Solid-phase synthesis of a novel phalloidin analog with on-bead and off-bead actin-binding activity
| Autor: | David M. Perrin, Mihajlo Todorovic, Antoine Blanc |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Phalloidin Chinese hamster ovary cell Metals and Alloys macromolecular substances General Chemistry 010402 general chemistry 01 natural sciences Fluorescence Catalysis 3. Good health 0104 chemical sciences Surfaces Coatings and Films Electronic Optical and Magnetic Materials chemistry.chemical_compound Solid-phase synthesis Phallotoxin chemistry Polymerization Materials Chemistry Ceramics and Composites Biophysics Actin Derivative (chemistry) |
| Zdroj: | Chemical Communications. 55:385-388 |
| ISSN: | 1364-548X 1359-7345 |
| DOI: | 10.1039/c8cc08379g |
| Popis: | Specific effectors of actin polymerization have found use as dynamic probes of cellular morphology that may be used to gauge cellular response to stimuli and drugs. Of various natural products that target actin, phalloidin is one of the most potent and selective inhibitors of actin depolymerization. Phalloidin and related members of the phallotoxin family are macrocyclic heptapeptides bearing a characteristic and rigidifying transannular tryptathionine bridge. Here we describe a solid-phase synthesis of a new phalloidin analog as a prototype for library development with the potential for on- and off-bead screening. To validate our method, we labelled the phalloidin derivative with a fluorescent dye which stained actin in CHO cells. Furthermore, a bioassay was developed allowing actin polymerization on beads carrying a phalloidin derivative. |
| Databáze: | OpenAIRE |
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