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Reagentes e instrumentos para imunologia, biologia celular e biologia molecular.

Valproic acid [99-66-1]

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Referência HY-10585-5g

Tamanho : 5g

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Marca : MedChemExpress

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Description

Valproic acid (VPA) is an orally active HDAC inhibitor, with IC₅₀ in the range of 0.5 and 2 mM. Valproic acid inhibits HDAC1 (IC₅₀, 400 μM), and induces proteasomal degradation of HDAC2. Valproic acid activates Notch1 signaling and inhibits proliferation in small cell lung cancer (SCLC) cells. Valproic acid is used in the epilepsy, bipolar disorder, metabolic disease, HIV infection and prevention of migraine headaches^[1]^[2]^[3]^[4]^[5]^[6]^[7].

IC₅₀ & Target^[5]^[6]

HDAC1

400 μM (IC₅₀)

HDAC

0.5-2 mM (IC₅₀)

HDAC2

Autophagy

Mitophagy

Cellular Effect

Cell Line	Type	Value	Description	References
A498	IC₅₀	2141.25 μM Compound: VPA	Antiproliferative activity against human A498 cells assessed as cell growth inhibition incubated for 24 hrs by MTT assay Antiproliferative activity against human A498 cells assessed as cell growth inhibition incubated for 24 hrs by MTT assay	[PMID: 34111829]
A549	IC₅₀	>1000 nM Compound: VPA	Antiproliferative activity against human A549 cells after 3 days Antiproliferative activity against human A549 cells after 3 days	[PMID: 18294844]
A549	IC₅₀	>1 μM Compound: VPA	Antiproliferative activity against human A549 cells after 3 days Antiproliferative activity against human A549 cells after 3 days	[PMID: 18294844]
Caco-2	IC₅₀	>1000 μM Compound: VPA	Growth inhibition of human Caco2 cells after 48 hrs by MTT assay Growth inhibition of human Caco2 cells after 48 hrs by MTT assay	[PMID: 25304896]
Caco-2	IC₅₀	>1 mM Compound: VPA	Growth inhibition of human Caco2 cells after 48 hrs by MTT assay Growth inhibition of human Caco2 cells after 48 hrs by MTT assay	[PMID: 25304896]
CAKI-1	IC₅₀	2825.37 μM Compound: VPA	Antiproliferative activity against human CAKI-1 cells assessed as cell growth inhibition incubated for 24 hrs by MTT assay Antiproliferative activity against human CAKI-1 cells assessed as cell growth inhibition incubated for 24 hrs by MTT assay	[PMID: 34111829]
HCT-116	IC₅₀	4.66 μM Compound: Valproic acid	Antiproliferative activity against human HCT-116 cells measured after 24 hrs by MTT assay Antiproliferative activity against human HCT-116 cells measured after 24 hrs by MTT assay	[PMID: 37875056]
HeLa	IC₅₀	1 mM Compound: VPA	Growth inhibition of human HeLa cells after 48 hrs by MTT assay Growth inhibition of human HeLa cells after 48 hrs by MTT assay	[PMID: 25304896]
HeLa	IC₅₀	1000 μM Compound: VPA	Growth inhibition of human HeLa cells after 48 hrs by MTT assay Growth inhibition of human HeLa cells after 48 hrs by MTT assay	[PMID: 25304896]
HeLa	IC₅₀	4.66 μM Compound: Valproic acid	Antiproliferative activity against human HeLa cells measured after 24 hrs by MTT assay Antiproliferative activity against human HeLa cells measured after 24 hrs by MTT assay	[PMID: 37875056]
HeLa	IC₅₀	7.24 mM Compound: Valproic acid	Inhibition of HDAC in human Hela cells nuclear extracts by fluorimetric assay Inhibition of HDAC in human Hela cells nuclear extracts by fluorimetric assay	[PMID: 19520580]
HeLa	IC₅₀	995 μM Compound: VPA	Inhibition of human HDAC in HeLa cells Inhibition of human HDAC in HeLa cells	[PMID: 18294844]
Hepatocyte	EC₅₀	11.73 μM Compound: 4	Reduction of propionyl-CoA in human hepatocytes derived from propionic acidemia patient pretreated for 30 mins followed by 13C-isoleucine addition and measured after 1 hr by MS/MS analysis Reduction of propionyl-CoA in human hepatocytes derived from propionic acidemia patient pretreated for 30 mins followed by 13C-isoleucine addition and measured after 1 hr by MS/MS analysis	[PMID: 33848153]
HepG2	IC₅₀	4.66 μM Compound: Valproic acid	Antiproliferative activity against human HepG2 cells measured after 24 hrs by MTT assay Antiproliferative activity against human HepG2 cells measured after 24 hrs by MTT assay	[PMID: 37875056]
