Valproic acid sodium salt An HDAC inhibitor with anticancer, anti-inflammatory and neuroprotective effects

Valproic acid sodium salt (CAS 1069-66-5)

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Sinónimo: Sodium valproate, 2-Propylpentanoic acid . Na, Sodium 2-propylpentanoate
Solicitud: An HDAC inhibitor with anticancer, anti-inflammatory and neuroprotective effects
Número de CAS: 1069-66-5
Pureza: ≥98%
Peso Molecular: 166.19
Fórmula Molecular: C8H15O2•Na
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Valproic Acid, Sodium Salt is a branched chain fatty acid which is reported to inhance central GABAergic neurotransmission and inhibit Sodium Channel Protein (Na+ channels). This compound is also reported to cause inositol depletion, activate the ERK pathway, inhibit GSK-3α and GSK-3β. Valproic Acid has been reported to be a potent inhibitor of HDAC (histone deacetylase) in vitro (IC50 = 400 μM for HDAC1), thereby relieving HDAC-dependent transcriptional repression and causes the hyperacetylation of histones in cultured cells. In animal studies, Valproic Acid has been observed to reduce tumor growth and metastasis formation. Additionally, Valproic Acid is reported to activate Wnt-dependent gene expression and to mimic trichostatin A (sc-3511) in the inhibition of histone deacetylase. This compound is also an inhibitor of the CYP2C9 enzyme.

Metabolites of Valproic Acid are also available as:
Valproic Acid (sc-213144)
3-Hydroxy Valproic Acid (sc-209599)
3-Keto Valproic Acid Sodium Salt (sc-216476)
4-Hydroxy Valproic Acid Sodium Salt (Mixture of Diastereomers) (sc-216870)
rac 5-Hydroxy Valproic Acid Sodium Salt (sc-208266)
Valproic Acid β-D-Glucuronide Allyl Ester (sc-220360)
Valproic Acid β-D-Glucuronide (sc-213145)

Labelled forms of Valproic Acid are available as:
Valproic Acid-d6 (sc-213146)
Valproic Acid-d6 β-D-Glucuronide (sc-220361)
rac 5-Hydroxy Valproic Acid-d7 Sodium Salt (sc-219789)


References

1. Della Paschoa, O E., et al., 1998. Modelling of the pharmacodynamic interaction between phenytoin and sodium valproate. British journal of pharmacology. 125(7): 1610-6. PMID: 9884091
2. Tunnicliff, G., et al., 1999. Actions of sodium valproate on the central nervous system. Journal of physiology and pharmacology : an official journal of the Polish Physiological Society. 50(3): 347-65. PMID: 10574466
3. Phiel, C J., et al., 2001. Histone deacetylase is a direct target of valproic acid, a potent anticonvulsant, mood stabilizer, and teratogen. The Journal of biological chemistry. 276(39): 36734-41. PMID: 11473107
4. Göttlicher, M., et al., 2001. Valproic acid defines a novel class of HDAC inhibitors inducing differentiation of transformed cells. The EMBO journal. 20(24): 6969-78. PMID: 11742974
5. Gökçe, Selim., et al., 2010. Valproic acid-associated vanishing bile duct syndrome. Journal of child neurology. 25(7): 909-11. PMID: 20388938

Estado de Materia :
Solid
Solubilidad :
Soluble in water (50 mg/ml), ethanol (~30 mg/ml), DMSO (50 mM), DMF (~5 mg/ml), and methanol.
ALMACENAMIENTO :
Store at 4° C
Punto de Fusión :
>320° C
Indice de Refracción :
n20D ~1.44 (Predicted)
IC50 :
Aldehyde reductase: IC50 = 89 µM (pig); Histone deacetylase HD2: IC50 = 128 µM (Maize (Zea mays)); Aldose reductase: IC50 = 380 µM (rat); HDAC1: IC50 = 400 µM
Datos Ki :
GABA-A receptor; anion channel: Ki>0.1 mM (human); GABA-A receptor; anion channel: Ki>0.1 mM (rat); CYP2C9 isoform: Ki= 0.6 mM (human)
Para Uso Exclusivo en Investigación. No está diseñado para uso en diagnosis o terapia.
WGK Alemania :
3
RTECS :
YV7876000
PubChem CID :
16760703
Indice de Merck :
14:9913
Número MDL :
MFCD00078604
Número EC :
213-961-8
SMILES :
CCCC(CCC)C(=O)[O-].[Na+]

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PMID: # 28153532  Segura-Ulate, I. et al. 2017. Neuropharmacology. 117: 149-157.

PMID: # 27343825  2016. Mol. Cell. Neurosci. 75: 27-35.

PMID: # 20381581  Liu, B. et al. 2010. Exp. Hematol. 38: 685-695.

PMID: # 14871994  Takai, N. et al. 2004. Clin. Cancer Res. 10: 1141-1149.

PMID: # 402258  Pinder, RM. et al. 1977. Drugs. 13: 81-123.

PMID: # 10812195  Johannessen, CU. et al. 2000 Aug-Sep. Neurochem. Int. 37: 103-110.

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