Home Epigenetics DNA Methyltransferase inhibitor β-thujaplicin

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β-thujaplicin DNA Methyltransferase inhibitor

Cat.No.S4771

β-Thujaplicin (β-TH, Hinokitiol, 4-Isopropyltropolone) is a toxic tropolone derivative present in the heartwood of western red cedar (Thuja plicata) and is used as a preservative and antimicrobial additive in a number of commercial goods. Hinokitiol is a component of essential oils isolated from Chymacyparis obtusa, reduces Nrf2 expression, and decreases DNMT1 and UHRF1 mRNA and protein expression, with anti-infective, anti-oxidative, and anti-tumor activities.
β-thujaplicin DNA Methyltransferase inhibitor Chemical Structure

Chemical Structure

Molecular Weight: 164.20

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Chemical Information, Storage & Stability

Molecular Weight 164.20 Formula

C10H12O2

 Storage (From the date of receipt)
CAS No. 499-44-5 Download SDF Storage of Stock Solutions

Synonyms Hinokitiol, 4-Isopropyltropolone Smiles CC(C)C1=CC(=O)C(=CC=C1)O

Solubility

In vitro
Batch:

DMSO : 32 mg/mL (194.88 mM)
(Moisture-contaminated DMSO may reduce solubility. Use fresh, anhydrous DMSO.)

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Mass Concentration Volume Molecular Weight

In vivo
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Method for preparing in vivo formulation: Take μL DMSO master liquid, next addμL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O, mix and clarify.

Method for preparing in vivo formulation: Take μL DMSO master liquid, next add μL Corn oil, mix and clarify.

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Mechanism of Action

In vitro
In lung cancer cells, hinokitiol inhibits cell proliferation by inducing the p53-independent DNA damage response, autophagy (not apoptosis), S-phase cell cycle arrest, and senescence. Hinokitiol induces autophagy in lung adenocarcinoma cells but not in human lung stromal fibroblasts. It induces cellular senescence in both human lung cancer cells and lung stromal fibroblasts[1]. Treatment with hinokitiol reveals a concentration-dependent inhibition of migration of B16-F10 melanoma cells. It appears to achieve this effect by reducing the expression of MMP-1 and by suppressing the phosphorylation of mitogen- activated protein kinase (MAPK) signaling molecules such as extracellular signal-regulated kinase (ERK) 1/2, p38 MAPK and c-Jun N-terminal kinases (JNK). On the other hand, hinokitiol treatment reverses IκB-α degradation and inhibits the phosphorylation of p65 nuclear factor kappa B (NF-κB) and cJun in B16-F10 cells. In addition, hinokitiol suppresses the translocation of p65 NF-κB from the cytosol to the nucleus, suggesting reduced NF-κB activation[2].
In vivo
Hinokitiol reduces tumor growth, potentially through the attenuation of tumorigenicity, and induces DNA damage and autophagy to suppress tumor progression[1]. In vivo study demonstrates that hinokitiol treatment significantly reduces the total number of mouse lung metastatic nodules and improves histological alterations in B16-F10 injected C57BL/6 mice[2].
References

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