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MilliporeSigma

647925

Sigma-Aldrich

Trichostatin A

from Streptomyces sp., ≥98% (HPLC), lyophilized solid, HDAC inhibitor, Calbiochem®

Synonym(s):

Trichostatin A, Streptomyces sp., 4,6-Dimethyl-7-[ p-dimethylaminophenyl]-7-oxahepta-2,4-dienohydroxamic Acid, TSA, HDAC Inhibitor IX

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About This Item

Empirical Formula (Hill Notation):
C17H22N2O3
CAS Number:
Molecular Weight:
302.37
MDL number:
UNSPSC Code:
12352200
NACRES:
NA.77
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Product Name

Trichostatin A, Streptomyces sp., A potent and reversible, cell-permeable inhibitor of histone deacetylase.

Quality Level

description

RTECS - MI5215000

assay

≥98% (HPLC)

form

lyophilized solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

color

off-white

solubility

ethanol: 1 mg/mL
DMSO: 20 mg/mL
methanol: soluble

shipped in

ambient

storage temp.

−20°C

SMILES string

N(O)C(=O)\C=C\C(=C\C(C)C(=O)c1ccc(cc1)N(C)C)\C

InChI

1S/C17H22N2O3/c1-12(5-10-16(20)18-22)11-13(2)17(21)14-6-8-15(9-7-14)19(3)4/h5-11,13,22H,1-4H3,(H,18,20)/b10-5+,12-11+

InChI key

RTKIYFITIVXBLE-WKWSCTOISA-N

General description

A potent and reversible inhibitor of histone deacetylase. Blocks cell cycle progression at the G1 phase in HeLa cells and induces a 12-fold increase in intracellular levels of gelsolin. Induces reversion of oncogenic ras-tranformed NIH 3T3 cells to a normal morphology. Inhibits IL-2 gene expression (IC50 = 73 nM) in Jurkat cells and shows immunosuppressive activity in a mouse model. IC50 = 6 nM for HDAC1; 38 nM for HDAC4, and 8.6 nM for HDAC6A.
A potent and reversible, cell-permeable inhibitor of histone deacetylase. Blocks cell cycle progression at the G1 phase in HeLa cells and induces a 12-fold increase in intracellular levels of gelsolin. Induces reversion of oncogenic ras-transformed NIH/3T3 cells to a normal morphology. Inhibits IL-2 gene expression (IC50 = 73 nM) in Jurkat cells and shows immunosuppressive activity in a mouse model. Down-regulates p57kip2 in Hep 3Bcells. IC50 = 6 nM for HDAC1; 38 nM for HDAC4, and 8.6 nM for HDAC6A. 10 mM (500 µg/165 µl) solution of Trichostatin A, Streptomyces sp. (Cat. No. 647926) in DMSO is also available.

Biochem/physiol Actions

Cell permeable: yes
Primary Target
histone deactylase
Product does not compete with ATP.
Reversible: yes
Target IC50: 73 nM inhibiting IL-2 gene expressionin Jurkat cells

Preparation Note

Following reconstitution in DMSO, aliquot and freeze (-20°C). Following reconstitution in ethanol, refrigerate (4°C). DMSO stock solutions are stable for up to 6 months at -20°C. Ethanol stock solutions are stable for up to 3 months at 4°C.

Other Notes

Furumai, R., et al. 2001. Proc. Natl. Acad. Sci. USA98, 87.
Gray, S.G. and Ekstrom, T.J. 1998. Biochem. Biophys. Res. Commun. 245, 423.
Takahashi, I., et al. 1996. J. Antibiot. 49, 453.
Taunton, J., et al. 1996. Science 272, 408.
Futamura, M., et al. 1995. Oncogene 10, 1119.
Hoshikawa, Y., et al. 1994. Exp. Cell Res. 214, 189.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Harmful (C)

Storage Class

10 - Combustible liquids

wgk_germany

WGK 3


Certificates of Analysis (COA)

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Gilles Flouriot et al.
Journal of molecular biology, 432(7), 2253-2270 (2020-02-28)
The baseline level of transcription, which is variable and difficult to quantify, seriously complicates the normalization of comparative transcriptomic data, but its biological importance remains unappreciated. We show that this currently neglected ingredient is essential for controlling gene network multistability
Xudong Sun et al.
Journal of dairy science, 103(9), 8388-8397 (2020-07-06)
Exogenous molecules derived from catabolic states (e.g., fatty acids, β-hydroxybutyrate) during periods of stress such as the periparturient period or pathogen challenges [e.g., lipopolysaccharide (LPS)] can trigger an inflammatory response in tissues such as the liver and the mammary gland.
Mariana Bresque et al.
The Journal of biological chemistry, 298(3), 101711-101711 (2022-02-13)
Acute and chronic inflammations are key homeostatic events in health and disease. Sirtuins (SIRTs), a family of NAD-dependent protein deacylases, play a pivotal role in the regulation of these inflammatory responses. Indeed, SIRTs have anti-inflammatory effects through a myriad of

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