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ChemicalBook--->CAS DataBase List--->410536-97-9

410536-97-9

410536-97-9 Structure

410536-97-9 Structure
IdentificationBack Directory
[Name]

SIRTINOL
[CAS]

410536-97-9
[Synonyms]

SIRTINOL
SIR TWO INHIBITOR NAPHTHOL
2-[(2-HYDROXYNAPHTHALEN-1-YLMETHYLENE)AMINO]-N-(1-PHENETHYL)BENZAMIDE
2-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]-N-(1-phenylethyl)benzamide
2-{[(2-hydroxynaphthalen-1-yl)Methylidene]aMino}-N-(2-phenylethyl)benzaMide
(E)-2-((2-hydroxynaphthalen-1-yl)methyleneamino)-N-(1-phenylethyl)benzamide
[Molecular Formula]

C26H22N2O2
[MDL Number]

MFCD00810186
[MOL File]

410536-97-9.mol
[Molecular Weight]

394.47
Chemical PropertiesBack Directory
[Melting point ]

119-120℃
[Boiling point ]

659.2±50.0 °C(Predicted)
[density ]

1.16
[storage temp. ]

−20°C
[solubility ]

Soluble in DMSO (up to 30 mg/ml).
[form ]

Yellow solid
[pka]

7.85±0.50(Predicted)
[color ]

Pale yellow
[Water Solubility ]

Soluble in water, DMSO and methanol
[Stability:]

Stable for 1 year from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
Hazard InformationBack Directory
[Usage]

Sirtinol is a known inhibitor of the NAD+-Dependent Protein Desuccinylase and Demalonylase Sirt5 and exhibits anticancer properties.
[Biological Activity]

Cell-permeable, selective sirtuin deacetylase inhibitor (IC 50 values are 38, 68 and 131 μ M at SIRT2, Sir2p and SIRT1 respectively) that has no effect on HDAC1 activity. Significantly decreases growth and viability of PCa and HEK293T cells in vitro .
[Description]

Sirtinol (410536-97-9) is an inhibitor of sirtuin family enzymes including human SIRT1 (IC50=60 μM), human SIRT2 (IC50=58 μM), and yeast Sir2 (IC50=48 μM) with no inhibition of human HDAC1. Active in vivo and in purified enzyme studies. Cell permeable.
[Uses]

Sirtinol is a cell permeable specific inhibitor of sirtuin NAD-dependant deacetylases
[Uses]

Sirtinol is a known inhibitor of the NAD+-Dependent Protein Desuccinylase and Demalonylase Sirt5 and exhibits anticancer properties.
[Definition]

ChEBI: Sirtinol is a benzamide obtained by formal condensation of the carboxy group of 2-{[(2-hydroxy-1-naphthyl)methylene]amino}benzoic acid with the amino group of 1-phenylethylamine. It has a role as an anti-inflammatory agent, an EC 3.5.1.98 (histone deacetylase) inhibitor and a Sir2 inhibitor. It is a member of benzamides, an aldimine and a member of naphthols. It is functionally related to an anthranilic acid.
[General Description]

A cell-permeable 2-hydroxy-1-naphthaldehyde derivative that acts as a specific and direct inhibitor of the sirtuin class of deacetylase activity with no affect on human HDAC1 (IC50 = 48 μM, 131 μM and 58 μM for ySir2, hSIRT1 and hSIRT2, respectively). Reported to inhibit Sir2p transcriptional silencing activity in vivo (IC50 = 25 μM), and NAD-dependent histone deacetylase activity of purified recombinant yeast Sir2p and human SIRT2 in vitro (IC50 = 70 μM and 40 μM, respectively). A 10 mM (1 mg/254 μl) solution of Sirtinol (Cat. No. 566321) in DMSO is also available.
[Biochem/physiol Actions]

Cell permeable: yes
[storage]

Store at -20°C
[References]

1) Ota et al. (2006) SIRT1 inhibitor, Sirtinol, induces senescence-like growth arrest with attenuated Ras-MAPK signaling in human cancer cells; Oncogene, 25 176 2) Mai et al. (2005) Design, synthesis and biological evaluation of sirtinol analogues as class III histone/protein deacetylase (Sirtuin) inhibitors; J. Med. Chem. 48 7789 3) Grozinger et al. (2001) Identification of a class of small molecule inhibitors of the sirtuin family of NAD-dependent deacetylases by phenotypic screening; J. Biol. Chem. 276 38837 4) Koering et al. (2002) Human telomeric position effect is determined by chromosomal context and telomeric chromatin integrity; EMBO Rep. 3 1055
Safety DataBack Directory
[WGK Germany ]

3
Spectrum DetailBack Directory
[Spectrum Detail]

SIRTINOL(410536-97-9)MS
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