Oxaloacetic acid

Manufactured by Merck Group

Sourced in United States

Oxaloacetic acid is a dicarboxylic acid that plays a crucial role in the tricarboxylic acid (TCA) cycle, also known as the Krebs cycle. It is an important intermediate in cellular metabolism, serving as a key component in the oxidation of carbohydrates, fats, and proteins to generate energy in the form of ATP. Oxaloacetic acid is used in various laboratory and research applications.

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Lab products found in correlation

Acetyl coa, by Merck Group (7 mentions) Adenosine triphosphate (atp), by Merck Group (5 mentions) L malic acid, by Merck Group (4 mentions) Pyruvic acid, by Merck Group (4 mentions) Malic acid, by Merck Group (4 mentions) Sodium pyruvate, by Merck Group (3 mentions) Antimycin a, by Merck Group (3 mentions) Tridecanoic acid, by Merck Group (3 mentions) Amitriptyline, by MP Biomedicals (3 mentions) Succinic acid, by MP Biomedicals (3 mentions) Pyruvic acid, by MP Biomedicals (3 mentions) Alpha ketoglutarate, by Merck Group (3 mentions) D9 progesterone, by CDN Isotopes (3 mentions) D7 glucose, by Cambridge Isotopes (3 mentions) D3 leucine, by Cambridge Isotopes (3 mentions) Phenylalanine d8, by Cambridge Isotopes (3 mentions) Tryptophan d5, by Cambridge Isotopes (3 mentions) D5 hippuric acid, by CDN Isotopes (3 mentions) D5 indole acetic acid, by CDN Isotopes (3 mentions) Bromophenylalanine, by Merck Group (3 mentions)

39 protocols using oxaloacetic acid

Metabolite Standards for Biochemical Analysis

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Metabolite standards were obtained at high purity. If not otherwise indicated, the product number refers to Sigma-Aldrich: sodium citrate (71635), sodium isocitrate (I1252), cis-aconitic acid (A3412), sodium α-ketoglutarate (K2010), sodium succinate (14160), succinic semialdehyde (Santa Cruz Biotechnology, F1114), sodium fumarate (F1506), L-malic acid (M6413), sodium pyruvate (P2256), oxaloacetic acid (O4126), iron acetate (FeAc, 339199), FeCl₂ (372870), FeCl₃ (157740), Fe(ClO₄)₂ (334081), Fe(ClO₄)₃ (309281), ferrocene (F408), FeS(268704), H₃PO₄ (P5811), 2-mercaptoethanol (Merck Millipore, 805740), cysteine (30095), DL-ethionine (E5139), dimethylsulfoxid (D8418), homocysteic acid (69453), NaHSO₃ (Acros Organics, 41944), methionine (M9375), ammonium peroxydisulfate (Fischer Scientific, 10219790), sodium sulfite Na₂SO₃ (Fischer Scientific, 10070400), sodium sulfate Na₂SO₄ (Fischer Scientific, 10493372). All water was obtained commercially at UPLC-MS purity (Biosolve Chemicals, Cat no. 23214102).

Keller M.A., Kampjut D., Harrison S.A, & Ralser M. (2017). Sulfate radicals enable a non-enzymatic Krebs cycle precursor. Nature ecology & evolution, 1, 0083.

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Metabolite Standards for Biochemical Analysis

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Keller M.A., Kampjut D., Harrison S.A, & Ralser M. (2017). Sulfate radicals enable a non-enzymatic Krebs cycle precursor. Nature ecology & evolution, 1, 0083.

