566320

Sirtinol

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.

• Synonym(e): Sirtinol, 2-[(2-Hydroxynaphthalen-1-ylmethylene)amino]-N-(1-phenethyl)benzamide, Sir Two Inhibitor Naphthol, SIRT1 Inhibitor I, SIRT1/2 Inhibitor I, SIRT2 Inhibitor III
• Empirische Formel (Hill-System): C₂₆H₂₂N₂O₂
• CAS-Nummer: 410536-97-9
• Molekulargewicht: 394.47
• MDL number: MFCD00810186
• UNSPSC Code: 12352200
• NACRES: NA.77
• Assay: ≥97% (HPLC)
• Form: solid
• Quality level: 100
• Storage condition: OK to freeze, protect from light

Eigenschaften

• Quality Level: 100
• assay: ≥97% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze, protect from light
• color: yellow
• solubility: DMSO: 1 mg/mL
• shipped in: ambient
• storage temp.: −20°C
• SMILES string: N([C@@H](C)c4ccccc4)C(=O)c1c(cccc1)N\C=C2\c3c(cccc3)C=CC\2=O
• InChI: 1S/C26H22N2O2/c1-18(19-9-3-2-4-10-19)28-26(30)22-13-7-8-14-24(22)27-17-23-21-12-6-5-11-20(21)15-16-25(23)29/h2-18,27H,1H3,(H,28,30)/b23-17-/t18-/m0/s1
• InChI key: YUGODMKHHCZZOI-ZVTCDHROSA-N

Beschreibung

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.

A cell-permeable 2-hydroxy-1-napthaldehyde derivative that acts as a specific and a direct inhibitor of sirtuin class of histone deacetylase (HDAC) activity. Does not affect human HDAC1. Reported to block Sir2p transcriptional silencing activity in vivo (IC₅₀ = 25 µM) and NAD-dependent HDAC activity in purified recombinant yeast Sir2p and human SIRT2 in vitro (IC₅₀ = 68 µM and 38 µM, respectively).

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Human HDAC1

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 48 µM, 131 µM and 58 µM for ySir2, hSIRT1 and hSIRT2

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Other Notes

Mai, A., et al. 2005. J. Med. Chem.48, 7789.
Grozinger, C.M., et al. 2001. J. Biol. Chem.276, 38837.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Sicherheitshinweise

• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 1