Trichostatin A (synthetic)

AdipoGen Life Sciences
Product Code: AG-CN2-0523
CodeSizePrice
AG-CN2-0523-M0011 mg£90.00
Quantity:
AG-CN2-0523-M0055 mg£250.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
Ambient
Storage:
+4°C

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
TSA; A300; R-(E,E)-7-(4-(Dimethylamino)phenyl)-N-hydroxy- 4,6-dimethyl-7-oxo-2,4-heptadienamide
Appearance:
Off-white solid.
CAS:
58880-19-6
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
After reconstitution, prepare aliquots and store at -20°C.
Hazards:
H302, H312, H315, H319, H332, H335
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
InChiKey:
RTKIYFITIVXBLE-QEQCGCAPSA-N
Long Description:
Chemical. CAS: 58880-19-6. Formula: C17H22N2O3. MW: 302.4. Synthetic. Originally isolated from Streptomyces hygroscopicus.. Antibiotic, antifungal and antiprotozoal agent. Potent and reversible, cell permeable inhibitor of class I and II histone deacetylases (HDACs). Anticancer, immunosuppressive, antifibrogenic compound. Induces apoptosis and cell growth arrest at both G1 and G2/M phases. Also inactivates mitotic spindle checkpoint. Enhances the efficacy of anticancer agents that target DNA. Downregulates DNA methyltransferase DNMT1 and affects DNA methylation. Telomerase inhibitor. Smooth muscle cell proliferation inhibitor. Anti-inflammatory and inhibits osteoclastogenesis and bone resorption. Promotes either self-renewal or differentiation of embryonic stem cells.
MDL:
MFCD03848392
Molecular Formula:
C17H22N2O3
Molecular Weight:
302.4
Package Type:
Vial
Precautions:
P261, P271, P280, P301, P312, P304, P340, P302, P352
Product Description:
Antibiotic, antifungal and antiprotozoal agent. Potent and reversible, cell permeable inhibitor of class I and II histone deacetylases (HDACs). Anticancer, immunosuppressive, antifibrogenic compound. Induces apoptosis and cell growth arrest at both G1 and G2/M phases. Also inactivates mitotic spindle checkpoint. Enhances the efficacy of anticancer agents that target DNA. Downregulates DNA methyltransferase DNMT1 and affects DNA methylation. Telomerase inhibitor. Smooth muscle cell proliferation inhibitor. Anti-inflammatory and inhibits osteoclastogenesis and bone resorption. Promotes either self-renewal or differentiation of embryonic stem cells.
Purity:
>95% (HPLC)
Signal word:
Warning
SMILES:
C[C@H](C=C(/C)C=CC(=O)NO)C(=O)C1=CC=C(C=C1)N(C)C
Solubility Chemicals:
Soluble in DMSO, ethanol, methanol, dimethyl formamide, acetonitrile or chloroform. Insoluble in water or hexane.
Source / Host:
Synthetic. Originally isolated from Streptomyces hygroscopicus.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 3 years after receipt when stored at -20°C.

References

A new antifungal antibiotic, trichostatin: N. Tsuji, et al.; J. Antibiot. (Tokyo) 29, 1 (1976) | Screening for new antitrichomonal substances of microbial origin and antitrichomonal activity of trichostatin A: K. Otoguro, et al.; J. Antibiot. (Tokyo) 41, 461 (1988) | Potent and specific inhibition of mammalian histone deacetylase both in vivo and in vitro by trichostatin A: M. Yoshida, et al.; J. Biol. Chem. 265, 17174 (1990) | Selective inhibition of IL-2 gene expression by trichostatin A, a potent inhibitor of mammalian histone deacetylase: I. Takahashi, et al.; J. Antibiot. (Tokyo) 49, 453 (1996) | Trichostatin A modulates expression of p21waf1/cip1, Bcl-xL, ID1, ID2, ID3, CRAB2, GATA-2, hsp86 and TFIID/TAFII31 mRNA in human lung adenocarcinoma cells: B. Eickhoff, et al.; Biol. Chem. 381, 107 (2000) | Trichostatin A is a histone deacetylase inhibitor with potent antitumor activity against breast cancer in vivo: D.M. Vigushin, et al.; Clin. Cancer Res. 7, 971 (2001) | Trichostatin A, a histone deacetylase inhibitor, suppresses collagen synthesis and prevents TGF-beta(1)-induced fibrogenesis in skin fibroblasts: K. Rombouts, et al.; Exp. Cell Res. 278, 184 (2002) | The histone deacetylase inhibitor Trichostatin A modulates CD4+ T cell responses: J.M. Moreira, et al.; BMC Cancer 3, 30 (2003) | Mechanism of histone deacetylase inhibitor Trichostatin A induced apoptosis in human osteosarcoma cells: M.S. Roh, et al.; Apoptosis 9, 583 (2004) | Cell growth inhibition and gene expression induced by the histone deacetylase inhibitor, trichostatin A, on human hepatoma cells: T. Chiba, et al.; Oncology 66, 481 (2004) | A histone deacetylase inhibitor, trichostatin A, enhances radiosensitivity by abrogating G2/M arrest in human carcinoma cells: I.A. Kim, et al.; Cancer Res. Treat. 37, 122 (2005) | Mitotic spindle checkpoint inactivation by trichostatin a defines a mechanism for increasing cancer cell killing by microtubule-disrupting agents: M. Dowling, et al.; Cancer Biol. Ther. 4, 197 (2005) | Trichostatin A, an inhibitor of histone deacetylase, inhibits smooth muscle cell proliferation via induction of p21(WAF1): H. Okamoto, et al.; J. Atheroscler. Thromb. 13, 183 (2006) | Induction of apoptosis and inhibition of telomerase activity by trichostatin A, a histone deacetylase inhibitor, in human leukemic U937 cells: H.J. Woo, et al.; Exp. Mol. Pathol. 82, 77 (2007) | Trichostatin A down-regulate DNA methyltransferase 1 in Jurkat T cells: R. Januchowski, et al.; Cancer Lett. 246, 313 (2007) | Trichostatin A causes p53 to switch oxidative-damaged colorectal cancer cells from cell cycle arrest into apoptosis: C. Habold, et al.; J. Cell Mol. Med. 12, 607 (2008) | Anti-inflammatory effect of Trichostatin-A on murine bone marrow-derived macrophages: S.B. Han & J.K. Lee; Arch. Pharm. Res. 32, 613 (2009) | Trichostatin A inhibits osteoclastogenesis and bone resorption by suppressing the induction of c-Fos by RANKL: H.N. Kim, et al.; Eur. J. Pharmacol. 623, 22 (2009) | Trichostatin A inhibits expression of cathepsins in experimental osteoarthritis: W.P. Chen, et al.; Rheumatol. Int. 31, 1325 (2011) | Histone Deacetylase Inhibitors in Cell Pluripotency, Differentiation, and Reprogramming: A. Kretsovali, et al.; Stem Cells Int. 2012, 1 (2012) | HDAC inhibitors increase NRF2-signaling in tumour cells and blunt the efficacy of co-adminstered cytotoxic agents: M. McMahon, et al.; PLoS One 9, e114055 (2014)

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