Latrunculin A

Cayman Chemical Item Number 10010630

NSC 613011 (CAS 76343-93-6)

Latrunculin A (CAS 76343-93-6)

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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)1,2 and in cells (0.5 μM, 30 min).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

1 Coué, M., Brenner, S.L., Spector, I., et al. Inhibition of actin polymerization by latrunculin A. FEBS Lett 213(2) 316-318 (1987).

2 Yarmola, E.G., Somasundaram, T., Boring, T.A., et al. Actin-latrunculin A structure and function. J Biol Chem 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. Toxicol Appl Pharmacol 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. J Cell Biochem 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. Exp Eye Res 77 181-188 (2003).

Synonyms
  • NSC 613011
Formal Name (4R)-​[(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
CAS Number 76343-93-6
Molecular Formula C22H31NO5S
Formula Weight 421.6
Formulation A solution in ethanol
Purity ≥98%
Stability 1 year
Storage -20°C
Shipping Wet ice in continental US; may vary elsewhere
SMILES
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C/C(CC/C=C/C=C\[C@@H]​(C)​CC[C@@H]​1C[C@@H]​2C[C@@]​([C@H]​3NC(SC3)​=O)​(O)​O1)​=C/C(O2)​=O
InCHI Code
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​1S/C22H31NO5S/c1-15-7-5-3-4-6-8-16(2)​11-20(24)​27-18-12-17(10-9-15)​28-22(26,13-18)​19-14-29-21(25)​23-19/h3-5,7,11,15,17-19,26H,6,8-10,12-14H2,1-2H3,(H,23,25)​/b4-3+,7-5-,16-11-/t15-,17-,18-,19+,22-/m1/s1
InCHI Key
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DDVBPZROPPMBLW-IZGXTMSKSA-N

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Size Price Quantity Subtotal
25 µg $29.00 $0.00
50 µg $55.00 $0.00
100 µg $104.00 $0.00
500 µg $464.00 $0.00
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Pricing updated 2014-04-18. Prices are subject to change without notice.

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