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JASPLAKINOLIDE

Product Name
JASPLAKINOLIDE
CAS No.
102396-24-7
Chemical Name
JASPLAKINOLIDE
Synonyms
NSC 613009;JASPLAKINOLIDE;GQWYWHOHRVVHAP-DHKPLNAMSA-N;JASPLAKINOLIDE, JASPIS JOHNSTONI;Jasplakinolide, Actin polymerization and stabilization inducer;Jasplakinolide, Jaspis johnstoni - CAS 102396-24-7 - Calbiochem;Cyclo[(3R)-3-(4-hydroxyphenyl)-β-alanyl-(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-L-alanyl-2-bromo-N-methyl-D-tryptophyl];(3S,6R,9R,13S,15R,16E,19S)-3,5,13,15,17,19-Hexamethyl-6-[(2-bromo-1H-indole-3-yl)methyl]-9-(4-hydroxyphenyl)-12-oxa-2,5,8-triazacyclononadeca-16-ene-1,4,7,11-tetraone;[3S,6R,9R,13S,15R,19S,16E,(+)]-6-[(2-Bromo-1H-indol-3-yl)methyl]-9-(4-hydroxyphenyl)-3,5,13,15,17,19-hexamethyl-2,5,8-triaza-12-oxacyclononadecan-16-ene-1,4,7,11-tetrone
CBNumber
CB0703307
Molecular Formula
C36H45BrN4O6
Formula Weight
709.67
MOL File
102396-24-7.mol
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JASPLAKINOLIDE Property

Melting point:
110℃ (decomposition)
storage temp. 
-20°C
solubility 
DMSO: >2mg/mL
form 
Off-white solid
color 
off white to beige
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Safety

RIDADR 
3172
WGK Germany 
3
RTECS 
GX7000000
HazardClass 
6.1(b)
PackingGroup 
III
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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
J4580
Product name
Jasplakinolide
Purity
≥97% (HPLC)
Packaging
100μg
Price
$761
Updated
2025/07/31
Sigma-Aldrich
Product number
420107-M
Product name
Jasplakinolide, <i>Jaspis johnstoni</i>
Purity
A cell-permeable F-actin probe.
Packaging
1 unit
Price
$195.3
Updated
2025/07/31
Cayman Chemical
Product number
11705
Product name
Jasplakinolide
Purity
≥98%
Packaging
50μg
Price
$169
Updated
2024/03/01
Cayman Chemical
Product number
11705
Product name
Jasplakinolide
Purity
≥98%
Packaging
100μg
Price
$287
Updated
2024/03/01
Tocris
Product number
2792
Product name
Jasplakinolide
Purity
≥97%(HPLC)
Packaging
100U
Price
$374
Updated
2021/12/16
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JASPLAKINOLIDE Chemical Properties,Usage,Production

Description

Jasplakinolide is a natural macrocyclic peptide first isolated from a marine sponge. It potently inhibits the proliferation of PC3 prostate carcinoma cells (IC50 = 35 nM) by binding F-actin (KD = 15 nM). This binding of jasplakinolide to actin, which is competitive with phalloidin, stabilizes actin filaments in vitro but disrupts actin filaments and induces irregular polymerization of monomeric actin in vivo. This compound is used to investigate the role of actin in diverse cellular roles, such as motility, transport, and development.

Uses

Jasplakinolide is a natural macrocyclic peptide first isolated from a marine sponge. It potently inhibits the proliferation of PC3 prostate carcinoma cells (IC50 = 35 nM) by binding F-actin (KD = 15 nM). This binding of jasplakinolide to actin, which is competitive with phalloidin, stabilizes actin filaments in vitro but disrupts actin filaments and induces irregular polymerization of monomeric actin in vivo. This compound is used to investigate the role of actin in diverse cellular roles, such as motility, transport, and development.

Uses

Jasplakinolide has been used to analyze its influence on sciatic nerve guidance effect in vivo in chicken embryos. It has also been used to apply on the control cells for the treatment for blocking actin dynamics.

Uses

Jasplakinolide is a potent inhibitor of prostrate and breast carcinoma cell proliferation. Also acts as an actin stabilizing agent, affecting chromosome movement in studies.

