Trichostatin A CAS: 58880-19-6
MF: C17H22N2O3
MW: 302.37

Trichostatin A (CAS 58880-19-6)

Trichostatin A | CAS 58880-19-6 is rated 5.0 out of 5 by 3.
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Alternate Names: Trichostatin A is also known as TSA.
Application: Trichostatin A is a potent and non-competitive reversible inhibitor of HDAC in LNCaP human prostate cancer cells, as well as in MON and HeLa cells.
CAS Number: 58880-19-6
Purity: ≥98%
Molecular Weight: 302.37
Molecular Formula: C17H22N2O3
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data (including water content).
DISCOUNT: Bulk orders of Chemicals totaling $1,000 or more receive a 5% discount.
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Trichostatin A (TSA) is a potent and non-competitive reversible inhibitor of HDAC (histone deacetylase) with a Ki of 3.4 nM. In HeLa cells, Trichostatin A blocked cell cycle progression at G1 and induced a 12-fold increase in intracellular levels of gelsolin. In cells latently infected with HIV-1, Trichostatin A induced the transcriptional activation of the HIV-1 promoter, which resulted in a marked increase in virus production. In NIH 3T3 cells, Trichostatin A induced reversion of oncogenic ras-transformed cells to a normal morphology. In Jurkat cells, Trichostatin A inhibited IL-2 gene expression and displayed immunosuppressive activity in a mouse model. Induces increased acetylation of GATA4, a cardiac-specific transcription factor and increases cardiac muscle cell differentiation. In normal rat fibroblasts, induced Friend cell differentiation and inhibited the G1 and G2 phases of the cell cycle. Trichostatin A is a useful tool for induction of hyperacetylation of cellular histones and for further elucidation of their role in gene expression. Trichostatin A is also known as TSA, and [R-(E,E)]-7-[4-(Dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide.


References

1. Yoshida, M., et al., 1990. Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A. The Journal of biological chemistry. 265(28): 17174-9. PMID: 2211619

2. Futamura, M., et al., 1995. Trichostatin A inhibits both ras-induced neurite outgrowth of PC12 cells and morphological transformation of NIH3T3 cells. Oncogene. 10(6): 1119-23. PMID: 7700637

3. Hoshikawa, Y., et al., 1994. Trichostatin A induces morphological changes and gelsolin expression by inhibiting histone deacetylase in human carcinoma cell lines. Experimental cell research. 214(1): 189-97. PMID: 8082721

4. Van Lint, C., et al., 1996. Transcriptional activation and chromatin remodeling of the HIV-1 promoter in response to histone acetylation. The EMBO journal. 15(5): 1112-20. PMID: 8605881

5. Takahashi, I., et al., 1996. Selective inhibition of IL-2 gene expression by trichostatin A, a potent inhibitor of mammalian histone deacetylase. The Journal of antibiotics. 49(5): 453-7. PMID: 8682722

6. Kawamura, Teruhisa., et al., 2005. Acetylation of GATA-4 is involved in the differentiation of embryonic stem cells into cardiac myocytes. The Journal of biological chemistry. 280(20): 19682-8. PMID: 15764815

7. Pan, Lina., et al., 2007. Histone deacetylase inhibitor trichostatin a potentiates doxorubicin-induced apoptosis by up-regulating PTEN expression. Cancer. 109(8): 1676-88. PMID: 17330857

Physical State :
Solid
Solubility :
Soluble in water (Partly Miscible), ethanol (2 mg/mL), DMSO (20 mg/mL), acetonitrile, DMF (30 mg/mL), and methanol.
Storage :
Store at -20° C
Melting Point :
144° C (dec.)
Density :
~1.1 g/cm3 (Predicted)
Refractive Index :
n20D 1.58
Optical Activity :
α20D 136, c = 0.3 in methanol
IC50 :
the activity of the HDAC1 : IC50 = 70 nM; IL-2 gene expression : IC50 = 73 nM (Jurkat cells)
Ki Data :
HDAC: Ki= 3.4 nM
pK Values :
pKa: 8.93, pKb: 1.96
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
RTECS :
MI5215000
PubChem CID :
Merck Index :
14: 9649
MDL Number :
MFCD03848392
SMILES :
CC(C=C(C)C=CC(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C

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Certificate of Analysis

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Trichostatin A (CAS 58880-19-6)  Product Citations

See how others have used Trichostatin A (CAS 58880-19-6). Click on the entry to view the PubMed entry .

