T8552

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
• 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

Properties

• 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)

Description

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.[1]

Application

Trichostatin A (TSA) has been used during the production of cloned mouse embryos[2]. TSA has also been used as a histone deacetylase (HDAC) inhibitor in LNCaP human prostate cancer cells[3], as well as in MON and HeLa cells[4].

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.

Trichostatin A inhibits histone deacetylase at nanomolar concentrations; resultant histone hyperacetylation leads to chromatin relaxation and modulation of gene expression.

Features and Benefits

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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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves