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Isocitric acid

Manufactured by Merck Group
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Sourced in United States, Germany

Isocitric acid is a chemical compound used in various laboratory applications. It is a tricarboxylic acid that occurs naturally in the human body and plays a role in the citric acid cycle. Isocitric acid is commonly used as a reference standard and in the analysis of biological samples.

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Lab products found in correlation

Citric acid, by Merck Group (7 mentions) Succinic acid, by Merck Group (6 mentions) Malic acid, by Merck Group (5 mentions) Fumaric acid, by Merck Group (4 mentions) Ethyl acetate, by Kanto Chemical (3 mentions) Diethyl ether, by Kanto Chemical (3 mentions) Toluene, by Kanto Chemical (3 mentions) Lactic acid, by Merck Group (3 mentions) Pyruvic acid, by Merck Group (3 mentions) Citric, by Merck Group (2 mentions) Pyruvic, by Merck Group (2 mentions) Glycolic, by Merck Group (2 mentions) Malonic, by Merck Group (2 mentions) Succinic, by Merck Group (2 mentions) Fumaric, by Merck Group (2 mentions) Malic, by Merck Group (2 mentions) Sodium chloride (nacl), by Kanto Chemical (2 mentions) Lactic, by Merck Group (2 mentions) O methoxyamine hydrochloride, by Merck Group (2 mentions) 2 hydroxybutyric, by Merck Group (2 mentions)

17 protocols using isocitric acid

1

GC-MS Analysis of Organic Acids

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The 14 OA standards (pyruvic, lactic, glycolic, 2-hydroxybutyric, 3-hydroxybutyric, malonic, succinic, fumaric, α-ketoglutaric, malic, 2-hydroxyglutaric, cis-aconitic, citric, and isocitric acid), and O-methoxyamine hydrochloride were purchased from Sigma-Aldrich (St. Louis, MO, USA). N-Methyl-N-(tert-butyldimethylsilyl) trifluoroacetamide (MTBSTFA) + 1% tert-butyldimetheylchlorosilane (TBDMCS) was obtained from Thermo Scientific (Bellefonte, PA, USA). Toluene, diethyl ether, ethyl acetate, and sodium chloride of pesticide grade were supplied by Kanto Chemical (Tokyo, Japan). All other chemicals were of analytical grade and used as received.
Lee H., Choi B., Oh S., Park H., Popova E., Paik M.J, & Kim H. (2023). Dynamics of Organic Acids during the Droplet-Vitrification Cryopreservation Procedure Can Be a Signature of Oxidative Stress in Pogostemon yatabeanus. Plants, 12(19), 3489.
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2

Comprehensive Characterization of Bioactive Compounds

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The compounds 2,2′-azinobis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), 6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid (Trolox), 2,4,6-tri(2-pyridyl)-s-triazine (TPTZ), methanol, malic acid, oxalic acid, citric acid, isocitric acid, quinic acid, ferulic acid, galacturonic acid, and succinic acid were purchased from Sigma-Aldrich (Steinheim, Germany). On the other hand, (−)-epicatechin, (+)-catechin, procyanidin B2, chlorogenic acid, neochlorogenic acid, cryptochlorogenic acid, caffeic acid, dicaffeoylquinic acid, p-coumaric acid, myricetin, isoquercitrin, cyanidin-3-O-galactoside, and cyanidin-3-O-glucoside were purchased from Extrasynthese (Lyon, France). Acetonitrile for ultra-performance liquid chromatography (UPLC; Gradient grade) and ascorbic acid were from Merck (Darmstadt, Germany).
Lachowicz S., Oszmiański J., Wilczyńska M., Zaguła G., Saletnik B, & Puchalski C. (2020). Impact Mineralization of Chokeberry and Cranberry Fruit Juices Using a New Functional Additive on the Protection of Bioactive Compounds and Antioxidative Properties. Molecules, 25(3), 659.
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3

