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Merck
CN

428021

Latrunculin A

from Latrunculia magnifica, ≥95% (HPLC), solid, actin polymerization inhibitor, Calbiochem

Synonym(s):

Latrunculin A, Latrunculia magnifica

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About This Item

Empirical Formula (Hill Notation):
C22H31NO5S
CAS Number:
76343-93-6
Molecular Weight:
421.55
MDL number:
MFCD27977552
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Product Name

Latrunculin A, Latrunculia magnifica, Latrunculin A, CAS 76343-93-6, is a cell-permeable marine toxin that disrupts microfilament organization in cultured cells by the formation of a 1:1 complex with monomeric G-actin (KD = 200 nM).

SMILES string

S1C[C@H](NC1=O)[C@@]2(O[C@H]3C[C@@H](OC(=O)\C=C(/CC\C=C\C=C/[C@H](CC3)C)\C)C2)O

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

description

Merck USA index - 14, 8378

assay

≥95% (HPLC)

form

solid

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze
protect from light

color

white

solubility

DMSO: 25 mg/mL

shipped in

ambient

storage temp.

−20°C

Quality Level

100

Related Categories

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Biochem/physiol Actions

Cell permeable: yes
Kd = 200 nM in formation of a 1:1 complex with monomeric G-actin
Primary Target
G-actin
Product does not compete with ATP.
Reversible: no

Disclaimer

Toxicity: Harmful (C)

General description

A cell-permeable marine toxin from the Red Sea sponge Latrunculia magnifica that disrupts microfilament organization in cultured cells by the formation of a 1:1 complex with monomeric G-actin (Kd = 200 nM). Also a potent inhibitor of microfilament-mediated processes in sperm, eggs, and embryos.
A cell-permeable marine toxin that disrupts microfilament organization in cultured cells by the formation of a 1:1 complex with monomeric G-actin (Kd = 200 nM). Also a potent inhibitor of microfilament-mediated processes in sperm, eggs, and embryos. A 1 mM (50 µg/119 µl) solution of Latrunculin A, Latrunculia magnifica Cat. No. 428026 in DMSO is also available.

Other Notes

Ayscough, K.R., et al. 1997. J. Cell Biol. 137, 399.
Spector, I., et al. 1989. Cell Motil. Cytoskeleton 13, 127.
Coue, M., et al. 1987. FEBS Lett. 213, 316.
Schatten, G., et al. 1986. Exp. Cell Res. 166, 191.
Spector, I., et al. 1983. Science 219, 493.

Packaging

Packaged under inert gas

Preparation Note

Following reconstitution aliquot and freeze (-20°C). Stock solutions are stable for up to 3 months at -20°C.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Camille Curantz et al.
PLoS biology, 20(10), e3001807-e3001807 (2022-10-11)
Developing tissues can self-organize into a variety of patterned structures through the stabilization of stochastic fluctuations in their molecular and cellular properties. While molecular factors and cell dynamics contributing to self-organization have been identified in vivo, events channeling self-organized systems
Ao Liu et al.
Molecular biology of the cell, 32(20), ar5-ar5 (2021-08-05)
Mitochondrial division is an important cellular process in both normal and pathological conditions. The dynamin GTPase Drp1 is a central mitochondrial division protein, driving constriction of the outer mitochondrial membrane (OMM). In mammals, the OMM protein mitochondrial fission factor (Mff)
Microtubule retrograde flow retains neuronal polarization in a fluctuating state.
Schelski, et al.
Science Advances, 8, eabo2336-eabo2336 (2022)
Lia Mara Gomes Paim et al.
Proceedings of the National Academy of Sciences of the United States of America, 119(12), e2119381119-e2119381119 (2022-03-17)
Cytokinesis is the final step of cell division during which a contractile ring forms a furrow that partitions the cytoplasm in two. How furrow ingression is spatiotemporally regulated and how it is adapted to complex cellular environments and developmental transitions
Sabrya C Carim et al.
iScience, 26(6), 106903-106903 (2023-06-28)
Animal cell cytokinesis requires activation of the GTPase RhoA (Rho1 in Drosophila), which assembles an F-actin- and myosin II-dependent contractile ring (CR) at the equatorial plasma membrane. CR closure is poorly understood, but involves the multidomain scaffold protein, Anillin. Anillin
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