76343-94-7

Basic information

• Product Name: LATRUNCULIN B
• Synonyms: LATRUNCULIN B;LATRUNCULIN B, LATRUNCULIA MAGNIFICA;LAT-B;LatrunculinBfromLutrunculiamagnifica;LATRUNCULIN B, LUTRUNCULIA MAGNIFICA;NSC 339663;Latrunculin B from Latruncula magnifica;(4R)-4-[(1R,4S,5Z,9Z,13R,15R)-15-hydroxy-4,9-dimethyl-11-oxo-12,16-dioxabicyclo[11.3.1]heptadeca-5,9-dien-15-yl]-1,3-thiazolidin-2-one
• CAS NO: 76343-94-7
• Molecular Formula: C20H29NO5S
• Molecular Weight: 395.51
• Mol File: 76343-94-7.mol
• Article Data: 5

Chemical Properties

• Appearance: light yellow/solid
• Density: 1.178 g/cm³
• Refractive Index: 1.533
• Storage Temp.: −20°C
• Solubility: DMSO: soluble
• Stability: 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.
• CAS DataBase Reference: LATRUNCULIN B(CAS DataBase Reference)
• NIST Chemistry Reference: LATRUNCULIN B(76343-94-7)
• EPA Substance Registry System: LATRUNCULIN B(76343-94-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 76343-94-7(Hazardous Substances Data)

Usage

Description

Latrunculin B is a macrocyclic toxin produced by the Red Sea sponge Latruncula magnifica. It is a potent actin polymerization inhibitor that disrupts microfilament organization, causing shortening and thickening of stress fibers. It is active in cell culture and is significantly more potent than cytochalasins in disrupting microfilament-mediated processes. Effective doses for latrunculin B vary depending on the cell type but are frequently in the low micromolar range. Note that latrunculin B is slowly inactivated by fetal bovine serum.

Uses

1. Used in Cell Biology Research:
Latrunculin B is used as an actin polymerization inhibitor for elucidating the molecular mechanisms of motile processes in cell biology.
2. Used in Actin Depolymerization Studies:
Latrunculin B is used as a depolymerizing agent for actin filaments in various experiments, helping researchers understand the role of actin in cellular processes.
3. Used in Dendritic Cell Research:
Latrunculin B is used as a component in bone marrow-derived dendritic cell (BMDC) complete medium to study the formation of tubules from phagosomes in dendritic cells.
4. Used in Pharmaceutical Applications:
Although not explicitly mentioned in the provided materials, latrunculin B's ability to disrupt actin polymerization and microfilament organization could potentially be applied in the development of drugs targeting cellular processes related to actin dynamics, such as cancer cell migration and invasion.

Biochem/physiol Actions

Primary TargetActin polymerization

References

1) Coue?et al. (1987),?Inhibition of actin polymerization by latrunculin; FEBS Lett.,?213?316 2) Spector?et al. (1989),?Latrunculins-novel marine macrolides that disrupt microfilament organization and affect cell growth; Cell Motil. Cytoskeleton,?13?127 3) Wakatsuki?et al. (2001),?Effects of cytochalasin D and latrunculin B on mechanical properties of cells; J. Cell. Sci.,?114?1025 4) Cha?et al. (2004),?The lateral mobility of NHE3 on the apical membrane of renal epithelial OK cells is limited by the PDZ domain proteins NHERF1/2 but is dependent on an intact actin cytoskeleton as determined by FRAP; Prog. Clin. Biol. Res.,?230 4 5) Herrera (2021), Cell cultures, transfection and treatments. protocols.io???https://dx.doi.org/10.17504/protocols.io.77ehrje [Focus Citation]

InChI:InChI=1/C20H29NO5S/c1-13-5-3-4-6-14(2)9-18(22)25-16-10-15(8-7-13)26-20(24,11-16)17-12-27-19(23)21-17/h3,5,9,13,15-17,24H,4,6-8,10-12H2,1-2H3,(H,21,23)/b5-3+,14-9-/t13-,15-,16-,17+,20-/m1/s1

Upstream product

• 105917-28-0 6,7-(Z)-15-OMe-Latrunculin B 
• 101915-87-1 6,7-(Z)-N-PMB-15-OMe-Latrunculin B 
• 861821-43-4 dimethyl 2-((R)-3-(4-methoxybenzyl)-2-oxothiazolidin-4-yl)-2-oxoethyl-phosphonate 
• 861821-42-3 (R)-4-[(E)-(5R,8S)-5-(tert-Butyl-dimethyl-silanyloxy)-8-methyl-undec-2-en-9-ynoyl]-3-(4-methoxy-benzyl)-thiazolidin-2-one 
• 646994-48-1 4-[2,4-dihydroxy-6-(3-methyl-hex-4-ynyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one 
• 101860-51-9 (-)-4-acetyl-3-(4-methoxybenzyl)-thiazolidinon-2-one 
• 646994-44-7 (3R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-methyl-non-7-ynal 
• 646994-43-6 ((1R,4S)-1-Allyl-4-methyl-hept-5-ynyloxy)-tert-butyl-dimethyl-silane 
• 646994-49-2 (R)-4-[(2R,4S,6R)-4-Hydroxy-2-methoxy-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-2-yl]-3-(4-methoxy-benzyl)-thiazolidin-2-one 
• 646994-46-9 (R)-4-[(5R,8S)-5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-8-methyl-undec-9-ynoyl]-3-(4-methoxy-benzyl)-thiazolidin-2-one 
• 1053714-70-7 Trifluoro-methanesulfonic acid (2R,4S,6R)-2-methoxy-2-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-4-yl ester 
• 646994-51-6 (R)-3-(4-Methoxy-benzyl)-4-((Z)-(1R,10S,13R,15R)-15-methoxy-5,10-dimethyl-3-oxo-2,14-dioxa-bicyclo[11.3.1]heptadec-4-en-8-yn-15-yl)-thiazolidin-2-one 
• 928112-44-1 (Z)-3-Methyl-oct-2-en-6-ynoic acid (2R,4R,6R)-2-methoxy-2-[(R)-3-(4-methoxy-benzyl)-2-oxo-thiazolidin-4-yl]-6-((S)-3-methyl-hex-4-ynyl)-tetrahydro-pyran-4-yl ester 
• 2436-90-0 (S)-(+)-dihydromyrcene 

Downstream Products

• 76376-32-4 latrunculin-C 

Relevant articles and documents

Examination of the olefin-olefin ring closing metathesis to prepare Latrunculin B

Three subunits of the potent actin polymerization inhibitor Latrunculin B were synthesized and assembled using olefin-olefin ring closing metathesis chemistry to close the 14-membered macrocycle. Metathesis reactions of substrates with various remote protecting group patterns were examined and gave 6,7-E-lactones as the preferred products.

Catalysis-Based Total Synthesis of Latrunculin B

The highly selective actin-binding latrunculins (e.g. 1) play a prominent role as probe molecules in chemical biology. A highly concise, productive, and inherently flexible approach to 1 illustrates the excellent profile and use of metal-catalyzed C-C bond formations.

Total Synthesis of (+)-Latrunculin B

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