15N magnetic resonance hyperpolarization via the reaction of parahydrogen with 15N-propargylcholine.
(15)N-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 (15)N resonance. Among the different isomers formed upon hydrogenation of (15)N-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 (15)N enhancement has been attained through a retro-INEPT ((15)N-(1)H) experiment. T(1) of the hyperpolarized (15)N 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 (15)N polarized signal. Insights into the good cellular uptake of the compound have been gained.
Dipartimento di Chimica IFM, University of Torino, V. P. Giuria 7, 10125 Torino, Italy.
Francesca
F
Reineri
Alessandra
A
Viale
Silvano
S
Ellena
Diego
D
Alberti
Tommaso
T
Boi
Giovanni Battista
GB
Giovenzana
Roberto
R
Gobetto
Samuel S D
SS
Premkumar
Silvio
S
Aime
D045744:Cell Line, Tumor; D002794:Choline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism; D004705:Endocytosis; D005260:Female; D006801:Humans; D006865:Hydrogenation; D007536:Isomerism; D009682:Magnetic Resonance Spectroscopy / Q000379:methods*; D009587:Nitrogen Isotopes / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D010293:Pargyline / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism
D009587:Nitrogen Isotopes; D010293:Pargyline; D002794:Choline