Tubastatin A
| Code | Size | Price |
|---|
| AG-CR1-3900-M010 | 10 mg | £65.00 |
Quantity:
Prices exclude any Taxes / VAT
Overview
Regulatory Status: RUO
Shipping:
-20°C
Storage:
+4°C (short term) -20°C (long term).
Documents
Further Information
Alternate Names/Synonyms:
N-hydroxy-4-[(1,2,3,4-tetrahydro-2-methyl-5H-pyrido[4,3-b]indol-5-yl)methyl] benzamide
Appearance:
Off-white solid.
CAS:
1252003-15-8
EClass:
32160000
Form (Short):
solid
Handling Advice:
Keep cool and dry.Protect from light.
InChi:
InChI=1S/C20H21N3O2/c1-22-11-10-19-17(13-22)16-4-2-3-5-18(16)23(19)12-14-6-8-15(9-7-14)20(24)21-25/h2-9,25H,10-13H2,1H3,(H,21,24)
InChiKey:
GOVYBPLHWIEHEJ-UHFFFAOYSA-N
Long Description:
Chemical. CAS: 1252003-15-8. Formula: C20H21N3O2. MW: 335.4. Cell permeable potent and selective class IIb histone deacetylase 6 (HDAC6) inhibitor (IC50=15nM, >1000-fold selective against other HDACs and 60-fold for HDAC8). Neuroprotective. Effectively prevents neuronal cell death (by >95% at 10µM) upon oxidative stress induction by HCA and selectively induces cellular alpha-tubulin, but not histone H4, hyperacetylation (2.5 to 5µM) in primary rat cortical neuron cultures. Improves cognition in Alzheimer's disease transgenic mice. Exhibits cardioprotective and anticancer chemotherapeutic activities. Reduces tumor growth and cell proliferation and induces cell cycle arrest in G1. Inhibits TNFalpha (IC50=272nM) and IL-6 (IC50=712nM) in LPS-stimulated human THP-1 macrophages and displays anti-inflammatory activity in animal models. Antileishmanial. HDAC6 deacetylates tubulin, HSP90 and the core histones (H2A, H2B, H3, H4). Histone deacetylases act via the formation of large multiprotein complexes. HDAC6 plays an important role in microtubule-dependent cell motility, transcriptional regulation, degradation of misfolded proteins and cell cycle and is involved in autophagy, inflammation, cancer and neurodegeneration.
MDL:
MFCD18071463
Molecular Formula:
C20H21N3O2
Molecular Weight:
335.4
Package Type:
Vial
Product Description:
Cell permeable potent and selective class IIb histone deacetylase 6 (HDAC6) inhibitor (IC50=15nM, >1000-fold selective against other HDACs and 60-fold for HDAC8). Neuroprotective. Effectively prevents neuronal cell death (by >95% at 10µM) upon oxidative stress induction by HCA and selectively induces cellular alpha-tubulin, but not histone H4, hyperacetylation (2.5 to 5µM) in primary rat cortical neuron cultures. Improves cognition in Alzheimer's disease transgenic mice. Exhibits cardioprotective and anticancer chemotherapeutic activities. Reduces tumor growth and cell proliferation and induces cell cycle arrest in G1. Inhibits TNFalpha (IC50=272nM) and IL-6 (IC50=712nM) in LPS-stimulated human THP-1 macrophages and displays anti-inflammatory activity in animal models. Antileishmanial. HDAC6 deacetylates tubulin, HSP90 and the core histones (H2A, H2B, H3, H4). Histone deacetylases act via the formation of large multiprotein complexes. HDAC6 plays an important role in microtubule-dependent cell motility, transcriptional regulation, degradation of misfolded proteins and cell cycle and is involved in autophagy, inflammation, cancer and neurodegeneration.
Purity:
>98% (HPLC)
SMILES:
CN1CCC2=C(C1)C1=CC=CC=C1N2CC1=CC=C(C=C1)C(=O)NO
Solubility Chemicals:
Soluble in DMSO.
Transportation:
Non-hazardous
UNSPSC Category:
Biochemical Reagents
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.
References
Rational design and simple chemistry yield a superior, neuroprotective HDAC6 inhibitor, tubastatin A: K.V. Butler, et al.; JACS 132, 10842 (2010) | Histone deacetylase 6 and heat shock protein 90 control the functions of Foxp3(+) T-regulatory cells: E.F. de Zoeten, et al.; Mol. Cell Biol. 31, 2066 (2011) | Second-generation histone deacetylase 6 inhibitors enhance the immunosuppressive effects of Foxp3+ T-regulatory cells: J.H. Kalin, et al.; J. Med. Chem. 55, 639 (2012) | Selective histone deacetylase 6 inhibitors bearing substituted urea linkers inhibit melanoma cell growth: J.A. Bergman, et al.; J. Med. Chem. 55, 9891 (2012) | HDAC6 inhibition restores ciliary expression and decreases tumor growth: S.A. Gradilone, et al.; Cancer Res. 73, 2259 (2013) | Tubastatin, a selective histone deacetylase 6 inhibitor shows anti-inflammatory and anti-rheumatic effects: S. Vishwakarma, et al.; Int. Immunopharmacol. 16, 72 (2013) | HDAC6 inhibition results in tau acetylation and modulates tau phosphorylation and degradation in oligodendrocytes: M. Noack, et al.; Glia 62, 535 (2014) | Histone deacetylase 6 inhibition improves memory and reduces total tau levels in a mouse model of tau deposition: M.L. Selenica, et al.; Alzheimers Res. Ther. 6, 12 (2014) | Tubastatin A/ACY-1215 improves cognition in Alzheimer's disease transgenic mice: L. Zhang, et al.; J. Alzheimers Dis. 41, 1193 (2014) | Selective inhibitor of histone deacetylase 6 (tubastatin A) suppresses proliferation of hepatitis C virus replicon in culture of human hepatocytes: M.V. Kozlov, et al.; Biochem. 79, 637 (2014) | The antileishmanial activity of isoforms 6- and 8-selective histone deacetylase inhibitors: Q. Sodji, et al.; Bioorg. Med. Chem. Lett. 24, 4826 (2014) | Targeting histone deacetylase 6 mediates a dual anti-melanoma effect: Enhanced antitumor immunity and impaired cell proliferation: K.V. Woan, et al.; Mol. Oncol. 9, 1447 (2015)