HL-60	IC₅₀	1.7 mM Compound: VPA	Cytotoxicity against human HL60 cells after 24 to 48 hrs by trypan blue dye exclusion method Cytotoxicity against human HL60 cells after 24 to 48 hrs by trypan blue dye exclusion method	[PMID: 25304896]
HL-60	IC₅₀	1700 μM Compound: VPA	Growth inhibition of human HL60 cells after 48 hrs by MTT assay Growth inhibition of human HL60 cells after 48 hrs by MTT assay	[PMID: 25304896]
HT-29	IC₅₀	>1000 μM Compound: VPA	Growth inhibition of human HT-29 cells after 48 hrs by MTT assay Growth inhibition of human HT-29 cells after 48 hrs by MTT assay	[PMID: 25304896]
HT-29	IC₅₀	>1 mM Compound: VPA	Growth inhibition of human HT-29 cells after 48 hrs by MTT assay Growth inhibition of human HT-29 cells after 48 hrs by MTT assay	[PMID: 25304896]
HuT78	IC₅₀	1800 μM Compound: VPA	Growth inhibition of human HUT78 cells after 48 hrs by MTT assay Growth inhibition of human HUT78 cells after 48 hrs by MTT assay	[PMID: 25304896]
HUVEC	IC₅₀	1.5 mM Compound: valproic acid	Inhibition of LPS-induced tissue factor activity in HUVEC preincubated for 4 hrs assessed after 4 hrs of LPS challenge by one stage clotting assay Inhibition of LPS-induced tissue factor activity in HUVEC preincubated for 4 hrs assessed after 4 hrs of LPS challenge by one stage clotting assay	[PMID: 17675290]
HUVEC	IC₅₀	2 mM Compound: valproic acid	Inhibition of TNF-alpha-induced tissue factor activity in HUVEC preincubated for 4 hrs assessed after 4 hrs of TNFalpha challenge by one stage clotting assay Inhibition of TNF-alpha-induced tissue factor activity in HUVEC preincubated for 4 hrs assessed after 4 hrs of TNFalpha challenge by one stage clotting assay	[PMID: 17675290]
K562	IC₅₀	>1000 μM Compound: VPA	Growth inhibition of human K562 cells after 48 hrs by MTT assay Growth inhibition of human K562 cells after 48 hrs by MTT assay	[PMID: 25304896]
K562	IC₅₀	>1 mM Compound: VPA	Growth inhibition of human K562 cells after 48 hrs by MTT assay Growth inhibition of human K562 cells after 48 hrs by MTT assay	[PMID: 25304896]
MCF7	IC₅₀	0.23 mM Compound: 7	Antiproliferative activity against human MCF7 cells assessed as cell growth inhibition Antiproliferative activity against human MCF7 cells assessed as cell growth inhibition	[PMID: 34826681]
MCF7	IC₅₀	230 μM Compound: VPA	Growth inhibition of human MCF7 cells after 48 hrs by MTT assay Growth inhibition of human MCF7 cells after 48 hrs by MTT assay	[PMID: 25304896]
MCF7	IC₅₀	4.66 μM Compound: Valproic acid	Antiproliferative activity against human MCF7 cells measured after 24 hrs by MTT assay Antiproliferative activity against human MCF7 cells measured after 24 hrs by MTT assay	[PMID: 37875056]
Sf21	IC₅₀	>1000 μM Compound: Valproate	Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake Inhibition of human BSEP expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake	[PMID: 21965623]
Sf21	IC₅₀	>1000 μM Compound: Valproate	Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake Inhibition of Sprague-Dawley rat Bsep expressed in plasma membrane vesicles of Sf21 cells assessed as inhibition of ATP-dependent [3H]taurocholate uptake	[PMID: 21965623]

In Vitro

Valproic acid (VPA) (0-15 mM; 24 and 72 h) inhibits Hela cell growth in a dose- and time- dependent manner^[1].
Valproic acid (10 mM; 24 h) significantly attenuates the activities of total, cytosol and nuclear HDACs^[1].
Valproic acid (0-15 mM; 24 h) induces a G1 phase arrest at 1–3 mM and a G2/M phase arrest at 10 mM, and increases the percentage of sub-G1 cells in HeLa cells. Valproic acid also induces necrosis, apoptosis and lactate dehydrogenase (LDH) release^[1].
Valproic acid (0-20 mM; 24 h) activates Tcf/Lef-dependent transcription and synergizes with lithium^[2].
Valproic acid (0-5 mM; 0-18 h) increases β-catenin levels in Neuro2A cells^[2].
Valproic acid (0-2 mM; 0-24 h) stimulates phosphorylation of AMPK and ACC in hepatocytes^[5].
Valproic acid (0-10 mM; 2 days) induces Notch1 signaling and morphologic differentiation, suppresses production of NE tumor markers in SCLC cells^[6].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Viability Assay^[1]

Cell Line:	HeLa cells
Concentration:	0, 1, 3, 5, 10 and 15 mM
Incubation Time:	24 and 72 h
Result:	HeLa cell growth was dose- and time-dependently decreased with an IC₅₀ of ~10 and 4 mM at 24 and 72 h.

