| Identification | Back Directory | [Name]
LATRUNCULIN A | [CAS]
76343-93-6 | [Synonyms]
LAT-A
NSC 613011
LATRUNCULIN A
Latrunculin A (LAT-A)
LATRUNCULIN A, LATRUNCULIA MAGNIFICA
Latrunculin A, Latrunculia magnifica - CAS 76343-93-6 - Calbiochem
4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-Hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl)-2-thiazolidinone
(4R)-4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-Hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-2-thiazolidinone
2-Thiazolidinone, 4-[(1R,4Z,8E,10Z,12S,15R,17R)-17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl]-, (4R)-
[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
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 | [Molecular Formula]
C22H31NO5S | [MDL Number]
MFCD00272613 | [MOL File]
76343-93-6.mol | [Molecular Weight]
421.55 |
| Chemical Properties | Back Directory | [alpha ]
D24 +152° (c = 1.2 in chloroform) | [storage temp. ]
-20°C | [solubility ]
DMSO: soluble
| [form ]
waxy solid
| [color ]
yellow
| [Stability:]
Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months. |
| Hazard Information | Back Directory | [Description]
Actin disruption is used to study cell functions in vitro (e.g., migration, endocytosis) and in vivo (e.g., tumor cell invasion). Latrunculin A is a bioactive 2-thiazolidinone macrolide derived from sponges that sequesters G-actin and prevents F-actin assembly. It binds monomeric actin with 1:1 stoichiometry and can be used to block actin polymerization both in vitro (Kd = 0.2 μM) and in cells (0.5 μM, 30 min).{ Latrunculin A (1-10 μM) causes depolymerization of tumor cell cytoskeleton within ten minutes. Overnight treatment of cells with latrunculin A (10 μM) strongly suppresses actin synthesis. Prolonged cell treatment blocks dexamethasone-induced changes in actin cytoskeleton with no effect on cell viability. | [Uses]
Latrunculin A has been used as medium supplementation for A549 cells to determine the internalization mechanism of CAV9 in A549 human lung carcinoma cells. | [Uses]
Latrunculin A, Latrunculia magnifica is a stabilizer of monomeric G-actin and polymerization inhibitor. | [Definition]
ChEBI: A bicyclic macrolide natural product consisting of a 16-membered bicyclic lactone attached to the rare 2-thiazolidinone moiety. It is obtained from the Red Sea sponge Latrunculia magnifica and from the Fiji Islands sponge Cacospongia myc
fijiensis. Latrunculin A inhibits actin polymerisation, microfilament organsation and microfilament-mediated processes. | [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. | [Biochem/physiol Actions]
Latrunculin A inhibits actin polymerization by a different mechanism than cytochalasins. Latrunculin A disrupts microfilament-mediated processes. | [storage]
Store at -20°C | [References]
1) Coue et al. (1987), Inhibition of actin polymerization by latrunculin; FEBS Lett., 213 316
2) Spector et al. (1989), Latrunculins-novel marine macrolides that disrupt microfilament organization and affect cell growth; Cell Motil. Cytoskeleton, 13 127
3) Wang et al. (2005), Differential effects of latrunculin-A on myofibrils in cultures of skeletal muscle cells: Insights into mechanisms of myofibrillogenesis; Cell Motil. Cytoskeleton, 62 35
4) Reggiori et al. (2005), The actin cytoskeleton is required for selective types of autophagy, but not for non-specific autophagy, in the yeast Saccharomyces cerevisiae; Mol. Biol. Cell, 16 5843
5) Asadi et al. (2016) A Genetic Screen for Fission Yeast Gene Deletion Mutants Exhibiting Hypersensitivity to Latrunculin A; G3 Genes Genomes Genetics, 6 3399 [Focus Citation] |
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