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044973 Jasplakinolide CAS: 102396-24-7

Specifications
References
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
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.
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
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