NMR Spectroscopic Method to Identify and Classify Thiol-Trapping Agents: Revival of Michael Acceptors for Drug Discovery

Speed trap: Cysteamine reacts in DMSO with electrophilic double bonds to afford Michael adducts (see scheme), whereas no trapping reaction takes place in apolar solvents. A simple and quick NMR spectroscopic method to identify Michael acceptors and sort them into reversible and irreversible thiol si...

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Veröffentlicht in:	Angewandte Chemie (International ed.) 2011-01, Vol.50 (2), p.467-471
Hauptverfasser:	Avonto, Cristina, Taglialatela-Scafati, Orazio, Pollastro, Federica, Minassi, Alberto, Di Marzo, Vincenzo, De Petrocellis, Luciano, Appendino, Giovanni
Format:	Artikel
Sprache:	eng
Schlagworte:	Antineoplastic Agents - chemical synthesis Antineoplastic Agents - chemistry Biological Products - chemical synthesis Biological Products - chemistry Cell Line Cysteamine - chemistry Dimethyl Sulfoxide - chemistry Drug Discovery Humans Magnetic Resonance Spectroscopy - methods Michael addition natural products Neoplasms - drug therapy NMR spectroscopy Sulfhydryl Compounds - chemistry thiols
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Beschreibung
Zusammenfassung:	Speed trap: Cysteamine reacts in DMSO with electrophilic double bonds to afford Michael adducts (see scheme), whereas no trapping reaction takes place in apolar solvents. A simple and quick NMR spectroscopic method to identify Michael acceptors and sort them into reversible and irreversible thiol sinks is validated biologically in a cellular assay sensitive to thiol‐trapping agents. DMSO=dimethyl sulfoxide.
ISSN:	1433-7851 1521-3773
DOI:	10.1002/anie.201005959