401250-M

Ilimaquinone

A cell-permeable marine sponge metabolite with anti-microbial, anti-HIV, anti-inflammatory, and anti-mitotic properties.

• Synonym(s): Ilimaquinone, 3-[(Decahydro-1β,2β,4aβ-trimethyl-5-methylene-1-napthyl)methyl]-2-hydroxy-5-methoxybenzoquinone, IQ
• Empirical Formula (Hill Notation): C₂₂H₃₀O₄
• CAS Number: 71678-03-0
• Molecular Weight: 358.47
• UNSPSC Code: 12352200

Properties

• Quality Level: 100
• assay: ≥98% (HPLC)
• form: solid
• manufacturer/tradename: Calbiochem^®
• storage condition: OK to freeze; protect from light
• color: red
• solubility: DMSO: 200 mg/mL
• storage temp.: −20°C
• InChI: 1S/C22H30O4/c1-13-7-6-8-18-21(13,3)10-9-14(2)22(18,4)12-15-19(24)16(23)11-17(26-5)20(15)25/h11,14,18,24H,1,6-10,12H2,2-5H3/t14-,18+,21+,22+/m0/s1
• InChI key: JJWITJNSXCXULM-YVUMSICPSA-N

Description

General description

A cell-permeable marine sponge metabolite that induces complete and reversible breakdown of Golgi membranes into smaller vesicular structures, possibly through the activation of heterotrimeric G-proteins. Blocks protein transport at the cis-Golgi and depolymerizes microtubules. Also possesses anti-HIV activity and the ability to inhibit the cytotoxicity of ricin and diphtheria toxin.

A cell-permeable marine sponge metabolite with anti-microbial, anti-HIV, anti-inflammatory, and anti-mitotic properties. Induces a complete and reversible breakdown of Golgi membranes into smaller vesicular structures and causes depolymerization of microtubules. Inhibits cellular methylations through its interaction with S-adenosylhomocysteinase. Blocks the cytotoxicity of ricin and diphtheria toxin. Acts as an inhibitor of the RNase H activity of HIV-1.

Biochem/physiol Actions

Primary Target
Induces a complete and reversible breakdown of Golgi membranes into smaller vesicular structures and causes depolymerization of microtubules.

Warning

Toxicity: Standard Handling (A)

Other Notes

Radeke, H.S., et al. 1999. Chem. Biol. 6, 639.
Radeke, H.S., and Snapper, M.L. 1998. Bioorg. Med. Chem.6, 1227.
Jamora, C., et al. 1997. Cell 91, 617.
Nambiar, M.P., and Wu, H.C. 1995. Exp. Cell Res. 219, 671.
Loya, S., and Hizi, A. 1993. J. Biol. Chem. 268, 9323.
Takizawa, P.A., et al. 1993. Cell 73, 1079.
Veit, B., et al. 1993. J. Cell Biol. 122, 1197.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Safety Information

• Storage Class: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable