Introduction：Basic information about CAS 6953-61-3|1-Naphthohydroxamic acid, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | 1-Naphthohydroxamic acid |
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| CAS Number | 6953-61-3 | Molecular Weight | 187.195 |
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| Density | 1.3±0.1 g/cm3 | Boiling Point | / |
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| Molecular Formula | C11H9NO2 | Melting Point | / |
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| MSDS | ChineseUSA | Flash Point | / |
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Names
| Name | N-hydroxynaphthalene-1-carboxamide |
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| Synonym | More Synonyms |
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1-Naphthohydroxamic acid BiologicalActivity
| 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]. |
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| Related Catalog | Research Areas >>CancerSignaling Pathways >>Cell Cycle/DNA Damage >>HDACSignaling Pathways >>Epigenetics >>HDAC |
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| Target | HDAC8:14 μM (IC50) HDAC1:>100 μM (IC50) HDAC6:>100 μM (IC50) |
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| 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. |
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| 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. |
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| 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. |
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Chemical & Physical Properties
| Density | 1.3±0.1 g/cm3 |
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| Molecular Formula | C11H9NO2 |
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| Molecular Weight | 187.195 |
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| Exact Mass | 187.063324 |
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| PSA | 49.33000 |
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| LogP | 1.49 |
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| Appearance of Characters | white to tan |
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| Index of Refraction | 1.678 |
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| InChIKey | JRZGPWOEHDOVMC-UHFFFAOYSA-N |
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| SMILES | O=C(NO)c1cccc2ccccc12 |
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| Storage condition | 2-8°C |
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| Water Solubility | DMSO: ≥5mg/mL |
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Toxicological Information
CHEMICAL IDENTIFICATION - RTECS NUMBER :
- QJ1894500
- CHEMICAL NAME :
- 1-Naphthalenecarboxamide, N-hydroxy-
- CAS REGISTRY NUMBER :
- 6953-61-3
- BEILSTEIN REFERENCE NO. :
- 2094470
- LAST UPDATED :
- 199612
- DATA ITEMS CITED :
- 1
- MOLECULAR FORMULA :
- C11-H9-N-O2
- MOLECULAR WEIGHT :
- 187.21
- WISWESSER LINE NOTATION :
- L66J BVMQ
HEALTH HAZARD DATAACUTE TOXICITY DATAMUTATION DATA - TYPE OF TEST :
- Mutation in microorganisms
- TEST SYSTEM :
- Bacteria - Salmonella typhimurium
- DOSE/DURATION :
- 2500 nmol/plate
- REFERENCE :
- MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 135,139,1984
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Safety Information
| Risk Phrases | 52 |
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| RIDADR | NONH for all modes of transport |
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| RTECS | QJ1894500 |
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| HS Code | 2924299090 |
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Customs
| HS Code | 2924299090 |
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| Summary | 2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0% |
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Synonyms
| 1-NAPHTHALENECARBOXAMIDE,N-HYDROXY |
| a-Naphthohydroxamic acid |
| N-hydroxynaphthalene-1-carboxamide |
| 1-Naphthalenecarboxamide, N-hydroxy- |
| N-Hydroxy-1-naphthamide |
| 1-naphthohydroxamic acid |
