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Latrunculin A (Synonyms: NSC 613011)

Catalog No.GC15671

A reversible inhibitor of actin assembly

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Latrunculin A Chemical Structure

Cas No.: 76343-93-6

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Sample solution is provided at 25 µL, 10mM.

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Background

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).[1],[2],[3] Latrunculin A (1-10 μM) causes depolymerization of tumor cell cytoskeleton within ten minutes.[4] Overnight treatment of cells with latrunculin A (10 μM) strongly suppresses actin synthesis.[5] Prolonged cell treatment blocks dexamethasone-induced changes in actin cytoskeleton with no effect on cell viability.[6]

References
[1]. Coué, M., Brenner, S.L., Spector, I., et al. Inhibition of actin polymerization by latrunculin A. FEBS Letters 213(2), 316-318 (1987).
[2]. Yarmola, E.G., Somasundaram, T., Boring, T.A., et al. Actin-latrunculin A structure and function. The Journal of Biological Chemisty 275(36), 28120-28127 (2000).
[3]. Loubéry, S., Wilhelm, C., Hurbain, I., et al. Different microtubule motors move early and late endocytic compartments. Traffic 9, 492-509 (2008).
[4]. Hayot, C., Debeir, O., Van Ham, P., et al. Characterization of the activities of actin-affecting drugs on tumor cell migration. Toxicology and Applied Pharmacology 211, 30-40 (2006).
[5]. Lyubimova, A., Bershadsky, A.D., and Ben-Ze'ev, A. Autoregulation of actin synthesis requires the 3'-UTR of actin mRNA and protects cells from actin overproduction. Journal of Cellular Biochemistry 76, 1-12 (1999).
[6]. Liu, X., Wu, Z., Sheibani, N., et al. Low dose latrunculin-A inhibits dexamethasone-induced changes in the actin cytoskeleton and alters extracellular matrix protein expression in cultured human trabecular meshwork cells. Experimental Eye Research 77, 181-188 (2003).

Chemical Properties

Cas No. 76343-93-6 SDF
Synonyms NSC 613011
Chemical Name (R)-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)thiazolidin-2-one
Canonical SMILES O[C@@](C1)([C@H]2NC(SC2)=O)O[C@H](CC[C@@H](/C=C\C=C\CC/C(C)=C\3)C)C[C@H]1OC3=O
Formula C22H31NO5S M.Wt 421.6
Solubility 25mg/mL in ethanol, or in DMSO Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.
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