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C0494

Cambinol

Name: Cambinol
Brand: SIGMA

≥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

NACRES:

NA.77

PubChem Substance ID:

329774799

UNSPSC Code:

12352200

MDL number:

MFCD09057543

Assay:

≥97% (HPLC)

Form:

powder

Quality level:

100

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Quality Level

100

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

Related Categories

Bioactive Small Molecule Inhibitors

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, 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.

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.

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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Certificates of Analysis (COA)

Lot/Batch Number

0000485161

0000480762

0000119570

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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)

Sirtuin 1 and 2 inhibitors enhance the inhibitory effect of sorafenib in hepatocellular carcinoma cells.

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

We offer a variety of small molecule research tools, such as transcription factor modulators, inhibitors of chromatin modifying enzymes, and agonists/antagonists for target identification and validation in gene regulation research; a selection of these research tools is shown below.

Global Trade Item Number

SKU	GTIN
C0494-5MG	04061832824130
C0494-25MG	04061832824123

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