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Merck

C0494

Sigma-Aldrich

Cambinol

≥97% (HPLC), white, powder

Szinonimák:

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

Bejelentkezésa Szervezeti és Szerződéses árazás megtekintéséhez


About This Item

Tapasztalati képlet (Hill-képlet):
C21H16N2O2S
CAS-szám:
Molekulatömeg:
360.43
MDL-szám:
UNSPSC kód:
12352200
PubChem Substance ID:
NACRES:
NA.77

Minőségi szint

Teszt

≥97% (HPLC)

Forma

powder

szín

white

oldhatóság

DMSO: ≥10 mg/mL

tárolási hőmérséklet

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)

Nemzetközi kémiai azonosító kulcs

RVNSQVIUFZVNAU-UHFFFAOYSA-N

Alkalmazás

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

Biokémiai/fiziológiai hatások

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.

Tulajdonságok és előnyök

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.

Tárolási osztály kódja

11 - Combustible Solids

WGK

WGK 3

Lobbanási pont (F)

Not applicable

Lobbanási pont (C)

Not applicable

Egyéni védőeszköz

dust mask type N95 (US), Eyeshields, Gloves


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Analitikai tanúsítványok (COA)

Lot/Batch Number

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Dokumentumtár megtekintése

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)
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)
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)
Marie Gamal et al.
Current issues in molecular biology, 45(6), 5005-5017 (2023-06-27)
Liver cancer is a prevalent form of cancer worldwide. While research has shown that increasing sphingomyelin (SM) hydrolysis by activating the cell surface membrane-associated neutral sphingomyelinase 2 (nSMase2) can control cell proliferation and apoptosis, the role of total glutathione depletion

Cikkek

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.

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