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Kinetic Assay for MDH Inhibition

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MDH inhibition assays were performed at room temperature on a HP8453a spectrophotometer in kinetic mode using UV–vis Chemstation software (Agilent Technologies) in methacrylate cuvettes (Fisher Scientific, 14955128) with a final volume of 1 mL for both control and test reactions. MDH (from porcine heart, 901643, Sigma-Millipore) was added to a 50 mM KPi pH 7 buffer for a final concentration of 2 nM. Compounds were dissolved in DMSO at 100 times concentration; 10 μL of compound was used for a final DMSO concentration of 1%. After compound addition, the cuvette was mixed by pipetting up and down 5 times with a p1000, and the cuvette was then incubated for 5 min at room temperature. The reaction was initiated by the addition of 200 μM nicotinamide adenine dinucleotide (54839, Sigma-Aldrich) and 200 μM oxaloacetic acid (324427, Sigma-Aldrich), and the rate was monitored at 340 nm. A negative control was included in each run, in which 10 μL of DMSO without the compound was added. The reactions were monitored for 90 s, and the initial rates were divided by the initial rate of the negative control to obtain the % inhibition and % enzyme activity. For dose–response curves, three replicates were done for each concentration, the graphs were generated using GraphPad Prism version 9.1.1 (San Diego, CA).

O’Donnell H.R., Tummino T.A., Bardine C., Craik C.S, & Shoichet B.K. (2021). Colloidal Aggregators in Biochemical SARS-CoV-2 Repurposing Screens. Journal of medicinal chemistry.

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Biochemical Assay Protocol Compendium

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Bio-Rad protein assay kit was purchased from Bio-Rad; sodium pyruvate, malic acid, succinic acid, ascorbic acid, N,N,N′,N′-tetramethyl-p-phenylenediamine (TMPD), palmitoyl-L-carnitine, rotenone, antimycin A, oligomycin, coenzyme A trilithium salt (CoA-SH), acetyl-CoA, oxaloacetic acid, thiamine pyrophosphate (TPP), 5,5-dithiobis-(2-nitrobenzoic acid) (DTNB), 2,6-dichlorophenolindophenol (DCPIP), carbonyl cyanide-4-(trifluoromethoxy)phenylhydrazone (CCCP), phosphoenolpyruvate (PEP), ADP, ATP, NAD⁺, NADH, NADPH, KCN, pyruvate kinase, lactate dehydrogenase, cytochrome c, and decylubiquinone were from Sigma; KO was a generous gift of Aker BioMarine ASA (Oslo, Norway). Antibodies against AAC and UCP2 were from Santa Cruz Biotechnology (sc-11433 and sc-6526); antibodies against OXPHOS proteins were from Mitosciences (ab110413). Kits for the assay of triglycerides and total cholesterol were purchased from Futura System. Plasma insulin concentration was analyzed with a Mercodia Ultrasensitive Mouse Insulin kit. Luciferase ATP assay kit was from Sigma and Lipid Hydroperoxide (LPO) assay kit was from Merck. All other reagents were of analytical grade.

Ferramosca A., Conte A, & Zara V. (2015). Krill Oil Ameliorates Mitochondrial Dysfunctions in Rats Treated with High-Fat Diet. BioMed Research International, 2015, 645984.

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Citrate Synthase Activity Assay

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Citrate synthase activity was determined using a previously described protocol (36 (link)). Acetyl-CoA (0.3 mM, Sigma-Aldrich) and oxaloacetic acid (0.5 mM, Sigma-Aldrich) were used as substrates for citrate synthase and 5,5-dithiobis (2-nitrobenzoic acid) (DTNB, 0.1mM, Sigma-Aldrich) were used to generate color. The reaction was activated with 10 μg snap-freeze cell lysate in reaction buffer (0.1 M Tris-HCl, pH 8.00). The absorbance was measured at 412 nm using a SpectraMax iD3 Multi-Mode Microplate Reader (Molecular Devices, Shanghai, China).

Ye X., Wei X., Liao J., Chen P., Li X., Chen Y., Yang Y., Zhao Q., Sun H., Pan L., Chen G., He X., Lyu J, & Fang H. (2021). 4-Hydroxyphenylpyruvate Dioxygenase-Like Protein Promotes Pancreatic Cancer Cell Progression and Is Associated With Glutamine-Mediated Redox Balance. Frontiers in Oncology, 10, 617190.

