Trichostatin A A potent and non-competitive reversible inhibitor of HDAC

Trichostatin A (CAS 58880-19-6)

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Sinónimo: TSA;[R-(E,E)]-7-[4-(Dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide
Solicitud: A potent and non-competitive reversible inhibitor of HDAC
Número de CAS: 58880-19-6
Pureza: ≥98%
Peso Molecular: 302.37
Fórmula Molecular: C17H22N2O3
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Trichostatin A (TSA) is a potent and non-competitive reversible inhibitor of histone deacetylases (HDAC) with a Ki of 3.4 nM. In HeLa cells, TSA blocked cell cycle progression at G1 and induced a 12-fold increase in intracellular levels of gelsolin. In cells latently infected with HIV-1, TSA induced the transcriptional activation of the HIV-1 promoter, which resulted in a marked increase in virus production. In NIH 3T3 cells, TSA induced reversion of oncogenic ras-transformed cells to a normal morphology. In Jurkat cells, TSA 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 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. A glucoside analog of Trichostatin A is also offered as Trichostatin C (sc-202369). Trichostatin A is an inhibitor of TERT, HDAC1, HDAC4 and HDAC6.


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

Estado de Materia :
Solid
Solubilidad :
Soluble in water (Partly Miscible), ethanol (2 mg/mL), DMSO (20 mg/mL), acetonitrile, DMF (30 mg/mL), and methanol.
ALMACENAMIENTO :
Store at -20° C
Punto de Fusión :
144° C (dec.)
Densidad :
~1.1 g/cm3 (Predicted)
Indice de Refracción :
n20D 1.58
Actividad Óptica :
α20/D 136°, c = 0.3 in methanol
IC50 :
the activity of the HDAC1 : IC50 = 70 nM; IL-2 gene expression : IC50 = 73 nM (Jurkat cells)
Datos Ki :
HDAC: Ki= 3.4 nM
Valores de pK :
pKa: 8.93, pKb: 1.96
Para Uso Exclusivo en Investigación. No está diseñado para uso en diagnosis o terapia.
WGK Alemania :
3
RTECS :
MI5215000
PubChem CID :
444732
Indice de Merck :
14: 9649
Número MDL :
MFCD03848392
SMILES :
C[C@H](/C=C(\\C)/C=C/C(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C

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Trichostatin A  Menciones del Producto

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Citaciones 1 a 10 de un total de 18

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

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

PMID: # 25936755  Alexanian, AR. et al. 2015. The international journal of biochemistry & cell biology. 64: 190-4.

PMID: # 25639887  Schmauss, C. et al. 2015. Sci Rep. 5: 8171.

PMID: # 25376115  Balliu, M. et al. 2014. Journal of cellular and molecular medicine.

PMID: # 23665234  Alexanian, AR. et al. 2013. The international journal of biochemistry & cell biology. 45: 1633-8.

PMID: # 24088168  Kuo, HY. et al. 2013. Anal. Chem. 85: 10635-42.

PMID: # 17892546  Segura-Pacheco, B. et al. 2007. Genet Vaccines Ther. 5: 10.

PMID: # 16818616  Qin, H. et al. 2006. Cancer Res. 66: 6477-6481.

PMID: # 15781658  Rahmani, M. et al. 2005. Cancer Res. 65(6): 2422-2432.

Citaciones 1 a 10 de un total de 18
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