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A New Ir‐NHC Catalyst for Signal Amplification by Reversible Exchange in D(2)O

NMR signal amplification by reversible exchange (SABRE) has been observed for pyridine, methyl nicotinate, N‐methylnicotinamide, and nicotinamide in D(2)O with the new catalyst [Ir(Cl)(IDEG)(COD)] (IDEG=1,3‐bis(3,4,5‐tris(diethyleneglycol)benzyl)imidazole‐2‐ylidene). During the activation and hyperp...

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Autores principales: Spannring, Peter, Reile, Indrek, Emondts, Meike, Schleker, Philipp P. M., Hermkens, Niels K. J., van der Zwaluw, Nick G. J., van Weerdenburg, Bram J. A., Tinnemans, Paul, Tessari, Marco, Blümich, Bernhard, Rutjes, Floris P. J. T., Feiters, Martin C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5089654/
https://www.ncbi.nlm.nih.gov/pubmed/27258850
http://dx.doi.org/10.1002/chem.201601211
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author Spannring, Peter
Reile, Indrek
Emondts, Meike
Schleker, Philipp P. M.
Hermkens, Niels K. J.
van der Zwaluw, Nick G. J.
van Weerdenburg, Bram J. A.
Tinnemans, Paul
Tessari, Marco
Blümich, Bernhard
Rutjes, Floris P. J. T.
Feiters, Martin C.
author_facet Spannring, Peter
Reile, Indrek
Emondts, Meike
Schleker, Philipp P. M.
Hermkens, Niels K. J.
van der Zwaluw, Nick G. J.
van Weerdenburg, Bram J. A.
Tinnemans, Paul
Tessari, Marco
Blümich, Bernhard
Rutjes, Floris P. J. T.
Feiters, Martin C.
author_sort Spannring, Peter
collection PubMed
description NMR signal amplification by reversible exchange (SABRE) has been observed for pyridine, methyl nicotinate, N‐methylnicotinamide, and nicotinamide in D(2)O with the new catalyst [Ir(Cl)(IDEG)(COD)] (IDEG=1,3‐bis(3,4,5‐tris(diethyleneglycol)benzyl)imidazole‐2‐ylidene). During the activation and hyperpolarization steps, exclusively D(2)O was used, resulting in the first fully biocompatible SABRE system. Hyperpolarized (1)H substrate signals were observed at 42.5 MHz upon pressurizing the solution with parahydrogen at close to the Earth's magnetic field, at concentrations yielding barely detectable thermal signals. Moreover, 42‐, 26‐, 22‐, and 9‐fold enhancements were observed for nicotinamide, pyridine, methyl nicotinate, and N‐methylnicotinamide, respectively, in conventional 300 MHz studies. This research opens up new opportunities in a field in which SABRE has hitherto primarily been conducted in CD(3)OD. This system uses simple hardware, leaves the substrate unaltered, and shows that SABRE is potentially suitable for clinical purposes.
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spelling pubmed-50896542016-11-09 A New Ir‐NHC Catalyst for Signal Amplification by Reversible Exchange in D(2)O Spannring, Peter Reile, Indrek Emondts, Meike Schleker, Philipp P. M. Hermkens, Niels K. J. van der Zwaluw, Nick G. J. van Weerdenburg, Bram J. A. Tinnemans, Paul Tessari, Marco Blümich, Bernhard Rutjes, Floris P. J. T. Feiters, Martin C. Chemistry Full Papers NMR signal amplification by reversible exchange (SABRE) has been observed for pyridine, methyl nicotinate, N‐methylnicotinamide, and nicotinamide in D(2)O with the new catalyst [Ir(Cl)(IDEG)(COD)] (IDEG=1,3‐bis(3,4,5‐tris(diethyleneglycol)benzyl)imidazole‐2‐ylidene). During the activation and hyperpolarization steps, exclusively D(2)O was used, resulting in the first fully biocompatible SABRE system. Hyperpolarized (1)H substrate signals were observed at 42.5 MHz upon pressurizing the solution with parahydrogen at close to the Earth's magnetic field, at concentrations yielding barely detectable thermal signals. Moreover, 42‐, 26‐, 22‐, and 9‐fold enhancements were observed for nicotinamide, pyridine, methyl nicotinate, and N‐methylnicotinamide, respectively, in conventional 300 MHz studies. This research opens up new opportunities in a field in which SABRE has hitherto primarily been conducted in CD(3)OD. This system uses simple hardware, leaves the substrate unaltered, and shows that SABRE is potentially suitable for clinical purposes. John Wiley and Sons Inc. 2016-06-03 2016-06-27 /pmc/articles/PMC5089654/ /pubmed/27258850 http://dx.doi.org/10.1002/chem.201601211 Text en © 2016 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Spannring, Peter
Reile, Indrek
Emondts, Meike
Schleker, Philipp P. M.
Hermkens, Niels K. J.
van der Zwaluw, Nick G. J.
van Weerdenburg, Bram J. A.
Tinnemans, Paul
Tessari, Marco
Blümich, Bernhard
Rutjes, Floris P. J. T.
Feiters, Martin C.
A New Ir‐NHC Catalyst for Signal Amplification by Reversible Exchange in D(2)O
title A New Ir‐NHC Catalyst for Signal Amplification by Reversible Exchange in D(2)O
title_full A New Ir‐NHC Catalyst for Signal Amplification by Reversible Exchange in D(2)O
title_fullStr A New Ir‐NHC Catalyst for Signal Amplification by Reversible Exchange in D(2)O
title_full_unstemmed A New Ir‐NHC Catalyst for Signal Amplification by Reversible Exchange in D(2)O
title_short A New Ir‐NHC Catalyst for Signal Amplification by Reversible Exchange in D(2)O
title_sort new ir‐nhc catalyst for signal amplification by reversible exchange in d(2)o
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5089654/
https://www.ncbi.nlm.nih.gov/pubmed/27258850
http://dx.doi.org/10.1002/chem.201601211
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