15N magnetic resonance hyperpolarization via the reaction of parahydrogen with 15N-Propargylcholine

Francesca Reineri; Alessandra Viale; Silvano Ellena; Diego Alberti; Tommaso Boi; Giovanni Battista Giovenzana; Roberto Gobetto; Samuel S.D. Premkumar; Silvio Aime

doi:10.1021/ja209884h

¹⁵N magnetic resonance hyperpolarization via the reaction of parahydrogen with ¹⁵N-Propargylcholine

Francesca Reineri, Alessandra Viale, Silvano Ellena, Diego Alberti, Tommaso Boi, Giovanni Battista Giovenzana, Roberto Gobetto, Samuel S.D. Premkumar, Silvio Aime

Dipartimento di Scienze del Farmaco

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

Abstract

¹⁵N-Propargylcholine has been synthesized and hydrogenated with para-H ₂. Through the application of a field cycling procedure, parahydrogen spin order is transferred to the ¹⁵N resonance. Among the different isomers formed upon hydrogenation of ¹⁵N- propargylcholine, only the nontransposed derivative contributes to the observed N-15 enhanced emission signal. The parahydrogen-induced polarization factor is about 3000. The precise identification of the isomer responsible for the observed ¹⁵N enhancement has been attained through a retro-INEPT ( ¹⁵N- ¹H) experiment. T ₁ of the hyperpolarized ¹⁵N resonance has been estimated to be ca. 150 s, i.e., similar to that reported for the parent propargylcholine (144 s). Experimental results are accompanied by theoretical calculations that stress the role of scalar coupling constants (J _HN and J _HH) and of the field dependence in the formation of the observed ¹⁵N polarized signal. Insights into the good cellular uptake of the compound have been gained.

Lingua originale	Inglese
pagine (da-a)	11146-11152
Numero di pagine	7
Rivista	Journal of the American Chemical Society
Volume	134
Numero di pubblicazione	27
DOI	https://doi.org/10.1021/ja209884h
Stato di pubblicazione	Pubblicato - 11 lug 2012

Accesso al documento

10.1021/ja209884h

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title = "15N magnetic resonance hyperpolarization via the reaction of parahydrogen with 15N-Propargylcholine",

abstract = "15N-Propargylcholine has been synthesized and hydrogenated with para-H 2. Through the application of a field cycling procedure, parahydrogen spin order is transferred to the 15N resonance. Among the different isomers formed upon hydrogenation of 15N- propargylcholine, only the nontransposed derivative contributes to the observed N-15 enhanced emission signal. The parahydrogen-induced polarization factor is about 3000. The precise identification of the isomer responsible for the observed 15N enhancement has been attained through a retro-INEPT ( 15N- 1H) experiment. T 1 of the hyperpolarized 15N resonance has been estimated to be ca. 150 s, i.e., similar to that reported for the parent propargylcholine (144 s). Experimental results are accompanied by theoretical calculations that stress the role of scalar coupling constants (J HN and J HH) and of the field dependence in the formation of the observed 15N polarized signal. Insights into the good cellular uptake of the compound have been gained.",

author = "Francesca Reineri and Alessandra Viale and Silvano Ellena and Diego Alberti and Tommaso Boi and Giovenzana, {Giovanni Battista} and Roberto Gobetto and Premkumar, {Samuel S.D.} and Silvio Aime",

year = "2012",

month = jul,

day = "11",

doi = "10.1021/ja209884h",

language = "English",

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journal = "Journal of the American Chemical Society",

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T1 - 15N magnetic resonance hyperpolarization via the reaction of parahydrogen with 15N-Propargylcholine

AU - Reineri, Francesca

AU - Viale, Alessandra

AU - Ellena, Silvano

AU - Alberti, Diego

AU - Boi, Tommaso

AU - Giovenzana, Giovanni Battista

AU - Gobetto, Roberto

AU - Premkumar, Samuel S.D.

AU - Aime, Silvio

PY - 2012/7/11

Y1 - 2012/7/11

N2 - 15N-Propargylcholine has been synthesized and hydrogenated with para-H 2. Through the application of a field cycling procedure, parahydrogen spin order is transferred to the 15N resonance. Among the different isomers formed upon hydrogenation of 15N- propargylcholine, only the nontransposed derivative contributes to the observed N-15 enhanced emission signal. The parahydrogen-induced polarization factor is about 3000. The precise identification of the isomer responsible for the observed 15N enhancement has been attained through a retro-INEPT ( 15N- 1H) experiment. T 1 of the hyperpolarized 15N resonance has been estimated to be ca. 150 s, i.e., similar to that reported for the parent propargylcholine (144 s). Experimental results are accompanied by theoretical calculations that stress the role of scalar coupling constants (J HN and J HH) and of the field dependence in the formation of the observed 15N polarized signal. Insights into the good cellular uptake of the compound have been gained.

AB - 15N-Propargylcholine has been synthesized and hydrogenated with para-H 2. Through the application of a field cycling procedure, parahydrogen spin order is transferred to the 15N resonance. Among the different isomers formed upon hydrogenation of 15N- propargylcholine, only the nontransposed derivative contributes to the observed N-15 enhanced emission signal. The parahydrogen-induced polarization factor is about 3000. The precise identification of the isomer responsible for the observed 15N enhancement has been attained through a retro-INEPT ( 15N- 1H) experiment. T 1 of the hyperpolarized 15N resonance has been estimated to be ca. 150 s, i.e., similar to that reported for the parent propargylcholine (144 s). Experimental results are accompanied by theoretical calculations that stress the role of scalar coupling constants (J HN and J HH) and of the field dependence in the formation of the observed 15N polarized signal. Insights into the good cellular uptake of the compound have been gained.

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U2 - 10.1021/ja209884h

DO - 10.1021/ja209884h

M3 - Article

SN - 0002-7863

VL - 134

SP - 11146

EP - 11152

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

IS - 27