S7942
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:
Molecular Weight:
394.47
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352203
MDL number:
Product Name
Sirtinol, ≥95% (HPLC)
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+
SMILES string
CC(NC(=O)c1ccccc1\N=C\c2c(O)ccc3ccccc23)c4ccccc4
InChI key
UXJFDYIHRJGPFS-WPWMEQJKSA-N
assay
≥95% (HPLC)
form
solid
solubility
DMSO: soluble
storage temp.
−20°C
Quality Level
Gene Information
human ... SIRT1(23411), SIRT2(22933)
Related Categories
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
H Mutoh et al.
The American journal of physiology, 261(1 Pt 1), G65-G70 (1991-07-01)
We examined the role of reduced glutathione as a defense mechanism against acid-induced gastric mucosal cell damage in vitro. Cellular stores of reduced glutathione were depleted by reaction with diethyl maleate (DEM) or 1-chloro-2,4-dinitrobenzene (CDNB) and increased by reaction with
Jorge Gracia-Sancho et al.
Cardiovascular research, 85(3), 514-519 (2009-10-10)
Resveratrol activates Sirtuin 1 (SIRT1), a nicotinamide adenine dinucleotide-dependent deacetylase which modulates metabolic homeostasis and improves several pathophysiological features present in diseases of ageing. In particular, it has been shown that SIRT1 activation improves endothelial dysfunction and suppresses vascular inflammation
Wenhao Zheng et al.
International immunopharmacology, 45, 135-147 (2017-02-19)
Osteoarthritis (OA) is a degenerative joint disease characterized by cartilage degradation and inflammation. Fisetin, a polyphenol extracted from fruits and vegetables, has been reported to have anti-inflammatory effects. Our study aimed to investigate the effect of fisetin on OA both
Dong Ryeol Ryu et al.
Aging cell, 18(2), e12904-e12904 (2019-01-08)
Although it is known that the expression and activity of sirtuin 1 (Sirt1) decrease in the aged kidney, the role of interaction between Sirt1 and hypoxia-inducible factor (HIF)-1α is largely unknown. In this study, we investigated whether HIF-1α could be
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