Key Documents

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

Pricing and availability is not currently available.

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Properties

Quality Segment

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

Description

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.

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This Item	566323	SML1685	SML1568
Sigma-Aldrich C0494 Cambinol	Sigma-Aldrich 566323 SIRT1/2 Inhibitor IV, Cambinol	Sigma-Aldrich SML1685 Ribocil-C	Sigma-Aldrich SML1568 ZINC05626394
form powder	form solid	form powder	form powder
assay ≥97% (HPLC)	assay ≥95% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)
Quality Level 100	Quality Level 100	Quality Level 100	Quality Level 100
storage temp. room temp	storage temp. 2-8°C	storage temp. 2-8°C	storage temp. 2-8°C
solubility DMSO: ≥10 mg/mL	solubility DMSO: 100 mg/mL, ethanol: 5 mg/mL	solubility DMSO: 20 mg/mL, clear	solubility DMSO: 25 mg/mL, clear
color white	color white	color white to beige	color white to beige

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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