Perspectives on hyperpolarised solution‐state magnetic resonance in chemistry

Dumez, Jean‐Nicolas

doi:10.1002/mrc.4496

Cited by 11 publications

(7 citation statements)

References 53 publications

(191 reference statements)

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“…Hyperpolarization of nuclear spins allows to enhance NMR signal by several orders of magnitude at magnetic fields of a few tesla. [1][2][3][4] The obtained hyperpolarized (HP) molecules can be used as contrast agents for metabolic studies and molecular imaging. 5,6 Currently, in this context the most important HP compound is pyruvate which is metabolized to lactate in vivo.…”

Section: Introductionmentioning

confidence: 99%

“…Hyperpolarization of nuclear spins allows one to enhance the NMR signal by several orders of magnitude at magnetic fields of a few tesla. − The obtained hyperpolarized (HP) molecules can be used as contrast agents for metabolic studies and molecular imaging. , Currently, in this context, the most important HP compound is pyruvate, which is metabolized to lactate in vivo . In tumor tissues, the rates of aerobic glycolysis and reduction of pyruvate to lactate are usually significantly higher compared to those of normal tissues (the so-called Warburg effect).…”

Section: Introductionmentioning

confidence: 99%

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Parahydrogen-Induced Polarization of 1-¹³C-Acetates and 1-¹³C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters

et al. 2019

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13 C-hyperpolarized carboxylates, such as pyruvate and acetate, are emerging molecular contrast agents for MRI visualization of various diseases, including cancer. Here we present a systematic study of 1 H and 13 C parahydrogen-induced polarization of acetate and pyruvate esters with ethyl, propyl and allyl alcoholic moieties. It was found that allyl pyruvate is the most efficiently hyperpolarized compound from those under study, yielding 21% and 5.4% polarization of 1 H and 13 C nuclei, respectively, in CD 3 OD solutions. Allyl pyruvate and ethyl acetate were also hyperpolarized in aqueous phase using homogeneous hydrogenation with parahydrogen over water-soluble rhodium catalyst. 13 C polarization of 0.82% and 2.1% was obtained for allyl pyruvate and ethyl acetate, respectively. 13 C-hyperpolarized methanolic and aqueous solutions of allyl pyruvate and ethyl acetate were employed for in vitro MRI visualization, demonstrating the prospects for translation of the presented approach to biomedical in vivo studies.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Parahydrogen-Induced Polarization of 1-¹³C-Acetates and 1-¹³C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters

et al. 2019

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“…65 Dynamic Nuclear Polarization (DNP) can provide major increases in NMR sensitivity. 66 Currently, this is specialized and expensive area of research. However, it is likely that further developments in instrumentation and methodology will allow more widespread use of DNP for small molecule structure elucidation in the future.…”

Section: Discussionmentioning

confidence: 99%

The use of indirectly bonded ¹³C‐¹H (INCH) shift correlation spectra for ab initio structure elucidation of natural products and other complex organic compounds; A personal and historical perspective

Reynolds

2016

Concepts Magnetic Resonance

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This article reviews the use of long-range shift correlation spectra for structure elucidation of natural products and other complex organic compounds from the early 1980's to the present. Much of it is written from the personal viewpoint of someone who has been involved in this area of research since its earliest days. The first section covers the early use of long-range correlation spectra in the 1980's. The second section covers the development of specialized pulse sequences for this type of acquisition. It begins with three 13 C-detected sequences, followed by heteronuclear multiple bond correlation (HMBC) and some modified versions of HMBC and, finally, longer range correlation sequences based on the heteronuclear single quantum multiple bond correlation sequence. The third section covers various sequences designed to distinguish between 2-bond and longer range 13 C-1 H correlations. Unfortunately, none of these can make this distinction for non-protonated carbons. Only the 1,1-ADEQUATE sequence can make this distinction but its very low sensitivity limits its usefulness. The next section focuses on ways of avoiding getting incorrect structures of organic compounds, an ongoing problem in natural product research. The last section includes likely shortterm developments and possible long-term developments in NMR methodology that would be beneficial for small molecule structure elucidation. K E Y W O R D S 1,1-ADEQUATE, constant-time inverse-detection gradient accord rescaled, correlation by long-range coupling constants, FLOCK, heteronuclear 2-bond correlation, heteronuclear multiple bond correlation, heteronuclear single quantum multiple bond correlation, long-range 13 C-1 H correlation spectra, structure elucidation, X-nucleus CORrelation with Fixed Evolution time

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“…SABRE is mainly observed for hetrocyclic organic compounds [123]. SABRE is a powerful hyperpolarization technique but it is restricted in application to selected molecules.…”

Section: Applicationsmentioning

confidence: 99%

Rapid-melt Dynamic Nuclear Polarization

Sharma¹,

Janssen²,

Leggett³

et al. 2015

Journal of Magnetic Resonance

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Perspectives on hyperpolarised solution‐state magnetic resonance in chemistry

Cited by 11 publications

References 53 publications

Parahydrogen-Induced Polarization of 1-¹³C-Acetates and 1-¹³C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters

Parahydrogen-Induced Polarization of 1-¹³C-Acetates and 1-¹³C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters

The use of indirectly bonded ¹³C‐¹H (INCH) shift correlation spectra for ab initio structure elucidation of natural products and other complex organic compounds; A personal and historical perspective

Rapid-melt Dynamic Nuclear Polarization

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Perspectives on hyperpolarised solution‐state magnetic resonance in chemistry

Cited by 11 publications

References 53 publications

Parahydrogen-Induced Polarization of 1-13C-Acetates and 1-13C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters

Parahydrogen-Induced Polarization of 1-13C-Acetates and 1-13C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters

The use of indirectly bonded 13C‐1H (INCH) shift correlation spectra for ab initio structure elucidation of natural products and other complex organic compounds; A personal and historical perspective

Rapid-melt Dynamic Nuclear Polarization

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Parahydrogen-Induced Polarization of 1-¹³C-Acetates and 1-¹³C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters

Parahydrogen-Induced Polarization of 1-¹³C-Acetates and 1-¹³C-Pyruvates Using Sidearm Hydrogenation of Vinyl, Allyl, and Propargyl Esters

The use of indirectly bonded ¹³C‐¹H (INCH) shift correlation spectra for ab initio structure elucidation of natural products and other complex organic compounds; A personal and historical perspective