Latrunculin A
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Basic information
- CAS
76343-93-6- Standard SMILES
C/C1=C/C(=O)O[C@@H]2C[C@@H](CC[C@H](C)/C=C\C=C\CC1)O[C@@](O)([C@@H]1CSC(=O)N1)C2- InChIKey
DDVBPZROPPMBLW-IZGXTMSKSA-N- Molecular formula
- C22H31NO5S
- Average molar mass
- 421.6 g/mol
- Monoisotopic mass
- 421.19229426
Overview
Latrunculin A is a bicyclic macrolide natural product consisting of a 16-membered bicyclic lactone attached to the rare 2-thiazolidinone moiety. It is obtained from the Red Sea sponge Latrunculia magnifica and from the Fiji Islands sponge Cacospongia mycofijiensis. Latrunculin A inhibits actin polymerisation, microfilament organsation and microfilament-mediated processes. It has a role as a metabolite, a toxin and an actin polymerisation inhibitor. It is a macrolide, an oxabicycloalkane, a thiazolidinone and a cyclic hemiketal.
Names & identifiers
- Preferred name
- Latrunculin A
- IUPAC
- (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
- English name
- LATRUNCULIN A
- Molecular formula
- C22H31NO5S
- Molecular weight
- 421.55
Names & synonyms
latrunculin a76343-93-6LAT-ALatA(+)-latrunculin ANSC 613011SRQ9WWM084LATRUNCULIN(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-oneDTXSID90893488NSC-613011CHEBI:69136
Show more names
Latrunculin A (LAT-A)LATRUNCULIN A, LATRUNCULIA MAGNIFICALatrunculin A (LAT-A), Actin polymerization inhibitorLatrunculin A, Latrunculia magnifica - CAS 76343-93-6 - Calbiochem4-[(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)-2-thiazolidinone(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]-2-thiazolidinone
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)-2-Thiazolidinone, 4-(17-hydroxy-5,12-dimethyl-3-oxo-2,16-dioxabicyclo(13.3.1)nonadeca-4,8,10-trien-17-yl)-, (1R*,4Z,8E,10Z,12S*,15R*,17R*(R*))-(+)-(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-one2-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)-RefChem:152463DTXCID501323505(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(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
Properties
Computed structural propertiesFilling in
- XLogP
- 3.7
- Topological polar surface area
- 110 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 1
- Heavy atoms
- 29
- Formal charge
- 0
- Complexity
- 703
Physicochemical properties
- alpha
- 24 · D24 +152° (c = 1.2 in chloroform)
- storage temp.
- -20 °C · -20°C
- solubility
- DMSO: soluble
- form
- waxy solid
- color
- yellow
- biological source
- sea sponge
- optical activity
- 144.423 · +144.423 (CHCl3)
- Stability
- 1 year · Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20° for up to 3 months.
- InChIKey
- DDVBPZROPPMBLW-IZGXTMSKSA-N
- SMILES
- 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
- FDA UNII
- 9 WWM084 · SRQ9WWM084
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 2 · GHS02
- Signal word
- Danger
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- Signal word
- Danger
- Symbol(GHS)
- GHS02
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H225
- Precautionary statements
- P210-P233-P240-P241-P242-P243-P280-P303+P361+P353-P370+P378-P403+P235-P501
Chemistry & industry
Applications
DescriptionActin disruption is used to study cell functions in vitro (e.g., migration, endocytosis) and in vivo (e.g., tumor cell invasion). Latrunculin A is a bioactive 2-thiazolidinone macrolide derived from sponges that sequesters G-actin and prevents F-actin assembly. It binds monomeric actin with 1:1 stoichiometry and can be used to block actin polymerization both in vitro (Kd = 0.2 μM) and in cells (0.5 μM, 30 min).{ Latrunculin A (1-10 μM) causes depolymerization of tumor cell cytoskeleton within ten minutes. Overnight treatment of cells with latrunculin A (10 μM) strongly suppresses actin synthesis. Prolonged cell treatment blocks dexamethasone-induced changes in actin cytoskeleton with no effect on cell viability.
UsesLatrunculin A, Latrunculia magnifica is a stabilizer of monomeric G-actin and polymerization inhibitor.
UsesLatrunculin A has been used as medium supplementation for A549 cells to determine the internalization mechanism of CAV9 in A549 human lung carcinoma cells.
General DescriptionLatrunculin 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. It forms a complex by binding with the nucleotide cleft of actin for actin filaments elongation.
Additional notes
DefinitionChEBI: A bicyclic macrolide natural product consisting of a 16-membered bicyclic lactone attached to the rare 2-thiazolidinone moiety. It is obtained from the Red Sea sponge Latrunculia magnifica and from the Fiji Islands sponge Cacospongia myc fijiensis. Latrunculin A inhibits actin polymerisation, microfilament organsation and microfilament-mediated processes.
Related reactions
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Compound notes
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