| Company Name: |
Sigma-Aldrich |
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021-61415566 800-8193336 |
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- Salermide
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- $40.00
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2026-05-11
- CAS:1105698-15-4
- Purity: 97.62%
- Supply Ability: 10g
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| | N-[3-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]phenyl]-α-methylbenzeneacetamide Basic information | | Background |
| Product Name: | N-[3-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]phenyl]-α-methylbenzeneacetamide | | Synonyms: | N-[3-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]phenyl]-α-methylbenzeneacetamide;Salermide;N-{3-[(2-Hydroxy-naphthalen-1-ylmethylene)-amino]-phenyl}-2-phenyl-propionamide;SIRT1/2 Inhibitor VIII, Salermide;CS-2458;SIRT1/2 Inhibitor VIII, Salermide - CAS 1105698-15-4 - Calbiochem;N-[3-[[(2-HYDROXY-1-NAPHTHALENYL)METHYLENE]AMINO]PHENYL]-A-METHYL-BENZENEACETAMIDE;Benzeneacetamide, N-[3-[[(2-hydroxy-1-naphthalenyl)methylene]amino]phenyl]-α-methyl- | | CAS: | 1105698-15-4 | | MF: | C26H22N2O2 | | MW: | 394.47 | | EINECS: | | | Product Categories: | | | Mol File: | 1105698-15-4.mol | ![N-[3-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]phenyl]-α-methylbenzeneacetamide Structure](CAS/20181012/GIF/1105698-15-4.gif) |
| | N-[3-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]phenyl]-α-methylbenzeneacetamide Chemical Properties |
| Melting point | >250 °C | | 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 Codes | Xi | | Risk Statements | 43-52/53 | | Safety Statements | 36/37-61 | | WGK Germany | 3 | | Storage Class | 11 - Combustible Solids |
| | N-[3-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]phenyl]-α-methylbenzeneacetamide Usage And Synthesis |
| 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. Salermide is an inhibitor of SIRT1 and SIRT2, causing tumor-specific apoptotic cell death. In MOLT4 leukemia cells, salermide causes 90% apoptosis within 72 hours (IC50 ~20 μM) by reactivating proapototic genes that are repressed by SIRT1. | | 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). | | Background | The reverse amide Salermide is a strong inhibitor of the sirtuin proteins SirT1 and SirT2. Sirtuins are nicotinamide adenine dinucleotide-dependent protein deacetylases involved in cell aging and lifespan regulation. Nuclear SirT1 is implicated in regulating apoptosis, cellular senescence, aging, and longevity; SirT2 is involved in cytoskeletal regulation and progression through mitosis. Exposure of human cancer cell lines to Salermide results in the reactivation of proapoptotic genes repressed by SirT1 and tumor-specific cell death. Salermide treatment of human breast cancer cells leads to decreased SirT1 expression and increased acetylation and activation of p53. Inhibition of both SirT1 and SirT2 by Salermide is required to induce p53 acetylation and cell death. Salermide treatment of human pancreatic cancer cells potentiates the anticancer effects of a cytotoxin, reducing pancreatic cancer cell progression and stopping the cell cycle at G1. | | References | [1] E LARA. Salermide, a Sirtuin inhibitor with a strong cancer-specific proapoptotic effect[J]. Oncogene, 2008, 28 6: 781-791. DOI:10.1038/onc.2008.436
[2] MATTHIEU Y. PASCO. Characterization of Sirtuin Inhibitors in Nematodes Expressing a Muscular Dystrophy Protein Reveals Muscle Cell and Behavioral Protection by Specific Sirtinol Analogues[J]. Journal of Medicinal Chemistry, 2009, 53 3: 1407-1411. DOI:10.1021/jm9013345
[3] YONGBO ZHAO . Interactions between SIRT1 and MAPK/ERK regulate neuronal apoptosis induced by traumatic brain injury in vitro and in vivo[J]. Experimental Neurology, 2012, 237 2: Pages 489-498. DOI:10.1016/j.expneurol.2012.07.004 |
| | N-[3-[[(2-Hydroxy-1-naphthalenyl)methylene]amino]phenyl]-α-methylbenzeneacetamide Preparation Products And Raw materials |
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