NSC 3852

HDAC inhibitor CAS# 3565-26-2

NSC 3852

Catalog No. BCC2423----Order now to get a substantial discount!

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Chemical structure

NSC 3852

3D structure

Chemical Properties of NSC 3852

Cas No. 3565-26-2 SDF Download SDF
PubChem ID 19103 Appearance Powder
Formula C9H6N2O2 M.Wt 174.16
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 100 mM in DMSO and to 10 mM in ethanol
Chemical Name 5-nitrosoquinolin-8-ol
SMILES C1=CC2=C(C=CC(=C2N=C1)O)N=O
Standard InChIKey RZWRYPGAUIOOMK-UHFFFAOYSA-N
Standard InChI InChI=1S/C9H6N2O2/c12-8-4-3-7(11-13)6-2-1-5-10-9(6)8/h1-5,12H
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 NSC 3852

DescriptionHistone deacetylase inhibitor. Causes cell differentiation and antiproliferative activity in MCF-7 human breast cancer cells in vitro and displays antitumor activity in vivo.

NSC 3852 Dilution Calculator

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NSC 3852 Molarity Calculator

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Preparing Stock Solutions of NSC 3852

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 5.7418 mL 28.7092 mL 57.4185 mL 114.8369 mL 143.5462 mL
5 mM 1.1484 mL 5.7418 mL 11.4837 mL 22.9674 mL 28.7092 mL
10 mM 0.5742 mL 2.8709 mL 5.7418 mL 11.4837 mL 14.3546 mL
50 mM 0.1148 mL 0.5742 mL 1.1484 mL 2.2967 mL 2.8709 mL
100 mM 0.0574 mL 0.2871 mL 0.5742 mL 1.1484 mL 1.4355 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 NSC 3852

NSC 3852 is a potent inhibitor of histone deacetylase [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.

In MCF-7 human breast cancer cells, NSC 3852 induced the formation of the DMPO-OH adduct, which was catalyzed by superoxide dismutase. The result suggested that NSC 3852 induced generation of superoxide and reactive oxygen species (ROS), which produced DNA damage and induced apoptosis. Also, NSC 3852 resulted in cells accumulation in G0, hypophosphorylated retinoblastoma protein(Rb) and reduced E2F1 and Myc protein [1]. In HS68 cell, NSC 3852 inhibited Toxoplasma gondii tachyzoite propagation with EC50 value of 78.6 nM. Also, in human red blood cells, NSC 3852 inhibited Plasmodium falciparum growth with EC50 value of 1.3 μM. NSC 3852 inhibited Toxoplasma gondii tachyzoite propagation by involving redox reactions [2].

References:
[1].  Martirosyan A, Leonard S, Shi X, et al. Actions of a histone deacetylase inhibitor NSC3852 (5-nitroso-8-quinolinol) link reactive oxygen species to cell differentiation and apoptosis in MCF-7 human mammary tumor cells. J Pharmacol Exp Ther, 2006, 317(2): 546-552.
[2].  Strobl JS, Seibert CW, Li Y, et al. Inhibition of Toxoplasma gondii and Plasmodium falciparum infections in vitro by NSC3852, a redox active antiproliferative and tumor cell differentiation agent. J Parasitol, 2009, 95(1): 215-223.

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References on NSC 3852

Inhibition of Toxoplasma gondii and Plasmodium falciparum infections in vitro by NSC3852, a redox active antiproliferative and tumor cell differentiation agent.[Pubmed:18837587]

J Parasitol. 2009 Feb;95(1):215-23.

We searched the National Cancer Institute (NCI) compound library for structures related to the antitumor quinoline NSC3852 (5-nitroso-8-quinolinol) and used a computer algorithm to predict the antiprotozoan activity for each of 13 structures. Half of these compounds inhibited Toxoplasma gondii tachyzoite propagation in human fibroblasts at < or =1 microM. The active compounds comprise a series of low-molecular-weight quinolines bearing nitrogen substituents in the ring-5 position. NSC3852 (EC(50) 80 nM) and NSC74949 (EC(50) 646 nM) were the most potent. NSC3852 also inhibited Plasmodium falciparum growth in human red blood cells (EC(50) 1.3 microM). To investigate the mechanism for NSC3852's anti-T. gondii activity, we used chemiluminescence assays to detect reactive oxygen species (ROS) formation in freshly isolated tachyzoites and in infected host cells; the absence of ROS generation by NSC3852 in these assays indicated NSC3852 does not redox cycle in T. gondii. Inhibitors of enzyme sources of free radicals such as superoxide anion, nitric oxide (NO), and their reaction product peroxynitrite did not interfere with the anti-T. gondii activity of NSC3852. However, inhibition of T. gondii tachyzoite propagation by NSC3852 involved redox reactions because tachyzoites were protected from NSC3852 by inclusion of the cell permeant superoxide dismutase mimetic, MnTMPyP, or N-acetylcysteine in the culture medium. We conclude that the Prediction of Activity Spectra for Substances (PASS) computer program is useful in finding new compounds that inhibit T. gondii tachyzoites in vitro and that NSC3852 is a potent T. gondii inhibitor that acts by indirect generation of oxidative stress in T. gondii.

