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J4580

Sigma-Aldrich

Jasplakinolide

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

Synonym(s):

Jaspamide

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About This Item

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

product name

Jasplakinolide, ≥97% (HPLC)

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.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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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
Long-range self-organization of cytoskeletal myosin II filament stacks
Hu S, et al.
Nature Cell Biology, 19(2), 133-133 (2017)
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
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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