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HomeProduct name listEMBELIN

EMBELIN

Synonym(s):2,5-Dihydroxy-3-undecyl-2,5-cyclohexadiene-1,4-dione;Apoptosis Activator III, Embelin - CAS 550-24-3 - Calbiochem;Embelic acid;Embelin, Embelia ribes, XIAP inhibitor, Embelin, 2,5-Dihydroxy-3-undecyl-1,4-benzoquinone;Emberine

  • CAS NO.:550-24-3
  • Empirical Formula: C17H26O4
  • Molecular Weight: 294.39
  • MDL number: MFCD00016369
  • EINECS: 208-979-8
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-19 15:53:33
EMBELIN Structural

What is EMBELIN?

Description

Embelin (550-24-3) inhibits?the lysine acetyl transferase PCAF?in vitro and in vivo?(in vitro?IC50=7.2 mM). Inhibits H3K9 acetylation in mouse liver tissue while leaving levels of H3K14, H4K8, H4K12 unchanged.1? Also inhibits X-linked inhibitor of apoptosis (XIAP) (IC50 = 4.1 μM, competing with Smac peptide). Binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Induces apoptosis and alters gene expression profiles in breast cancer cells.3?Possesses anti-inflammatory and analgesic activity?in vivo.4?Cell-permeable.

Chemical properties

Orange Solid

The Uses of EMBELIN

Embelin is a natural benzoquinone found in plants of the Myrsinaceae family. Embelin has a wide range of biological activity as it inhibits the growth of bacteria, fungi, protozoa and parasites. Embel in also displays contraceptive and pro-apoptotic properties.

The Uses of EMBELIN

Embelin is a natural benzoquinone found in plants of the Myrsinaceae family. Embelin has a wide range of biological activity as it inhibits the growth of bacteria, fungi, protozoa and parasites. Embelin also displays contraceptive and pro-apoptotic properties.

What are the applications of Application

Embelin is an anti-nociceptive, anti-inflammatory, and anti-oxidant agent also shown to induce apoptosis

Definition

ChEBI: A member of the class of dihydroxy-1,4-benzoquinones that is 2,5-dihydroxy-1,4-benzoquinone which is substituted by an undecyl group at position 3. Isolated from Lysimachia punctata and Embelia ribes, it exhibits antimicrobial, an ineoplastic and inhibitory activity towards hepatitis C protease.

Biological Activity

Cell-permeable, non-peptide inhibitor of X-linked inhibitor of apoptosis (XIAP) (IC 50 = 4.1 μ M in competition binding assay with Smac peptide); binds to the BIR3 domain, preventing XIAP interaction with caspase-9 and Smac. Inhibits cell growth, induces apoptosis and activates caspase-9 in prostate cancer cells (IC 50 4-6 μ M), but has a weaker effect on normal prostate cells (IC 50 = 19-20 μ M). Overcomes the protective effect of XIAP on apoptosis in XIAP-transfected Jurkat cells. Anti-tumor, analgesic and anti-inflammatory in vivo .

References

1) Modak?et al. (2013),?Probing p300/CBP associated factor (PCAF)-dependent pathways with a small molecule inhibitor; ACS Chem. Biol.,?8?1311 2) Nikolovska-Coleska?et al. (2004),?Discovery of embelin as a cell-permeable, small-molecular weight inhibitor of XIAP through structure-based computational screening of a traditional herbal medicine three-dimensional structure database; J. Med. Chem.,?47?2430 3) Shah?et al.?(2016),?Embelin inhibits proliferation, induces apoptosis and alters gene expression profiles in breast cancer cells; Pharmacol. Rep.,?68?638 4) Chitra?et al. (1994),?Antitumor, anti-inflammatory and analgesic property of embelin, a plant product.; Chemotherapy,?40?109

Properties of EMBELIN

Melting point: 142-143°C
Boiling point: 356.15°C (rough estimate)
Density  1.131
refractive index  1.4230 (estimate)
storage temp.  Keep in dark place,Inert atmosphere,2-8°C
solubility  DMSO: >10 mg/mL
form  solid
pka 2.84±0.50(Predicted)
color  Dark orange
Sensitive  Light Sensitive
Stability: Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.

Safety information for EMBELIN

Signal word Warning
Pictogram(s)
ghs
Health Hazard
GHS08
Precautionary Statement Codes P201:Obtain special instructions before use.
P308+P313:IF exposed or concerned: Get medical advice/attention.

Computed Descriptors for EMBELIN

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