Trichostatin A
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| Category | Antibiotics |
| Catalog number | BBF-03423 |
| CAS | 58880-19-6 |
| Molecular Weight | 302.37 |
| Molecular Formula | C17H22N2O3 |
| Purity | 98% |
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Description
Trichostatin A, also known as TSA, is an HDAC inhibitor. TSA inhibits the eukaryotic cell cycle during the beginning of the growth stage. TSA can be used to alter gene expression by interfering with the removal of acetyl groups from histones (histone deacetylases, HDAC) and therefore altering the ability of DNA transcription factors to access the DNA molecules inside chromatin. It is a member of a larger class of histone deacetylase inhibitors (HDIs or HDACIs) that have a broad spectrum of epigenetic activities.
Specification
| Related CAS | 58880-19-6 (R-isomer) 122292-85-7 (S-isomer) |
| Synonyms | TSA; Antibiotic A-300; 7-(4-(Dimethylamino)phenyl)-N-hydroxy-4,6-dimethyl-7-oxo-2,4-heptadienamide |
| Storage | Store at-20°C |
| IUPAC Name | (2E,4E,6R)-7-[4-(dimethylamino)phenyl]-N-hydroxy-4,6-dimethyl-7-oxohepta-2,4-dienamide |
| Canonical SMILES | CC(C=C(C)C=CC(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C |
| InChI | 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 |
| Source | Streptomyces sp. |
Properties
| Appearance | White Solid Powder |
| Application | Reprogramming |
| Antibiotic Activity Spectrum | fungi |
| Melting Point | 144°C (dec.) |
| Density | 1.139 g/cm3 |
| Solubility | Soluble in ethanol, methanol, DMF or DMSO. Limited water solubility. |
Reference Reading
1.Trichostatin A Protects Liver against Septic Injury through Inhibiting Toll-Like Receptor Signaling.
Kim SJ1, Park JS1, Lee DW1, Lee SM1. Biomol Ther (Seoul). 2016 Apr 11. doi: 10.4062/biomolther.2015.176. [Epub ahead of print]
Sepsis, a serious clinical problem, is characterized by a systemic inflammatory response to infection and leads to organ failure. Toll-like receptor (TLR) signaling is intimately implicated in hyper-inflammatory responses and tissue injury during sepsis. Histone deacetylase (HDAC) inhibitors have been reported to exhibit anti-inflammatory properties. The aim of this study was to investigate the hepatoprotective mechanisms of trichostatin A (TSA), a HDAC inhibitor, associated with TLR signaling pathway during sepsis. The anti-inflammatory properties of TSA were assayed in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Polymicrobial sepsis was induced in mice by cecal ligation and puncture (CLP), a clinically relevant model of sepsis. The mice were intraperitoneally received TSA (1, 2 or 5 mg/kg) 30 min before CLP. The serum and liver samples were collected 6 and 24-h after CLP. TSA inhibited the increased production of tumor necrosis factor (TNF)-α and interleukin (IL)-6 in LPS-stimulated RAW264.
2.Inhibition of Histone Deacetylases Enhances the Osteogenic Differentiation of Human Periodontal Ligament Cells.
Huynh NC1,2, Everts V3, Pavasant P1,4, Ampornaramveth RS2. J Cell Biochem. 2016 Jun;117(6):1384-95. doi: 10.1002/jcb.25429. Epub 2015 Nov 26.
One of the characteristics of periodontal ligament (PDL) cells is their plasticity. Yet, the underlying mechanisms responsible for this phenomenon are unknown. One possible mechanism might be related to epigenetics, since histone deacetylases (HDACs) have been shown to play a role in osteoblast differentiation. This study was aimed to investigate the role of HDACs in osteogenic differentiation of human PDL (hPDL) cells. HDAC inhibitor trichostatin A (TSA) had no effect on cell viability as was assessed by MTT assay. Osteogenic and adipogenic differentiation was analyzed by gene expression, ALP activity and mineral deposition. Western blotting was used to investigate the effect of TSA on histone acetylation and protein expression. In the presence of the HDAC inhibitor osteogenic differentiation was induced; osteoblast-related gene expression was increased significantly. ALP activity and mineral nodule formation were also enhanced. Inhibition of HDACs did not induce differentiation into the adipocyte lineage.
3.The histone deacetylase inhibitor trichostatin A suppresses murine innate allergic inflammation by blocking group 2 innate lymphoid cell (ILC2) activation.
Toki S1, Goleniewska K1, Reiss S1, Zhou W1, Newcomb DC2, Bloodworth MH3, Stier MT3, Boyd KL3, Polosukhin VV1, Subramaniam S4, Peebles RS Jr2. Thorax. 2016 Apr 12. pii: thoraxjnl-2015-207728. doi: 10.1136/thoraxjnl-2015-207728. [Epub ahead of print]
BACKGROUND: Group 2 innate lymphoid cells (ILC2) are an important source of the type 2 cytokines interleukin (IL)-5 and IL-13 that are critical to the allergic airway phenotype. Previous studies reported that histone deacetylase (HDAC) inhibition by trichostatin A (TSA) downregulated adaptive allergic immune responses; however, the effect of HDAC inhibition on the early innate allergic immune response is unknown. Therefore, we investigated the effect of TSA on innate airway inflammation mediated by ILC2 activation.
4.Absence of nucleolus formation in raccoon dog-porcine interspecies somatic cell nuclear transfer embryos results in embryonic developmental failure.
Jeon Y1, Nam YH, Cheong SA, Kwak SS, Lee E, Hyun SH. J Reprod Dev. 2016 Apr 10. [Epub ahead of print]
Interspecies somatic cell nuclear transfer (iSCNT) can be a solution for preservation of endangered species that have limited oocytes. It has been reported that blastocyst production by iSCNT is successful even if the genetic distances between donors and recipients are large. In particular, domestic pig oocytes can support the development of canine to porcine iSCNT embryos. Therefore, we examined whether porcine oocytes may be suitable recipient oocytes for Korean raccoon dog iSCNT. We investigated the effects of trichostatin A (TSA) treatment on iSCNT embryo developmental patterns and nucleolus formation. Enucleated porcine oocytes were fused with raccoon dog fibroblasts by electrofusion and cleavage, and blastocyst development and nucleolus formation were evaluated. To our knowledge, this study is the first in which raccoon dog iSCNT was performed using porcine oocytes; we found that 68.5% of 158 iSCNT embryos had the ability to cleave.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
