| Size | Price | Stock | Qty |
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| 250mg |
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| 500mg |
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| 5g |
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| Other Sizes |
| Targets |
The compound Diethyl succinate (specifically, hyperpolarized diethyl 1-¹³C 2,3-d₂ succinate) acts as a metabolic substrate for the Tricarboxylic Acid (TCA) cycle. After cellular uptake and hydrolysis by esterases, it is metabolized by TCA cycle enzymes, including succinate dehydrogenase. [1]
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| ln Vivo |
After intravenous (i.v.) or intraperitoneal (i.p.) injection of hyperpolarized diethyl succinate (10-20 μmol) into normal mice, downstream TCA cycle metabolites (malate, succinate, fumarate, aspartate) were detected in vivo within seconds using ¹³C magnetic resonance spectroscopy (MRS), demonstrating its metabolism in real-time. [1]
The metabolic profile of hyperpolarized diethyl succinate was altered following pre-treatment of mice with 3-nitropropionate (an irreversible inhibitor of succinate dehydrogenase), evidenced by a significant reduction in the downstream succinate resonance in ¹³C MRS. [1] ¹³C magnetic resonance imaging (MRI) using a True FISP sequence showed that after i.v. injection, the hyperpolarized compound and its metabolites were initially localized in the cardiovascular region (heart) and later accumulated in the bladder/ureters. After i.p. injection, the signal remained primarily within the peritoneal cavity. [1] |
| Animal Protocol |
Hyperpolarized diethyl succinate was generated via parahydrogen-induced polarization (PHIP) of diethyl 1-¹³C 2,3-d₂ fumarate in an aqueous catalyst solution (20 mM final concentration in 9:1 H₂O:D₂O, pH ~6 after hydrogenation). [1]
For in vivo studies, male BALB/c mice were anesthetized. A 0.5 mL aliquot of the hyperpolarized solution (containing 10 μmol of compound for i.v. or 20 μmol for i.p.) was injected via tail vein catheter or directly into the peritoneal cavity. [1] ¹³C MRS data were acquired starting immediately after injection, using a single 30° pulse every 5-9 seconds for about 1 minute. ¹³C MRI was performed using a True FISP sequence (flip angles of 40°, 60°, or 80°) with images acquired every 9 seconds. [1] For inhibition studies, mice were pre-treated with an i.p. injection of 200 μL of a 5 mg/mL (42 mM) 3-nitropropionate solution (pH 8.5) and imaged 20 minutes later. [1] |
| ADME/Pharmacokinetics |
After injection, the hyperpolarized diethyl succinate is thought to enter the cell, where its ester group is hydrolyzed by esterases to generate succinic acid, which then enters the tricarboxylic acid cycle for metabolism. [1] In a 9:1 H₂O:D₂O solvent system, the in vivo spin-lattice relaxation time (T₁) of the hyperpolarized ¹³C-labeled diethyl succinate carbonyl group was measured to be 38 ± 4 seconds, enabling signal detection for more than 3 minutes. [1] Real-time ¹³C magnetic resonance spectroscopy (MRS) showed that the metabolite appeared within 5 seconds after injection and lasted for about 1 minute. [1]
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| Toxicity/Toxicokinetics |
Diethyl succinate is non-toxic and commonly used in flavorings and seasonings. [1] In the described experiment, the hydrogenation catalyst (rhodium complex) was co-injected with the hyperpolarizing compound (2.75-5.5 μmol per injection). In this study, the animals tolerated multiple injections and no acute adverse reactions were reported. [1] The authors point out that if it is to be applied clinically, a method for removing the catalyst before injection needs to be developed. [1]
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| References | |
| Additional Infomation |
Diethyl succinate is a fatty acid ester. It has been reported in cacti (Opuntia ficus-indica), Guyana kurupita cactus (Couroupita guianensis), and other organisms with relevant data. Diethyl succinate is a metabolite found or produced in Saccharomyces cerevisiae. See also: Succinic acid, di-C8-26-alkyl ester (note moved here). Diethyl succinate is a neutral molecule suitable for hyperpolarization at near-physiological pH (final injection pH approximately 6), unlike succinic acid, which requires extremely high pH values for optimal polarization. [1]
The PHIP hyperpolarization process of diethyl succinate is very rapid (polarization transfer takes about 4 seconds, generating an injectable sample every 3-4 minutes), much faster than the dynamic nuclear polarization (DNP) method, which may take 90 minutes or more. [1] Compared to hyperpolarized 1-¹³C pyruvate (which can show single-step metabolism), hyperpolarized diethyl succinate can image multiple steps in the tricarboxylic acid cycle in real time. [1] This compound holds promise as a diagnostic imaging agent for real-time assessment of tricarboxylic acid cycle metabolism in diseases such as cancer and neurodegenerative diseases. [1] |
| Molecular Formula |
C8H14O4
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|---|---|
| Molecular Weight |
174.1944
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| Exact Mass |
174.089
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| CAS # |
123-25-1
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| Related CAS # |
Diethyl succinate-13C4;1628796-56-4;Diethyl succinate-d4;52089-62-0
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| PubChem CID |
31249
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| Appearance |
Colorless to light yellow liquid
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| Density |
1.0±0.1 g/cm3
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| Boiling Point |
218.4±8.0 °C at 760 mmHg
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| Melting Point |
-20 °C
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| Flash Point |
90.6±0.0 °C
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| Vapour Pressure |
0.1±0.4 mmHg at 25°C
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| Index of Refraction |
1.423
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| LogP |
1.26
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| Hydrogen Bond Donor Count |
0
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| Hydrogen Bond Acceptor Count |
4
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| Rotatable Bond Count |
7
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| Heavy Atom Count |
12
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| Complexity |
135
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O(C([H])([H])C([H])([H])[H])C(C([H])([H])C([H])([H])C(=O)OC([H])([H])C([H])([H])[H])=O
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| InChi Key |
DKMROQRQHGEIOW-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H14O4/c1-3-11-7(9)5-6-8(10)12-4-2/h3-6H2,1-2H3
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| Chemical Name |
diethyl butanedioate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 250 mg/mL (~1435.21 mM)
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (11.94 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 5.7409 mL | 28.7043 mL | 57.4086 mL | |
| 5 mM | 1.1482 mL | 5.7409 mL | 11.4817 mL | |
| 10 mM | 0.5741 mL | 2.8704 mL | 5.7409 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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