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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
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 (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, 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

3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801 18930552037
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
ProdList
15848
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69
Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
sales@meilune.com
Country
China
ProdList
4654
Advantage
58
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
18521735133 18521732826;
Fax
021-50323701
Email
market@aladdin-e.com
Country
China
ProdList
25015
Advantage
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Shanghai Tauto Biotech Co., Ltd.
Tel
021-51320588
Fax
0086-21-51320502
Email
tauto@tautobiotech.com
Country
China
ProdList
3989
Advantage
66
ChemStrong Scientific Co.,Ltd
Tel
0755-0755-66853366 13670046396
Fax
0755-28363542
Email
sales@chem-strong.com
Country
China
ProdList
17994
Advantage
56
Sigma-Aldrich
Tel
021-61415566 800-8193336
Email
orderCN@merckgroup.com
Country
China
ProdList
51471
Advantage
80
EMMX Biotechnology LLC
Tel
888-539-0666
Fax
888-539-0666
Email
info@emmx.com
Country
United States
ProdList
8449
Advantage
60
Shanghai EFE Biological Technology Co., Ltd.
Tel
021-65675885 18964387627
Fax
021-65675885
Email
info@efebio.com
Country
China
ProdList
9709
Advantage
58
Shanghai YuanYe Biotechnology Co., Ltd.
Tel
021-61312847; 18021002903
Fax
QQ:3008007432
Email
3008007409@qq.com
Country
China
ProdList
27322
Advantage
60
Beijing Solarbio Science & Tecnology Co., Ltd.
Tel
010-50973130 4009686088
Email
3193328036@qq.com
Country
China
ProdList
29797
Advantage
68

76343-93-6, LATRUNCULIN ARelated Search:


  • [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