Ilimaquinone An ADP-ribosylation factor (ARF) and β-COP to the Golgi membrane inhibitor

Ilimaquinone (CAS 71678-03-0)

Ilimaquinone | CAS 71678-03-0 is rated 5.0 out of 5 by 1.
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Synonym: IQ; Imaquinone
Application: An ADP-ribosylation factor (ARF) and β-COP to the Golgi membrane inhibitor
CAS Number: 71678-03-0
Purity: ≥98%
Molecular Weight: 358.47
Molecular Formula: C22H30O4
* Refer to Certificate of Analysis for lot specific data (including water content).
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Ilimaquinone is a natural marine metabolite shown to have antiinflammatory, antimicrobial, and antimitotic properties. Ilimaquinone has also been described to block diptheria toxin and the cytotoxicity of ricin. Golgi membrane studies reveal that exposure to ilimaquinone results in the formation of vesiculated Golgi membranes and blockage of the secretory pathway, which can be reversed with the removal of ilimaquinone. Additionally, ilimaquinone has been shown to block the association of the ADP-ribosylation factor (ARF) and β-COP to the Golgi membrane, and depolarize cytoplasmic microtubules. Further studies report that the vesiculation of Golgi membranes through Ilimaquinone takes place by the activation of heterotrimeric G proteins. Biochemical assays from HIV studies suggest that ilimaquinone belongs to a group of marine metabolites with anti-HIV activity. Ilimaquinone studies suggest that it has the ability to induce anti-proliferative affects through GADD153-mediated pathway modifications.


References

1. Takizawa, P.A., et al. 1993. Cell. 73: 1079-1090. PMID: 8513494
2. Veit, B., et al. 1993. J. Cell Biol. 122: 1197-1206. PMID: 8104190
3. Jamora, C., et al. 1997. Cell. 91: 617-626. PMID: 9393855
4. Dinter, A., et al. 1998. Histochem. Cell Biol. 109: 571-590. PMID: 9681636
5. Radeke, H.S., et al. 1999. Chem. Biol. 6: 639-647. PMID: 10467129
6. Tziveleka, L.A., et al. 2003. Curr Top Med Chem. 3: 1512-1535. PMID: 14529524
7. Lu, P.H., et al. 2007. Eur. J. Pharmacol. 556: 45-54. PMID: 17140562

Physical State :
Solid
Solubility :
Soluble in DMSO (25 mg/ml), and ethanol (25 mg/ml).
Storage :
Store at -20° C
Melting Point :
204.22° C (Predicted)
Boiling Point :
~478.4° C at 760 mmHg (Predicted)
Density :
~1.1 g/cm3 (Predicted)
Refractive Index :
n20D 1.55
IC50 :
P388: IC50 = 0.2 ug/ml (Mus musculus); A549: IC50 = 0.4 ug/ml (human); A2780: IC50 = 10.9 µM (human); Adenosylhomocysteinase: IC50 = 40 µM (human)
pK Values :
pKa: 2.92
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
3
PubChem CID :
72291
Merck Index :
14: 4898
MDL Number :
MFCD00274432
SMILES :
C[C@H]1CC[C@]2([C@H]([C@]1(C)CC3=C(C(=O)C=C(C3=O)OC)O)CCCC2=C)C

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Certificate of Analysis

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Ilimaquinone  Product Citations

See how others have used Ilimaquinone. Click on the entry to view the PubMed entry .

Citations 1 to 1 of 1 total

PMID: # 27281477  Massarweh, A. et al. 2016. J. Lipid Res. 57: 1477-91.

Citations 1 to 1 of 1 total

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Rated 5 out of 5 by from Lu et al Lu et al. (PubMed ID 17140562) found that ilimaquinone induced a concentration-dependent anti-proliferative effect in several cancer lines by increasing G(1) phase arrest and subsequent G(1) phase apoptosis. -SCBT Publication Review
Date published: 2015-07-10
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