Purification and expression of CYP27A1

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Dioleoyl phosphatidylcholine and bovine heart cardiolipin were from Avanti Polar Lipids (Alabaster, AL). 2-Hydroxypropyl-β-cyclodextrin (HP-β-CD) was from Cerestar (Hammond, IN). Vitamin D3, NADPH and isocitric acid (tri-sodium salt) were from Sigma-Aldrich (Sydney, Australia) and 5β-cholestane-3α,7α,12α-triol was from Steraloids (Newport, RI). Lumisterol3 (L3) was purchased from Toronto Research Chemicals (Toronto, Canada) and was purified before use on a Brownlee Aquapore C18 column (25 cm × 1 cm, 10 μm particle size) using a gradient of methanol in water (64–100% methanol) for 15 min followed by 100% methanol for 45 min at a flow rate of 1.5 ml/min. (25R)-27-Hydroxycholesterol and (25S)-27-hydroxycholesterol were from Cayman Chemical (Ann Arbor, MI).
Human CYP27A1 with the N-terminal mitochondrial target sequence removed and a six histidine tag added to the C-terminus was expressed in E. coli and purified by Ni affinity- and octyl Sepharose-chromatography, as described previously [26 (link)]. Human adrenodoxin reductase, and mouse and human adrenodoxin were also expressed in E. coli and purified as described before [27 (link)–30 (link)].
Tuckey R.C., Li W., Ma D., Cheng C.Y., Wang K.M., Kim T.K., Jeayeng S, & Slominski A.T. (2018). CYP27A1 acts on the pre-vitamin D3 photoproduct, lumisterol, producing biologically active hydroxy-metabolites. The Journal of steroid biochemistry and molecular biology, 181, 1-10.
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4

Comprehensive Metabolite Analysis Protocol

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Acetic acid, lactic acid (LA), pyruvic acid (PA), citric acid (CA), isocitric acid (ICA), succinic acid (SA), 2-hydroxy-glutaric acid (2-OHGA), a ketoglutaric acid (αKG), oxaloAcetic acid (OA), malic acid (MA), fumaric acid (FA), methyl malonic acid (MMA), maleic acid (MAEA) and formic acid were all purchased from Sigma Aldrich (Milwaukee, WI) in the highest purity available. 1-Ethyl-3-dimethylaminopropyl carbodiimide (EDC) was purchased from Acros Organics (Thermo Fisher Scientific, Waltham, MA). HPLC-grade acetonitrile and methanol were purchased from Sigma Aldrich, and water was purified using in house Milli-Q water purification system. Brominated derivatization agents 4-BNMA, 3-methyl-N-methylbenzylamine (3-BNMA), and 4-bromo-n-methylaniline (4-BMA) were purchased from Sigma Aldrich and 2-(4-Bromophenyl)-N-methylethanamine (B-MPEA) was purchased from Combi-locks Inc. (San Diego, CA). Isotope standards sodium lactate 13C3 (LAi), citric D4(2,2,4,4) acid (CAi), fumaric 13C4 acid (FAi), sodium pyruvate 13C3 (PAi), and α-ketoglutaric D6 acid (αKGi) were purchased from Isotec (Sigma Aldrich, Milwaukee, WI) and succinic D6 acid (SAi), and disodium 2 hydroxy glutarate D3(2,3,3) (2OHGAi) were purchased from CDN Isotopes (Pointe-Claire, Canada).
Marquis B.J., Louks H.P., Bose C., Wolfe R.R, & Singh S.P. (2017). A New Derivatization Reagent for HPLC–MS Analysis of Biological Organic Acids. Chromatographia, 80(12), 1723-1732.
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5

