SIRTINOL

SIRTINOL Basic information
Product Name:SIRTINOL
Synonyms:{2-[(2-Hydroxynaphthalen-1-ylmethylene)amino]}-N-(1-phenethyl)benzamide (Sirtinol);2-[(2-HYDROXYNAPHTHALEN-1-YLMETHYLENE)AMINO]-N-(1-PHENETHYL)BENZAMIDE;SIRTINOL;SIR TWO INHIBITOR NAPHTHOL;(E)-2-((2-hydroxynaphthalen-1-yl)methyleneamino)-N-(1-phenylethyl)benzamide;2-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]-N-(1-phenylethyl)benzamide;2-{[(2-hydroxynaphthalen-1-yl)Methylidene]aMino}-N-(2-phenylethyl)benzaMide;Sirtinol - CAS 410536-97-9 - Calbiochem
CAS:410536-97-9
MF:C26H22N2O2
MW:394.47
EINECS:
Product Categories:Inhibitors;Inhibitor;Other enzyme inhibitors and activators;Other Enzyme Inhibitors.
Mol File:410536-97-9.mol
SIRTINOL Structure
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
pka7.85±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.
Safety Information
WGK Germany 3
MSDS Information
ProviderLanguage
SigmaAldrich English
SIRTINOL Usage And Synthesis
DescriptionSirtinol (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.
UsesSirtinol is a known inhibitor of the NAD+-Dependent Protein Desuccinylase and Demalonylase Sirt5 and exhibits anticancer properties.
UsesSirtinol is a cell permeable specific inhibitor of sirtuin NAD-dependant deacetylases
DefinitionChEBI: 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 DescriptionA 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 ActivityCell-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 ActionsCell permeable: yes
storageStore at -20°C
References1) Ota et al. (2006) SIRT1 inhibitor, Sirtinol, induces senescence-like growth arrest with attenuated Ras-MAPK signaling in human cancer cells; Oncogene, 25 176 2) Mai et al. (2005) Design, synthesis and biological evaluation of sirtinol analogues as class III histone/protein deacetylase (Sirtuin) inhibitors; J. Med. Chem. 48 7789 3) Grozinger et al. (2001) Identification of a class of small molecule inhibitors of the sirtuin family of NAD-dependent deacetylases by phenotypic screening; J. Biol. Chem. 276 38837 4) Koering et al. (2002) Human telomeric position effect is determined by chromosomal context and telomeric chromatin integrity; EMBO Rep. 3 1055
SIRTINOL Preparation Products And Raw materials
Doxorubicin hydrochloride BEZ235 (NVP-BEZ235, Dactolisib) SU 4312 Troglitazone Veliparib (+)-Camptothecin SRT1720 AGK2 6-CHLORO-2,3,4,9-TETRAHYDRO-1H-CARBAZOLE-1-CARBOXAMIDE Aristoforin CYCLOPAMINE SIRTINOL 1-((PHENYLIMINO)METHYL)NAPHTHALEN-2-OL 2-((O-TOLYLIMINO)METHYL)PHENOL 2-AMINO-N-(1-PHENYL-ETHYL)-BENZAMIDE

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