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1-Naphthohydroxamicacid structure, CAS 6953-61-3

1-Naphthohydroxamicacid

CAS Number6953-61-3

Synonyms1-NAPHTHALENECARBOXAMIDE,N-HYDROXY; a-Naphthohydroxamic acid; N-hydroxynaphthalene-1-carboxamide; N-Hydroxy-1-naphthamide; 1-naphthohydroxamic acid

Molecular FormulaC11H9NO2

Molecular Weight187.195

Purity

Density1.3±0.1 g/cm3

Boiling Point

Melting Point

Flash Point

Appearancewhite to tan

EINECS

MSDSChineseEnglish

Symbol

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Cat. No.: 2A-9087213 Purity:
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Quality Control of [ 6953-61-3 ] SDS Specification MoL

COA NMR CNMR HPLC LC-MS
Chemical & Physical Properties
CAS Number6953-61-3
Catalog No.2A-9087213
Chinese Name1-萘羟肟酸
Synonyms1-NAPHTHALENECARBOXAMIDE,N-HYDROXY; a-Naphthohydroxamic acid; N-hydroxynaphthalene-1-carboxamide; N-Hydroxy-1-naphthamide; 1-naphthohydroxamic acid
Molecular FormulaC11H9NO2
Molecular Weight187.195
Density1.3±0.1 g/cm3
Appearancewhite to tan
Water SolubilityDMSO: ≥5mg/mL
Storage Condition2-8°C
Application1-Naphthohydroxamic acid (Compound 2) is a potent and selective HDAC8 inhibitor with an IC50 of 14 μM. 1-Naphthohydroxamic acid is more selective for HDAC8 than class I HDAC1 and class II HDAC6 (IC50
HTC2924299090
SMILESO=C(NO)c1cccc2ccccc12
InChIInChI=1S/C11H9NO2/c13-11(12-14)10-7-3-5-8-4-1-2-6-9(8)10/h1-7,14H,(H,12,13)
InChI KeyJRZGPWOEHDOVMC-UHFFFAOYSA-N
MSDSmsds/87213_2_6953_61_3.pdf
Bioactivity1-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]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Cell Cycle/DNA Damage >> HDAC Signaling Pathways >> Epigenetics >> HDAC Target 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]. 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]. 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. References [1]. Krennhrubec K, et al. Design and evaluation of 'Linkerless' hydroxamic acids as selective HDAC8 inhibitors. Bioorg Med Chem Lett. 2007 May 15;17(10):2874-8. [2]. Oehme I, et al. Histone deacetylase 8 in neuroblastoma tumorigenesis. Clin Cancer Res. 2009 Jan 1;15(1):91-9. Chemical & Physical Properties Density 1.3±0.1 g/cm3 Molecular Formula C11H9NO2 Molecular Weight 187.195 Exact Mass 187.063324 PSA 49.33000 LogP 1.49 Appearance of Characters white to tan Index of Refraction 1.678 InChIKey JRZGPWOEHDOVMC-UHFFFAOYSA-N SMILES O=C(NO)c1cccc2ccccc12 Storage condition 2-8°C Water Solubility DMSO: ≥5mg/mL
Use of1-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]. Properties Name N-hydroxynaphthalene-1-carboxamide Synonym More Synonyms 1-Naphthohydroxamic acid Biological Activity 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]. Related Catalog Research Areas >> Cancer Signaling Pathways >> Cell Cycle/DNA Damage >> HDAC Signaling Pathways >> Epigenetics >> HDAC HDAC8:14 μM (IC50) HDAC1:>100 μM (IC50) HDAC6:>100 μM (IC50) References [1]. Krennhrubec K, et al. Design and evaluation of 'Linkerless' hydroxamic acids as selective HDAC8 inhibitors. Bioorg Med Chem Lett. 2007 May 15;17(10):2874-8. [2]. Oehme I, et al. Histone deacetylase 8 in neuroblastoma tumorigenesis. Clin Cancer Res. 2009 Jan 1;15(1):91-9. Chemical & Physical Properties Molecular Formula C11H9NO2 Exact Mass 187.063324 PSA 49.33000 Appearance of Characters white to tan Index of Refraction 1.678 InChIKey JRZGPWOEHDOVMC-UHFFFAOYSA-N
Tax Rebate13.0%
SupervisionNone. MFN tariff: 6.5%. Ordinary tariff: 30.0%
Transport InfoProduct name: Purity: 98.0%
MSDS Transport InfoModule 14. Shipping information United Nations classification: inconsistent with United Nations classification standards UN number: not specified
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