Quantitative IDH1 Enzyme Activity Assay

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An in vitro enzyme activity assay for wild type IDH1 was performed as previously described (8 (link)). In brief, 20 ng purified IDH1 and YF variant proteins that were pre-treated with or without recombinant active tyrosine kinases in an in vitro kinase assay were added to 100 μl enzyme activity assay buffer (25mM Tris-HCl (pH7.5), 10 mM MgCl2, 5 mM DTT) containing 0.5 mM NADP+ (Sigma-Aldrich) and 1 mM isocitric acid (Sigma-Aldrich). To determine the wild type IDH1 activity in cells, endogenous IDH1 from 1×107 cells was bound to protein G-Sepharose 4 Fast Flow beads (Sigma-Aldrich) by immunoprecipitation using IDH1 antibody (CST). To test IDH1 activity in xenograft tumor tissues, around 2 mg of total tumor lysates were used. After immunoprecipitation, the IDH1-bound beads were washed 3 times and eluted using IDH1 peptide (CST). Then 10 ul of the supernatant was added to 100μl assay buffer (25mM Tris-HCl, pH7.5, 10 mM MgCl2, 5 mM DTT) containing 0.5 mM NADP+ and 1 mM isocitric acid. IDH1 activity was measured by recording absorbance of 340 nm in kinetic mode every 20 seconds for 15 minutes using a SpectraMax Plus spectrophotometer (Molecular Devices).
Chen D., Xia S., Wang M., Lin R., Li Y., Mao H., Aguiar M., Famulare C.A., Shih A.H., Brennan C.W., Gao X., Pan Y., Liu S., Fan J., Jin L., Song L., Zhou A., Mukherjee J., Pieper R.O., Mishra A., Peng J., Arellano M., Blum W.G., Lonial S., Boggon T.J., Levine R.L, & Chen J. (2019). Mutant and wild-type isocitrate dehydrogenase 1 share enhancing mechanisms involving distinct tyrosine kinase cascades in cancer. Cancer discovery, 9(6), 756-777.
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6

Kinetic Analysis of Mutant IDH1 and YF Variants

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20 ng purified IDH1 and YF variant proteins that pre-treated with or without recombinant active tyrosine kinases in an in vitro kinase assay were incubated with various concentrations of NADP+ (0–200 μM; Sigma-Aldrich) or isocitrate acid (0–200 μM; Sigma-Aldrich) and 1 mM isocitric Acid (Sigma-Aldrich) or 0.5 mM NADP+ (Sigma-Aldrich), respectively at 100 μl enzyme activity assay buffer (25 mM Tris-HCl pH7.5), 10 mM MgCl2, 5 mM DTT). Absorbance at 340 nm was measured every 20 seconds for 5 minutes using a SpectraMax Plus spectrophotometer (Molecular Devices).
20 ng purified IDH1 R132H and YF variants proteins that pre-treated with or without recombinant active tyrosine kinases in an in vitro kinase assay were incubated with various concentrations of NADPH (0–10μM; Sigma-Aldrich) and 1.5 mM α-KG (Sigma-Aldrich) or various concentrations of α-KG (0–1500 μM; Sigma-Aldrich) and 15 μM NADPH (Sigma-Aldrich) at 100 μl enzyme activity assay buffer (25 mM Tris-HCl (pH7.5), 10 mM MgCl2, 5 mM DTT). Absorbance at 340 nm was measured every 20 seconds for 5 minutes using a SpectraMax Plus spectrophotometer (Molecular Devices). Non-linear regression analysis (Michaelis-Menten) was performed in Graphpad Prism 6.0.
Chen D., Xia S., Wang M., Lin R., Li Y., Mao H., Aguiar M., Famulare C.A., Shih A.H., Brennan C.W., Gao X., Pan Y., Liu S., Fan J., Jin L., Song L., Zhou A., Mukherjee J., Pieper R.O., Mishra A., Peng J., Arellano M., Blum W.G., Lonial S., Boggon T.J., Levine R.L, & Chen J. (2019). Mutant and wild-type isocitrate dehydrogenase 1 share enhancing mechanisms involving distinct tyrosine kinase cascades in cancer. Cancer discovery, 9(6), 756-777.
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7

GC-MS Analysis of Organic Acids

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The 14 OA standards (pyruvic, lactic, glycolic, 2-hydroxybutyric, 3-hydroxybutyric, malonic, succinic, fumaric, α-ketoglutaric, malic, 2-hydroxyglutaric, cis-aconitic, citric, and isocitric acid), and O-methoxyamine hydrochloride were purchased from Sigma-Aldrich (St. Louis, MO, USA). N-Methyl-N-(tert-butyldimethylsilyl) trifluoroacetamide (MTBSTFA) + 1% tert-butyldimetheylchlorosilane (TBDMCS) was obtained from Thermo Scientific (Bellefonte, PA, USA). Toluene, diethyl ether, ethyl acetate, and sodium chloride of pesticide grade were supplied by Kanto Chemical (Tokyo, Japan). All other chemicals were of analytical grade and used as received.
Lee H., Choi B., Oh S., Park H., Popova E., Paik M.J, & Kim H. (2023). Dynamics of Organic Acids during the Droplet-Vitrification Cryopreservation Procedure Can Be a Signature of Oxidative Stress in Pogostemon yatabeanus. Plants, 12(19), 3489.
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8