Definition

ChEBI: A cyclodepsipeptide isolated from Jaspis splendens and has been shown to exhibit antineoplastic activity.

Biochem/physiol Actions

Jasplakinolide is an actin-specific reagent that promotes actin polymerization and stabilizes actin filaments. In vitro, Jasplakinolidet potently induces actin polymerization by stimulating actin filament nucleation and competes with phalloidin for actin binding (Kd = 15 nM). In vivo, Jasplakinolide has been found to disrupt actin filaments and induce polymerization of monomeric actin into amorphous masses, the exact mechanism of which has not been determined yet. Jasplakinolide differs from other actin stabilizers in that it is cell permeable. This peptide has fungicidal, insecticidal and antiproliferative activity, and is useful for investigating cell processes mediated by actin polymerization and depolymerization, such as cell adhesion, locomotion, endocytosis, and vesicle sorting and release.

storage

+4°C

References

[1] M R BUBB. Jasplakinolide, a cytotoxic natural product, induces actin polymerization and competitively inhibits the binding of phalloidin to F-actin.[J]. The Journal of Biological Chemistry, 1994, 269 21: 14869-14871.
[2] M R BUBB. Effects of jasplakinolide on the kinetics of actin polymerization. An explanation for certain in vivo observations.[J]. The Journal of Biological Chemistry, 2000, 275 7: 5163-5170. DOI: 10.1074/jbc.275.7.5163
[3] DAVID VAN GOOR. The role of actin turnover in retrograde actin network flow in neuronal growth cones.[J]. PLoS ONE, 2012: e30959. DOI: 10.1371/journal.pone.0030959
[4] XIAOYUN ZHANG. Actin stabilization by jasplakinolide affects the function of bone marrow-derived late endothelial progenitor cells.[J]. PLoS ONE, 2012: e50899. DOI: 10.1371/journal.pone.0050899
[5] TANJA EISEMANN. An advanced glioma cell invasion assay based on organotypic brain slice cultures.[J]. BMC Cancer, 2018: 103. DOI: 10.1186/s12885-018-4007-4

JASPLAKINOLIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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102396-24-7, JASPLAKINOLIDERelated Search:

Lipopolysaccharides Morpholine Paraformaldehyde Acrylic acid NS-398 Anthraquinone Sodium carboxymethyl cellulose Ribonucleic acid 2-Bromopyrrole N-[2-(2-BROMO-1H-INDOL-3-YL)ETHYL]ACETAMIDE 2-BROMO-1H-INDOLE GLYCYLGLYCINAMIDE HYDROBROMIDE CHEMBRDG-BB 9071718 2-AMINO-N-BENZYL-3-(1H-INDOL-3-YL)-PROPIONAMIDE JASPLAKINOLIDE

  • JASPLAKINOLIDE
  • Jasplakinolide, Jaspis johnstoni - CAS 102396-24-7 - Calbiochem
  • Cyclo[(3R)-3-(4-hydroxyphenyl)-β-alanyl-(2S,4E,6R,8S)-8-hydroxy-2,4,6-trimethyl-4-nonenoyl-L-alanyl-2-bromo-N-methyl-D-tryptophyl]
  • JASPLAKINOLIDE, JASPIS JOHNSTONI
  • (3S,6R,9R,13S,15R,16E,19S)-3,5,13,15,17,19-Hexamethyl-6-[(2-bromo-1H-indole-3-yl)methyl]-9-(4-hydroxyphenyl)-12-oxa-2,5,8-triazacyclononadeca-16-ene-1,4,7,11-tetraone
  • [3S,6R,9R,13S,15R,19S,16E,(+)]-6-[(2-Bromo-1H-indol-3-yl)methyl]-9-(4-hydroxyphenyl)-3,5,13,15,17,19-hexamethyl-2,5,8-triaza-12-oxacyclononadecan-16-ene-1,4,7,11-tetrone
  • NSC 613009
  • GQWYWHOHRVVHAP-DHKPLNAMSA-N
  • Jasplakinolide, Actin polymerization and stabilization inducer
  • 102396-24-7
  • Amines, Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals