CAS 76343-94-7

Latrunculin B

Description:

Latrunculin B is a natural product derived from the marine sponge Latrunculia magnifica, belonging to the class of compounds known as macrolides. It is primarily recognized for its potent ability to inhibit actin polymerization, making it a valuable tool in cell biology research for studying cytoskeletal dynamics. The compound exhibits a molecular formula that reflects its complex structure, which includes multiple rings and functional groups contributing to its biological activity. Latrunculin B is typically characterized by its solubility in organic solvents, such as dimethyl sulfoxide (DMSO), and its relatively low solubility in water. Its mechanism of action involves binding to monomeric G-actin, preventing the formation of filamentous F-actin, which is crucial for various cellular processes, including cell motility and division. Due to its specific targeting of the cytoskeleton, Latrunculin B has been utilized in various experimental settings to elucidate the roles of actin in cellular functions and to explore potential therapeutic applications in cancer and other diseases.

Formula: C₂₀H₂₉NO₅S

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

InChI key: InChIKey=NSHPHXHGRHSMIK-JRIKCGFMSA-N

SMILES: O[C@]1([C@]2(NC(=O)SC2)[H])C[C@]3(C[C@](O1)(CC[C@H](C)/C=C\CC/C(/C)=C\C(=O)O3)[H])[H]

Synonyms:

• Latrunculin B
• 2-Thiazolidinone, 4-(15-hydroxy-5,10-dimethyl-3-oxo-2,14-dioxabicyclo[11.3.1]heptadeca-4,8-dien-15-yl)-, [1R-[1R*,4Z,8Z,10S*,13R*,15R*(R*)]]-
• 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)-
• 2,13-Dioxabicyclo[11.3.1]heptadecane, 2-thiazolidinone deriv.
• (4R)-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]-2-thiazolidinone

Latrunculin B

CAS: 76343-94-7

Formula: C₂₀H₂₉NO₅S

Purity: ≥96%

Molecular weight: 395.5130

Ref: IN-DA00G265

Latrunculin B

CAS: 76343-94-7

Latrunculin B: alkaloid, inhibits actin polymerization, antifungal, antiprotozoal, modulates heart rhythm, studied in glaucoma.

Formula: C₂₀H₂₉NO₅S

Purity: 98%

Color and Shape: Solid

Molecular weight: 395.51

Ref: TM-T20636

Latrunculin B

CAS: 76343-94-7

Formula: C₂₀H₂₉NSO₅

Purity: (HPLC) ≥ 98.0%

Color and Shape: White to light-yellow solid, or colourless film

Molecular weight: 395.51

Ref: 7W-GL0565

Latrunculin B

Controlled Product

CAS: 76343-94-7

Formula: C₂₀H₂₉NO₅S

Color and Shape: Neat

Molecular weight: 395.513

Ref: TR-L177330

Latrunculin B

CAS: 76343-94-7

Latrunculin B is a natural compound that acts as a potent inhibitor of actin polymerization. It blocks the polymerization of actin monomers, leading to cell lysis and cell death. Latrunculin B has been shown to increase the motility of pluripotent stem cells and induce angiogenesis in vivo. However, this drug has no effect on the growth or survival of tumor cells in vitro. The mechanism by which latrunculin B induces these effects is still unclear and may be related to its ability to inhibit transcriptional regulation and protein synthesis in a model system. Latrunculin B has also been shown to be an inhibitor of P-glycoprotein (P-gp), one of the major drug efflux transporters found in human cells. This drug may have potential as a substrate for P-gp inhibitors that are being developed for cancer chemotherapy.

Formula: C₂₀H₂₉NO₅S

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 395.51 g/mol

Ref: 3D-BDA34394