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| | SIRTINOL Basic information |
| Product Name: | SIRTINOL | | Synonyms: | 2-[(2-HYDROXYNAPHTHALEN-1-YLMETHYLENE)AMINO]-N-(1-PHENETHYL)BENZAMIDE;SIRTINOL;SIR TWO INHIBITOR NAPHTHOL;(E)-2-((2-hydroxynaphthalen-1-yl)methyleneamino)-N-(1-phenylethyl)benzamide;2-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]-N-(1-phenylethyl)benzamide;2-{[(2-hydroxynaphthalen-1-yl)Methylidene]aMino}-N-(2-phenylethyl)benzaMide;{2-[(2-Hydroxynaphthalen-1-ylmethylene)amino]}-N-(1-phenethyl)benzamide (Sirtinol);Sirtinol - CAS 410536-97-9 - Calbiochem | | CAS: | 410536-97-9 | | MF: | C26H22N2O2 | | MW: | 394.47 | | EINECS: | | | Product Categories: | Inhibitors;Inhibitor;Other Enzyme Inhibitors.;Other enzyme inhibitors and activators | | Mol File: | 410536-97-9.mol |  |
| | SIRTINOL Chemical Properties |
| 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. |
| | SIRTINOL Usage And Synthesis |
| 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. | | 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 . | | 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 |
| | SIRTINOL Preparation Products And Raw materials |
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