Dimethyl malate

Manufactured by Merck Group

Sourced in United States

Dimethyl malate is a chemical compound commonly used as a laboratory reagent. It serves as a precursor in organic synthesis reactions. The compound has the chemical formula C₄H₈O₄.

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Malate (93 citations)

7 protocols using dimethyl malate

Cell proliferation under metabolite and oxygen conditions

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Prior to the assay, cells were grown without selective drugs for 48 hr under standard culture conditions. Cells were then plated under standard culture conditions and at the indicated densities. Twenty-four hours after plating, cells were treated with the indicated concentrations of dimethyl alpha-ketoglutarate (Sigma), dimethyl malate (Sigma), or L-alanine (Sigma) and cultured under the indicated oxygen conditions. Cells were counted every 24 hr, and counts were normalized to cell number at initial time of treatment; i.e., 24 hr after plating the cells.

Smith B., Schafer X.L., Ambeskovic A., Spencer C.M., Land H, & Munger J. (2016). Addiction to Coupling of the Warburg Effect with Glutamine Catabolism in Cancer Cells. Cell reports, 17(3), 821-836.

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Cell proliferation under metabolite and oxygen conditions

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Smith B., Schafer X.L., Ambeskovic A., Spencer C.M., Land H, & Munger J. (2016). Addiction to Coupling of the Warburg Effect with Glutamine Catabolism in Cancer Cells. Cell reports, 17(3), 821-836.

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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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Cell Line Cultivation and Characterization

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A549, MiaPaCa2, DAN-G, SW1990, MPanc96, SUIT2-013-NQO1+/−, HPAFII, ASPC1, PL45, H596, Hs766T, BxPC3, MBA-MD-231+/−, and MCF7 cell lines were obtained from ATCC, tested for mycoplasma contamination and grown in complete Dulbecco's Modified Eagle's Medium (DMEM) with 10 % fetal bovine serum (FBS). H2122 and H661 cell lines were a generous gift from Dr. John Minna at UTSW. SUIT2-013 and MDA-MB-231 NQO1 deficient and proficient cell lines were generated as previously described [24 (link)]. DMEM (Glutamine free) was purchased from Sigma-Aldrich. FBS was purchased from Fischer Scientific. Glutamine, GSH-reduced ethyl ester, OAA, and dimethyl malate were purchased from Sigma. IMR90 cells lines were grown in MEM with 10 % FBS. All cells were incubated at 37° with 5 % CO₂.

Chakrabarti G., Moore Z.R., Luo X., Ilcheva M., Ali A., Padanad M., Zhou Y., Xie Y., Burma S., Scaglioni P.P., Cantley L.C., DeBerardinis R.J., Kimmelman A.C., Lyssiotis C.A, & Boothman D.A. (2015). Targeting glutamine metabolism sensitizes pancreatic cancer to PARP-driven metabolic catastrophe induced by ß-lapachone. Cancer & Metabolism, 3, 12.

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Metabolic Tracing of Carbon Sources

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PF-05175157 was provided by ChemicalBook, and lovastatin was obtained from MedChem Express. [U-¹³C]-glucose, [1,6-¹³C]-glucose, [3-²H]-glucose, [1-²H]-glucose, [6,6-²H]-glucose, and [U-¹³C]-glutamine were purchased from Cambridge Isotope Laboratories. Antimycin A, amino acids, pyruvate, oxalo acetate, α-ketoglutarate, citrate, malate, acetate, dimethyl α-ketoglutarate, triethyl citrate, dimethyl malate, and all general chemicals were obtained from Sigma unless otherwise described.

Liu M., Wang Y., Yang C., Ruan Y., Bai C., Chu Q., Cui Y., Chen C., Ying G, & Li B. (2020). Inhibiting both proline biosynthesis and lipogenesis synergistically suppresses tumor growth. The Journal of Experimental Medicine, 217(3), e20191226.

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Metabolic Enzyme Assay Protocol

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Reagents including the following: ADP (Sigma, A5285, St. Louis, USA), NAD (Sigma, N0632), NADH (Sigma, N8129), malate acid (Sigma, 02288), α-ketoglutaric acid (Sigma, 75890), dimethyl malate (Sigma, 374318), and dimethyl 2-oxoglutarate (Sigma, 349631). Enzymes including the following: malic dehydrogenase (Sigma, M2634), L-glutamic dehydrogenase (Sigma, G2501), and citrate synthase (Roche, 2168342). Antibodies including the following: ME2 (Abcam, 139686, Cambridge, USA), HIF-1α (Abcam, 16066), and β-actin (HUABIO, M1210-2, Hangzhou, China).

You D., Du D., Zhao X., Li X., Ying M, & Hu X. (2021). Mitochondrial malic enzyme 2 promotes breast cancer metastasis via stabilizing HIF-1α under hypoxia. Chinese Journal of Cancer Research, 33(3), 308-322.

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Metabolic Enzyme Activity Assay

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Reagents including the following: ADP (Sigma, A5285); NAD (Sigma, N0632); NADH (Sigma, N8129); malate acid (Sigma, 02288); α-ketoglutaric acid (Sigma, 75890); dimethyl malate (Sigma, 374318); dimethyl 2-oxoglutarate (Sigma, 349631). Enzymes including the following: malic dehydrogenase (Sigma, M2634); L-glutamic dehydrogenase (Sigma, G2501); citrate synthase (Roche, 2168342).
Antibodies including the following: ME2 (Abcam, 139686), HIF-1α (Abcam, 16066), β-actin (HUABIO, M1210-2).

You D., Du D., Zhao X., Li X., Ying M., & Hu X. (2021). Mitochondrial Malic Enzyme 2 Promotes Breast Cancer Metastasis via Stabilizing HIF-1α Under Hypoxia.

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