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1-NAPHTHOHYDROXAMIC ACID

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1-NAPHTHOHYDROXAMIC ACID Basic information

Product Name:
1-NAPHTHOHYDROXAMIC ACID
Synonyms:
  • HDAC Inhibitor XIX, Compound 2 - CAS 6953-61-3 - Calbiochem
  • Naphthalene-1-carbohydroximic acid
  • N-Hydroxy-1-naphthalenecarboxamide
  • a-Naphthohydroxamic acid
  • NSC 57457
  • HDAC Inhibitor XIX, Compound 2
  • N-HYDROXYNAPHTHALENE-1-CARBOXAMIDE
  • alpha-naphthohydroxamicacid
CAS:
6953-61-3
MF:
C11H9NO2
MW:
187.19
Product Categories:
  • Hydroxylamines
  • Hydroxylamines (N-Substituted)
Mol File:
6953-61-3.mol
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1-NAPHTHOHYDROXAMIC ACID Chemical Properties

Melting point:
176-178 °C
Density 
1.291±0.06 g/cm3(Predicted)
storage temp. 
2-8°C
solubility 
DMSO: ≥5mg/mL
pka
8.91±0.30(Predicted)
form 
White solid
color 
white to tan
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Safety Information

Risk Statements 
52
WGK Germany 
3
RTECS 
QJ1894500
HS Code 
2928009090
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1-NAPHTHOHYDROXAMIC ACID Usage And Synthesis

Uses

1-Naphthohydroxamic Acid is a potent HDAC inhibitor with efficacy against HDAC8, HDAC1 and HDAC6.

Biochem/physiol Actions

1-Naphthohydroxamic Acid is a cell-permeable, potent, and selective histone deacetylase 8 (HDAC8) inhibitor. 1-Naphthohydroxamic acid selectively inhibits HDAC8 (IC50 = 14 μM) over class I HDAC1 and class II HDAC6 (IC50 >100 μM). Treatment of cells with 1-Naphthohydroxamic acid does not increase neither global histone H4 nor tubulin acetylation . Also in contrast to the pan-HDAC inhibitors the compound is not reducing total intracellular HDAC activity.

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].

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.

IC 50

HDAC8: 14 μM (IC50); HDAC1: >100 μM (IC50); HDAC6: >100 μM (IC50)

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