Tricarballylic acid
(Synonyms: 三碳烯丙酸) 目录号 : GC63238
Tricarballylic acid (β-Carboxyglutaric acid, Propane-1,2,3-tricarboxylic acid) is an inhibitor of aconitase and therefore interferes with the Krebs cycle.
Cas No.:99-14-9
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Tricarballylic acid (β-Carboxyglutaric acid, Propane-1,2,3-tricarboxylic acid) is an inhibitor of aconitase and therefore interferes with the Krebs cycle.
| Cas No. | 99-14-9 | SDF | |
| 别名 | 三碳烯丙酸 | ||
| 分子式 | C6H8O6 | 分子量 | 176.12 |
| 溶解度 | 储存条件 | Store at RT | |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 5.6779 mL | 28.3897 mL | 56.7795 mL |
| 5 mM | 1.1356 mL | 5.6779 mL | 11.3559 mL |
| 10 mM | 0.5678 mL | 2.839 mL | 5.6779 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Effect of Tricarballylic acid, a nonmetabolizable rumen fermentation product of trans-aconitic acid, on Mg, Ca and Zn utilization of rats
J Nutr 1988 Feb;118(2):183-8.PMID:3339476DOI:10.1093/jn/118.2.183.
trans-Aconitic acid has been implicated in magnesium deficiency of ruminants since the 1960s, but recent experiments indicated that much of it can be converted by rumen bacteria to Tricarballylic acid (TCBA). Rats were used as experimental models in the studies described here because analogous experiments in ruminants would have been very expensive. When TCBA was fed to young male Sprague-Dawley rats as 2% of an AIN-76A diet with marginal (200 mg/kg) or adequate (500 mg/kg) Mg, virtually all of the dietary acid was recovered in the urine. Mg and Ca absorptions were unaffected by TCBA but urinary losses of Mg, Ca and Zn were higher than in pair-fed controls. TCBA was highly correlated (r = 0.93) with titratable acid excretion, and Mg, Ca and Zn retentions were reduced by 90, 35 and 56%, respectively. Rats fed 2% citric acid, a structurally similar but metabolizable acid, excreted more Zn than controls but did not excrete excess Mg or Ca. Since TCBA led to a depletion of Mg and other cations, it could be a contributing factor in the etiology of the Mg deficiency known as grass tetany in ruminants. Additional work in ruminants now seems warranted.
Synthesis, chemical speciation and SOD mimic assays of tricarballylic acid-copper(II) and imidazole-tricarballylic acid-copper(II) complexes
J Inorg Biochem 2009 Feb;103(2):219-26.PMID:19026447DOI:10.1016/j.jinorgbio.2008.10.007.
The coordination behavior of copper(II) with Tricarballylic acid (H(3)TCA) and imidazole (Imz) is described. Speciation in aqueous solution has been determined at 25 degrees C and 0.15M NaCl ionic strength by potentiometric measurements and EPR characterization of the species. Two new compounds CuTCAH.3H(2)O and CuTCAHImz.2H(2)O were obtained and characterized by elemental analysis diffuse reflectance, FTIR (Fourier transform infrared spectroscopy), EPR and thermal behavior. Their in vitro superoxide dismutase-mimetic activities have been tested.
Structure Activity Relationship for Fumonisin Phytotoxicity
Chem Res Toxicol 2021 Jun 21;34(6):1604-1611.PMID:33891387DOI:10.1021/acs.chemrestox.1c00057.