Western Blot Analysis^[1]^[2]^[5]

Cell Line:	HeLa cells, Neuro2A cells or primary mouse hepatocytes
Concentration:	10 mM (HeLa); 0, 2, and 5 mM (Neuro2A); 0.2, 0.4, 0.8, 1.2 and 2 mM (hepatocytes)
Incubation Time:	10 mM (HeLa); 0, 2, and 5 mM (Neuro2A); 0.2, 0.4, 0.8, 1.2 and 2 Mm (hepatocytes)
Result:	Increased the form of acetylated histone 3. Reduced PARP, induced cleavage PARP, and downregulated Bcl-2. Increased β-catenin levels. Increased the phosphorylation of AMPK and ACC.

Cell Cycle Analysis^[1]

Cell Line:	HeLa cells
Concentration:	0, 1, 3, 5, 10 and 15 mM
Incubation Time:	24 h
Result:	Induced a G1 phase arrest at 1–3 mM, significantly induced a G2/M phase arrest at 10 mM, and increased the percentage of sub-G1 cells in HeLa cells in a dose-dependent manner at 24 h.

In Vivo

Valproic acid (VPA) (500 mg/kg; i.p.; daily for 12 days) inhibits tumor angiogenesis in mice transplanted with Kasumi-1 cells^[3].
Valproic acid (350 mg/kg; i.p.; once) enhances social behavior in rats^[4].
Valproic acid (0.26% (w/v); p.o. via drinking water; 14 days) decreases liver mass, hepatic fat accumulation, and serum glucose in obese mice without hepatotoxicity^[5].
The solution of this product, when dissolved in Saline, is acidic. Before administration to animals, the pH must be adjusted to neutral (pH=7) with sodium hydroxide (e.g., 1M NaOH).

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model:	Female BALB/c nude mice, Kasumi-1 tumor model^[3]
Dosage:	500 mg/kg
Administration:	Intraperitoneal injection, daily for 12 days
Result:	Inhibited tumor growth and tumor angiogenesis. Inhibited the mRNA and protein expression of VEGF, VEGFR2 and bFGF. Inhibited HDAC activity and increased acetylation of histone H3. Enhanced the accumulation of hyperacetylated histone H3 on VEGF promoters.

Animal Model:	Timed-pregnant Long Evans rats^[4]
Dosage:	350 mg/kg
Administration:	Intraperitoneal injection, once
Result:	Demonstrated more social investigation and play fighting than control animals.

Animal Model:	Obese phenotype of ob/ob mice^[5]
Dosage:	0.26% (w/v)
Administration:	Oral via drinking water, 14 days
Result:	Revealed a marked reduction in the accumulation of fats in the liver as compared with the untreated mice, significantly decreased liver mass to body mass, decreased serum triglyceride concentrations, and did not induce hepatotoxicity.

Masse moléculaire

144.21

Formule

C₈H₁₆O₂

CAS No.

99-66-1

Appearance

Liquid (Density: 0.92 g/cm³)

Color

Colorless to light yellow

SMILES

CCCC(CCC)C(O)=O

Structure Classification

Ketones, Aldehydes, Acids

Initial Source

Endogenous metabolite

Livraison

Room temperature in continental US; may vary elsewhere.

Stockage

Store at room temperature 3 years

In solvent	-80°C	2 years
	-20°C	1 year

Solvant et solubilité

In Vitro:

DMSO : 100 mg/mL (693.43 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

0.1 M NaOH : 5 mg/mL (34.67 mM; Need ultrasonic)

H₂O : 2.5 mg/mL (17.34 mM; ultrasonic and warming and heat to 60°C)

Preparing
Stock Solutions

Concentration Solvent Mass	1 mg	5 mg	10 mg

1 mM	6.9343 mL	34.6717 mL	69.3433 mL
5 mM	1.3869 mL	6.9343 mL	13.8687 mL
10 mM	0.6934 mL	3.4672 mL	6.9343 mL

View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 1 year; -20°C, 6 months. When stored at -80°C, please use it within 1 year. When stored at -20°C, please use it within 6 months.