Citations 1 to 10 of 29 total

PMID: # 33807238  Di Fede, E.|Ottaviano, E.|Grazioli, P.|Ceccarani, C.|Galeone, A.|Parodi, C.|Colombo, EA.|Bassanini, G.|Fazio, G.|Severgnini, M.|Milani, D.|Verduci, E.|Vaccari, T.|Massa, V.|Borghi, E.|Gervasini, C.| et al. 2021. Int J Mol Sci. 22:

PMID: # 31268348  2019. Am. J. Physiol. Lung Cell Mol. Physiol. 317: L332-L346.

PMID: # 27477692  Sauer, M.|Schuldner, M.|Hoffmann, N.|Cetintas, A.|Reiners, KS.|Shatnyeva, O.|Hallek, M.|Hansen, HP.|Gasser, S.|von Strandmann, EP.| et al. 2017. Oncogene. 36: 933-941.

PMID: # 28467410  Moon, BS.|Yun, HM.|Chang, WH.|Steele, BH.|Cai, M.|Choi, SH.|Lu, W.| et al. 2017. PLoS Biol. 15: e2001220.

PMID: # 28122578  Parasramka, M. et al. 2017. Mol. Cancer. 16: 22.

PMID: # 28869038  Gaspar, L.|Howald, C.|Popadin, K.|Maier, B.|Mauvoisin, D.|Moriggi, E.|Gutierrez-Arcelus, M.|Falconnet, E.|Borel, C.|Kunz, D.|Kramer, A.|Gachon, F.|Dermitzakis, ET.|Antonarakis, SE.|Brown, SA.| et al. 2017. Elife. 6:

PMID: # 28855586  2017. Sci Rep. 7: 9984.

PMID: # 27990351  Venkatesh, I. et al. 2016. Neuroepigenetics. 8: 19-26.

PMID: # 27345839  Serebryannyy, LA.|Cruz, CM.|de Lanerolle, P.| et al. 2016. Sci Rep. 6: 28460.

PMID: # 27529070  Chen, D. et al. 2016. Biomed Res Int. 2016: 5173205.

Citations 1 to 10 of 29 total

For how long is Trichostatin A stable when kept at 37° C, dissolved in DMSO?

Asked by: SCM4
While we do not have information regarding stability at 37°C in DMSO, the product is stable for 2 years at -20°C in powder form, for 2 weeks at 4°C when dissolved in DMSO, and for 6 months at -80°C when dissolved in DMSO.
Answered by: Tech Service 11
Date published: 2017-03-02
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Rated 5 out of 5 by from It has been demonstrated (PubMed ID 2211619) It has been demonstrated (PubMed ID 2211619) that Trichostatin A (TSA) causes a significant increase in histone acetylation in various mammalian cell lines: 3Y1, W3Y, DS19, HeLa and F9. -SCBT Publication Review
Date published: 2015-06-13
Rated 5 out of 5 by from One publication (PubMed ID 7700637) reports One publication (PubMed ID 7700637) reports that TSA does have an affect on an early stage in the NGF-signaling pathway, which is governed by ras. PC12, NIH/3T3 cells were used. -SCBT Publication Review
Date published: 2015-06-13
Rated 5 out of 5 by from An increase in expression of acetylated Ac An increase in expression of acetylated Ac-Histone H4 was observed after treatment with Trichostatin A, catalog # sc-3511 by Western Blot analysis. NIH/3T3 cells were treated with Trichostatin A prior to lysis. -SCBT QC
Date published: 2015-05-07
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