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AdipoGen Life Sciences
Ilimaquinone
320
CHF
CHF 320.00
In stock
AG-CN2-0038-C100100 µgCHF 320.00
| Product Details | |
|---|---|
| Synonyms | 3-[(Decahydro-1α,2β,4aβ-trimethyl-5-methylene-1-naphthyl)methyl]-2-hydroxy-5-methoxybenzoquinone; IQ |
| Product Type | Chemical |
| Properties | |
| Formula | C22H30O4 |
| MW | 358.5 |
| CAS | 71678-03-0 |
| Source/Host Chemicals | Isolated from Anthelia sp. |
| Purity Chemicals | ≥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 |
| 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 |
| 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. |
| Documents | |
| MSDS |
 Download PDF |
| Product Specification Sheet | |
| Datasheet |
Download PDF |
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
- 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)
- Comparison of the biological properties of several marine sponge-derived sesquiterpenoid quinones: C.A. Motti, et al.; Molecules 12, 1376 (2007)
- A new structural class of S-adenosylhomocysteine hydrolase inhibitors: B.G. Kim, et al.; Bioorg. Med. Chem. 17, 6707 (2009)
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