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Santacruzamate A (CAY10683)

HDAC inhibitor, potent and selective CAS# 1477949-42-0

Santacruzamate A (CAY10683)

Catalog No. BCC5488----Order now to get a substantial discount!

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Chemical structure

Santacruzamate A (CAY10683)

3D structure

Chemical Properties of Santacruzamate A (CAY10683)

Cas No. 1477949-42-0 SDF Download SDF
PubChem ID 72946782 Appearance Powder
Formula C15H22N2O3 M.Wt 278.35
Type of Compound N/A Storage Desiccate at -20°C
Synonyms CAY-10683
Solubility DMSO : ≥ 100 mg/mL (359.26 mM)
*"≥" means soluble, but saturation unknown.
Chemical Name ethyl N-[4-oxo-4-(2-phenylethylamino)butyl]carbamate
SMILES CCOC(=O)NCCCC(=O)NCCC1=CC=CC=C1
Standard InChIKey HTOYBIILVCHURC-UHFFFAOYSA-N
Standard InChI InChI=1S/C15H22N2O3/c1-2-20-15(19)17-11-6-9-14(18)16-12-10-13-7-4-3-5-8-13/h3-5,7-8H,2,6,9-12H2,1H3,(H,16,18)(H,17,19)
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 Santacruzamate A (CAY10683)

DescriptionSantacruzamate A is a potent and selective histone deacetylase inhibitor.

References:
[1]. Pavlik CM, et al. Santacruzamate A, a potent and selective histone deacetylase inhibitor from the Panamanian marine cyanobacterium cf. Symploca sp. (PMID:24164245 PMCID:PMC3879121). Journal of Natural Products [2013, 76(11):2026-2033]

Santacruzamate A (CAY10683) Dilution Calculator

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Santacruzamate A (CAY10683) Molarity Calculator

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Preparing Stock Solutions of Santacruzamate A (CAY10683)

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.5926 mL 17.963 mL 35.926 mL 71.852 mL 89.815 mL
5 mM 0.7185 mL 3.5926 mL 7.1852 mL 14.3704 mL 17.963 mL
10 mM 0.3593 mL 1.7963 mL 3.5926 mL 7.1852 mL 8.9815 mL
50 mM 0.0719 mL 0.3593 mL 0.7185 mL 1.437 mL 1.7963 mL
100 mM 0.0359 mL 0.1796 mL 0.3593 mL 0.7185 mL 0.8981 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 Santacruzamate A (CAY10683)

Santacruzamate A (CAY10683) is a potent and selective inhibitor of histone deacetylase with IC50 values of 0.112 and 433 nM for HDAC2 and HDAC6, respectively [1].

Histone deacetylases (HDACs) 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.

Santacruzamate A (CAY10683) is a potent and selective HDAC inhibitor. Natural and synthetic santacruzamate A inhibited HDAC2 with IC50 values of 119 and 112 pM respectively and inhibited HDAC6 with IC50 values of 434 and 433 nM, respectively. Santacruzamate A was 700-fold more potent than SAHA for HDAC2. However, santacruzamate A inhibited HDAC4 with IC50 values of >1 µM. In HCT-116 colon carcinoma cells, natural and synthetic santacruzamate A inhibited cell growth with GI50 values of 29.4 and 28.3 µM, respectively. In HuT-78 cutaneous T-cell lymphoma cells, both inhibited cell growth with GI50 values of 1.4 and 1.3 µM, respectively [1].

Reference:
[1].  Pavlik CM, Wong CY, Ononye S, et al. Santacruzamate A, a potent and selective histone deacetylase inhibitor from the Panamanian marine cyanobacterium cf. Symploca sp. J Nat Prod, 2013, 76(11): 2026-2033.

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References on Santacruzamate A (CAY10683)

Pharmacological or transcriptional inhibition of both HDAC1 and 2 leads to cell cycle blockage and apoptosis via p21(Waf1/Cip1) and p19(INK4d) upregulation in hepatocellular carcinoma.[Pubmed:29484736]

Cell Prolif. 2018 Jun;51(3):e12447.

OBJECTIVES: Histone deacetylases (HDACs) are commonly dysregulated in cancer and represent promising therapeutic targets. However, global HDAC inhibitors have shown limited efficacy in the treatment of solid tumours, including hepatocellular carcinoma (HCC). In this study, we investigated the therapeutic effect of selectively inhibiting HDAC1 and 2 in HCC. METHODS: HDAC1 inhibitor Tacedinaline (CI994), HDAC2 inhibitor Santacruzamate A (CAY10683), HDAC1/2 common inhibitor Romidepsin (FK228) and global HDAC inhibitor Vorinostat (SAHA) were used to treat HCC cells. Cell cycle, apoptosis and the protein levels of CDKs and CDKNs were performed to evaluate HCC cell growth. Inhibition of HDAC1/2 by RNAi was further investigated. RESULTS: Combined inhibition of HDAC1/2 led to HCC cell morphology changes, growth inhibition, cell cycle blockage and apoptosis in vitro and suppressed the growth of subcutaneous HCC xenograft tumours in vivo. p21(Waf1/Cip1) and p19(INK)(4d) , which play roles in cell cycle blockage and apoptosis induction, were upregulated. Inhibition of HDAC1/2 by siRNA further demonstrated that HDAC1 and 2 cooperate in blocking the cell cycle and inducing apoptosis via p19(INK)(4d) and p21(Waf1/Cip1) upregulation. Finally, H3K18, H3K56 and H4K12 in the p19(INK)(4d) and p21(Waf1/Cip1) promoter regions were found to be targets of HDAC1/2. CONCLUSIONS: Pharmacological or transcriptional inhibition of HDAC1/2 increases p19(INK)(4d) and p21(Waf1/Cip1) expression, decreases CDK expression and arrests HCC growth. These results indicated a potential pharmacological mechanism of selective HDAC1/2 inhibitors in HCC therapy.

Description

Santacruzamate A (CAY-10683) is a potent and selective HDAC2 inhibitor with an IC50 of 119 pM.

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