NSC-1125476, Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone, 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

Product NameNSC-1125476, Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone, 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
CAS14513-15-6
MFC21H16N2O2S
MW360.43
EINECS
MOL File14513-15-6.mol

Chemical Properties

Melting point	235 °C(dec.)
Density	1.41±0.1 g/cm3(Predicted)
storage temp.	room temp
solubility	DMSO: ≥10mg/mL
form	White solid
pka	7.24±0.25(Predicted)
color	White to Off-White
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)
InChIKey	RVNSQVIUFZVNAU-UHFFFAOYSA-N
SMILES	Oc1ccc2ccccc2c1CC3=C(NC(=S)NC3=O)c4ccccc4

Safety Information

Hazard Codes	Xn
Risk Statements	22
WGK Germany	3
HS Code	2933.59.8000
Storage Class	11 - Combustible Solids

Usage And Synthesis

Uses

SIRT1/2 Inhibitor IV, Cambinol is an inhibitor of SIRT1, SIRT2, and SIRT5.

Uses

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.

in vivo

Cambinol is well tolerated in mice (100 mg/kg) and inhibits growth of Burkitt lymphoma xenografts. No significant weight loss occurs in cambinol-treated animals relative to controls. Inhibitors of NAD-dependent deacetylases may constitute novel anticancer agents^[1].

IC 50

SIRT1: 56 μM (IC₅₀); SIRT2: 59 μM (IC₅₀)

storage

Store at -20°C

References

heltweg b, gatbonton t, schuler ad, et al. antitumor activity of a small-molecule inhibitor of human silent information regulator 2 enzymes. cancer res. 2006 apr 15;66(8):4368-77.laemmle a, lechleiter a, roh v, et al. inhibition of sirt1 impairs the accumulation and transcriptional activity of hif-1α protein under hypoxic conditions. plos one. 2012;7(3):e33433.

NSC-1125476, Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone, 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 Supplier

NSC-1125476, Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone, 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 manufacturers

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