| Identification | Back 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 Properties | Back 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 Information | Back 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 |
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