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.

InChI

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)

InChIKey

UXJFDYIHRJGPFS-UHFFFAOYSA-N

SMILES

C(NC(C1=CC=CC=C1)C)(=O)C1=CC=CC=C1N=CC1=C2C(C=CC=C2)=CC=C1O

Safety Information

WGK Germany 

3

MSDS

• Language:English Provider:SigmaAldrich

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] H OTA. Sirt1 inhibitor, Sirtinol, induces senescence-like growth arrest with attenuated Ras-MAPK signaling in human cancer cells.[J]. Oncogene, 2006, 25 2: 176-185. DOI:10.1038/sj.onc.1209049
[2] ANTONELLO MAI. Design, Synthesis, and Biological Evaluation of Sirtinol Analogues as Class III Histone/Protein Deacetylase (Sirtuin) Inhibitors[J]. Journal of Medicinal Chemistry, 2005, 48 24: 7789-7795. DOI:10.1021/jm050100l
[3] C. GROZINGER. Identification of a Class of Small Molecule Inhibitors of the Sirtuin Family of NAD-dependent Deacetylases by Phenotypic Screening*[J]. The Journal of Biological Chemistry, 2001, 48 17: 38837-38843. DOI:10.1074/jbc.m106779200
[4] CATHERINE ELAINE KOERING. Human telomeric position effect is determined by chromosomal context and telomeric chromatin integrity.[J]. EMBO Reports, 2002, 3 11: 1055-1061. DOI:10.1093/embo-reports/kvf215

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