Valproic acid (VPA)

For research use only.

Catalog No.S3944 Synonyms: 2-Propylvaleric Acid, Valproate

20 publications

Valproic acid (VPA) Chemical Structure

CAS No. 99-66-1

Valproic acid (VPA, 2-Propylvaleric Acid, Valproate) is a fatty acid with anticonvulsant properties used in the treatment of epilepsy. It is also a histone deacetylase (HDAC) inhibitor and is under investigation for treatment of HIV and various cancers. Valproic acid (VPA) induces autophagy and mitophagy by upregulation of BNIP3 and mitochondrial biogenesis by upregulating PGC-1α. Valproic acid activates Notch-1 signaling.

Selleck's Valproic acid (VPA) has been cited by 20 publications

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Description Valproic acid (VPA, 2-Propylvaleric Acid, Valproate) is a fatty acid with anticonvulsant properties used in the treatment of epilepsy. It is also a histone deacetylase (HDAC) inhibitor and is under investigation for treatment of HIV and various cancers. Valproic acid (VPA) induces autophagy and mitophagy by upregulation of BNIP3 and mitochondrial biogenesis by upregulating PGC-1α. Valproic acid activates Notch-1 signaling.
Targets
HDAC1 [1]
(Cell-free assay)
0.4 mM
In vitro

Valproic acid (VPA), like lithium, activates Wnt-dependent gene expression, but unlike lithium, VPA does not inhibit GSK-3β in vivo. VPA can inhibit GSK-3β-mediated phosphorylation of a CREB peptide in vitro. VPA may activate Wnt-dependent gene expression through inhibition of HDAC, which in turn leads to both increased expression of β-catenin and de-repression of Tcf/Lef (as well as activation of other HDAC-regulated genes). In vitro, VPA can stimulate glutamic acid decarboxylase, which is involved in GABA biosynthesis, and inhibit GABA transaminase, succinic semialdehyde dehydrogenase, and α-ketoglutarate dehydrogenase, enzymes involved in GABA degradation[1]. Valproic acid relieves HDAC-dependent transcriptional repression and causes hyperacetylation of histones in cultured cells and in vivo. VPA induces differentiation and/or apoptosis of carcinoma cells, PML-RAR-transformed hematopoietic progenitor cells and leukemic blasts from AML patients[2]. In addition to selectively inhibiting the catalytic activity of class I HDACs, VPA also induces proteasomal degradation of HDAC2[3].