Actions of a histone deacetylase inhibitor NSC3852 (5-nitroso-8-quinolinol) link reactive oxygen species to cell differentiation and apoptosis in MCF-7 human mammary tumor cells.[Pubmed:16497787]

J Pharmacol Exp Ther. 2006 May;317(2):546-52.

NSC3852 (5-nitroso-8-quinolinol) has cell differentiation and antiproliferative activity in human breast cancer cells in tissue culture and antitumor activity in mice bearing P388 and L1210 leukemic cells. We investigated the mechanism of NSC3852 action in MCF-7 human breast cancer cells using electron spin resonance (ESR). Reactive oxygen species (ROS) were detected in MCF-7 cell suspensions incubated with NSC3852 using the spin trap 5,5-dimethyl-1-pyrroline-N-oxide (DMPO). Formation of the DMPO-OH adduct was quenched by the addition of superoxide dismutase but not by catalase, and we concluded that superoxide was generated in the NSC3852-treated cells. The flavoprotein inhibitor diphenylene iodonium suppressed ROS production, providing evidence for the involvement of a flavin-dependent enzyme system in the ROS response to NSC3852. A biologically significant oxidative response to NSC3852 occurred in MCF-7 cells. An early marker of oxidative stress was a decrease in the [glutathione]/[glutathione disulfide] ratio 1 h after NSC3852 addition. Oxidative DNA damage, marked by the presence of 8-oxoguanine, and DNA-strand breakage occurred in cells exposed to NSC3852 for 24 h. Apoptosis peaked 48 h after exposure to NSC3852. Pretreatment with the glutathione precursor N-acetyl-l-cysteine (NAC) prevented DNA-strand breakage and apoptosis. Pretreatment with NAC also reversed NSC3852 decreases in E2F1, Myc, and phosphorylated retinoblastoma protein, indicative of redox-sensitive pathway(s) in MCF-7 cells during G(1) phase of the cell cycle. We conclude that ROS formation is involved in the apoptotic and cell differentiation responses to NSC3852 in MCF-7 cells.

Differentiation-inducing quinolines as experimental breast cancer agents in the MCF-7 human breast cancer cell model.[Pubmed:15450938]

Biochem Pharmacol. 2004 Nov 1;68(9):1729-38.

The purpose of this work is to develop agents for cancer differentiation therapy. We showed that five antiproliferative quinoline compounds in the National Cancer Institute database stimulated cell differentiation at growth inhibitory concentrations (3-14 microM) in MCF-7 human breast tumor cells in vitro. The differentiation-inducing quinolines caused lipid droplet accumulation, a phenotypic marker of differentiation, loss of Ki67 antigen expression, a cell cycle marker indicative of exit into G0, and reduced protein levels of the G1--S transcription factor, E2F1. The antimalarial quinolines, chloroquine, hydroxychloroquine and quinidine had similar effects in MCF-7 cells, but were 3-10 times less potent than the NSC compounds. NSC3852 and NSC86371 inhibited histone deacetylase (HDAC) activity in vitro and caused DNA damage and apoptosis in MCF-7 cells, consistent with their differentiation and antiproliferative activities. However, the HDAC assay results showed that for other compounds, direct HDAC enzyme inhibition was not required for differentiation activity. E2F1 protein was suppressed by all differentiation quinolines, but not by non-differentiating analogs, quinoline and primaquine. At equivalent antiproliferative concentrations, NSC69603 caused the greatest decrease in E2F1 protein (90%) followed by antimalarials quinidine and hydroxychloroquine. NSC69603 did not cause DNA damage. The other NSC compounds caused DNA damage and apoptosis and reduced E2F1 levels. The physicochemical properties of NSC3852, NSC69603, NSC86371, and NSC305819 predicted they are drug candidates suitable for development as experimental breast tumor cell differentiation agents. We conclude DNA damage and reductions in E2F1 protein are mechanistically important to the differentiation and antiproliferative activities of these quinoline drug candidates.

Description

Histone deacetylase inhibitor

Keywords:

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