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Key Documents

J4580

Sigma-Aldrich

Jasplakinolide

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

Sinônimo(s):

Jaspamide

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About This Item

Fórmula empírica (Notação de Hill):
C36H45BrN4O6
Número CAS:
Peso molecular:
709.67
Número MDL:
Código UNSPSC:
12352200
ID de substância PubChem:
NACRES:
NA.77

product name

Jasplakinolide, ≥97% (HPLC)

Nível de qualidade

Ensaio

≥97% (HPLC)

forma

film (colorless)

cor

off-white to beige

solubilidade

DMSO: >2 mg/mL

Condições de expedição

wet ice

temperatura de armazenamento

−20°C

cadeia de caracteres 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

chave InChI

GQWYWHOHRVVHAP-DHKPLNAMSA-N

Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable


Certificados de análise (COA)

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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
P Preira et al.
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Pia M Sörensen et al.
ACS chemical biology, 7(9), 1502-1508 (2012-06-26)
Although small molecule actin modulators have been widely used as research tools, only one cell-permeable small molecule inhibitor of actin depolymerization (jasplakinolide) is commercially available. We report that the natural product cucurbitacin E inhibits actin depolymerization and show that its
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
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