Trichostatin A (TSA)

Alias: TSA; (+)-Trichostatin A; Trichostatin A; Trichostatin A (R-isomer)
Cat No.:V0258 Purity: ≥98%
Trichostatin A (also called TSA) is a novel, potent and specific inhibitor of histone deacetylase (HDAC) with potential anticancer activity.
Trichostatin A (TSA) Chemical Structure CAS No.: 58880-19-6
Product category: HDAC
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Trichostatin A (also called TSA) is a novel, potent and specific inhibitor of histone deacetylase (HDAC) with potential anticancer activity. Its IC50 value for HDAC inhibition is 1.8 nM. Additionally, at low nanomolar concentrations, it reversibly and noncompetivively inhibits HDAC in both fractionated cell nuclear extracts and cultured mammalian cells. It possesses cytostatic and differentiating qualities as an antifungal antibiotic agent. A study looking at TSA's impact on human breast cancer cell lines found that TSA significantly increased histone H4 hyperacetylation and inhibited the proliferation of breast carcinoma cell lines (IC50 124.4 ± 120.4 nM) compared to all other cell lines (IC50 2.4 ± 0.5 nM).

Biological Activity I Assay Protocols (From Reference)
Targets
HDAC ( IC50 = 1.8 nM )
ln Vitro

Trichostatin A has a mean IC50 of 124.4 nM (range, 26.4-308.1 nM) and is more effective against ERα-expressing cell lines than ERα-negative cell lines in inhibiting the growth of eight breast carcinoma cell lines: MCF-7, T-47D, ZR-75-1, BT-474, MDA-MB-231, MDA-MB-453, CAL 51, and SK-BR-3. With a mean IC50 of 2.4 nM (range, 0.6-2.6 nM), trichomestatin A inhibits HDAC activity in a manner consistent across all breast cancer cell lines, causing pronounced hyperacetylation of histone H4.[1] Trichostatin A inhibits these HDACs to a similar degree with IC50 values of 6 nM, 38 nM, and 8.6 nM, respectively, in contrast to Trapoxin (TPX) and Chlamydocin, which potently inhibit HDAC1 or HDAC4 but not HDAC6.[2] When MIA PaCa-2 cells are treated with 100 ng/mL of trichostatin A, they express transforming growth factor β type II receptor (TβRII). This is achieved by bringing p300 and PCAF together in a Sp1-NF-Y HDAC complex, which binds the TβRII promoter's DNA element. This process is linked to the simultaneous acetylation of Sp1 and a general reduction in the complex's HDAC content.[4]

ln Vivo
In the rat mammary carcinoma model induced by the N-methyl-N-nitrosourea carcinogen, 4 weeks of administration of Trichostatin A at a dose of 0.5 mg/kg shows strong antitumor activity without detectable toxicity at doses as high as 5 mg/kg.[1] In nontransgenic and spinal muscular atrophy (SMA) model mice, a single intraperitoneal dose of 10 mg/kg Trichostatin A causes modest increases in survival motor neuron (SMN) gene expression as well as elevated levels of acetylated H3 and H4 histones. In SMA model mice, administration of 10 mg/kg/day of Trichostatin A improves survival, attenuates weight loss, and improves motor behavior.[5]
Enzyme Assay
Each of the following breast cancer cell lines is used to prepare total cellular extracts: MCF-7, T-47D, ZR-75-1, BT-474, MDA-MB-231, MDA-MB-453, CAL 51, or SK-BR-3. A 20 μL crude cell extract (~2.5 ×105 cells) is incubated for 60 minutes at 25 °C with 1 μL (~1.5 × 106 cpm) of [3H]acetyl-labeled histone H4 peptide substrate (NH2-terminal residues 2–20) that has been acetylated with [3H]acetic acid, sodium salt (3.7 GBq/mmol) by an in vitro incorporation method. These conditions are followed by different concentrations of Trichostatin A in 0.1% (v/v) ethanol or 0.1% (v/v) ethanol as vehicle control. Scintillation counting is used to quantify the released [3H]acetate after each 200 μL reaction is extracted with 600 μL of ethyl acetate and quenched with 50 μL of 1 M HCl/0.16 M acetic acid. In order to fit inhibition data to the appropriate dose-response curve, IC50 values are graphically determined using nonlinear regression.
Cell Assay
For 72 hours, cells are cultivated in a 96-well plate at a density of 1×103 cells per well using 100 μL of full-dose DMEM, either with or without the HDAC inhibitor Trichostatin A. With a CCK-8 cell proliferation kit, the WST-8 assay is used to quantify cytotoxicity. A microplate reader is used to measure the absorbance at 450 nm. Three separate experiments are conducted, and each experiment is run in triplicate.
Animal Protocol
Rats: For four weeks, twelve rats are randomly assigned to receive 500 μg/kg Trichostatin A in 50 μL DMSO or 50 μL DMSO as the vehicle control by subcutaneous injection twice a week. Subsequent studies involve a randomization of 30 rats to receive daily subcutaneous injections of 500 μg/kg Trichostatin A in 50 μL DMSO, or 50 μL DMSO as the vehicle control, every day for 4 weeks. Each animal's body mass, estimated tumor volumes, and weekly tumor measurements are documented. Once the 4-week study period is over, the animals are sacrificed, and any palpable tumors are removed and instantly frozen in liquid nitrogen. Tumors that are less than 2 cm in diameter or that are ulcerating are removed from the study.
References

[1]. Clin Cancer Res . 2001 Apr;7(4):971-6.

[2]. Proc Natl Acad Sci U S A . 2001 Jan 2;98(1):87-92.

[3]. Cancer Res . 2003 Nov 1;63(21):7291-300.

[4]. J Biol Chem . 2005 Mar 18;280(11):10047-54.

[5]. J Clin Invest . 2007 Mar;117(3):659-71.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C17H22N2O3
Molecular Weight
302.4
Exact Mass
302.16
Elemental Analysis
C, 67.53; H, 7.33; N, 9.26; O, 15.87
CAS #
58880-19-6
Appearance
Solid powder
SMILES
C[C@H](/C=C(\C)/C=C/C(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C
InChi Key
RTKIYFITIVXBLE-QEQCGCAPSA-N
InChi Code
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
Chemical Name
(2E,4E,6R)-7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide
Synonyms
TSA; (+)-Trichostatin A; Trichostatin A; Trichostatin A (R-isomer)
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: 23~50 mg/mL (76.1~165.4 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Solubility (In Vivo)
1% DMSO+30% polyethylene glycol+1% Tween 80, pH 4: 6mg/mL
 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.3069 mL 16.5344 mL 33.0688 mL
5 mM 0.6614 mL 3.3069 mL 6.6138 mL
10 mM 0.3307 mL 1.6534 mL 3.3069 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

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Biological Data
  • Trichostatin A (TSA)

  • Trichostatin A (TSA)

    Trichostatin A (TSA)

  • Trichostatin A (TSA)
    TSA increases survival, attenuates weight loss, and enhances motor behavior of SMA mice.J Clin Invest.2007 Mar;117(3):659-71.
    Trichostatin A (TSA)
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