14513-15-6
14513-15-6 structure
- Name: Cambinol
- Chemical Name: 5-[(2-hydroxynaphthalen-1-yl)methyl]-6-phenyl-2-sulfanylidene-1H-pyrimidin-4-one
- CAS Number: 14513-15-6
- Molecular Formula: C21H16N2O2S
- Molecular Weight: 360.429
- Catalog: Signaling Pathways Cell Cycle/DNA Damage Sirtuin
- Create Date: 2016-09-02 04:07:58
- Modify Date: 2024-01-08 12:54:10
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Cambinol is a SIRT1 and SIRT2 inhibitor with IC50 values of 56 and 59 μM, respectively.
| Name | 5-[(2-hydroxynaphthalen-1-yl)methyl]-6-phenyl-2-sulfanylidene-1H-pyrimidin-4-one |
|---|---|
| Synonyms |
cambinol
5-[(2-Hydroxy-1-naphthyl)methyl]-6-phenyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone 4(1H)-Pyrimidinone, 2,3-dihydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo- SIRT1/2 Inhibitor IV,Cambinol |
| Description | Cambinol is a SIRT1 and SIRT2 inhibitor with IC50 values of 56 and 59 μM, respectively. |
|---|---|
| Related Catalog | |
| Target |
SIRT1:56 μM (IC50) SIRT2:59 μM (IC50) |
| In Vitro | Cambinol inhibits NAD-dependent deacetylase activity of human SIRT1 and SIRT2. Inhibition of SIRT1 activity with cambinol during genotoxic stress leads to hyperacetylation of key stress response proteins and promotes cell cycle arrest. Treatment of BCL6-expressing Burkitt lymphoma cells with cambinol as a single agent induces apoptosis, which is accompanied by hyperacetylation of BCL6 and p53. Cambinol has only weak inhibitory activity against SIRT5 (42% inhibition at 300 μM) and no activity against SIRT3[1]. |
| 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]. |
| Cell Assay | .The reporter construct with or without varying amounts of GAL4-BCL6 expression plasmid are introduced into NCI-H460 cells using calcium phosphate method. A plasmid containing cytomegalovirus (CMV)-driven β-galactosidase reporter (50 ng) is cotransfected to control for transfection efficiency. Sixteen hours after transfection, cells are treated with 100 μM cambinol of DMSO (control) for 24 hours and the luciferase and β-galactosidase activity is measured[1]. |
| Animal Admin | Mice: Cambinolat the dose of 100 mg/kg, or vehicle are administered i.v. through tail vein injection or i.p. daily from day 5 to 19 (five injections per week). The dose of 100 mg/kg cambinol is the highest dose that could be administered as a single i.v. injection due to limited solubility of the drug. Tumor size is measured thrice a week using caliper and the tumor volumes are calculated[1]. |
| References |
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Boiling Point | 667ºC at 760mmHg |
| Melting Point | 235 °C(dec.) |
| Molecular Formula | C21H16N2O2S |
| Molecular Weight | 360.429 |
| Flash Point | 357.2ºC |
| Exact Mass | 360.093262 |
| PSA | 100.97000 |
| LogP | 4.71 |
| Vapour Pressure | 2.12E-18mmHg at 25°C |
| Index of Refraction | 1.771 |
| Symbol |
GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H302-H319 |
| Precautionary Statements | P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xn: Harmful; |
| Risk Phrases | R22 |
| RIDADR | NONH for all modes of transport |