1. Cell Cycle/DNA Damage Epigenetics
  2. HDAC
  3. 1-Naphthohydroxamic acid

1-Naphthohydroxamic acid (Compound 2) is a potent and selective HDAC8 inhibitor with an IC50 of 14 μM. 1-Naphthohydroxamic acid is more selectively for HDAC8 than class I HDAC1 and class II HDAC6 (IC50 >100 μM). 1-Naphthohydroxamic acid does not increase global histone H4 acetylation and also does not reduce total intracellular HDAC activity.1-Naphthohydroxamic acid can induce tubulin acetylation.

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1-Naphthohydroxamic acid Chemical Structure

1-Naphthohydroxamic acid Chemical Structure

CAS No. : 6953-61-3

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10 mM * 1 mL in DMSO
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Based on 1 publication(s) in Google Scholar

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Description

1-Naphthohydroxamic acid (Compound 2) is a potent and selective HDAC8 inhibitor with an IC50 of 14 μM. 1-Naphthohydroxamic acid is more selectively for HDAC8 than class I HDAC1 and class II HDAC6 (IC50 >100 μM). 1-Naphthohydroxamic acid does not increase global histone H4 acetylation and also does not reduce total intracellular HDAC activity[1][2].1-Naphthohydroxamic acid can induce tubulin acetylation[3].

IC50 & Target[1]

HDAC8

14 μM (IC50)

HDAC1

>100 μM (IC50)

HDAC6

>100 μM (IC50)

In Vitro

1-Naphthohydroxamic acid (compound 2; 20-40 µM; 0-144  hours; BE(2)-C, SK-N-BE(2) and SH-SY5Y cells) treatment reduces cell numbers in a concentration-dependent manner[2].
1-Naphthohydroxamic acid (compound 2) at concentrations in the range of its in vitro IC50 against HDAC8 results in reduced cell density and outgrowth of neurite-like structures that stained positive for neurofilament.1-Naphthohydroxamic acid reduces the formation of clones in soft-agar concentration dependently[2].
When either cell type (HeLa and HEK293 cells) is treated with 1-Naphthohydroxamic acid (compound 2; 0.8 µM, 4 µM, 20 µM or 100 µM), only tubulin becomes hyperacetylated[1].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Cell Proliferation Assay[2]

Cell Line: BE(2)-C, SK-N-BE(2) and SH-SY5Y cells
Concentration: 20 µM, 40 µM
Incubation Time: 0 hours, 24 hours, 48 hours, 72 hours, 96 hours, and 144  hours
Result: Reduced cell numbers in a concentration-dependent manner.
In Vivo

Dose-limiting toxicities (DLTs) of 1-Naphthohydroxamic acid (compound 2; 0-40 mg/kg; intraperitoneal injection; daily; for 10 day; NMRI Foxn1 nude mice) include weight loss and signs of liver toxicity, as evidenced by elevated plasma liver enzymes and detection of necrotic areas on histological liver examination. 1-Naphthohydroxamic acid has the maximum tolerable doses at 50 mg/kg per day. At these concentrations, neither body weight nor blood parameters are critically changed[3].
Pharmacokinetic studies after intraperitoneal administration of the inhibitors identified the half-life of 1-Naphthohydroxamic acid to be ~15 min, with a plasma peak concentration of ~30 μM[3].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

Animal Model: NMRI Foxn1 nude mice[3]
Dosage: 0 mg/kg, 50 mg/kg, 100mg/kg, 200 mg/kg, 300 mg/kg 400 mg/kg
Administration: Intraperitoneal injection; daily; for 10 days
Result: Dose-limiting toxicities (DLTs) included weight loss and signs of liver toxicity, as evidenced by elevated plasma liver enzymes and detection of necrotic areas on histological liver examination.
Molecular Weight

187.19

Formula

C11H9NO2

CAS No.
Appearance

Solid

Color

White to off-white

SMILES

O=C(C1=C2C=CC=CC2=CC=C1)NO

Shipping

Room temperature in continental US; may vary elsewhere.

Storage
Powder -20°C 3 years
4°C 2 years
In solvent -80°C 2 years
-20°C 1 year
Solvent & Solubility
In Vitro: 

DMSO : 125 mg/mL (667.77 mM; Need ultrasonic; Hygroscopic DMSO has a significant impact on the solubility of product, please use newly opened DMSO)

Preparing
Stock Solutions
Concentration Solvent Mass 1 mg 5 mg 10 mg
1 mM 5.3422 mL 26.7108 mL 53.4217 mL
5 mM 1.0684 mL 5.3422 mL 10.6843 mL
View the Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

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Purity & Documentation
References

Complete Stock Solution Preparation Table

* Please refer to the solubility information to select the appropriate solvent. Once prepared, please aliquot and store the solution to prevent product inactivation from repeated freeze-thaw cycles.
Storage method and period of stock solution: -80°C, 2 years; -20°C, 1 year. When stored at -80°C, please use it within 2 years. When stored at -20°C, please use it within 1 year.

Optional Solvent Concentration Solvent Mass 1 mg 5 mg 10 mg 25 mg
DMSO 1 mM 5.3422 mL 26.7108 mL 53.4217 mL 133.5541 mL
5 mM 1.0684 mL 5.3422 mL 10.6843 mL 26.7108 mL
10 mM 0.5342 mL 2.6711 mL 5.3422 mL 13.3554 mL
15 mM 0.3561 mL 1.7807 mL 3.5614 mL 8.9036 mL
20 mM 0.2671 mL 1.3355 mL 2.6711 mL 6.6777 mL
25 mM 0.2137 mL 1.0684 mL 2.1369 mL 5.3422 mL
30 mM 0.1781 mL 0.8904 mL 1.7807 mL 4.4518 mL
40 mM 0.1336 mL 0.6678 mL 1.3355 mL 3.3389 mL
50 mM 0.1068 mL 0.5342 mL 1.0684 mL 2.6711 mL
60 mM 0.0890 mL 0.4452 mL 0.8904 mL 2.2259 mL
80 mM 0.0668 mL 0.3339 mL 0.6678 mL 1.6694 mL
100 mM 0.0534 mL 0.2671 mL 0.5342 mL 1.3355 mL
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1-Naphthohydroxamic acid
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