SIRTINOL
Background- Product Name
- SIRTINOL
- CAS No.
- 410536-97-9
- Chemical Name
- SIRTINOL
- Synonyms
- SIRTINOL;SIRTINOL USP/EP/BP;Sirtinol, 10 mM in DMSO;SIR TWO INHIBITOR NAPHTHOL;Sirtinol - CAS 410536-97-9 - Calbiochem;2-{[(2-hydroxy-1-naphthyl)methylene]amino}-N-(1-phenylethyl)benzamide;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)methylene)amino)-N-(1-phenylethyl)benzamide;2-{[(2-hydroxynaphthalen-1-yl)Methylidene]aMino}-N-(2-phenylethyl)benzaMide
- CBNumber
- CB7748565
- Molecular Formula
- C26H22N2O2
- Formula Weight
- 394.47
- MOL File
- 410536-97-9.mol
SIRTINOL Property
- 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
- WGK Germany
- 3
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P405Store locked up.
N-Bromosuccinimide Price
- Product number
- S7942
- Product name
- Sirtinol
- Purity
- ≥95% (HPLC)
- Packaging
- 1mg
- Price
- $109
- Updated
- 2025/07/31
- Product number
- S7942
- Product name
- Sirtinol
- Purity
- ≥95% (HPLC)
- Packaging
- 5mg
- Price
- $389
- Updated
- 2025/07/31
- Product number
- 566321
- Product name
- Sirtinol
- Purity
- InSolution, ≥97%, inhibitor of sirtuin class of histone deacetylase (HDAC) activity
- Packaging
- 1mg
- Price
- $98.6
- Updated
- 2025/07/31
- Product number
- 566320
- Product name
- Sirtinol
- Packaging
- 5mg
- Price
- $298
- Updated
- 2025/07/31
- Product number
- 10523
- Product name
- Sirtinol
- Purity
- ≥98%
- Packaging
- 5mg
- Price
- $68
- Updated
- 2024/03/01
SIRTINOL Chemical Properties,Usage,Production
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
Background
Sirtinol is a cell-permeable inhibitor of sirtuin NAD+-dependent histone deacetylases. It inhibits yeast sirtuin Sir2p with an IC50 value of 68 μM, and inhibits human SIRT1 and SIRT2 with IC50 values of 131 μM and 38 μM, respectively. Sirtinol does not inhibit human HDAC1 activity. It elevates endogenous levels of reactive oxygen species to induce apoptosis in cancer cells. Sirtinol inhibits proliferation of non-small cell lung cancer cells and suppresses inflammatory activity in human dermal microvascular endothelial cells. Sirtinol also activates the auxin signaling transduction pathway in Arabidopsis, altering plant growth and development.
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
SIRTINOL Preparation Products And Raw materials
Raw materials
Preparation Products
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