SirReal2

SIGMA/SML1514 - ≥98% (HPLC)

Synonym: 2-(4,6-Dimethyl-pyrimidin-2-ylsulfanyl)-N-(5-naphthalen-1-ylmethyl-thiazol-2-yl)-acetamide; SirReal 2

CAS Number: 709002-46-0
Empirical Formula (Hill Notation): C₂₂H₂₀N₄OS₂
Molecular Weight: 420.55
Linear Formula: C₂₂H₂₀N₄OS₂
Product Type: Chemical

assay	≥98% (HPLC)
color	white to beige
form	powder
InChI	1S/C22H20N4OS2/c1-14-10-15(2)25-22(24-14)28-13-20(27)26-21-23-12-18(29-21)11-17-8-5-7-16-6-3-4-9-19(16)17/h3-10,12H,11,13H2,1-2H3,(H,23,26,27)
InChI key	MENNDDDTIIZDDN-UHFFFAOYSA-N
Quality Level	100
SMILES string	CC1=NC(SCC(NC2=NC=C(S2)CC3=CC=CC4=C3C=CC=C4)=O)=NC(C)=C1
solubility	DMSO: 20 mg/mL, clear
storage temp.	−20°C

Application:	Sirtuin-rearranging ligand 2 (SirReal2) has been used as a positive control to evaluate in vivo sirtuin 2 (SIRT2) inhibition by RK-9123016 and NPD11033.
Biochem/physiol Actions:	SirReal2 is a potent and selective inhibitor of Sirt2, an NAD-dependent lysine deacetylase that has been implicated in the pathogenesis of cancer, inflammation, and neurodegeneration. SirReal2 has an IC₅₀ value of 140 nM and is >1000-fold selective for Sirt2 over Sirt1 and Sirt3. SirReal2 is believed to act through a ligand-induced structural rearrangement of the active site, binding at an adjacent pocket to lock Sirt2 in an open conformation. SirReal2 caused to tubulin hyperacetylation in HeLa cells and destabilization of the checkpoint protein BubR1, consistent with Sirt2 inhibition.
Biochem/physiol Actions:	SirReal2 is a potent and selective inhibitor of Sirt2.
Packaging:	5, 25 mg in glass bottle

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