AdipoGen Life Sciences

Latrunculin A

CHF 150.00
In stock
AG-CN2-0027-C100100 µgCHF 150.00
AG-CN2-0027-C500500 µgCHF 560.00
More Information
Product Details
Synonyms LAT-A; NSC 613011
Product Type Chemical
Properties
Formula

C22H31NO5S

MW 421.6
Merck Index 14: 5378
CAS 76343-93-6
Source/Host Chemicals Isolated from Latrunculia magnifica.
Purity Chemicals ≥97% (HPLC)
Appearance Colorless viscous film
Solubility Soluble in DMSO (25mg/ml) or ethanol (25mg/ml).
Identity Determined by 1H-NMR.
InChi Key DDVBPZROPPMBLW-IZGXTMSKSA-N
Smiles O=C(SC1)N[C@]1([H])[C@](C2)(O)O[C@@H](C[C@H]2O3)CC[C@H](C)/C=C\C=C\CC/C(C)=C\C3=O
Shipping and Handling
Shipping AMBIENT
Short Term Storage +4°C
Long Term Storage -20°C
Handling Advice Protect from light.
Use/Stability Stable for at least 2 years after receipt when stored at -20°C.
Store solutions at -20°C in the dark.
Documents
MSDS Download PDF
Product Specification Sheet
Datasheet Download PDF
Description
  • Cell permeable marine toxin [1].
  • Disrupts microfilament-mediated processes [2].
  • Actin polymerization inhibitor in vitro and in vivo by the formation of a 1:1 complex with monomeric G-actin [1, 2, 3, 6].
  • Depolymerizes actin filaments (F-actin) [3].
  • Potent phagocytosis inhibitor [4].
  • Anticancer compound [7, 8]. Suppresses hypoxia-induced HIF-1 activation in tumor cells [7]. Inhibits tumor cell invasion [7].
  • Acts via a different mechanism than cytochalasins.
Product References
  1. Latrunculins: novel marine toxins that disrupt microfilament organization in cultured cells: I. Spector, et al.; Science 219, 493 (1983)
  2. Latrunculin inhibits the microfilament-mediated processes during fertilization, cleavage and early development in sea urchins and mice: G. Schatten, et al.; Exp. Cell Res. 166, 191 (1986)
  3. Inhibition of actin polymerization by latrunculin: A: M. Coue, et al.; FEBS Lett. 213, 316 (1987)
  4. Latrunculin A is a potent inhibitor of phagocytosis by macrophages: C.A. de Oliveira & B. Mantovani; Life Sci. 43, 1825 (1988)
  5. Latrunculins-novel marine macrolides that disrupt microfilament organization and affect cell growth: I. Comparison with cytochalasin D: I. Spector, et al.; Cell Motil. Cytoskeleton 13, 127 (1989)
  6. Actin-latrunculin A structure and function. Differential modulation of actin-binding protein function by latrunculin A: E.G. Yarmola, et al.; J. Biol. Chem. 275, 28120 (2000)
  7. Latrunculin A and its C-17-O-carbamates inhibit prostate tumor cell invasion and HIF-1 activation in breast tumor cells: K.A. Sayed, et al.; J. Nat. Prod. 71, 396 (2008)
  8. Latrunculin a has a strong anticancer effect in a peritoneal dissemination model of human gastric cancer in mice: H. Konishi, et al.; Anticancer Res. 29, 2091 (2009)
  9. Nucleolar asymmetry and the importance of septin integrity upon cell cycle arrest: U. Rai, et al.; PLoS ONE 12, e0174306 (2017)
  10. Trogocytosis of ligand-receptor complex and its intracellular transport in CD30 signaling: M. Nakashima, et al.; Biol Cell. 110, 109 (2018)
  11. Integrating chemical and mechanical signals through dynamic coupling between cellular protrusions and pulsed ERK activation: J.M. Yang, et al.; Nat. Comm. 9, 4673 (2018)
  12. Rap1 organizes lymphocyte front-back polarity via RhoA signaling and talin1: Y. Ueda, et al.; iScience 26, 107292 (2023)
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