Latrunculin A

Names

[ Name ]:
Latrunculin A

[Synonym ]:
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
Latrunculin A
(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]-1,3-thiazolidin-2-one
latruculin A
(4R)-4-[(1R,4S,5Z,7E,11Z,15R,17R)-17-hydroxy-4,11-dimethyl-13-oxo-14,18-dioxabicyclo[13.3.1]nonadeca-5,7,11-trien-17-yl]-1,3-thiazolidin-2-one
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 (incomplete stereochemistry)
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)-
LAT-A

Biological Activity

[Description]:

Latrunculin A (LAT-A) is a toxin isolated from the red sea sponge Latrunculia magnifica, binds to actin monomers, inhibits polymerization of actin, with Kds of 0.1, 0.4, 4.7 μM and 0.19 μM for ATP-actin, ADP-Pi-actin, ADP-actin and G-actin, respectively[1][2].

[Related Catalog]:

Signaling Pathways >> Cytoskeleton >> Arp2/3 Complex

Research Areas >> Others

[Target]

Kd: 0.1 μM (ATP-actin), 0.4 μM (ADP-Pi-actin), 4.7 μM (ADP-actin)[2], 0.19 μM (G-actin)[2]

[References]

[1]. Fujiwara I, et al. Latrunculin A Accelerates Actin Filament Depolymerization in Addition to Sequestering Actin Monomers. Curr Biol. 2018 Oct 8;28(19):3183-3192.e2.

[2]. Coué M, et al. Inhibition of actin polymerization by latrunculin A. FEBS Lett. 1987 Mar 23;213(2):316-8.

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Molecular Formula ]:
C₂₂H₃₁NO₅S

[ Molecular Weight ]:
421.550

[ Exact Mass ]:
421.192291

[ PSA ]:
110.16000

[ LogP ]:
4.14

[ Index of Refraction ]:
1.533

[ Storage condition ]:
-20℃

MSDS

Click to get detail MSDS

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Inhibitory mechanism of FAT4 gene expression in response to actin dynamics during Src-induced carcinogenesis.

PLoS ONE 10(2) , e0118336, (2015)

Oncogenic transformation is characterized by morphological changes resulting from alterations in actin dynamics and adhesive activities. Emerging evidence suggests that the protocadherin FAT4 acts as ...

Ca(2+) permeation and/or binding to CaV1.1 fine-tunes skeletal muscle Ca(2+) signaling to sustain muscle function.

Skelet. Muscle 5 , 4, (2015)

Ca(2+) influx through CaV1.1 is not required for skeletal muscle excitation-contraction coupling, but whether Ca(2+) permeation through CaV1.1 during sustained muscle activity plays a functional role ...

Activation of the pleiotropic drug resistance pathway can promote mitochondrial DNA retention by fusion-defective mitochondria in Saccharomyces cerevisiae.

G3 (Bethesda) 4(7) , 1247-58, (2014)

Genetic and microscopic approaches using Saccharomyces cerevisiae have identified many proteins that play a role in mitochondrial dynamics, but it is possible that other proteins and pathways that pla...