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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
Molecular Weight:
421.55
MDL Number:
MFCD27977552
MOL File:
76343-93-6.mol
MSDS File:
SDS
Last updated:2023-06-30 15:45:59

LATRUNCULIN A Properties

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.
FDA UNII SRQ9WWM084

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS02
Signal word  Danger
Hazard statements  H225
Precautionary statements  P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501
WGK Germany  3
NFPA 704
3
0 0

LATRUNCULIN A price More Price(15)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich L5163 Latrunculin A from sea sponge, ≥85% (HPLC), waxy solid 76343-93-6 100μg $368 2024-03-01 Buy
Sigma-Aldrich 428021 Latrunculin A, Latrunculia magnifica - CAS 76343-93-6 - Calbiochem 76343-93-6 100μG $287 2023-06-20 Buy
Cayman Chemical 10010630 Latrunculin A ≥98% 76343-93-6 25μg $49 2024-03-01 Buy
Cayman Chemical 10010630 Latrunculin A ≥98% 76343-93-6 50μg $92 2024-03-01 Buy
Cayman Chemical 10010630 Latrunculin A ≥98% 76343-93-6 100μg $134 2024-03-01 Buy
Product number Packaging Price Buy
L5163 100μg $368 Buy
428021 100μG $287 Buy
10010630 25μg $49 Buy
10010630 50μg $92 Buy
10010630 100μg $134 Buy

LATRUNCULIN A Chemical Properties,Uses,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 (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

-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

Global( 53)Suppliers
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[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