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L5163

Sigma-Aldrich

Latrunculin A

from sea sponge, ≥85% (HPLC), waxy solid

Synonym(s):

LAT-A, [1R-[1R*, 4Z, 8E, 10Z, 12S*, 15R*, 17R*(R*)]]-4-(17-Hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-17-yl)-2-thiazolidinone

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About This Item

Empirical Formula (Hill Notation):
C22H31NO5S
CAS Number:
76343-93-6
Molecular Weight:
421.55
UNSPSC Code:
12352200
PubChem Substance ID:
329817620
NACRES:
NA.77
Pricing and availability is not currently available.

biological source

sea sponge

Quality Level

200

assay

≥85% (HPLC)

form

waxy solid

mol wt

421.6

solubility

DMSO: soluble
ethanol: soluble

storage temp.

−20°C

SMILES string

C[C@H]1CC[C@@H]2C[C@H](C[C@@](O)(O2)[C@@H]3CSC(=O)N3)OC(=O)C=C(C)CC\C=C\C=C1

InChI

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

DDVBPZROPPMBLW-IZGXTMSKSA-N

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1 of 4

This Item
47144548190226424
2-(N-Ethylanilino)ethanol 99%

117684

2-(N-Ethylanilino)ethanol

2-(Methylamino)ethanol ≥98%

471445

2-(Methylamino)ethanol

(±)-1-(2-Furyl)ethanol ≥99.0% (GC)

48190

(±)-1-(2-Furyl)ethanol

2-(Methylthio)ethanol 99%

226424

2-(Methylthio)ethanol

assay

99%

assay

≥98%

assay

≥99.0% (GC)

assay

99%

Quality Level

100

Quality Level

200

Quality Level

100

Quality Level

100

bp

268 °C (lit.)

bp

159 °C (lit.)

bp

167-170 °C

bp

169-171 °C (lit.)

form

solid

form

liquid

form

-

form

liquid

mp

36-38 °C (lit.)

mp

-

mp

-

mp

-

functional group

amine

functional group

amine, hydroxyl

functional group

hydroxyl

functional group

hydroxyl, thioether

General description

Latrunculin A, a toxin extracted from the red sea sponge Latrunculia magnifica. It participates in vitro in the morphological alteration of the polymerization of pure actin.[1] It forms a complex by binding with the nucleotide cleft of actin for actin filaments elongation.[2]

Application

Latrunculin A has been used as medium supplementation for A549 cells to determine the internalization mechanism of CAV9 in A549 human lung carcinoma cells.[3]

Biochem/physiol Actions

Latrunculin A inhibits actin polymerization by a different mechanism than cytochalasins. Latrunculin A disrupts microfilament-mediated processes.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCM1155
SLCL5222
SLCK7387
SLCJ8037
SLCJ2780

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E G Yarmola et al.
The Journal of biological chemistry, 275(36), 28120-28127 (2000-06-22)
Latrunculin A is used extensively as an agent to sequester monomeric actin in living cells. We hypothesize that additional activities of latrunculin A may be important for its biological activity. Our data are consistent with the formation of a 1:1
Peter J Wen et al.
Nature communications, 7, 12604-12604 (2016-09-01)
Vesicle fusion is executed via formation of an Ω-shaped structure (Ω-profile), followed by closure (kiss-and-run) or merging of the Ω-profile into the plasma membrane (full fusion). Although Ω-profile closure limits release but recycles vesicles economically, Ω-profile merging facilitates release but
Zhanghan Wu et al.
Nature communications, 9(1), 136-136 (2018-01-13)
Immune cells exhibit stimulation-dependent traveling waves in the cortex, much faster than typical cortical actin waves. These waves reflect rhythmic assembly of both actin machinery and peripheral membrane proteins such as F-BAR domain-containing proteins. Combining theory and experiments, we develop
Keiichiro Kushiro et al.
Scientific reports, 7(1), 4244-4244 (2017-06-28)
During metastasis, cancer cells are exposed to various three-dimensional microstructures within the body, but the relationship between cancer migration and three-dimensional geometry remain largely unclear. Here, such geometric effects on cancerous cells were investigated by characterizing the motility of various
Maureen Möckel et al.
Journal of virology, 93(16) (2019-05-31)
Dynamin GTPases, best known for their role in membrane fission of endocytic vesicles, provide a target for viruses to be exploited during endocytic uptake. Recently, we found that entry of herpes simplex virus 1 (HSV-1) into skin cells depends on
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