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J4580

Sigma-Aldrich

Jasplakinolide

≥97% (HPLC), film (colorless), actin polymerization promoter

Synonyme(s) :

Jaspamide

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About This Item

Formule empirique (notation de Hill):
C36H45BrN4O6
Numéro CAS:
102396-24-7
Poids moléculaire :
709.67
Numéro MDL:
MFCD00873735
Code UNSPSC :
12352200
ID de substance PubChem :
329815735
Nomenclature NACRES :
NA.77

product name

Jasplakinolide, ≥97% (HPLC)

Niveau de qualité

100

Pureté

≥97% (HPLC)

Forme

film (colorless)

Couleur

off-white to beige

Solubilité

DMSO: >2 mg/mL

Conditions d'expédition

wet ice

Température de stockage

−20°C

Chaîne 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](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

Clé InChI

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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Certificats d'analyse (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)
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.
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
P Preira et al.
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
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