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Culturing HepG2 and LO-2 Liver Cells

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Human hepatocellular liver carcinoma cell line (HepG2) and human normal liver cell line (LO‐2) were obtained directly from the cell bank of Shanghai Institute of Life Sciences (China). HepG2 cells and LO‐2 cells were cultured in DMEM medium supplemented with 10% fetal bovine serum (FBS) and 1% penicillin‐streptomycin (100 IU/mL penicillin and 100 mg/mL streptomycin) in a 5% carbon dioxide (CO₂) humidified air atmosphere at 37°C. Cell culture reagents (FBS and DMEM) were purchased from HyClone (Logan, Utah, USA, 10091130, 1249101). Oxaloacetic acid was purchased from Sigma (St. Louis, MO, 328‐42‐7). Oxaloacetic acid powder was dissolved in phosphate‐buffered saline (PBS) and pH adjusting to approximately 7.0 with NaOH. Because OA was relatively unstable in solution and the pH gradually increased over 2 h, it must be with the current use.

Kuang Y., Han X., Xu M, & Yang Q. (2018). Oxaloacetate induces apoptosis in HepG2 cells via inhibition of glycolysis. Cancer Medicine, 7(4), 1416-1429.

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Citrate Synthase Activity Assay

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All frozen samples were thawed at 4°C and all solutions used in this assay (Srere, 1969 ) were kept at 30°C. The spectrophotometer was set at 412 nm wavelength and programmed to maintain a constant temperature at 30°C. Pre-warmed 0.325 ml 100 mM Tris buffer (pH 8.0), 50 μl DTNB (55′-dithiobis-(2-nitrobenzoic acid), Sigma, St. Louis, MO, United States), 50 μl Acetyl CoA (Sigma) were added to each cuvette. Soleus and plantaris muscle samples were diluted 1:100 and 1:50, respectively, in 100 mM Tris buffer (pH 8.0) just before use. Dilute sample homogenate was added (25 μl) to the cuvette and the reactions were initialized with the addition of 50 μl of oxaloacetic acid (Sigma) and mixed by gentle pipetting. The OD₄₁₂ was recorded every minute for 5 min and the average change in OD for the last 4 min was used to calculate the citrate synthase activity. Activity (μmole/g/min) was calculated as: [(Δ OD/minute × dilution factor × 20 × 20)/13.6] and then normalized to protein concentration of each sample (nmol/mg protein/min) and used for comparisons between groups.

Hyatt J.P., Brown E.A., Deacon H.M, & McCall G.E. (2019). Muscle-Specific Sensitivity to Voluntary Physical Activity and Detraining. Frontiers in Physiology, 10, 1328.

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Fluorescent Copper Sensor Synthesis

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Diethylenetriamine,
terephthalaldehyde, copper(II) nitrate (pentahydrate), sodium borohydride,
and solvents were obtained from Sigma Aldrich. All acids used in the
specificity test were obtained from Fisher Scientific, with the exception
of oxalic acid, oxaloacetic acid, and uric acid, which were obtained
from Sigma Aldrich. Highest purity available was used in every case,
and HPLC-grade solvents were used. All black 96 well assay plates
(Microfluor 2Black Microtiter) were obtained from Thermo Scientific.
All plates were read with a Bio-Tek FLx-800 fluorescence plate reader
(BioTek, Winooski, VT) on the “top read” setting with
sensitivity set to 60. NMR was performed on a Bruker Avance III Ultrashield
400 Plus spectrometer (Bruker BioSpin Corporation, Billerica, MA).
Mass spectrometry was performed on an Advion expression CMS Electrospray
Ionization instrument (Advion, Ithica, NY). All graphs and associated
calculations were produced and performed using GraphPad Prism software
(San Diego, CA).