Analytical Reagents and Standards Sourcing

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The analytical reagents and solvents (HPLC grade) used for analysis were purchased from Sigma-Aldrich (Castle Hill, NSW, Australia), Fisher Chemical (Loughborough, UK), BDH AnalaR (Kilsyth, VIC, Australia), Univar Ajax Chemicals (Sydney, NSW, Australia), and Chem-Supply (Gillman, SA, Australia). The sugar standards, including glucose, fructose, and sucrose; L-ascorbic acid; organic acids including citric acid, fumaric acid, isocitric acid, maleic acid, malic acid, quinic acid, shikimic acid, succinic acid and tartaric acid; phenolic standards, including caffeic acid, catechin, chlorogenic acid, p-coumaric acid, ellagic acid, epicatechin, gallic acid, kaempferol, luteolin, myricetin, quercetin, quercetin-3-glucoside and rutin, were purchased from Sigma-Aldrich. Microbial media were purchased from Thermo Fisher Scientific (Melbourne, VIC, Australia).
Seididamyeh M., Phan A.D., Sivakumar D., Netzel M.E., Mereddy R, & Sultanbawa Y. (2023). Valorisation of Three Underutilised Native Australian Plants: Phenolic and Organic Acid Profiles and In Vitro Antimicrobial Activity. Foods, 12(3), 623.
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9

Quantification of Citric Acid Compounds

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Analytical grade citric acid, iso-citric acid, and citric acid-2,2,4,4-d4 were obtained from Sigma-Aldrich (St. Louis, MO, USA). HPLC grade methanol was purchased from Merck Co. (Darmstadt, Germany) with a purity of 99.8%. Purified water was prepared with a Milli-Q system (MA, USA).
Jahani R., van Ruth S., Weesepoel Y., Alewijn M., Kobarfard F., Faizi M., Shojaee AliAbadi M.H., Mahboubi A., Nasiri A, & Yazdanpanah H. (2022). Comparison of Portable and Benchtop Near-Infrared Spectrometers for the Detection of Citric Acid-adulterated Lime Juice: A Chemometrics Approach. Iranian Journal of Pharmaceutical Research : IJPR, 21(1), e128372.
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10

Comprehensive HPLC Analysis of Metabolites

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Amino acids, and organic acids HPLC quality standards proline (Pro), isoleucine (Ile), leucine (Leu), asparagine (Asn), aspartic acid (Asp), glutamine (Gln), glutamic acid (Glu), lysine (Lys), methionine (Met), histidine (His), phenylalanine (Phe), arginine (Arg), tyrosine (Tyr), tryptophan (Trp), 5 amino acid derivatives: O-acetyl-serine, thiamine, glutathione reduced (GSH), S-adenosyl-methionine (SAM), glutathione oxidized (GSSG), fumaric acid, succinic acid, malic acid, phospho(enol)pyruvic acid, cis-aconitic acid, shikimic acid, citric acid, isocitric acid, gluconic acid, 2 phosphorylated sugars: d-glucose 6-phosphate, trehalose 6-Phosphate, 4 secondary metabolites: gallic acid, azelaic acid, kaempferol, chlorogenic acid, and two internal standards: Lactitol and Taurine, were purchased from Sigma-Aldrich (Saint Quentin, France).
Ultra-pure water was prepared by a Milli-Q Advantage A10 system (Darmstadt, Germany), Acetonitrile (ACN) and Methanol (MeOH) Optima LC–MS grade were purchased from Fisher (Leicester, UK), Formic Acid (FA) LC–MS grade and perchloric acid (PCA) were purchased from Merck (Darmstadt, Germany).
Ghosson H., Schwarzenberg A., Jamois F, & Yvin J.C. (2018). Simultaneous untargeted and targeted metabolomics profiling of underivatized primary metabolites in sulfur-deficient barley by ultra-high performance liquid chromatography-quadrupole/time-of-flight mass spectrometry. Plant Methods, 14, 62.
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