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S7942 Sigma-Aldrich

Sirtinol

≥95% (HPLC)

Synonym: 2-[(2-Hydroxynaphthalen-1-ylmethylene)amino]-N-(1-phenethyl)benzamide

  • CAS Number 410536-97-9

  • Empirical Formula (Hill Notation) C26H22N2O2

  • Molecular Weight 394.47

  •  MDL number MFCD00810186

  •  PubChem Substance ID 24899771

  •  NACRES NA.77

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Properties

Related Categories Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Biochemicals and Reagents, Cell Biology, Cell Signaling and Neuroscience,
Quality Level   200
assay   ≥95% (HPLC)
form   solid
solubility   DMSO: soluble
storage temp.   −20°C
SMILES string   CC(NC(=O)c1ccccc1\N=C\c2c(O)ccc3ccccc23)c4ccccc4
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
Gene Information   human ... SIRT1(23411), SIRT2(22933)

Description

Application

HUVEC were treated with sirtinol to study the effect on induction of transcription factor Krüppel-like factor 2.4 Sirtinol was used to treat human embryonic kidney cells to study the effect on the expression on Werner syndrome protein.5

Biochem/physiol Actions

Sirtinol inhibits yeast Sir2p transcriptional silencing activity in vivo, yeast Sir2p and human SIRT2 deacetylase activity in vitro. It inhibits the physiological regulators of platelet aggregation such as thrombin and collagen, attenuates intracellular Ca2+ release and formation thromboxane B2. It may increase levels of cAMP by inhibition of cAMP phosphodiesterase and inhibit the aggregation of platelets.2 Sirtinol reduces inflammatory responses of human dermal microvascular endothelial cells to TNF-α and IL-1β.3

Sirtinol inhibits yeast Sir2p transcriptional silencing activity in vivo, yeast Sir2p, and human SIRT2 deacetylase activity in vitro.

Features and Benefits

This compound is a featured product for Gene Regulation research. Click here to discover more featured Gene Regulation products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles

Articles

Discover Bioactive Small Molecules for Gene Regulation

The loss of regulation of gene expression is a key component to many human disease states, including neurodegenerative disorders, autoimmune conditions and, most prominently, cancers. Regulation of g...
Keywords: Acetylations, Epigenetics, Gene expression, Genomics, Methylations, PAGE, Post translational modifications, Transcription

Histone Modification and Chromatin Remodeling

Gene expression is governed by complex mechanisms including transcription factor binding to DNA and coordinated changes in chromatin structure. The primary protein components of chromatin are the his...
Savita Bagga, PhD.
BioFiles v7 n3, 2012, 10–16
Keywords: Acetylations, Amplification, Cancer, Cell culture, Chromatin immunoprecipitation, Cloning, DNA purification, Diseases, Epigenetics, Gene expression, Immunoprecipitation, Indicators, Methylations, Microarray Analysis, Polymerase chain reaction, Polymerase chain reaction - quantitative, Polymorphisms, Purification, Sequencing, Transcription, Whole genome amplification

Peer-Reviewed Papers
15

References

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EPI010 Sirtuin 2 (SIRT2) Inhibitor Screening Assay Kit, 100 assays in 96 well plates

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