Jasplakinolide (high purity)

Specifications / Handling

More Information
Product Details
Synonyms	Jaspamide; NSC 613009
Product Type	Chemical
Properties
Formula	C₃₆H₄₅BrN₄O₆
MW	709.7
CAS	102396-24-7
Source/Host Chemicals	Isolated from Jaspis splendens.
Purity Chemicals	≥98% (HPLC)
Appearance	Off-white solid.
Solubility	Soluble in ethanol, methanol or DMSO.
Identity	Determined by MS.
InChi Key	GQWYWHOHRVVHAP-DHKPLNAMSA-N
Smiles	C[C@H]1C[C@@H](C)\C=C(C)\C[C@H](C)C(=O)N[C@@H](C)C(=O)N(C)[C@H](CC2=C(Br)NC3=C2C=CC=C3)C(=O)N[C@H](CC(=O)O1)C1=CC=C(O)C=C1
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Protect from light.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Cell permeable, non-fluorescent F-actin probe [3, 8, 12].
Potent inducer of actin polymerization and stabilization [3, 8, 12].
Competes with phallotoxins for actin binding [3].
Antifungal and antiparasitic compound [1, 2, 9].
Antiproliferative and anticancer compound [3, 4, 5].
Apoptosis enhancer/inducer [6, 10].
Tool used for autophagy/phagocytosis research [7, 11, 13].

Product References

Jasplakinolide, a cyclodepsipeptide from the marine sponge, Jaspis sp: P. Crews, et al.; Tetrahedron Lett. 27, 2797 (1986)
Jaspamide, a modified peptide from a Jaspis sponge, with insecticidal and antifungal activity: T.M. Zabriskie, et al.; JACS 108, 3123 (1986)
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)
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)
Growth modulation and differentiation of acute myeloid leukemia cells by jaspamide: I. Fabian, et al.; Exp. Hematol. 23, 583 (1995)
Actin stabilization by jasplakinolide enhances apoptosis induced by cytokine deprivation: S.C. Posey & B.E. Bierer; J. Biol. Chem. 274, 4259 (1999)
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)
Jasplakinolide. An actin-specific reagent that promotes actin polymerization: A. Holzinger; Methods Mol. Biol. 161, 109 (2001) (Review)
Effect of jasplakinolide on the growth, invasion, and actin cytoskeleton of Plasmodium falciparum: Y. Mizuno, et al.; Parasitol. Res. 88, 844 (2002)
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)
Clearance of a Hirano body-like F-actin aggresome generated by jasplakinolide: F. Lázaro-Diéguez, et al.; Autophagy 4, 717 (2008)
Jasplakinolide: an actin-specific reagent that promotes actin polymerization: A. Holzinger; Methods Mol. Biol. 586, 71 (2009) (Review)
Dynamic macrophage "probing" is required for the efficient capture of phagocytic targets: R.S. Flannagan, et al.; J. Cell Biol. 191, 1205 (2010)

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