| Identification | Back Directory | [Name]
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 | [CAS]
14513-15-6 | [Synonyms]
Cambinol
NSC 112546
NSC-1125476
SIRT1/2 Inhibitor IV
CAMBINOL;NSC-1125476
Cambinol - NSC 112546
SIRT1/2 Inhibitor IV, Cambinol
5-[(2-hydroxy-1-naphthyl)methyl]-2-mercapto-6-phenyl-4(3H)-Pyrimidinone
5-[(2-Hydroxy-1-naphthyl)methyl]-6-phenyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone
5-(2-Hydroxynaphthalen-1-ylmethyl)-6-phenyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one
Tetrahydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-4(1H)-Pyrimidinone
5-[(2-Hydroxynaphthalen-1-yl)methyl]-6-phenyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
4(1H)-Pyrimidinone, 2,3-dihydro-5-[(2-hydroxy-1-naphthalenyl)methyl]-6-phenyl-2-thioxo-
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)-Pyrimidin
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 | [Molecular Formula]
C21H16N2O2S | [MDL Number]
MFCD09057543 | [MOL File]
14513-15-6.mol | [Molecular Weight]
360.435 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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
| [Uses]
SIRT1/2 Inhibitor IV, Cambinol is an inhibitor of SIRT1, SIRT2, and SIRT5. | [Biological Activity]
sirt1/2 inhibitor iv (cambinol) is a small-molecule inhibitor of sirt1 and sirt2 with ic50 values of 56 ?m and 59 ?m, respectively [1].sirtuin 1 (sirt1) and sirt2 are nad-dependent deacetylases and are members of sirtuin family protein. sirt1 regulate pathways in metabolism, inflammation and tumorigenesis and sirt2 functions as a tubulin deacetylase[2].sirt1/2 inhibitor iv is a cell-permeable sirt1 and sirt2 inhibitor. sirt1/2 inhibitor iv inhibited human sirt1 and sirt2 nad-dependent deacetylase activity with ic50 values of 56 and 59 ?mol/l, respectively. in nci h460 lung cancer cell line, combined inhibition of sirt2 and hdac6 with sirt1/2 inhibitor iv and trichostatin a resulted in hyperacetylation of tubulin. sirt1/2 inhibitor iv also increased acetylation of p53. in p53-positive lung cancer cell line nci h460, sirt1/2 inhibitor iv mediated inhibition of sirt1 sensitized cells to etoposide in p53-independent manner [1].in a mouse xenograft model, sirt1/2 inhibitor iv (100 mg/kg) administered i.v. into the tail vein or i.p. daily for 2 weeks (five injections per week) reduced tumor growth [1]. in mice pre-treated with cambinol for 2 hours and then exposed to 6% oxygen for 6 hours, cambinol significantly reduced epo mrna in the kidney and the liver [2]. | [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. |
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| Company Name: |
Sigma-Aldrich
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| Telephone: |
021-61415566 800-8193336 |
| Website: |
https://www.sigmaaldrich.cn |
| Company Name: |
TCI Chemicals
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| Telephone: |
021-67121386, 800-988-0390 |
| Website: |
www.tcichemicals.com |
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