Fumonisins are mycotoxins produced by a number of species of Fusarium and Aspergillus. They are polyketides that possess a linear polyol structure with two Tricarballylic acid side chains and an amine moiety. Toxicity results from their inhibition of Ceramide Synthase (CerS), which perturbs sphingolipid concentrations. The tricarballylic side chains and amine group of fumonisins are key molecular features responsible for inhibiting CerS, however their individual contributions toward overall toxicity are not fully understood. We have recently reported novel, deaminated fumonisins produced by A. niger and have identified an enzyme (AnFAO) responsible for their synthesis. Here we performed a structure/function activity assay to investigate the individual contributions of the Tricarballylic acid and amine toward overall fumonisin toxicity. Lemna minor was treated at 40 μM against FB1, hydrolyzed FB1 (hFB1), deaminated FB1 (FPy1), or hydrolyzed/deaminated (hFPy1). Four end points were monitored: plant dry weight, frond surface area, lipidomics, and metabolomics. Overall, hFB1 was less toxic than FB1 and FPy1 was less toxic than hFB1. hFPy1 which lacks both the amine group and tricarballylic side chains was also less toxic than FB1 and hFB1, however it was not significantly less toxic than FPy1. Lipidomic analysis showed that FB1 treatment significantly increased levels of phosphotidylcholines, ceramides, and pheophorbide A, while significantly decreasing the levels of diacylglycerides, sulfoquinovosyl diacylglycerides, and chlorophyll. Metabolomic profiling revealed a number of significantly increased compounds that were unique to FB1 treatment including phenylalanine, asymmetric dimethylarginine (ADMA), S-methylmethionine, saccharopine, and tyrosine. Conversely, citrulline, N-acetylornithine and ornithine were significantly elevated in the presence of hFB1 but not any of the other fumonisin analogues. These data provide evidence that although removal of the tricarballylic side chains significantly reduces toxicity of fumonisins, the amine functional group is a key contributor to fumonisin toxicity in L. minor and justify future toxicity studies in mammalian systems.
Production of Tricarballylic acid by rumen microorganisms and its potential toxicity in ruminant tissue metabolism
Br J Nutr 1986 Jul;56(1):153-62.PMID:3676191DOI:10.1079/bjn19860095.
1. Rumen microorganisms convert trans-aconitate to tricarballylate. The following experiments describe factors affecting the yield of tricarballylate, its absorption from the rumen into blood and its effect on mammalian citric acid cycle activity in vitro. 2. When mixed rumen microorganisms were incubated in vitro with Timothy hay (Phleum pratense L.) and 6.7 mM-trans-aconitate, 64% of the trans-aconitate was converted to tricarballylate. Chloroform and nitrate treatments inhibited methane production and increased the yield of tricarballylate to 82 and 75% respectively. 3. Sheep given gelatin capsules filled with 20 g trans-aconitate absorbed tricarballylate and the plasma concentration ranged from 0.3 to 0.5 mM 9 h after administration. Feeding an additional 40 g potassium chloride had little effect on plasma tricarballylate concentrations. Between 9 and 36 h there was a nearly linear decline in plasma tricarballylate. 4. Tricarballylate was a competitive inhibitor of the enzyme, aconitate hydratase (aconitase; EC 4.2.1.3), and the inhibitor constant, KI, was 0.52 mM. This KI value was similar to the Michaelis-Menten constant (Km) of the enzyme for citrate. 5. When liver slices from sheep were incubated with increasing concentrations of tricarballylate, [14C]acetate oxidation decreased. However, even at relatively high concentrations (8 mM), oxidation was still greater than 80% of the maximum. Oxidation of [14C]acetate by isolated rat liver cells was inhibited to a greater extent by tricarballylate. Concentrations as low as 0.5 mM caused a 30% inhibition of citric acid cycle activity.
Enrichment and Isolation of Rumen Bacteria That Reduce trans- Aconitic Acid to Tricarballylic acid
Appl Environ Microbiol 1985 Jan;49(1):120-6.PMID:16346691DOI:10.1128/aem.49.1.120-126.1985.
Bacteria from the bovine rumen capable of reducing trans-aconitate to tricarballylate were enriched in an anaerobic chemostat containing rumen fluid medium and aconitate. After 9 days at a dilution rate of 0.07 h, the medium was diluted and plated in an anaerobic glove box. Three types of isolates were obtained from the plates (a crescent-shaped organism, a pleomorphic rod, and a spiral-shaped organism), and all three produced tricarballylate in batch cultures that contained glucose and trans-aconitate. In glucose-limited chemostats (0.10 h), trans-aconitate reduction was associated with a decrease in the amount of reduced products formed from glucose. The crescent-shaped organism produced less propionate, the pleomorphic rod produced less ethanol, and the spiral made less succinate and possibly H(2). Aconitate reduction by the pleomorphic rod and the spiral organism was associated with a significant increase in cellular dry matter. Experiments with stock cultures of predominant rumen bacteria indicated that Selenomonas ruminantium, a species taxonomically similar to the crescent-shaped isolate, was an active reducer of trans-aconitate. Strains of Bacteroides ruminicola, Butyrivibrio fibrisolvens, and Megasphaera elsdenii produced little if any tricarballylate. Wolinella succinogenes produced some tricarballylate. Based on its stability constant for magnesium (K(eq) = 115), tricarballylate could be a factor in the hypomagnesemia that leads to grass tetany.