| Identification | Back Directory | [Name]
N-[3-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]phenyl]-α-methylbenzeneacetamide | [CAS]
1105698-15-4 | [Synonyms]
CS-2458
Salermide
SIRT1/2 Inhibitor VIII, Salermide
SIRT1/2 Inhibitor VIII, Salermide - CAS 1105698-15-4 - Calbiochem
N-{3-[(2-Hydroxy-naphthalen-1-ylmethylene)-amino]-phenyl}-2-phenyl-propionamide
N-[3-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]phenyl]-α-methylbenzeneacetamide
N-[3-[[(2-HYDROXY-1-NAPHTHALENYL)METHYLENE]AMINO]PHENYL]-A-METHYL-BENZENEACETAMIDE
Benzeneacetamide, N-[3-[[(2-hydroxy-1-naphthalenyl)methylene]amino]phenyl]-α-methyl- | [Molecular Formula]
C26H22N2O2 | [MDL Number]
MFCD12912446 | [MOL File]
1105698-15-4.mol | [Molecular Weight]
394.47 |
| Chemical Properties | Back Directory | [Boiling point ]
666.7±50.0 °C(Predicted) | [density ]
1.16±0.1 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO: >10mg/mL | [form ]
Yellow solid | [pka]
7.90±0.50(Predicted) | [color ]
Yellow | [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO, DMF, or ethanol may be stored at -20°C for up to 1 month. | [InChI]
1S/C26H22N2O2/c1-18(19-8-3-2-4-9-19)26(30)28-22-12-7-11-21(16-22)27-17-24-23-13-6-5-10-20(23)14-15-25(24)29/h2-18,29H,1H3,(H,28,30)/b27-17+ | [InChIKey]
HQSSEGBEYORUBY-WPWMEQJKSA-N | [SMILES]
CC(C(=O)Nc1cccc(c1)\N=C\c2c(O)ccc3ccccc23)c4ccccc4 |
| Hazard Information | Back Directory | [Description]
The sirtuins (SIRTs) are a family of NAD+-dependent histone deacetylases involved in gene regulation that is relevant to, e.g., longevity, cancer, gene regulation, energy homeostasis, and apoptosis.1,2 Salermide is an inhibitor of SIRT1 and SIRT2, causing tumor-specific apoptotic cell death.3 In MOLT4 leukemia cells, salermide causes 90% apoptosis within 72 hours (IC50 ~20 μM) by reactivating proapototic genes that are repressed by SIRT1.3 | [Uses]
Salermide is an inhibitor of SIRT1, SIRT2, and HDAC. | [Definition]
ChEBI: N-[3-[(2-oxo-1-naphthalenylidene)methylamino]phenyl]-2-phenylpropanamide is a member of naphthalenes. | [General Description]
A cell-permeable 2-hydroxy-naphthaldehyde that acts as an inhibitor against sirtuins SirT1 and SirT2, members of class III HDACs. Salermide effectively inhibits the activity of both SirT1 and SirT2 (by 80% at 100 and 25 μM, respectively), while its structural analogue Sirtinol (Cat. Nos. 566320 and 566321), at 100 μM concentration, inhibits SirT2 only by up to 60% and is of no effect against SirT1. Salermide is also shown to be at least 2-fold more potent than Sirtinol (both at 100 μM) in killing leukemia KG1A and lymphoma Raji cultures. | [Biochem/physiol Actions]
Salermide is a novel Sirtuin 1 (Sirt1) and Sirtuin 2 (Sirt2) inhibitor (III histone deacetylases inhibitor). In vitro Salermide has a stronger inhibitory effect on Sirt2 than on Sirt1. Salermide induces massive apoptosis in tumor cells. The activity was ascribed to effect of Salermide to the reactivation of proapoptotic genes epigenetically repressed exclusively in cancer cells by Sirt1. Salermide is a stronger Sirtuin inhibitor than sirtinol (Cat. No.S7942). | [References]
1) Lara?et al. (2009), Salermide, a Sirtuin inhibitor with a strong cancer-specific proapoptotic effect; Oncogene,?28?781
2) Pasco?et al. (2010),?Characterization of sirtuin inhibitors in nematodes expressing a muscular dystrophy protein reveals muscle cell and behavioral protection by specific sirtinol analogues; J. Med. Chem.,?53?1407
3) Zhao?et al.?(2012),?Interactions between SIRT1 and MAPK/ERK regulate neuronal apoptosis induced by traumatic brain injury in vitro and in vivo; Exp. Neurol.,?237 489 |
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Spectrum Chemical Manufacturing Corp.
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021-021-021-67601398-809-809-809 15221380277 |
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www.spectrumchemical.com/oa_html/index.jsp?minisite=10020&respid=22372&language=us |
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Sigma-Aldrich
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021-61415566 800-8193336 |
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https://www.sigmaaldrich.cn |
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