2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)-

Names

[ Name ]:
2-Thiazolidinone,4-[(1R,4Z,8Z,10S,13R,15R)-15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl]-,(4R)-

[Synonym ]:
LATRUNCULIN B
LATRUNCULIN B,LATRUNCULIA MAGNIFICA
MFCD00270879
LAT-B
LatrunculinBfromLutrunculiamagnifica

Biological Activity

[Description]:

Latrunculin B, an antimicrobial marine alkaloid, is an actin polymerization inhibitor. Latrunculin B regulates pulmonary vein electrophysiological characteristics and attenuates stretch-induced arrhythmogenesis[1][2]. Antifungal and antiprotozoal activity.

[Related Catalog]:

Research Areas >> Infection

Signaling Pathways >> Anti-infection >> Fungal

[In Vitro]

Latrunculin B displays growth inhibition of HeLa cells with an IC50 value of 1.4 μM[1]. Latrunculin B modulates electrophysiological characteristics and arrhythmogenesis in pulmonary vein cardiomyocytes. Latrunculin B (100 nM) decreases the spontaneous electrical activity by 16±4% in pulmonary vein (PV) preparations. Latrunculin B (100 nM) decreases the late Na+ current, L-type Ca2+ current, Na+/Ca2+ exchanger current, and stretch-activated BKCa current in PV cardiomyocytes. Latrunculin B reduces the transient outward K+ current and ultra-rapid delayed rectifier K+ current, but increases the delayed rectifier K+ current in isolated PV cardiomyocytes. Latrunculin B (100 nM) decreases intracellular Ca2+ transient and sarcoplasmic reticulum Ca2+ content in PV cardiomyocytes. Latrunculin B attenuates stretch-induced increased spontaneous electrical activity and trigger activity[2].

[References]

[1]. Diaa T A Youssef, et al. Magnificines A and B, Antimicrobial Marine Alkaloids Featuring a Tetrahydrooxazolo[3,2-a]azepine-2,5( 3H,6H)-dione Backbone from the Red Sea Sponge Negombata magnifica. Mar Drugs. 2021 Apr 12;19(4):214.

[2]. Yen-Yu Lu, et al. Latrunculin B modulates electrophysiological characteristics and arrhythmogenesis in pulmonary vein cardiomyocytes. Clin Sci (Lond). 2016 May;130(9):721-32.

Chemical & Physical Properties

[ Molecular Formula ]:
C₂₀H₂₉NO₅S

[ Molecular Weight ]:
395.51300

[ Exact Mass ]:
395.17700

[ PSA ]:
110.16000

[ LogP ]:
3.63220

[ Storage condition ]:
20°C

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

Arabidopsis dynamin-related proteins, DRP2A and DRP2B, function coordinately in post-Golgi trafficking.

Biochem. Biophys. Res. Commun. 456(1) , 238-44, (2015)

Dynamin-related proteins (DRPs) are large GTPases involved in a wide range of cellular membrane remodeling processes. In Arabidopsis thaliana, two paralogous land plant-specific type DRPs, DRP2A and D...

Morphological effects on expression of growth differentiation factor 15 (GDF15), a marker of metastasis.

J. Cell Physiol. 229(3) , 362-73, (2014)

Cancer cells typically demonstrate altered morphology during the various stages of disease progression as well as metastasis. While much is known about how altered cell morphology in cancer is a resul...

The formation of cortical actin arrays in human trabecular meshwork cells in response to cytoskeletal disruption.

Exp. Cell Res. 328(1) , 164-71, (2014)

The cytoskeleton of human trabecular meshwork (HTM) cells is known to be altered in glaucoma and has been hypothesized to reduce outflow facility through contracting the HTM tissue. Latrunculin B (Lat...