Jasplakinolide

Names

[ Name ]:
Jasplakinolide

[Synonym ]:
(4R,7R,10S,13S,15E,17R,19S)-7-[(2-Bromo-1H-indol-3-yl)methyl]-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetrone
Jaspamide
jasplakinolide
jasplakinolide,jaspis johnstoni
1-Oxa-5,8,11-triazacyclononadec-15-ene-2,6,9,12-tetrone, 7-[(2-bromo-1H-indol-3-yl)methyl]-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-, (4R,7R,10S,13S,15E,17R,19S)-

Biological Activity

[Description]:

Jasplakinolide is a potent actin polymerization inducer and stabilizes pre-existing actin filaments. Jasplakinolide binds to F-actin competitively with phalloidin with a Kd of 15 nM. Jasplakinolide, a naturally occurring cyclic peptide from the marine sponge, has both fungicidal and anti-cancer activity[1][2].

[Related Catalog]:

Signaling Pathways >> Cytoskeleton >> Arp2/3 Complex

Research Areas >> Cancer

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

[In Vitro]

Jasplakinolide has an IC50 of 35 nM for the antiproliferative effect of jasplakinolide on PC3 prostate carcinoma cells[2]. Jasplakinolide (10 μM; for 2 hours) generates binucleated cells when applied during mitosis. Jasplakinolide induces the formation of F-actin-containing apical extensions in Toxoplasma gondii tachyzoites[2]. Jasplakinolide (1 mM; for 60 min) induces the formation of actin-containing apical extensions in isolated Toxoplasma gondii tachyzoites fixed[2].

[References]

[1]. Bubb MR, et al. Jasplakinolide, a cytotoxic natural product, induces actin polymerization and competitively inhibits the binding of phalloidin to F-actin. J Biol Chem. 1994 May 27;269(21):14869-71.

[2]. Holzinger A, et al. Jasplakinolide: an actin-specific reagent that promotes actin polymerization. Methods Mol Biol. 2009;586:71-87.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
968.3±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₃₆H₄₅BrN₄O₆

[ Molecular Weight ]:
709.670

[ Flash Point ]:
539.4±34.3 °C

[ Exact Mass ]:
708.252258

[ PSA ]:
140.83000

[ LogP ]:
4.24

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.553

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ RIDADR ]:
UN 3172

[ RTECS ]:
GX7000000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

Articles

Rapid changes in phospho-MAP/tau epitopes during neuronal stress: cofilin-actin rods primarily recruit microtubule binding domain epitopes.

PLoS ONE 6 , e20878, (2011)

Abnormal mitochondrial function is a widely reported contributor to neurodegenerative disease including Alzheimer's disease (AD), however, a mechanistic link between mitochondrial dysfunction and the ...

P2Y2 receptor signaling in neutrophils is regulated from inside by a novel cytoskeleton-dependent mechanism.

Exp. Cell Res. 336 , 242-52, (2015)

Functional selectivity, a process by which G-protein coupled receptors (GPCRs) can activate one signaling route while avoiding another, is regulated by ligand-mediated stabilization of specific recept...

Actin polymerization controls the activation of multidrug efflux at fertilization by translocation and fine-scale positioning of ABCB1 on microvilli.

Mol. Biol. Cell 23(18) , 3663-72, (2012)

Fertilization changes the structure and function of the cell surface. In sea urchins, these changes include polymerization of cortical actin and a coincident, switch-like increase in the activity of t...