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About This Item
Empirical Formula (Hill Notation):
C21H16N2O2S
CAS Number:
Molecular Weight:
360.43
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
12352200
MDL number:
Quality Level
assay
≥97% (HPLC)
form
powder
color
white
solubility
DMSO: ≥10 mg/mL
storage temp.
room temp
SMILES string
Oc1ccc2ccccc2c1CC3=C(NC(=S)NC3=O)c4ccccc4
InChI
1S/C21H16N2O2S/c24-18-11-10-13-6-4-5-9-15(13)16(18)12-17-19(14-7-2-1-3-8-14)22-21(26)23-20(17)25/h1-11,24H,12H2,(H2,22,23,25,26)
InChI key
RVNSQVIUFZVNAU-UHFFFAOYSA-N
Application
Cambinol has been used:
- as an inhibitor of sirutins (SIRT1 and 2) in hepatocarcinoma cell lines to test its effect on cellular viability and colony formation
- as a SIRT1 and SIRT2 inhibitor to test its effect on frizzled 7 (FZD7) expression in the breast cancer cells MDA-MB-231 and T-47D cells
- as a sirutin inhibitor in L929 cells to test its protective effect against tumor necrosis factor (TNF)-induced cell death
Biochem/physiol Actions
Cambinol is a Sirtuin (Human Silent Information Regulator) Type 1/2 Inhibitor.
Cambinol is a Sirtuin (Human Silent Information Regulator) Type 1/2 Inhibitor. Sirtuins are structurally and mechanistically unrelated to HDACs Class 1 & 2 deacetylases but share many protein targets. HDAC is a large complex enzyme family involved in epigenetic-control of gene expression. Sirt2 has an IC50 equal to 59 μM.
Cambinol, a β-naphthol compound, elicits antitumor activity and impairs the mitogen-activated protein kinase (MAPK) signaling. It has ability to inhibit the secretion of inflammatory cytokines including the tumor necrosis factor and interleukins. Cambinol can be a potential therapeutic agent for treating inflammatory diseases. It also aids protection in events of endotoxic and septic shock.
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
dust mask type N95 (US), Eyeshields, Gloves
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Frizzled 7 expression is positively regulated by SIRT1 and beta-catenin in breast cancer cells
Simmons Jr GE, et al.
PLoS ONE, 9(6), e98861-e98861 (2014)
The sirtuin inhibitor cambinol impairs MAPK signaling, inhibits inflammatory and innate immune responses and protects from septic shock
Lugrin J, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1833(6), 1498-1510 (2013)
Inhibition of sirtuins 1 and 2 impairs cell survival and migration and modulates the expression of P-glycoprotein and MRP3 in hepatocellular carcinoma cell lines
Ceballos MP, et al.
Toxicology Letters, 289(6), 63-74 (2018)