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L5163

Sigma-Aldrich

Latrunculin A

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

Synonym(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

Empirical Formula (Hill Notation):
C22H31NO5S
CAS Number:
Molecular Weight:
421.55
UNSPSC Code:
12352200
PubChem Substance ID:
NACRES:
NA.77

biological source

sea sponge

Quality Level

Assay

≥85% (HPLC)

form

waxy solid

mol wt

421.6

solubility

DMSO: soluble
ethanol: soluble

storage temp.

−20°C

SMILES string

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

InChI key

DDVBPZROPPMBLW-IZGXTMSKSA-N

Related Categories

General description

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.

Biochem/physiol Actions

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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