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C0494

Sigma-Aldrich

Cambinol

≥97% (HPLC), white, powder

Synonym(s):

5-(2-Hydroxynaphthalen-1-ylmethyl)-6-phenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one, 5-[(2-hydroxy-1-naphthyl)methyl]-2-mercapto-6-phenyl-4(3H)-Pyrimidinone, NSC-1125476, Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone

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About This Item

Empirical Formula (Hill Notation):
C21H16N2O2S
CAS Number:
14513-15-6
Molecular Weight:
360.43
MDL number:
MFCD09057543
UNSPSC Code:
12352200
PubChem Substance ID:
329774799
NACRES:
NA.77

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. 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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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)
Intracellular nicotinamide adenine dinucleotide promotes TNF-induced necroptosis in a sirtuin-dependent manner
Preyat N, et al.
Cell Death and Differentiation, 23(1), 29-40 (2016)
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)
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)
María Paula Ceballos et al.
European journal of pharmacology, 892, 173736-173736 (2020-11-22)
Multidrug resistance (MDR) counteracts the efficiency of sorafenib, an important first-line therapy for hepatocellular carcinoma (HCC). Sirtuins (SIRTs) 1 and 2 are associated with tumor progression and MDR. We treated 2D and 3D cultures (which mimic the features of in
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Discover Bioactive Small Molecules for Gene Regulation

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