Inhibitor of sirtuin deacetylases
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Sirtinol

Item No. 10523

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[[(2-hydroxy-1-naphthalenyl)methylene]amino]-N-(1-phenylethyl)-benzamide
CAS Number
410536-97-9
Synonyms
  • Sir Two Inhibitor Naphthol
Molecular Formula
C26H22N2O2
Formula Weight
394.5
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 15 mg/mlDMF:PBS (pH 7.2) (1:2): 0.3 mg/mlDMSO: 10 mg/ml
λmax
231, 317, 374, 439 nm
SMILES
O=C(N([H])C(C1=CC=CC=C1)C)C(C=CC=C2)=C2/N=C/C3=C(O)C=CC4=C3C=CC=C4
InChi Code
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/h2-18,29H,1H3,(H,28,30)/b27-17+
InChi Key
UXJFDYIHRJGPFS-WPWMEQJKSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    50 mg

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    Cayman Chemical
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    Product Description

    Sirtinol is a cell-permeable inhibitor of sirtuin NAD+-dependent deacetylases, inhibiting the yeast sirtuin Sir2p with an IC50 value of 68 μM and the human sirtuins SIRT1 and SIRT2 with IC50 values of 131 and 38 μM, respectively.1 It does not alter HDAC1 activity.1 Sirtinol inhibits the growth of cancer cells and suppresses inflammatory signaling in human dermal microvascular endothelial cells.2,3,4 In plants, sirtinol can be metabolized to 2-hydroxy-1-naphthoic acid, which activates auxin signaling and alters plant growth and development.5,6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Grozinger, C.M., Chao, E.D., Blackwell, H.E., et al. Identification of a class of small molecule inhibitors of the sirtuin family of NAD-dependent deacetylases by phenotypic screening. The Journal of Biological Chemisty 276(42), 38837-38843 (2001).

    2. Ota, H., Tokunaga, E., Chang, K., et al. Sirt1 inhibitor, sirtinol, induces senescence-like growth arrest with attenuated Ras-MAPK signaling in human cancer cells. Oncogene 25(2), 176-185 (2006).

    3. Cea, M., Soncini, D., Fruscione, F., et al. Synergistic interactions between HDAC and sirtuin inhibitors in human leukemia cells. PLoS One 6(7), 1-12 (2011).

    4. Orecchia, A., Scarponi, C., Di Felice, F., et al. Sirtinol treatment reduces inflammation in human dermal microvascular endothelial cells. PLoS One 6(9), 1-12 (2011).

    5. Zhao, Y., Dai, X., Blackwell, H.E., et al. SIR1, an upstream component in auxin signaling identified by chemical genetics. Science 301(5636), 1107-1110 (2003).

    6. Dai, X., Hayashi, K.i., Nozaki, H., et al. Genetic and chemical analyses of the action mechanisms of sirtinol in Arabidopsis. Proc. Natl. Acad. Sci. USA 102(8), 3129-3134 (2005).

    Product Citations

    Aragonès, G., Suárez, M., Ardid-Ruiz, A., et al. Dietary proanthocyanidins boost hepatic NAD+ metabolism and SIRT1 expression and activity in a dose-dependent manner in healthy rats. Sci. Rep. 6, 24977 (2016).