76343-89-0

Upstream product

• 67-56-1 methanol 
• 76343-93-6 latrunculin A 
• 76343-93-6 Latrunculin A 
• 76343-93-6 Latrunculin A 
• 76343-93-6 Latrunculin-A 

Downstream Products

• 76343-93-6 latrunculin A 
• 1220351-11-0 17-O-methyl-N-benzyllatrunculin A 
• 1220351-12-1 17-O-methyl-N-benzoyllatrunculin A 
• 1220351-13-2 17-O-methyl-N-(6'-methoxyphenylacetyl)latrunculin A 

Relevant academic research and scientific papers

Latrunculin-Based Macrolides and Their Uses

Latrunculin derivatives are disclosed, as are anti-invasive and cytotoxic uses for latrunculins and latrunculin derivatives, and semisyntheses of latrunculin derivatives. The latrunculins and latrunculin derivatives are useful, for example, in treating cancers.

Semisynthetic latrunculin derivatives as inhibitors of metastatic breast cancer: Biological evaluations, preliminary structure-activity relationship and molecular modeling studies

The microfilament cytoskeleton protein actin plays an important role in cell biology and affects cytokinesis, morphogenesis, and cell migration. These functions usually fail and become abnormal in cancer cells. The marine-derived macrolides latrunculins A and B, from the Red Sea sponge Negombata magnifica, are known to reversibly bind actin monomers, forming 1:1 stoichiometric complexes with G-actin, disrupting its polymerization. To identify novel therapeutic agents for effective treatment of metastatic breast cancer, several semisynthetic derivatives of latrunculin A with diverse steric, electrostatic, and hydrogen bond donor and acceptor properties were rationally prepared. Analogues were designed to modulate the binding affinity toward G-actin. Examples of these reactions are esterification, acetylation, and N-alkylation. Semisynthetic latrunculins were then tested for their ability to inhibit pyrene-conjugated actin polymerization, and subsequently assayed for their antiproliferative and anti-invasive properties against MCF7 and MDA-MB-231 cells using MTT and invasion assays, respectively.

On the Chemistry of Latrunculins A and B

The chemical behavior of latrunculins A (1) and (B) (Lat A and B) under a variety of reaction conditions is described.The combination of the macrolide, the THP-lactol, and the 2-thiazolidinone rings was found to result on interesting unpredicted chemical transformations.The structures of two new Lats, 6,7-epoxy-Lat A (3) and Lat M (4) isolated from Latrunculia magnifica, are discussed.

Marine Toxins of Latrunculia magnifica

Latrunculins A (1) and B (2) are the major extractable toxins of Latrunculia magnifica, constituting up to O.35 percent of the dry weight of the sponge.The structure of the compounds was determined by detailed spectral analysis, some minor chemical transformations, and X-ray crystallography.The latrunculins are the first-known 2-thiazolidinone-bearing marine macrolides.They were found to cause major alterations in specific cytoskeletal proteins.A retrosynthesis of the new compounds is suggested.

Latrunculin, a new 2-thiazolidinone macrolide from the marine sponge latrunculia magnifica

Three new toxins were isolated from the Red Sea sponge Latrunculia magnifica A full structure determination of these toxins, by spectroscopic methods, was aided by an X-ray diffraction analysis of a crystalline derivative (1b) of latrunculin-A. The Latrunculins exhibit a new class of 14 and 16 membered macrolides to which the rare 2-thiazolidinone moiety is attached. A biogenesis of these biologically active compounds is put forward.