A binder and modulator of F-actin
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Jasplakinolide

Item No. 11705

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
cyclo[(3R)-3-(4-hydroxyphenyl)-β-alanyl-8S-hydroxy-2S,4E,6R-trimethyl-4-nonenoyl-L-alanyl-2-bromo-N-methyl-D-tryptophyl]
CAS Number
102396-24-7
Synonyms
  • NSC 613009
Molecular Formula
C36H45BrN4O6
Formula Weight
709.7
Purity
≥95%
Formulation (Request formulation change)
A solid
Solubility(Learn about Variance in Solubility)
DMSO: SolubleEthanol: SolubleMethanol: Soluble
SMILES
C/C(C[C@H](C)C(N[C@@H](C)C(N(C)[C@H](CC1=C(Br)NC2=C1C=CC=C2)C(N[C@@H](C3=CC=C(O)C=C3)C4)=O)=O)=O)=C\[C@H](C)C[C@H](C)OC4=O
InChi Code
InChI=1S/C36H45BrN4O6/c1-20-15-21(2)17-23(4)47-32(43)19-30(25-11-13-26(42)14-12-25)40-35(45)31(18-28-27-9-7-8-10-29(27)39-33(28)37)41(6)36(46)24(5)38-34(44)22(3)16-20/h7-15,21-24,30-31,39,42H,16-19H2,1-6H3,(H,38,44)(H,40,45)/b20-15+/t21-,22-,23-,24-,30+,31+/m0/s1
InChi Key
GQWYWHOHRVVHAP-DHKPLNAMSA-N
Origin
Animal/Jaspis splendens
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    50 µg

    $237

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    Product Description

    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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    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).

    Product Citations

    Eisemann, T., Costa, B., Strelau, J., et al. An advanced glioma cell invasion assay based on organotypic brain slice cultures. BMC Cancer 18(1), 103 (2018).