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26647-82-5

26647-82-5 structure
26647-82-5 structure
  • Name: Succinyl phosphonate
  • Chemical Name: 4-oxo-4-phosphonobutanoic acid
  • CAS Number: 26647-82-5
  • Molecular Formula: C4H7O6P
  • Molecular Weight: 182.06900
  • Catalog: Research Areas Others
  • Create Date: 2016-06-06 20:56:04
  • Modify Date: 2024-01-13 19:37:10
  • Succinyl phosphonate is an inhibitor of the α-ketoglutarate dehydrogenase.

Name 4-oxo-4-phosphonobutanoic acid
Synonyms Butanoic acid,4-oxo-4-phosphono
succinyl phosphonate
Description Succinyl phosphonate is an inhibitor of the α-ketoglutarate dehydrogenase.
Related Catalog
In Vitro 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].
Cell Assay 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.

Molecular Formula C4H7O6P
Molecular Weight 182.06900
Exact Mass 181.99800
PSA 121.71000
Storage condition 2-8℃