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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

Nom du produit

Jasplakinolide, ≥97% (HPLC)

Niveau de qualité

100

Essai

≥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

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Certificats d'analyse (COA)

Lot/Batch Number
0000221890
0000219705
037M4716V
115M4734V

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Consulter la Bibliothèque de documents

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)
Kei H Kojo et al.
Plant & cell physiology, 54(9), 1491-1503 (2013-07-05)
In land plant cells, division planes are precisely predicted by the microtubule preprophase band and cortical actin microfilament pattern called the actin-depleted zone or actin microfilament twin peaks. However, the function of cortical actin microfilament patterning is not clear. In
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
Long-range self-organization of cytoskeletal myosin II filament stacks
Hu S, et al.
Nature Cell Biology, 19(2), 133-133 (2017)
E Kavanagh et al.
Cell death & disease, 3, e311-e311 (2012-05-18)
p57 (Kip2, cyclin-dependent kinase inhibitor 1C), often found downregulated in cancer, is reported to hold tumor suppressor properties. Originally described as a cyclin-dependent kinase (cdk) inhibitor, p57(KIP2) has since been shown to influence other cellular processes, beyond cell cycle regulation
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