Cell Data
Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID
HEK293 NXvQfYNYTnWwY4Tpc44h[XO|YYm= NYLXWIFqOSCvTR?= M323RWlv[3KnYYPlJIlvKHC{b4TlbY4h\Gm|dXzmbYRmKGm|b33ldoF{\SCuZY\lcEBqdiCKRVuyPVMh[2WubIOgZZQhOSCvTTDifUBqdW23bn;icI91 MnnQQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOTd3Nk[3N|IoRjF5NU[2O|MzRC:jPh?=
HEK293 MkXRSpVv[3Srb36gZZN{[Xl? NWnlfW5xOSCvTR?= NEew[ZVKdmO{ZXHz[UBqdiCJUmC3PEBxem:2ZXnuJIxmfmWuIHnuJGhGUzJ7MzDj[YxteyCjdDCxJI1OKGK7IHntcZVvd2Kub4S= MnvQQIEhfGG{Z3X0QUdg[myjbnunJIhz\WZ;J3j0eJB{Qi9xcIXicYVlNm6lYnmucoxuNm6raD7nc5YwOTd3Nk[3N|IoRjF5NU[2O|MzRC:jPh?=
A549 NYjWOYR2TnWwY4Tpc44h[XO|YYm= M4HyVFE2OCC3TR?= NETUOZUzPCCqcoO= M2qzUGlvcGmkaYTpc44hd2ZiaIXtZY4hUESDQzDpckBCPTR7IHPlcIx{KGG|c3Xzd4VlKGG|IHnuZ5Jm[XOnIHnuJIhqe3SxbnWtTFQh[WOndInsZZRqd25iYYSgNVUxKHWPIHHmeIVzKDJ2IHjyd{BjgSCZZYP0[ZJvKGKub4S= M2ixV|xiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzF6Mkm0PFQ1Lz5zOEK5OFg1PDxxYU6=
GM15850 NUPETGtuTnWwY4Tpc44h[XO|YYm= Mn7rOFAxKHWP NHzsemIyOiCqcoO= M3njRmlvcGmkaYTpc44hd2ZiSFTBR{BqdiCqdX3hckBIVTF3OEWwJINmdGy|IHHzd4V{e2WmIHHzJIlv[3KnYYPlJIlvKHSxdHHsJIFk\XS7bHH0[YQhcGm|dH;u[UBt\X[nbDDheEA1ODBidV2gZYZ1\XJiMUKgbJJ{KGK7IGfld5Rmem5iYnzveEBidmGueYPpdy=> M324b|xiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzF4OUKxN|Y4Lz5zNkmyNVM3PzxxYU6=
PC12 MWXGeY5kfGmxbjDhd5NigQ>? MUWxJJVO NFTibFgzPCCqcoO= NF\IRppKdmS3Y4Tpc44hd2ZiYYX0c5Bp[We7IHnuJJJifCC|dHHicIUhcW6mdXPpZoxmKFCFMUKgZ4VtdHNiZYjwdoV{e2mwZzDBOVNVKGGucHjhMZN6dnWlbHXpckBie3Onc4Pl[EBieyCDNUPUJIFteGijLYP5cpVkdGWrbjDjcIViemGwY3WgZZQhOSC3TTDh[pRmeiB{NDDodpMh[nliZHXud4l1d22ndILpZ{BidmGueYPpdy=> MXW8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8yQDN7MUm0PUc,OTh|OUG5OFk9N2F-
PC12 NV\t[YlETnWwY4Tpc44h[XO|YYm= NIjie4syKHWP MoTnPVYhcHK| MmPUTY5lfWO2aX;uJI9nKGG3dH;wbIFogSCrbjDyZZQhe3SjYnzlJIlv\HWlaXLs[UBRSzF{IHPlcIx{KGW6cILld5NqdmdiRVfGVE1JTFF5NDDhd5Nme3OnZDDhd{B{d2y3YnzlJGVITlBvSFTRO|Qh[2ynYYLhcoNmKGG2IEGgeW0h[W[2ZYKgPVYhcHK|IHL5JIRmdnOrdH;t[ZRzcWNiYX7hcJl{cXN? M2qwWFxiKHSjcnfleF0oZ2KuYX7rK{BpemWoPTfoeJRxezpxL4D1Zo1m\C6wY3LpMo5tdS6waXiu[493NzF6M{mxPVQ6Lz5zOEO5NVk1QTxxYU6=
SK-N-MC NXfzcYx6TnWwY4Tpc44h[XO|YYm= MYSxJI1O NHzzc2c1QCCqcoO= NGixOXhKdmS3Y4Tpc44hd2ZiYYX0c5Bp[We7IHnuJIh2dWGwIGPLMW4uVUNiY3XscJMh\XiycnXzd4lv\yCHR1\QMWhFWTd2IHHzd4V{e2WmIHHzJJJm\HWldHnvckBqdiCHR1\QMWhFWTd2IHHn[5Jm\2G2aX;uJIF1KDFidV2gZYZ1\XJiNEigbJJ{KGK7IHTlcpNqfG:vZYTybYMh[W6jbInzbZM> NUfy[FlWRGFidHHy[4V1RSehYnzhcosoKGi{ZX[9K4h1fHC|Oj:vdJVjdWWmLn7jZokvdmyvLn7pbE5od3ZxMUizPVE6PDlpPkG4N|kyQTR7PD;hQi=>
HL60 NXnMVHh7TnWwY4Tpc44h[XO|YYm= NGHPfHkyKG2P M3\OVFI1KGi{cx?= NW\lOZJzUW6qaXLpeIlwdiCxZjDISGFEKGmwIHj1cYFvKEiONkCgZ4VtdHNiYYPz[ZN{\WRiYYOgbY5kemWjc3WgbY4hcGm|dH;u[UBJOyCjY3X0fYxifGmxbjDheEAyKG2PIHHmeIVzKDJ2IHjyd{BjgSCZZYP0[ZJvKGKub4T0bY5oKG2ndHjv[C=> MXy8ZUB1[XKpZYS9K39jdGGwazegbJJm\j1paIT0dJM7Ny:ydXLt[YQvdmOkaT7ucI0vdmmqLnfvek8zPTNyNEi5Okc,OjV|MES4PVY9N2F-

