresh growth medium in presence or absence of rescue metabolites, FK866 and BH3 mimetic drugs were added using the HP D300e Digital Dispenser (Hewlett-Packard Development Company). Cells were treated for 72 h before annexin-V-Hoechst staining was performed as described under measurements of cell death.
Daniels V.W., Zoeller J.J., van Gastel N., McQueeney K.E., Parvin S., Potter D.S., Fell G.G., Ferreira V.G., Yilma B., Gupta R., Spetz J., Bhola P.D., Endress J.E., Harris I.S., Carrilho E., Sarosiek K.A., Scadden D.T., Brugge J.S, & Letai A. (2021). Metabolic perturbations sensitize triple-negative breast cancers to apoptosis induced by BH3 mimetics. Science signaling, 14(686), eabc7405.
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8

Evaluating Cytotoxic Compound Effects

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Dimethylfumarate, Triton X 100, chloroquine, propidium iodide and staurosporine were obtained from Sigma-Aldrich (Hamburg, Germany). Oxaliplatin was purchased from Abcam (Cambridge, UK) rapamycin from Merck’s Calbiochem (Darmstadt, Germany) and RNAse from Qiagen (Hilden, Germany).
Kaluzki I., Hailemariam-Jahn T., Doll M., Kaufmann R., Balermpas P., Zöller N., Kippenberger S, & Meissner M. (2019). Dimethylfumarate Inhibits Colorectal Carcinoma Cell Proliferation: Evidence for Cell Cycle Arrest, Apoptosis and Autophagy. Cells, 8(11), 1329.
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9

Modulation of Lymphocyte Oxidative Stress

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Lymphocytes were pretreated for 18 hours with Auranofin (AUF, with the concentration 1 µg/mL for NK cells and 0,5 µg/mL for TIL and CAR T cells, if not indicated differently), DL-sulforaphane (SUL) or dimethyl fumarate (DMF) (all Sigma-Aldrich) at indicated concentrations. As all compounds were reconstituted in DMSO, control NK cells were pretreated with DMSO with an equivalent volume to the highest compound concentration. 100 U/mL Catalase (Sigma-Aldrich) were added to control lymphocytes just before exposure to oxidative stress. For N-acetylcysteine (NAC, Invitrogen) treatment, DMSO pretreated cells were incubated for 1 hour with 5 or 10 mM NAC prior to H2O2 treatment. For Nrf2 inhibition, NK cells were pretreated with 50 µM ML-385 (Sigma-Aldrich) in parallel to AUF. For H2O2 treatment, lymphocytes were washed and resuspended to 1×106 cells/mL in RPMI containing the indicated H2O2 (Sigma-Aldrich) concentration for 1 hour at 37°C 5% CO2. Cells were washed with medium and then used for further experiments.
Renken S., Nakajima T., Magalhaes I., Mattsson J., Lundqvist A., Arnér E.S., Kiessling R, & Wickström S.L. (2022). Targeting of Nrf2 improves antitumoral responses by human NK cells, TIL and CAR T cells during oxidative stress. Journal for Immunotherapy of Cancer, 10(6), e004458.
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10

Mitochondrial Function Assays

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Lipopolysaccharide, polyinosinic:polycytidylic acid (polyI:C), CpG ODN were purchased from Invivogen. 3-nitropropionic acid (NPA), succinate, succinate hexahydrate, glutamate, malate disodium-salt, fumarate, dimethyl-fumarate, dimethyl succinate, dimethyl malonate (DM), itaconic acid, thenoyltrifluoroacetone (TTFA), carbonilcyanide p-triflouromethoxyphenylhydrazone (FCCP), CCCP, oligomycin, rotenone, antimycin A, ubiquinone, sn-glycerol 3-phosphate, oxidized cytochrome c, adenosine tri-phosphate (ATP), adenosine di-phosphate (ADP), phenazine methosulfate (PMS) and digitonin were all from Sigma. Luciferin and luciferase were from Promega and Roche, respectively.
Garaude J., Acín-Pérez R., Martínez-Cano S., Enamorado M., Ugolini M., Nistal-Villán E., Hervás-Stubbs S., Pelegrín P., Sander L.E., Enríquez J.A, & Sancho D. (2016). Mitochondrial respiratory chain adaptations in macrophages contribute to antibacterial host defence. Nature immunology, 17(9), 1037-1045.
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