Monomethyl fumarate

Manufactured by Merck Group

Sourced in United States

Monomethyl fumarate is a laboratory reagent used in various applications for scientific research and analysis. It serves as a chemical building block and intermediate in organic synthesis. The core function of monomethyl fumarate is to provide a versatile platform for further chemical transformations and investigations, without interpretation or extrapolation on its intended use.

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8 protocols using monomethyl fumarate

Fumarate and Maleate Compound Preparation

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Dimethyl fumarate (DMF) (Sigma-Aldrich) was resuspended in 100% DMSO to 100mM and further diluted at indicated dilutions before use in all in-vitro experiments. For in-vivo experiments, DMF was dissolved in 100% DMSO or 0.8% methyl cellulose at 50mg/mL diluted at indicated dilutions before use.
Monomethyl fumarate (MMF), Diethyl fumarate (DEF), Dimethyl maleate (DMM), Diethyl maleate (DEM) and Fumaric acid (FA) were all obtained from (Sigma-Aldrich) and all resuspended in 100% DMSO to 100mM and further diluted at indicated dilutions before use in all in-vitro experiments.

Alwithenani A., Taha Z., Thomson M., Chen A., Wong B., Arulanandam R, & Diallo J.S. (2023). Unlocking the potential of dimethyl fumarate: enhancing oncolytic HSV-1 efficacy for wider cancer applications. Frontiers in Immunology, 14, 1332929.

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Monocyte Training and Restimulation Assay

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100 μL cells were added to flat bottom 96-well plates. After washing with warm PBS, monocytes were incubated with culture medium only as a negative control or 5 μg/mL of β-glucan, (β-1,3-(D)-glucan, kindly provided by Professor David Williams), 100 μM mono methyl-fumarate, or dimethyl-2-oxoglutarate (Sigma) for 24 hr (in 10% pooled human serum). Cells were washed once with 200 μL warm PBS and incubated for 5 days in culture medium with 10% serum and medium was changed once. Cells were restimulated with 200 μL RPMI, Escherichia coli LPS (serotype 055:B5, Sigma-Aldrich, 10 ng/mL), or Pam3Cys (EMC Microcollections, L2000, 10 μg/mL). After 24 hr, supernatants were collected and stored at −20°C (see Figure S1). In some experiments, cells were preincubated (before β-glucan training) for 1 hr with 10 nM rapamycin (Sigma), 50 μM BPTES (Sigma), 2 μg/mL Ceruline (Sigma), 100 μM 6-aminonicotinamide (Sigma), and 20 μM fluvastatin sodium hydrate (Sigma). Concentrations were selected as being the highest non-cytotoxic concentrations.

Arts R.J., Novakovic B., ter Horst R., Carvalho A., Bekkering S., Lachmandas E., Rodrigues F., Silvestre R., Cheng S.C., Wang S.Y., Habibi E., Gonçalves L.G., Mesquita I., Cunha C., van Laarhoven A., van de Veerdonk F.L., Williams D.L., van der Meer J.W., Logie C., O’Neill L.A., Dinarello C.A., Riksen N.P., van Crevel R., Clish C., Notebaart R.A., Joosten L.A., Stunnenberg H.G., Xavier R.J, & Netea M.G. (2016). Glutaminolysis and Fumarate Accumulation Integrate Immunometabolic and Epigenetic Programs in Trained Immunity. Cell metabolism, 24(6), 807-819.

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Glutathione Levels in Oligodendrocytes

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Cells were plated at 25,000 per well in a 96-well plate (Greiner Bio-One) and allowed to mature for 7 days in SATO medium supplemented with 0.5% FCS. Following 24 h treatment with sulforaphane (5 μM), monomethyl fumarate (Sigma-Aldrich) (90 µM), Protandim (LifeVantage) (60 µg/mL), OLs were washed with PBS, and total glutathione was measured in a white 96-wells plate (Greiner Bio-One), using GSH-Glo, according to manufacturer’s instructions (Promega, Madison, WI, USA). Luminescence was measured with a FLUOstar Galaxy fluorometer.

Lim J.L., van der Pol S.M., Baron W., McCord J.M., de Vries H.E, & van Horssen J. (2016). Protandim Protects Oligodendrocytes against an Oxidative Insult. Antioxidants, 5(3), 30.

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Fumarate and Maleate Compound Assays

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Assays were performed with the following reagents: dimethyl fumarate (DMF; 242926; Sigma Aldrich), monomethyl fumarate (MMF; 651419; Sigma Aldrich), dimethyl succinate (DMS; W239607; Sigma Aldrich), and buthionine sulfoximine (BSO; 14484; Cayman Chemical). The Nrf2 inhibitor ML385 (SML1833, Sigma Aldrich), Dimethyl maleate (238198; Sigma Aldrich), Diethyl fumarate (D95654: Sigma Alrich), Diethyl maleate (D97703; Sigma Aldrich), Diisobutyl fumarate (7283–69-4; TCI Chemicals) and Diisopropyl fumarate (7283–70-7; TCI Chemicals).

