TCS HDAC6 20b

Selective HDAC6 inhibitor CAS# 956154-63-5

TCS HDAC6 20b

Catalog No. BCC2427----Order now to get a substantial discount!

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TCS HDAC6 20b: 5mg $115 In Stock
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Chemical structure

TCS HDAC6 20b

3D structure

Chemical Properties of TCS HDAC6 20b

Cas No. 956154-63-5 SDF Download SDF
PubChem ID 23636017 Appearance Powder
Formula C26H44N2O4S M.Wt 480.7
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 100 mM in DMSO and to 100 mM in ethanol
Chemical Name S-[(6S)-7-(1-adamantylamino)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-7-oxoheptyl] 2-methylpropanethioate
SMILES CC(C)C(=O)SCCCCCC(C(=O)NC12CC3CC(C1)CC(C3)C2)NC(=O)OC(C)(C)C
Standard InChIKey DQZMLPMCOMRJOR-MOVGKWKRSA-N
Standard InChI InChI=1S/C26H44N2O4S/c1-17(2)23(30)33-10-8-6-7-9-21(27-24(31)32-25(3,4)5)22(29)28-26-14-18-11-19(15-26)13-20(12-18)16-26/h17-21H,6-16H2,1-5H3,(H,27,31)(H,28,29)/t18?,19?,20?,21-,26?/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of TCS HDAC6 20b

DescriptionSelective inhibitor of histone deacetylase 6 (HDAC6). Inhibits HCT116 growth in combination with taxol. Also inhibits growth of MCF-7 cells stimulated by estrogen.

TCS HDAC6 20b Dilution Calculator

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TCS HDAC6 20b Molarity Calculator

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Preparing Stock Solutions of TCS HDAC6 20b

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.0803 mL 10.4015 mL 20.803 mL 41.606 mL 52.0075 mL
5 mM 0.4161 mL 2.0803 mL 4.1606 mL 8.3212 mL 10.4015 mL
10 mM 0.208 mL 1.0401 mL 2.0803 mL 4.1606 mL 5.2007 mL
50 mM 0.0416 mL 0.208 mL 0.4161 mL 0.8321 mL 1.0401 mL
100 mM 0.0208 mL 0.104 mL 0.208 mL 0.4161 mL 0.5201 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on TCS HDAC6 20b

TCS HDAC6 20b is a potent and selective inhibitor of histone deacetylase 6 (HADC6) [1].

Histone deacetylases (HADC) are a series of enzymes that remove acetyl groups from an ε-N-acetyl lysine amino acid on a histone and make the histones to wrap the DNA more tightly, which prevent transcription. Mutation of HADC6 is associated with Alzheimer's disease.

In HCT116 cells, TCS HDAC6 20b increased ɑ-tubulin acetylation in a dose-dependent way without a significant increase in acetylated histone H4, which indicated that TCS HDAC6 20b selectively inhibit HDAC6 [1]. Treatment human colon cancer HCT116 cells with TCS HDAC6 20b (5 μM) and paclitaxel (PTX) (0.03 μM) inhibited cells growth by approximately 50%, which suggested that TCS HDAC6 20b has potential as drug candidates when used with PTX. In estrogen receptor ɑ (ERɑ) -positive breast cancer MCF-7 cells, treatment with 17β-estradiol (E2) (1 nM) increased cell growth by 40%, which was significantly blocked by TCS HDAC6 20b [2].

References:
[1].  Suzuki T, Kouketsu A, Itoh Y, et al. Highly potent and selective histone deacetylase 6 inhibitors designed based on a small-molecular substrate. J Med Chem, 2006, 49(16): 4809-4812.
[2].  Itoh Y, Suzuki T, Kouketsu A, et al. Design, synthesis, structure--selectivity relationship, and effect on human cancer cells of a novel series of histone deacetylase 6-selective inhibitors. J Med Chem, 2007, 50(22): 5425-5438.

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References on TCS HDAC6 20b

[Inhibition effect of N-acetyl-seryl-aspartyl-lysyl-proline on myofibroblast differentiation by regulating acetylated tubulin alpha in silicotic rat model].[Pubmed:26887263]

Zhonghua Lao Dong Wei Sheng Zhi Ye Bing Za Zhi. 2015 Nov;33(11):816-21.

OBJECTIVE: To explore the inhibition effect and mechanism of N-acetyl-seryl-aspartyl-lysyl-proline (Ac-SDKP)on myofibroblast differentiation via regulating acetylated tubulin alpha (Ac-Tub alpha)in vivo and in vitro. METHODS: Silicotic model were made by SiO2 douched and divided into 6 groups as follows: control (4w, 8w)group, silicotic model (4w, 8w)group and post-or pre-treatment by Ac-SDKP group. Pulmonary fibroblasts were divided into 5 groups: (1) control; (2) Ang II; (3) Ang II+Ac-SDKP; (4) Ang II+Valsartan; (5) Ang II+TCS histone deacetylase (HDAC)6 20b. The localization of Ac-Tub alpha and alpha-smooth muscle actin (SMA) were observed by immunohistochemical (IHC) and immunofluorescence staining. The protein levels of Ac-Tub alpha, alpha-SMA, collagen type I (col I) and HDAC6 were measured by western blot. RESULTS: In silicotic nodules and interstitial fibrosis area, positive expression of alpha-SMA, a classical marker of myofibroblast, was ob-served by IHC, accompanied with absence expression of Ac-Tub alpha. Furthermore, Ac-SDKP post-treatment could attenuate the levels of col I, alpha-SMA and HDAC6 to 48.39%, 52.63% and 70.18% compared with the silicotic 8w group respectively. And in Ac-SDKP pre-treatment group, compared with the silicotic 8w group, these protein levels were decreased to 32.26%, 64.91% and 54.39% respectively (P<0.05). The up-regulation of Ac-Tub alpha was found in Ac-SDKP post-and pre-treatment and increased to 3.00 and 2.90 folds compared with the silicotic 8w group. Compared with control group, the levels of alpha-SMA, HDAC6 and col I in Ang II group were up-regulated to 1.66, 3.56 and 4.00 folds accompanied with down-regulation of Ac-Tub by 44.44% (P<0.05). Pre-treatment with Valsartan, TCS HDAC6 20b or Ac-SDKP could inhibited all this changes induced by Ang II in vitro. CONCLUSION: Ac-SDKP can inhibit the myofibroblast differentiation and collagen deposition via sup-press HDAC6 and up-regulate the expression of Ac-Tub alpha in vivo and in vitro.

Design, synthesis, structure--selectivity relationship, and effect on human cancer cells of a novel series of histone deacetylase 6-selective inhibitors.[Pubmed:17929798]

J Med Chem. 2007 Nov 1;50(22):5425-38.

To uncover novel histone deacetylase 6 (HDAC6)-selective inhibitors and to elucidate the structural requirements for their inhibitory activity, we designed and prepared a series of thiolate analogues based on the structure of an HDAC6-selective substrate and evaluated their properties by Western blotting and enzyme assays. Several thiolate analogues were found to be potent and selective HDAC6 inhibitors. Study of the structure-selectivity relationship revealed that the presence of a bulky alkyl group and tert-butylcarbamate group in these compounds is important for HDAC6-selective inhibition. Compounds 16b and 20b, the most selective and active compounds in this series, exerted a synergistic inhibition of cancer cell growth in combination with paclitaxel. They also blocked the growth of estrogen receptor alpha-positive breast cancer MCF-7 cells that had been treated with estrogen. These findings suggested that HDAC6-selective inhibitors have potential as anticancer agents.

Description

Selective HDAC6 inhibitor

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