LATRUNCULIN A

Product Name: LATRUNCULIN A
CAS No.: 76343-93-6
Chemical Name: LATRUNCULIN A
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
CBNumber: CB1679575
Molecular Formula: C22H31NO5S
Formula Weight: 421.55
MOL File: 76343-93-6.mol

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LATRUNCULIN A Property

alpha: D24 +152° (c = 1.2 in chloroform)
storage temp.: -20°C
solubility: DMSO: soluble
form: waxy solid
color: yellow
optical activity: +144.423 （CHCl3）
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.

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Safety

WGK Germany: 3

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H225Highly Flammable liquid and vapour

Precautionary statements

P210Keep away from heat/sparks/open flames/hot surfaces. — No smoking.

P233Keep container tightly closed.

P240Ground/bond container and receiving equipment.

P241Use explosion-proof electrical/ventilating/lighting/…/equipment.

P242Use only non-sparking tools.

P243Take precautionary measures against static discharge.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.

P370+P378In case of fire: Use … for extinction.

P403+P235Store in a well-ventilated place. Keep cool.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: L5163
Product name: Latrunculin A
Purity: from sea sponge, ≥85% (HPLC), waxy solid
Packaging: 100μg
Price: $368
Updated: 2024/03/01

Sigma-Aldrich

Product number: 428021
Product name: Latrunculin A, Latrunculia magnifica - CAS 76343-93-6 - Calbiochem
Packaging: 100μG
Price: $287
Updated: 2023/06/20

Cayman Chemical

Product number: 10010630
Product name: Latrunculin A
Purity: ≥98%
Packaging: 25μg
Price: $49
Updated: 2024/03/01

Cayman Chemical

Product number: 10010630
Product name: Latrunculin A
Purity: ≥98%
Packaging: 50μg
Price: $92
Updated: 2024/03/01

Cayman Chemical

Product number: 10010630
Product name: Latrunculin A
Purity: ≥98%
Packaging: 100μg
Price: $134
Updated: 2024/03/01

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LATRUNCULIN A Chemical Properties,Usage,Production

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 (K_d = 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, Latrunculia magnifica is a stabilizer of monomeric G-actin and polymerization inhibitor.

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.

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

-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]

LATRUNCULIN A Preparation Products And Raw materials

Raw materials

Preparation Products

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LATRUNCULIN A Suppliers

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76343-93-6, LATRUNCULIN ARelated Search:

ReModelin S-Trityl-L-cysteine Colchicine 2-Fluoro-N-[2-(2-methyl-1H-indol-3-yl)ethyl]benzamide Polyurethane foam plastic LATRUNCULIN LATRUNCULIN B,LATRUNCULIN B, LATRUNCULIA MAGNIFICA,LATRUNCULIN B, LUTRUNCULIA MAGNIFICA ETHYL-3-METHYL-2-HEXENOATE SEC-BUTYL 3-METHYLBUT-2-ENOATE (7Z,9E)-dodeca-7,9-dienyl acetate METHYL-(TETRAHYDRO-PYRAN-2-YLMETHYL)-AMINE LATRUNCULIN 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

LAT-A

LATRUNCULIN A

LATRUNCULIN A, LATRUNCULIA MAGNIFICA

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

(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

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

NSC 613011

Latrunculin A, Latrunculia magnifica - CAS 76343-93-6 - Calbiochem

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)-

Latrunculin A (LAT-A)

76343-93-6

C22H31NO5S

Cytoskeleton and Extracellular Matrix

BioChemical

Actin Inhibitors and Probes

Cell Biology

Cell Signaling and Neuroscience