An NMR spectroscopic method to identify and classify thiol-trapping agents: Revival of michael acceptors for drug discovery?

Cristina Avonto; Orazio Taglialatela-Scafati; Federica Pollastro; Alberto Minassi; Vincenzo Di-Marzo; Luciano De-Petrocellis; Giovanni Appendino

doi:10.1002/anie.201005959

An NMR spectroscopic method to identify and classify thiol-trapping agents: Revival of michael acceptors for drug discovery?

Cristina Avonto
, Orazio Taglialatela-Scafati
, Federica Pollastro
, Alberto Minassi
, Vincenzo Di-Marzo
, Luciano De-Petrocellis
, Giovanni Appendino

Department of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

Abstract

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.

Original language	English
Pages (from-to)	467-471
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	2
DOIs	https://doi.org/10.1002/anie.201005959
Publication status	Published - 10 Jan 2011

Keywords

Michael addition
NMR spectroscopy
drug discovery
natural products
thiols

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10.1002/anie.201005959

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title = "An NMR spectroscopic method to identify and classify thiol-trapping agents: Revival of michael acceptors for drug discovery?",

abstract = "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.",

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AU - Taglialatela-Scafati, Orazio

AU - Pollastro, Federica

AU - Minassi, Alberto

AU - Di-Marzo, Vincenzo

AU - De-Petrocellis, Luciano

AU - Appendino, Giovanni

PY - 2011/1/10

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AB - 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.

KW - Michael addition

KW - NMR spectroscopy

KW - drug discovery

KW - natural products

KW - thiols

UR - https://www.scopus.com/pages/publications/78650855820

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DO - 10.1002/anie.201005959

M3 - Article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 2

ER -

An NMR spectroscopic method to identify and classify thiol-trapping agents: Revival of michael acceptors for drug discovery?

Abstract

Keywords

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