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L5163

Sigma-Aldrich

Latrunculin A

from sea sponge, ≥85% (HPLC), waxy solid

Synonyme(s) :

LAT-A, [1R-[1R*, 4Z, 8E, 10Z, 12S*, 15R*, 17R*(R*)]]-4-(17-Hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl)-2-thiazolidinone

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About This Item

Formule empirique (notation de Hill):
C22H31NO5S
Numéro CAS:
76343-93-6
Poids moléculaire :
421.55
Code UNSPSC :
12352200
ID de substance PubChem :
329817620
Nomenclature NACRES :
NA.77

Source biologique

sea sponge

Niveau de qualité

200

Pureté

≥85% (HPLC)

Forme

waxy solid

Poids mol.

421.6

Solubilité

DMSO: soluble
ethanol: soluble

Température de stockage

−20°C

Chaîne SMILES 

C[C@H]1CC[C@@H]2C[C@H](C[C@@](O)(O2)[C@@H]3CSC(=O)N3)OC(=O)C=C(C)CC\C=C\C=C1

InChI

1S/C22H31NO5S/c1-15-7-5-3-4-6-8-16(2)11-20(24)27-18-12-17(10-9-15)28-22(26,13-18)19-14-29-21(25)23-19/h3-5,7,11,15,17-19,26H,6,8-10,12-14H2,1-2H3,(H,23,25)/b4-3+,7-5-,16-11-/t15-,17-,18-,19+,22-/m1/s1

Clé InChI

DDVBPZROPPMBLW-IZGXTMSKSA-N

Description générale

Latrunculin A, a toxin extracted from the red sea sponge Latrunculia magnifica. It participates in vitro in the morphological alteration of the polymerization of pure actin. It forms a complex by binding with the nucleotide cleft of actin for actin filaments elongation.

Application

Latrunculin A has been used as medium supplementation for A549 cells to determine the internalization mechanism of CAV9 in A549 human lung carcinoma cells.

Actions biochimiques/physiologiques

Latrunculin A inhibits actin polymerization by a different mechanism than cytochalasins. Latrunculin A disrupts microfilament-mediated processes.

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

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Zhanghan Wu et al.
Nature communications, 9(1), 136-136 (2018-01-13)
Immune cells exhibit stimulation-dependent traveling waves in the cortex, much faster than typical cortical actin waves. These waves reflect rhythmic assembly of both actin machinery and peripheral membrane proteins such as F-BAR domain-containing proteins. Combining theory and experiments, we develop
Peter J Wen et al.
Nature communications, 7, 12604-12604 (2016-09-01)
Vesicle fusion is executed via formation of an Ω-shaped structure (Ω-profile), followed by closure (kiss-and-run) or merging of the Ω-profile into the plasma membrane (full fusion). Although Ω-profile closure limits release but recycles vesicles economically, Ω-profile merging facilitates release but
E G Yarmola et al.
The Journal of biological chemistry, 275(36), 28120-28127 (2000-06-22)
Latrunculin A is used extensively as an agent to sequester monomeric actin in living cells. We hypothesize that additional activities of latrunculin A may be important for its biological activity. Our data are consistent with the formation of a 1:1
M Coué et al.
FEBS letters, 213(2), 316-318 (1987-03-23)
Latrunculin A, a toxin purified from the red sea sponge Latrunculia magnifica, was found previously to induce striking reversible changes in the morphology of mammalian cells in culture and to disrupt the organization of their microfilaments. We now provide evidence
Maureen Möckel et al.
Journal of virology, 93(16) (2019-05-31)
Dynamin GTPases, best known for their role in membrane fission of endocytic vesicles, provide a target for viruses to be exploited during endocytic uptake. Recently, we found that entry of herpes simplex virus 1 (HSV-1) into skin cells depends on
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