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T8552

Sigma-Aldrich

Trichostatin A

≥98% (HPLC), from Streptomyces sp.

Synonym(s):

TSA, [R-(E,E)]-7-[4-(Dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide

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About This Item

Empirical Formula (Hill Notation):
C17H22N2O3
CAS Number:
58880-19-6
Molecular Weight:
302.37
MDL number:
MFCD03848392
UNSPSC Code:
12352200
PubChem Substance ID:
24900542
NACRES:
NA.77

biological source

Streptomyces sp.

Quality Level

300

Assay

≥98% (HPLC)

form

powder

solubility

methanol: soluble 1.90-2.10 mg/mL, clear, colorless to faint yellow or tan
DMF: soluble
DMSO: soluble
H2O: insoluble
acetone: slightly soluble
acetonitrile: soluble
benzene: slightly soluble
chloroform: slightly soluble
ethanol: soluble
ethyl acetate: slightly soluble
lower alcohols: soluble

storage temp.

−20°C

SMILES string

C[C@H](\C=C(C)\C=C\C(=O)NO)C(=O)c1ccc(cc1)N(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+/t13-/m1/s1

InChI key

RTKIYFITIVXBLE-QEQCGCAPSA-N

Gene Information

human ... HDAC1(3065) , HDAC4(9759) , HDAC6(10013) , HDAC8(55869)
mouse ... ENSMUSG00000061062(15181)
rat ... Hdac7a(84582)

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General description

Trichostatin A (TSA) is a potent and specific inhibitor of histone deacetylase (HDAC) activity. It is an antifungal antibiotic with cytostatic and differentiating properties in mammalian cell culture.

Application

Trichostatin A (TSA) has been used during the production of cloned mouse embryos. TSA has also been used as a histone deacetylase (HDAC) inhibitor in LNCaP human prostate cancer cells, as well as in MON and HeLa cells.

Biochem/physiol Actions

Trichostatin A (TSA) inhibits histone deacetylase at nanomolar concentrations; resultant histone hyperacetylation leads to chromatin relaxation and modulation of gene expression. May be involved in cell cycle progression of several cell types, inducing cell growth arrest at both G and G/M phases; may induce apoptosis. Enhances the efficacy of anticancer agents that target DNA. Trichostatin A serves as an epigenetic modifier.

Features and Benefits

This compound is a featured product for Apoptosis and Gene Regulation research. Discover more featured Apoptosis and Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Preparation Note

Trichostatin A is soluble in methanol at 1.90 - 2.10 mg/ml and yields a clear, colorless to faint yellow/tan solution. It is also soluble in DMSO, DMF, acetonitrile, ethanol and lower alcohols. Trichostatin A is sparingly soluble in chloroform, ethyl acetate, acetone, and benzene. However, it is insoluble in water.

WGK

WGK 3

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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