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

Dipartimento di Scienze del Farmaco

Risultato della ricerca: Contributo su rivista › Articolo in rivista › 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.

Lingua originale	Inglese
pagine (da-a)	467-471
Numero di pagine	5
Rivista	Angewandte Chemie - International Edition
Volume	50
Numero di pubblicazione	2
DOI	https://doi.org/10.1002/anie.201005959
Stato di pubblicazione	Pubblicato - 10 gen 2011

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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.",

keywords = "Michael addition, NMR spectroscopy, drug discovery, natural products, thiols",

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

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month = jan,

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An NMR spectroscopic method to identify and classify thiol-trapping agents: Revival of michael acceptors for drug discovery? / Avonto, Cristina; Taglialatela-Scafati, Orazio; Pollastro, Federica et al.
In: Angewandte Chemie - International Edition, Vol. 50, N. 2, 10.01.2011, pag. 467-471.

Risultato della ricerca: Contributo su rivista › Articolo in rivista › peer review

TY - JOUR

T1 - An NMR spectroscopic method to identify and classify thiol-trapping agents

T2 - Revival of michael acceptors for drug discovery?

AU - Avonto, Cristina

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

Y1 - 2011/1/10

N2 - 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.

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

SN - 1433-7851

VL - 50

SP - 467

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JO - Angewandte Chemie - International Edition

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IS - 2

ER -

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

Abstract

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