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Catalog No.GC17312

Jasplakinolide Chemical Structure

stabilizes pre-formed actin filaments and inhibits their disassembly

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Jasplakinolide is a natural macrocyclic peptide first isolated from a marine sponge. It potently inhibits the proliferation of PC3 prostate carcinoma cells (IC50 = 35 nM) by binding F-actin (KD = 15 nM).[1] This binding of jasplakinolide to actin, which is competitive with phalloidin, stabilizes actin filaments in vitro but disrupts actin filaments and induces irregular polymerization of monomeric actin in vivo.[1],[2] This compound is used to investigate the role of actin in diverse cellular roles, such as motility, transport, and development.[3],[4]

[1]. Bubb, M.R., Senderowicz, A.M.J., Sausville, E.A., et al. Jasplakinolide, a cytotoxic natural product, induces actin polymerization and competitively inhibits the binding of phalloidin to F-actin. The Journal of Biological Chemisty 269(21), 14869-14871 (1994).
[2]. Bubb, M.R., Spector, I., Beyer, B.B., et al. Effects of jasplakinolide on the kinetics of actin polymerization. An explanation for certain in vivo observations. The Journal of Biological Chemisty 275(7), 5163-5170 (2000).
[3]. Van Goor, D., Hyland, C., Schaefer, A.W., et al. The role of actin turnover in retrograde actin network flow in neuronal growth cones. PLoS One 7(2), (2012).
[4]. Zhang, X., Cui, X., Cheng, L., et al. Actin stabilization by jasplakinolide affects the function of bone marrow-derived late endothelial progenitor cells. PLoS One 7(11), (2012).

Chemical Properties

Cas No. 102396-24-7 SDF
Synonyms NSC 613009
Chemical Name (4R,7R,10S,13R,17R,19S,E)-7-((2-bromo-1H-indol-3-yl)methyl)-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetraone
Canonical SMILES BrC(NC1=CC=CC=C21)=C2C[C@H](C(N[C@@H](C(C=C3)=CC=C3O)CC(O[C@@H](C)C[C@@H](C)C=C(C)C[C@@H](C)C(N[C@H]4C)=O)=O)=O)N(C)C4=O
Formula C36H45BrN4O6 M.Wt 709.67
Solubility Soluble in ethanol, methanol and DMSO Storage Store at -20°C
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request

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Average Rating: 5 ★★★★★ (Based on Reviews and 35 reference(s) in Google Scholar.)

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