Hontz D., Hensley J., Hiryak K., Lee J., Luchetta J., Torsiello M., Venditto M., Lucent D., Terzaghi W., Mencer D., Bommareddy A, & VanWert A.L. (2020). A Copper(II) Macrocycle Complex for Sensing Biologically Relevant Organic Anions in a Competitive Fluorescence Assay: Oxalate Sensor or Urate Sensor?. ACS Omega, 5(31), 19469-19477.

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Comprehensive Biochemical Reagents Protocol

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HEPES (Pharmagrade), Tricine (Pharmagrade), La(III)chloride heptahydrate (99.999%), TEA chloride, Chelex 100 (sodium form), Zn(II)chloride (99.999%), pyruvic acid (98%), ATP, oxaloacetic acid, FBS, hygromycin B, geneticin, penicillin-streptomycin, hydrochloric acid (TraceSelect), and 70% nitric acid (ACS reagent) were purchased from Sigma-Aldrich. Anhydrous ethanol, diethylpyrocarbonate (high purity), sodium hydroxide 30% solution (suprapur), sodium chloride (puratronic, 99.999%; AlfaAesar), potassium chloride (puratronic, 99.997%; AlfaAesar) cesium chloride (99.999%; AlfaAesar), calcium chloride (99.99%; AlfaAesar), 50% cesium hydroxide solution (99.9%; AlfaAesar), D-glucose (AnalaR Normapur), and potassium hydroxide (99.98%) were purchased from VWR. 1,000 mM stock solutions of diethyl pyrocarbonate (DEPC) in anhydrous ethanol were prepared on the day of the experiments, kept on ice, and diluted into standard external solution immediately before use.

Neumaier F., Alpdogan S., Hescheler J, & Schneider T. (2020). Zn2+-induced changes in Cav2.3 channel function: An electrophysiological and modeling study. The Journal of General Physiology, 152(9), e202012585.

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Measurement of Mitochondrial Function

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Standard chemicals, 2-thenoyltrifluoroacetone (TTFA; #T27006), rotenone (#R8875), sodium azide BioXtra (#S8032), antimycin A (#A8674), dimethyl malonate (#04011), d-α tocopherol succinate (#T3126), 2,6-dichloroindophenol sodium salt hydrate (DCPIP; #D1878), phenazine methosulphate (PMS; #P9625), MTT (#M5655), acetyl CoA (#A2181), 5,5′-dithiobis(2-nitrobenzoic acid) (DTNB; #D218200), bovine serum albumin (#A6003), doxycycline hyclate (#D9891), 3-Nitropropionic acid (#N5636) and oxaloacetic acid (#O4126) were purchased from Sigma-Aldrich. Carbonyl cyanide p-trifluoro-methoxyphenyl hydrazone (FCCP; #BML-CM120-0010) was purchased from Enzo Life Sciences. Venetoclax (#2253-1) and IACS-010759 (#B2231-1) were purchased from Biovision Inc. Potassium phosphate monobasic (KH₂PO₄; #BP362-500) and ethylenediamine tetra acetic acid (EDTA; #BP118-500) were purchased from Fisher Scientific. Decylubiquinone was purchased from Abcam (#ab145233). Oligomycin was purchased from Merck Millipore (#495455). Triton X-100 (0694) was purchased from Amresco. Polybrene (#TR-1003-G) was purchased from Millipore. Puromycin (#631306) was purchased from Clontech.

Bajpai R., Sharma A., Achreja A., Edgar C.L., Wei C., Siddiqa A.A., Gupta V.A., Matulis S.M., McBrayer S.K., Mittal A., Rupji M., Barwick B.G., Lonial S., Nooka A.K., Boise L.H., Nagrath D, & Shanmugam M. (2020). Electron transport chain activity is a predictor and target for venetoclax sensitivity in multiple myeloma. Nature Communications, 11, 1228.

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