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S7942

Sigma-Aldrich

Sirtinol

≥95% (HPLC)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C26H22N2O2
CAS Number:
410536-97-9
Molecular Weight:
394.47
MDL number:
MFCD00810186
UNSPSC Code:
12352203
PubChem Substance ID:
24899771
NACRES:
NA.77

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)

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.

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Pricing

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Angela Orecchia et al.
PloS one, 6(9), e24307-e24307 (2011-09-21)
Histone deacetylases (HDAC) are key enzymes in the epigenetic control of gene expression. Recently, inhibitors of class I and class II HDAC have been successfully employed for the treatment of different inflammatory diseases such as rheumatoid arthritis, colitis, airway inflammation
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We previously reported that sphere-forming non-small cell lung cancer (NSCLC) tumor-initiating cells (TICs) have an altered activation of DNA damage response- and repair proteins and are refractory to DNA-damaging treatments. We analyzed whether chromatin organization plays a role in the
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