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ProductsBack/Ilimaquinone [71678-03-0]
Chemical Structure
Chemical Structure
Chemical Structure

Ilimaquinone [71678-03-0]

Research Use Only
AG-CN2-0038
AdipoGen Life Sciences
CAS Number71678-03-0
DownloadMSDS
Product group Chemicals
Estimated Purity>98%
Molecular Weight358.5
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Ilimaquinone
  • Delivery Days Customer
    10
  • CAS Number
    71678-03-0
  • Certification
    Research Use Only
  • Estimated Purity
    >98%
  • Molecular Formula
    C22H30O4
  • Molecular Weight
    358.5
  • Scientific Description
    Chemical. CAS: 71678-03-0. Formula: C22H30O4. MW: 358.5. Isolated from Anthelia sp. Cytoplasmic microtubule inhibitor. Cell permeable, antimicrobial, anti-inflammatory, antimitotic and cytotoxic compound. Induces a complete and reversible breakdown/disruption of Golgi membranes into smaller vesicular structures. Blocks the association of the ADP-ribosylation factor and beta-COP to the Golgi membrane. Blocks protein transport to the plasma membrane and inhibits gap junctional communication. HIV-1 inhibitor. Blocks the cytotoxicity of ricin and diphtheria toxin. S-Adenosylhomocysteinase hydrolase inhibitor and cellular methylations inhibitor. DNA polymerase beta lyase activity inhibitor. Anti-cancer compound. - 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 beta-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 beta lyase activity inhibitor [8]. Anti-cancer compound. [10].
  • SMILES
    [H][C@]12CCCC(=C)[C@]1(C)CC[C@@H](C)[C@]2(C)CC1=C(O)C(=O)C=C(OC)C1=O
  • Storage Instruction
    -20°C,2°C to 8°C
  • UNSPSC
    12352200

References

  • Ilimaquinone, a sesquiterpenoid quinone from a marine sponge: R.T. Luibrand, et al.; Tetrahedron 35, 609 (1979)
  • Microtubule independent vesiculation of Golgi membranes and the reassembly of vesicles into Golgi stacks: B. Veit, et al.; J. Cell. Biol. 122, 1197 (1993)
  • 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)
  • 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)
  • 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)
  • Golgi-disturbing agents: A. Dinter & E.G. Berger; Histochem. Cell Biol. 109, 571 (1998)
  • Interactions of (-)-ilimaquinone with methylation enzymes: implications for vesicular-mediated secretion: H.S. Radeke, et al.; Chem. Biol. 6, 639 (1999)
  • Marine sesquiterpenoids that inhibit the lyase activity of DNA polymerase beta: S. Cao, et al.; J. Nat. Prod. 67, 1716 (2004)
  • Ilimaquinone inhibits gap junctional communication in a connexin isotype-specific manner: V. Cruciani & S.O. Mikalsen; Exp. Cell Res. 304, 136 (2005)
  • Ilimaquinone, a marine sponge metabolite, displays anticancer activity via GADD153-mediated pathway: P.H. Lu, et al.; Eur. J. Pharmacol. 556, 45 (2007)