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Succinyl phosphonate

Catalog No.GC30030

Succinyl phosphonate is an α-ketoglutarate dehydrogenase (KGDHC) inhibitor, effective inhibits (KGDHC) in muscle, bacterial, brain, and cultured human fibroblasts.

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Succinyl phosphonate Chemical Structure

Cas No.: 26647-82-5

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2mg
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10mg
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Protocol

Cell experiment:

MTT assay is employed to test cellular viability. Serial dilutions of succinyl phosphonate (0.01-20 mM) are added to cells in fresh culture media. During the medium exchange before the succinyl phosphonate addition, glioblastoma cells are brought to DMEM with 1 g/L glucose, 1 mM pyruvate and 2 mM glutamax. The influence of succinyl phosphonate in minimal medium is studied in the earlier employed buffered salt solution[3].

References:

[1]. Biryukov AI, et al. Succinyl phosphonate inhibits alpha-ketoglutarate oxidative decarboxylation, catalyzed by alpha-ketoglutarate dehydrogenase complexes from E. coli and pigeon breast muscle. FEBS Lett. 1996 Mar 11;382(1-2):167-70.
[2]. Bunik VI, et al. Phosphonate analogues of alpha-ketoglutarate inhibit the activity of the alpha-ketoglutaratedehydrogenase complex isolated from brain and in cultured cells. Biochemistry. 2005 Aug 9;44(31):10552-61.
[3]. Bunik VI, et al. Inhibition of mitochondrial 2-oxoglutarate dehydrogenase impairs viability of cancer cells in a cell-specific metabolism-dependent manner. Oncotarget. 2016 May 3;7(18):26400-21.

Background

Succinyl phosphonate is an inhibitor of the α-ketoglutarate dehydrogenase.

Succinyl phosphonate is an α-Ketoglutarate phosphoanalogue. It is found to be an effective inhibitor of α-ketoglutarate oxidative decarboxylation, catalyzed by both muscle and bacterial α-ketoglutarate dehydrogenase complexes, as well as muscle α-ketoglutarate dehydrogenase[1]. At a concentration of 0.01 mM, succinyl phosphonate completely inhibits isolated brain KGDHC even in the presence of a 200-fold higher concentration of its substrate. In cultured human fibroblasts, 0.01 mM succinyl phosphonate produced 70% inhibition of α-ketoglutarate dehydrogenase complex. DESP and TESP are also inhibitory in the cell system, but only after preincubation, suggesting the release of their charged groups by cellular esterases[2]. Succinyl phosphonate inhibits 2-Oxoglutarate dehydrogenase , the first rate-limiting component of the mitochondrial multi-enzyme complex of oxidative decarboxylation of 2-oxoglutarate, in a highly selective and efficient manner[3].

[1]. Biryukov AI, et al. Succinyl phosphonate inhibits alpha-ketoglutarate oxidative decarboxylation, catalyzed by alpha-ketoglutarate dehydrogenase complexes from E. coli and pigeon breast muscle. FEBS Lett. 1996 Mar 11;382(1-2):167-70. [2]. Bunik VI, et al. Phosphonate analogues of alpha-ketoglutarate inhibit the activity of the alpha-ketoglutaratedehydrogenase complex isolated from brain and in cultured cells. Biochemistry. 2005 Aug 9;44(31):10552-61. [3]. Bunik VI, et al. Inhibition of mitochondrial 2-oxoglutarate dehydrogenase impairs viability of cancer cells in a cell-specific metabolism-dependent manner. Oncotarget. 2016 May 3;7(18):26400-21.

Chemical Properties

Cas No. 26647-82-5 SDF
Canonical SMILES O=C(O)CCC(P(O)(O)=O)=O
Formula C4H7O6P M.Wt 182.07
Solubility Water : ≥ 50 mg/mL (274.62 mM) Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 5.4924 mL 27.462 mL 54.9239 mL
5 mM 1.0985 mL 5.4924 mL 10.9848 mL
10 mM 0.5492 mL 2.7462 mL 5.4924 mL
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