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Ilimaquinone

AG-CN2-0038-C100 100 µg INQ
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Additional Information

Product Data
Synonyms 3-[(Decahydro-1α,2β,4aβ-trimethyl-5-methylene-1-naphthyl)methyl]-2-hydroxy-5-methoxybenzoquinone; IQ
Properties
Formula C22H30O4
MW 358.5
CAS 71678-03-0
Source/Host Isolated from Anthelia sp.
Purity ≥98% (HPLC)
Appearance Yellow solid.
Solubility Soluble in methanol, ethanol, DMSO or hexane.
Identity Determined by 1H-NMR and MS.
InChi Key JJWITJNSXCXULM-ZKZNVZPYSA-N
Product Type Chemical
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
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Product Description

  • Cytoplasmic microtubule inhibitor [2, 6].
  • Cell permeable, antimicrobial, anti-inflammatory, antimitotic and cytotoxic compound [1, 11].
  • Induces a complete and reversible breakdown/disruption of Golgi membranes into smaller vesicular structures [2, 6].
  • Blocks the association of the ADP-ribosylation factor and β-COP to the Golgi membrane [3, 6].
  • Blocks protein transport to the plasma membrane and inhibits gap junctional communication [2, 3, 9].
  • HIV-1 inhibitor [4].
  • Blocks the cytotoxicity of ricin and diphtheria toxin [5].
  • S-Adenosylhomocysteinase hydrolase inhibitor and cellular methylations inhibitor [7, 12].
  • DNA polymerase β lyase activity inhibitor [8].
  • Anti-cancer compound. [10].

Product References

  1. Ilimaquinone, a sesquiterpenoid quinone from a marine sponge: R.T. Luibrand, et al.; Tetrahedron 35, 609 (1979)
  2. Microtubule independent vesiculation of Golgi membranes and the reassembly of vesicles into Golgi stacks: B. Veit, et al.; J. Cell. Biol. 122, 1197 (1993)
  3. Complete vesiculation of Golgi membranes and inhibition of protein transport by a novel sea sponge metabolite, ilimaquinone: P.A. Takizawa, et al.; Cell 73, 1079 (1993)
  4. The interaction of illimaquinone, a selective inhibitor of the RNase H activity, with the reverse transcriptases of human immunodeficiency and murine leukemia retroviruses: S. Loya & A. Hizi; J. Biol. Chem. 268, 9323 (1993)
  5. Ilimaquinone inhibits the cytotoxicities of ricin, diphtheria toxin, and other protein toxins in Vero cells: M.P. Nambiar & H.C. Wu; Exp. Cell Res. 219, 671 (1995)
  6. Golgi-disturbing agents: A. Dinter & E.G. Berger; Histochem. Cell Biol. 109, 571 (1998)
  7. Interactions of (-)-ilimaquinone with methylation enzymes: implications for vesicular-mediated secretion: H.S. Radeke, et al.; Chem. Biol. 6, 639 (1999)
  8. Marine sesquiterpenoids that inhibit the lyase activity of DNA polymerase beta: S. Cao, et al.; J. Nat. Prod. 67, 1716 (2004)
  9. Ilimaquinone inhibits gap junctional communication in a connexin isotype-specific manner: V. Cruciani & S.O. Mikalsen; Exp. Cell Res. 304, 136 (2005)
  10. Ilimaquinone, a marine sponge metabolite, displays anticancer activity via GADD153-mediated pathway: P.H. Lu, et al.; Eur. J. Pharmacol. 556, 45 (2007)
  11. Comparison of the biological properties of several marine sponge-derived sesquiterpenoid quinones: C.A. Motti, et al.; Molecules 12, 1376 (2007)
  12. A new structural class of S-adenosylhomocysteine hydrolase inhibitors: B.G. Kim, et al.; Bioorg. Med. Chem. 17, 6707 (2009) 
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