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J4580

Sigma-Aldrich

Jasplakinolide

≥97% (HPLC)

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Synonym(s):
Jaspamide
Empirical Formula (Hill Notation):
C36H45BrN4O6
CAS Number:
102396-24-7
Molecular Weight:
709.67
MDL number:
MFCD00873735
UNSPSC Code:
12352200
PubChem Substance ID:
329815735
NACRES:
NA.77

Quality Level

100

Assay

≥97% (HPLC)

form

film (colorless)

color

off-white to beige

solubility

DMSO: >2 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

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](Cc2c(Br)[nH]c3ccccc23)C(=O)N[C@H](CC(=O)O1)c4ccc(O)cc4

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

InChI key

GQWYWHOHRVVHAP-DHKPLNAMSA-N

Application

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.

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.

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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The developmental and genetic basis of `clubfoot? in the peroneal muscular atrophy mutant mouse
Collinson J M, et al.
Development, 145(3), 160093-160093 (2018)
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Lab on a chip, 13(1), 161-170 (2012-11-14)
The deformability of circulating leukocytes plays an important role in the physiopathology of several diseases like sepsis or acute respiratory distress syndrome (ARDS). We present here a microfluidic method for the passive testing, sorting and separating of non-adherent cell populations
Jeffery C Noro et al.
Chemistry & biodiversity, 9(10), 2077-2095 (2012-10-20)
The discovery of novel natural products for drug development relies heavily upon a rich biodiversity, of which the marine environment is an obvious example. Marine natural product research has spawned several drugs and many other candidates, some of which are
Jelena Dinic et al.
Biochimica et biophysica acta, 1828(3), 1102-1111 (2012-12-19)
The relationship between ordered plasma membrane nanodomains, known as lipid rafts, and actin filaments is the focus of this study. Plasma membrane order was followed in live cells at 37°C using laurdan and di-4-ANEPPDHQ to report on lipid packing. Disrupting
Jose T Thaiparambil et al.
Molecular and cellular biology, 32(16), 3203-3217 (2012-06-13)
The proper orientation of the mitotic spindle is essential for mitosis; however, how these events unfold at the molecular level is not well understood. AMP-activated protein kinase (AMPK) regulates energy homeostasis in eukaryotes, and AMPK-null Drosophila mutants have spindle defects.
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