* Note: If you choose water as the stock solution, please dilute it to the working solution, then filter and sterilize it with a 0.22 μm filter before use.

Select the appropriate dissolution method based on your experimental animal and administration route.

For the following dissolution methods, please ensure to first prepare a clear stock solution using an In Vitro approach and then sequentially add co-solvents:
To ensure reliable experimental results, the clarified stock solution can be appropriately stored based on storage conditions. As for the working solution for in vivo experiments, it is recommended to prepare freshly and use it on the same day.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: 10% DMSO 40% PEG300 5% Tween-80 45% Saline
Solubility: ≥ 2.5 mg/mL (17.34 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 400 μL PEG300, and mix evenly; then add 50 μL Tween-80 and mix evenly; then add 450 μL Saline to adjust the volume to 1 mL.
Preparation of Saline: Dissolve 0.9 g sodium chloride in ddH₂O and dilute to 100 mL to obtain a clear Saline solution.
Protocol 2

Add each solvent one by one: 10% DMSO 90% (20% SBE-β-CD in Saline)
Solubility: ≥ 2.5 mg/mL (17.34 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown).
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL 20% SBE-β-CD in Saline, and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C, storage for one week): 2 g SBE-β-CD powder is dissolved in 10 mL Saline, completely dissolve until clear.
Protocol 3

Add each solvent one by one: 10% DMSO 90% Corn Oil
Solubility: ≥ 2.5 mg/mL (17.34 mM); Clear solution

This protocol yields a clear solution of ≥ 2.5 mg/mL (saturation unknown). If the continuous dosing period exceeds half a month, please choose this protocol carefully.
Taking 1 mL working solution as an example, add 100 μL DMSO stock solution (25.0 mg/mL) to 900 μL Corn oil, and mix evenly.

For the following dissolution methods, please prepare the working solution directly. It is recommended to prepare fresh solutions and use them promptly within a short period of time.
The percentages shown for the solvents indicate their volumetric ratio in the final prepared solution. If precipitation or phase separation occurs during preparation, heat and/or sonication can be used to aid dissolution.

Protocol 1

Add each solvent one by one: PBS
Solubility: 2 mg/mL (13.87 mM); Clear solution; Need ultrasonic
Protocol 2

Add each solvent one by one: Saline
Solubility: 50 mg/mL (346.72 mM); Suspended solution; Need ultrasonic and warming and heat to 60°C
Protocol 3

Add each solvent one by one: 50% PEG300 50% Saline
Solubility: 25 mg/mL (173.36 mM); Clear solution; Need ultrasonic
Protocol 4

Add each solvent one by one: 0.5% CMC/saline water
Solubility: 20 mg/mL (138.69 mM); Suspended solution; Need ultrasonic

Pureté et documentation

Purity: 99.89%

Fiche technique (283 KB) SDS (557 KB)

COA (245 KB) HNMR (220 KB) MS (71 KB) GC (262 KB)

Instruction de manipulation (2659 KB)

Références

[1]. Han BR, et al. Valproic acid inhibits the growth of HeLa cervical cancer cells via caspase-dependent apoptosis. Oncol Rep. 2013 Dec;30(6):2999-3005. [Content Brief]

[2]. Valproic acid, et al. Histone deacetylase is a direct target of valproic acid, a potent anticonvulsant, mood stabilizer, and teratogen. J Biol Chem. 2001 Sep 28;276(39):36734-41. [Content Brief]

[3]. Zhang ZH, et al. Valproic acid inhibits tumor angiogenesis in mice transplanted with Kasumi 1 leukemia cells. Mol Med Rep. 2013 Nov 28. [Content Brief]

[4]. Cohen OS, et al. Acute prenatal exposure to a moderate dose of valproic acid increases social behavior and alters gene expression in rats. Int J Dev Neurosci. 2013 Dec;31(8):740-50. [Content Brief]

[5]. Avery LB, et al. Valproic Acid Is a Novel Activator of AMP-Activated Protein Kinase and Decreases Liver Mass, Hepatic Fat Accumulation, and Serum Glucose in Obese Mice. Mol Pharmacol. 2014 Jan;85(1):1-10. [Content Brief]

[6]. Platta CS, et al. Valproic acid induces Notch1 signaling in small cell lung cancer cells. J Surg Res. 2008 Jul;148(1):31-7. [Content Brief]

[7]. Routy JP, et al. Valproic acid in association with highly active antiretroviral therapy for reducing systemic HIV-1 reservoirs: results from a multicentre randomized clinical study. HIV Med. 2012 May;13(5):291-6. [Content Brief]

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