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Merck

T8552

Trichostatin A

From Streptomyces sp., ≥98% (HPLC), Histone deacetylase (HDAC) inhibitor, powder

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
UNSPSC Code:
12352200
PubChem Substance ID:
24900542
NACRES:
NA.77
MDL number:
MFCD03848392

Product Name

Trichostatin A, ≥98% (HPLC), from Streptomyces sp.

SMILES string

C[C@H](\C=C(C)\C=C\C(=O)NO)C(=O)c1ccc(cc1)N(C)C

InChI key

RTKIYFITIVXBLE-QEQCGCAPSA-N

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

biological source

Streptomyces sp.

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

Quality Level

300

Gene Information

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

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

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.

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.

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.

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
0000492907
0000492907
0000396985
0000396985
0000382194

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  1. Which document(s) contains shelf-life or expiration date information for a given product?

    If available for a given product, the recommended re-test date or the expiration date can be found on the Certificate of Analysis.

  2. How do I get lot-specific information or a Certificate of Analysis?

    The lot specific COA document can be found by entering the lot number above under the "Documents" section.

  3. What is the shelf life of Product No. T8552, Trichostatin A?

    The  product has a recommended retest date (similar to a shelf life date) of 2 years.  The actual recommended retest date for each lot is on the Certificate of Analysis located at our website.

  4. How can I solubilize Product T8552, Trichostatin A?

    Trichostatin A is soluble in dimethyl sulfoxide (DMSO) and in ethanol, each at 1 mg/mL. It is also soluble in methanol at 2 mg/mL. It is insoluble in water.  Additional solubility information can be found on the data sheet on our website.

  5. How should solutions of Trichostatin A, Product T8552, be stored?

    Solutions at a concentration of 2 mg/mL in DMSO can be divided into aliquots and stored frozen at -20°C.

  6. Has Product T8552, Trichostatin A been endotoxin tested?

    Product T8552 has not been tested for any endotoxin levels, nor has it been cell culture tested.

  7. At what concentration can Product T8552, Trichostatin A, be used as an inhibitor of histone deacetylase?

    Trichostatin A inhibits histone deacetylase at nanomolar concentrations. Additional information may be found in the literature references cited on the product detail page for T8552.

  8. How do I find price and availability?

    There are several ways to find pricing and availability for our products. Once you log onto our website, you will find the price and availability displayed on the product detail page. You can contact any of our Customer Sales and Service offices to receive a quote.  USA customers:  1-800-325-3010 or view local office numbers.

  9. What is the Department of Transportation shipping information for this product?

    Transportation information can be found in Section 14 of the product's (M)SDS.To access the shipping information for this material, use the link on the product detail page for the product. 

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D M Vigushin et al.
Clinical cancer research : an official journal of the American Association for Cancer Research, 7(4), 971-976 (2001-04-20)
Trichostatin A (TSA), an antifungal antibiotic with cytostatic and differentiating properties in mammalian cell culture, is a potent and specific inhibitor of histone deacetylase (HDAC) activity. The purpose of this study was to evaluate the antiproliferative and HDAC inhibitory activity
Cheng Liu et al.
Cancer research, 67(6), 2626-2631 (2007-03-17)
Recent evidence has accumulated that the dynamic histone methylation mediated by histone methyltransferases and demethylases plays key roles in regulation of chromatin structure and transcription. In the present study, we show that SET and MYND domain-containing protein 3 (SMYD3), a
Teena Haritwal et al.
International journal of radiation biology, 95(4), 443-451 (2018-10-12)
Ionizing radiation is known to damage male reproductive system. Current study aims to study the mitigative effects of trichostatin A on male reproductive system and accompanying metabolite changes in testicular tissue of mice. Eight-week-old male C57 Bl/6J mice were exposed
Satoshi Kishigami et al.
The Journal of reproduction and development, 53(6), 1207-1215 (2007-10-17)
Without using sperm, artificial oocyte activation is essential for current assisted reproductive technologies, particularly somatic cell nuclear transfer and round spermatid injection. Strontium has been widely used as an activator of oocytes especially in the mouse, by which efficient oocyte
M Yoshida et al.
BioEssays : news and reviews in molecular, cellular and developmental biology, 17(5), 423-430 (1995-05-01)
Reversible acetylation at the epsilon-amino group of lysines located at the conserved domain of core histones is supposed to play an important role in the regulation of chromatin structure and its transcriptional activity. One promising strategy for analyzing the precise
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