Zaro B.W., Vinogradova E.V., Lazar D.C., Blewett M.M., Suciu R.M., Takaya J., Studer S., de la Torre J.C., Casanova J.L., Cravatt B.F, & Teijaro J.R. (2019). Dimethyl fumarate disrupts human innate immune signaling by targeting the IRAK4-MYD88 complex. Journal of immunology (Baltimore, Md. : 1950), 202(9), 2737-2746.

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Irradiation and Fumarate Exposure

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All experiments involving irradiation used the Xstrahl at 195 kV and 10 mA following the manufacturer’s instructions to achieve the desired level of irradiation in Grays. For addition of exogenous fumarate, 400 µM monomethyl-fumarate (Sigma) was added to the cell culture media immediately prior to irradiation.

Johnson T.I., Costa A.S., Ferguson A.N, & Frezza C. (2018). Fumarate hydratase loss promotes mitotic entry in the presence of DNA damage after ionising radiation. Cell Death & Disease, 9(9), 913.

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Cell Culture Conditions and Reagents for Cellular Assays

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HeLa, 293T, and COS7 cells were obtained from ATCC. MEFs were supplied by C. López-Otín (University of Oviedo, Oviedo, Spain). All cell lines were cultured in DMEM plus l-glutamine and pyruvate with 10% inactivated FBS and penicillin and streptomycin (Thermo Fisher Scientific) and maintained at 37°C and 5% CO₂. Reagents were obtained from the following sources: doxycycline hyclate (D9891; Sigma-Aldrich), actinonin (A6671; Sigma-Aldrich), FCCP (C2920; Sigma-Aldrich), MB (10–1472-5; Tebu.bio), Rotenone (R8875; Sigma-Aldrich), antimycin A (A8674; Sigma-Aldrich), oligomycin (495455; EMD Millipore), tunicamycin (T7765; Sigma-Aldrich), ISRIB (SML0843; Sigma-Aldrich), monomethyl fumarate (651419; Sigma-Aldrich), Mdivi-1 (M0199; Sigma-Aldrich), and paraquat dichloride hydrate (36541; Sigma-Aldrich). pCAGGS vectors containing WT (pCAGGS-OTC) and mutant (pCAGGS-ΔOTC) forms of ornithine-transcarbamylase were a gift from N. Hoogenraad (La Trobe University, Melbourne, Australia). Cells were treated during 6 h or 24 h with 30 µg/ml doxycycline, 50 µM actinonin, 10 µM FCCP, or 50 µM MB. Induction of ER stress was performed by treating the cells with 2.5 µg/ml (6 h) or 1 µg/ml (24 h) tunicamycin. ISRIB was used at 500 nM, monomethyl fumarate at 2.5 mM, Mdivi-1 at 50 µM, and paraquat at 400 µM.

Quirós P.M., Prado M.A., Zamboni N., D’Amico D., Williams R.W., Finley D., Gygi S.P, & Auwerx J. (2017). Multi-omics analysis identifies ATF4 as a key regulator of the mitochondrial stress response in mammals. The Journal of Cell Biology, 216(7), 2027-2045.

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Neuroprotective Mechanisms of Dimethyl Fumarate

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Dimethyl fumarate (DMF) and mono-methyl fumarate (MMF) were purchased from Sigma-Aldrich. Poly-d-lysine, DMSO and Glutamax were purchased from Sigma. HBSS, DMEM, fetal calf serum, Neurobasal medium, B-27 supplement were purchased from Invitrogen. LIVE/DEAD viability/cytotoxicity kit was purchased from Molecular Probes. The cytotoxicity detection kit plus (lactate dehydrogenase (LDH)) was purchased from Roche. The following primary antibodies were used in these experiments: rabbit anti-Nrf2 (1:200, Santa Cruz Biotechnology), rabbit anti-HO-1 (1:4000, Enzo Life Sciences), rabbit anti-β-tubulin (1:1000, Cell Signaling Technology), mouse anti-rat CD-3 (1:25, BD Biosciences), rabbit anti-myeloperoxidase (MPO) (1:300, DAKO), mouse anti-CD-68 (1:100, Abcam), and rabbit anti-iNOS (1:80, Abcam).

Lin R., Cai J., Kostuk E.W., Rosenwasser R, & Iacovitti L. (2016). Fumarate modulates the immune/inflammatory response and rescues nerve cells and neurological function after stroke in rats. Journal of Neuroinflammation, 13, 269.

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Preparation of Methylglyoxal and Fumarate Compounds

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Methylglyoxal (~40%) was obtained from Sigma-Aldrich (M0252). It was further dissolved in 0.9% normal saline or culturing media for in vivo and in vitro experiments, respectively. Diroximel fumarate (DRF) (Biogen) was dissolved in 10 mM citric acid / 0.5% carboxymethylcellulose / 0.02% Tween80 adjusted to pH 5.0. For in vitro studies, monomethyl fumarate (MMF) (Sigma-Aldrich # 651419) was initially dissolved to 500 mM in 100% DMSO. Subsequent dilutions of MMF were performed in culturing media.

Yousuf M.S., Moreno M.M., Li J., He L., Royer D., Zhang J., Woodall B.J., Grace P.M, & Price T.J. (2023). Diroximel fumarate acts through Nrf2 to attenuate methylglyoxal-induced nociception in mice and decreases ISR activation in DRG neurons. bioRxiv.

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