... Click to View More Cell Line Experimental Data

Assay
Methods Test Index PMID
Western blot
acetyl-H4; 

PubMed: 20025549     


Changes in histone acetylation after valproic acid (VPA) exposure. LS174T and HCT116 cells were exposed to varying concentrations of VPA for 16 hours. Cellular protein extracts were prepared, as described in Materials and Methods, and analyzed by immunoblot assay with antibody against acetylated histone H4 (acetyl-H4). β-actin was included as a control to show equivalent protein loading.

Acetyl-H3; 

PubMed: 30387821     


Chidamide and VPA promoted an increase in the levels of histone H3 acetylation in human MM cells (RPMI-8226 and U266). 

p-IKKα/β / IKKα/β / NF-κB p65 / IκBα; 

PubMed: 30387821     


(C) Effects of VPA (1 mM) on the expression levels of NF-κB pathway-associated proteins in U266 cells. (D) Effects of VPA (0.5 mM) on the expression levels of NF-κB pathway-associated proteins in RPMI8226 cells. IκBα, inhibitor of NF-κB; IKK, IκB kinase; NF-κB, nuclear factor-κB; p, phosphorylated; VPA, valproic acid.

20025549 30387821
Growth inhibition assay
Cell viability; 

PubMed: 28101176     


Inhibitory effect of various doses of VPA on CAL27 cell proliferation. CAL27 cells were treated with 0.5, 1.0, 1.5, 2.0, 2.5 and 3.0 mm/l VPA for 24, 48, 72, 96 and 120 h, respectively, in vitro. Cell viability was determined using MTT assay and analyzed as the percentage of the absorbance value compared with control. *P<0.05 vs. 0.0 mmol/l; #P<0.05 vs. 0 h. Error bars represent the standard error of the mean. VPA, valproic acid.

28101176
In vivo Valproic acid (VPA) increases the level of the inhibitory neurotransmitter γ-aminobutyric acid (GABA), with acute administration causing a 15-45% increase in GABA in the brains of rodents[1]. VPA also inhibits tumor growth and metastasis in animal experiments. It is a well-tolerated drug even during long-term treatment[2].

Protocol

Cell Research:

[1]

- Collapse
  • Cell lines: Neuro2A cells
  • Concentrations: 0.5-5 mM
  • Incubation Time: 24 h
  • Method:

    Neuro2A cells are treated with VPA (0.5-5 mM) or with TSA (300 nm) for 24 h and then histones are isolated. Histone acetylation is assessed by immunoblotting with an antibody specific to acetylated histone H4.


    (Only for Reference)
Animal Research:

[2]

- Collapse
  • Animal Models: Rats
  • Dosages: 1.25 mM/kg
  • Administration: i.p.
    (Only for Reference)

Solubility (25°C)

Chemical Information

Molecular Weight 144.21
Formula

C8H16O2

Density 0.9 g/mL at 25 °C
CAS No. 99-66-1
Storage 2 years -20°C liquid
Synonyms 2-Propylvaleric Acid, Valproate
Smiles CCCC(CCC)C(=O)O

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Clinical Trial Information

NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT04671589 Not yet recruiting Drug: Meropenem Injection Drug Toxicity Mabaret Al-Asafara Hospitals June 2021 Phase 4
NCT04384172 Recruiting Device: Tibial e-stim|Device: Genital e-stim Female Sexual Dysfunction|Spinal Cord Injuries University of Michigan|International Society for the Study of Women''s Sexual Health November 11 2020 Not Applicable
NCT03962829 Terminated Drug: mCPP|Drug: Placebo oral tablet Eating Behavior|Obesity University of Birmingham|University Hospital Birmingham February 1 2019 Not Applicable
NCT03681158 Completed Drug: sodium valproate Epilepsy Sanofi October 5 2018 Phase 1

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Cell Lines Assay Type Concentration Incubation Time Formulation Activity Description PMID