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L5163 Sigma-Aldrich

Latrunculin A

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

Synonym: 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

  • CAS Number 76343-93-6

  • Empirical Formula (Hill Notation) C22H31NO5S

  • Molecular Weight 421.55

  •  PubChem Substance ID 329817620

  •  NACRES NA.77

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Properties

Related Categories Actin Inhibitors and Probes, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules, Cell Biology, Cell Signaling and Neuroscience,
Quality Level   200
biological source   sea sponge
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

Description

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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