Technical Data

044973
CAS Number
102396-24-7
Grade
Highly Purified
MDL Number
MFCD00873735
Molecular Formula
C₃₆H₄₅BrN₄O₆
Molecular Weight
709.7
EU Commodity Code
38220090
Shipping Temp
RT
Storage Temp
-20°C
Jasplakinolide
Jaspamide; NSC 613009; cyclo[(3R)-3-(4-hydroxyphenyl)-β-alanyl-8S-hydroxy-2S,4E,6R-trimethyl-4-nonenoyl-L-alanyl-2-bromo-N-methyl-D-tryptophyl]

Cell permeable, non-fluorescent F-actin probe. Potent inducer of actin polymerization and stabilization. Competes with phallotoxins for actin binding. Antifungal and antiparasitic compound. Antiproliferative and anticancer compound. Apoptosis enhancer/inducer. Tool used for autophagy/phagocytosis research.

Source
Isolated from Jaspis splendens
Synonyms
Jaspamide; NSC 613009; cyclo[(3R)-3-(4-hydroxyphenyl)-β-alanyl-8S-hydroxy-2S,4E,6R-trimethyl-4-nonenoyl-L-alanyl-2-bromo-N-methyl-D-tryptophyl]
CAS No
102396-24-7
Molecular Weight
709.7
Molecular Formula
C₃₆H₄₅BrN₄O₆
Appearance
Supplied as an off-white solid.
Purity
≥98% (HPLC)
MS
Conforms to reference
Solubility
Ethanol, methanol or DMSO
Storage and Stability
May be stored at 4°C for short-term only. Stable for 12 months after receipt when stored at -20°C. Protect from light. For maximum recovery of product, centrifuge the original vial prior to removing the cap.

Intended for research use only. Not for use in human, therapeutic, or diagnostic applications.

References
1. Jasplakinolide, a cyclodepsipeptide from the marine sponge, Jaspis sp: P. Crews, et al.; Tetrahedron Lett. 27, 2797 (1986)|2. Jaspamide, a modified peptide from a Jaspis sponge, with insecticidal and antifungal activity: T.M. Zabriskie, et al.; JACS 108, 3123 (1986)|3. Jasplakinolide, a cytotoxic natural product, induces actin polymerization and competitively inhibits the binding of phalloidin to F-actin: M.R. Bubb, et al.; J. Biol. Chem. 269, 14869 (1994)|4. Jasplakinolide's inhibition of the growth of prostate carcinoma cells in vitro with disruption of the actin cytoskeleton: A.M. Senderowicz, et al.; J. Natl. Cancer Inst. 87, 46 (1995)|5. Growth modulation and differentiation of acute myeloid leukemia cells by jaspamide: I. Fabian, et al.; Exp. Hematol. 23, 583 (1995)|6. Actin stabilization by jasplakinolide enhances apoptosis induced by cytokine deprivation: S.C. Posey & B.E. Bierer; J. Biol. Chem. 274, 4259 (1999)|7. Alteration of actin organization by jaspamide inhibits ruffling, but not phagocytosis or oxidative burst, in HL-60 cells and human monocytes: I. Fabian, et al.; Blood 93, 3994 (1999)|8. Jasplakinolide. An actin-specific reagent that promotes actin polymerization: A. Holzinger; Methods Mol. Biol. 161, 109 (2001) (Review)|9. Effect of jasplakinolide on the growth, invasion, and actin cytoskeleton of Plasmodium falciparum: Y. Mizuno, et al.; Parasitol. Res. 88, 844 (2002)|10. Induction of apoptosis and CD10/neutral endopeptidase expression by jaspamide in HL-60 line cells: D.P. Cioca & K. Kitano; Cell. Mol. Life Sci. 59, 1377 (2002)|11. Clearance of a Hirano body-like F-actin aggresome generated by jasplakinolide: F. Lazaro-Diéguez, et al.; Autophagy 4, 717 (2008)|12. Jasplakinolide: an actin-specific reagent that promotes actin polymerization: A. Holzinger; Methods Mol. Biol. 586, 71 (2009) (Review)|13. Dynamic macrophage "probing" is required for the efficient capture of phagocytic targets: R.S. Flannagan, et al.; J. Cell Biol. 191, 1205 (2010)
USBio References
No references available
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