380315-80-0

Basic information

• Product Name: TENOVIN-1
• Synonyms: TENOVIN-1;N-[[[4-(Acetylamino)phenyl]amino]thioxomethyl]-4-(1,1-dimethylethyl)benzamide;N-[(4-acetaMidophenyl)carbaMothioyl]-4-tert-butylbenzaMide;Benzamide, N-[[[4-(acetylamino)phenyl]amino]thioxomethyl]-4-(1,1-dimethylethyl)-;N-[[[4-(Acetylamino)phenyl]amino]thioxomethyl]-4-(1,1-dimethylethyl)benzamide Tenovin 1;Tenovin 1 N-[[[4-(Acetylamino)phenyl]amino]thioxomethyl]-4-(1,1-dimethylethyl)benzamide;Tenovin-1, >=98%
• CAS NO: 380315-80-0
• Molecular Formula: C20H23N3O2S
• Molecular Weight: 369.487
• EINECS: 200-256-5
• Product Categories: Inhibitor;Inhibitors
• Mol File: 380315-80-0.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• Density: 1.238±0.06 g/cm3(Predicted)
• Storage Temp.: Store at +4°C
• Solubility: Soluble in DMSO (10 mg/ml with warming)
• PKA: 9.09±0.70(Predicted)
• Stability: Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20°C for up to 3 months.
• CAS DataBase Reference: TENOVIN-1(CAS DataBase Reference)
• NIST Chemistry Reference: TENOVIN-1(380315-80-0)
• EPA Substance Registry System: TENOVIN-1(380315-80-0)

Safety Data

• RIDADR: 3077
• Hazardous Substances Data: 380315-80-0(Hazardous Substances Data)

Usage

Description

Tenovin-1 is a small molecule activator of p53 transcriptional activity, functioning as a sirtuin inhibitor by targeting the deacetylase activity of human SIRT1 and SIRT2. It is known for its ability to elevate p53 expression in certain cell lines and decrease the growth of specific cancer cells. Despite its potential in cancer research, Tenovin-1 has limitations due to its poor water solubility.

Uses

Used in Cancer Research:
Tenovin-1 is used as a sirtuin inhibitor for the activation of p53 transcriptional activity. It is particularly effective in elevating p53 expression in MCF-7 cells and has shown to decrease the growth of BL2 Burkitt’s lymphoma and ARN8 melanoma cells. This makes it a valuable tool in understanding the role of p53 in cancer and potentially developing targeted therapies.
Used in Drug Development:
Due to its role in inhibiting the deacetylase activity of SIRT1 and SIRT2, Tenovin-1 is used as a starting point for the development of new drugs targeting the sirtuin family. These drugs may have applications in treating various diseases, including cancer, by modulating the activity of sirtuins and their associated pathways.
Used in Cellular Studies:
Tenovin-1 is used as a research tool in cellular studies to investigate the role of sirtuins and p53 in cell growth, differentiation, and apoptosis. Understanding these processes can provide insights into the development of cancer and the potential for targeted therapeutic interventions.

Biological Activity

p53 activator that protects against MDM2-mediated p53 degradation. Elevates levels of p53 and p21 CIP/WAF1 and induces expression from an endogenous p53-dependent promoter. Exhibits potent antiproliferative activity in vitro .

References

Lain et al. (2008), Discovery, in vivo activity, and mechanism of action of a small-molecule p53 activator; Cancer Cell, 13 454 Sonnemann et al. (2014), p53-dependent and p53-independent anticancer effects of different histone deacetylase inhibitors; Br. J. Cancer 110 656 Nihal et al. (2014), SIRT1 is upregulated in cutaneous T-cell lymphoma, and its inhibition induces growth arrest and apoptosis; Cell Cycle 13 632 Wilking et al. (2014), SIRT1 deacetylase is overexpressed in human melanoma and its small molecule inhibition imparts anti-proliferative response via p53 activation; Arch. Biochem. Biophys. 563 94 Marx et al. (2018), The sirtuin 1/2 inhibitor tenovin-1 induces a nonlinear apoptosis-inducing factor-dependent cell death in a p53 null Ewing’s sarcoma cell line; New Drugs 36 396 Bang et al. (2019), Tenovin-1 Induces Senescence and Decreases Wound-Healing Activity in Cultured Rat Primary Astrocytes; Biomol. Ther. (Seoul) 27 283

InChI:InChI=1S/C20H23N3O2S/c1-13(24)21-16-9-11-17(12-10-16)22-19(26)23-18(25)14-5-7-15(8-6-14)20(2,3)4/h5-12H,1-4H3,(H,21,24)(H2,22,23,25,26)

Upstream product

• 98-73-7 4-(1,1-dimethylethyl)benzoic acid 
• 540-72-7 sodium thiocyanide 
• 122-80-5 N-acetyl-p-phenylenediamine 
• 1710-98-1 p-tert-butyl benzoyl chloride 

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Synthesis and biological characterisation of sirtuin inhibitors based on the tenovins

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