Jasplakinolide

AdipoGen Life Sciences
Product Code: AG-CN2-0037
CodeSizePrice
AG-CN2-0037-C05050 ug£210.00
Quantity:
AG-CN2-0037-C100100 ug£340.00
Quantity:
Prices exclude any Taxes / VAT

Overview

Regulatory Status: RUO
Shipping:
Ambient
Storage:
+4deg;C

Images

1 / 1
Chemical Structure

Chemical Structure

Further Information

Alternate Names/Synonyms:
Jaspamide; NSC 613009
Appearance:
Off-white solid.
CAS:
102396-24-7
EClass:
32160000
Form (Short):
liquid
GHS Symbol:
GHS07
Handling Advice:
Protect from light.
Hazards:
H302, H312, H332
InChi:
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
InChiKey:
GQWYWHOHRVVHAP-DHKPLNAMSA-N
Long Description:
Chemical. CAS: 102396-24-7. Formula: C36H45BrN4O6. MW: 709.7. Isolated from Jaspis splendens. 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.
MDL:
MFCD00873735
Molecular Formula:
C36H45BrN4O6
Molecular Weight:
709.7
Package Type:
Vial
Precautions:
P261, P301, P312, P302, P352, P304, P340
Product 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].
Purity:
>98% (HPLC)
Signal word:
Warning
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
Solubility Chemicals:
Soluble in ethanol, methanol or DMSO.
Source / Host:
Isolated from Jaspis splendens.
Transportation:
Non-hazardous
UNSPSC Category:
Natural Products/Extracts
UNSPSC Number:
12352200
Use & Stability:
Stable for at least 2 years after receipt when stored at -20°C.

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. Lazaro-Di?guez, 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)

Related Products

Product NameProduct CodeSupplier 
Latrunculin AAG-CN2-0027AdipoGen Life Sciences Summary Details
PaclitaxelAG-CN2-0045AdipoGen Life Sciences Summary Details