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ProductsBack/Latrunculin A [76343-93-6]
Chemical Structure
Chemical Structure
Chemical Structure

Latrunculin A [76343-93-6]

Research Use Only
AG-CN2-0027
AdipoGen Life Sciences
CAS Number76343-93-6
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Product group Chemicals
Estimated Purity>96% (HPLC)
Molecular Weight421.6
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Overview

  • Supplier
    AdipoGen Life Sciences
  • Product Name
    Latrunculin A [76343-93-6]
  • Delivery Days Customer
    10
  • CAS Number
    76343-93-6
  • Certification
    Research Use Only
  • Estimated Purity
    >96% (HPLC)
  • Hazard Information
    Non-hazardous,Warning
  • Molecular Formula
    C22H31NO5S
  • Molecular Weight
    421.6
  • Scientific 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. - Chemical. CAS: 76343-93-6. Formula: C22H31NO5S. MW: 421.6. Isolated from Latrunculia magnifica. Cell permeable marine toxin. Disrupts microfilament-mediated processes. Actin polymerization inhibitor in vitro and in vivo by the formation of a 1:1 complex with monomeric G-actin. Depolymerizes actin filaments (F-actin). Potent phagocytosis inhibitor. Anticancer compound. Suppresses hypoxia-induced HIF-1 activation in tumor cells. Inhibits tumor cell invasion. Acts via a different mechanism than cytochalasins.
  • 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
  • Storage Instruction
    2°C to 8°C,-20°C
  • UNSPSC
    12352200

References

  • Latrunculins: novel marine toxins that disrupt microfilament organization in cultured cells: I. Spector, et al.; Science 219, 493 (1983)
  • 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)
  • Inhibition of actin polymerization by latrunculin: A: M. Coue, et al.; FEBS Lett. 213, 316 (1987)
  • Latrunculin A is a potent inhibitor of phagocytosis by macrophages: C.A. de Oliveira & B. Mantovani; Life Sci. 43, 1825 (1988)
  • 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)
  • 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)
  • 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)
  • 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)