title: Para-hydrogenated glucose derivatives as potential 13C-hyperpolarized probes for magnetic resonance imaging.
abstract: A set of molecules in which a glucose moiety is bound to a hydrogenable synthon has been synthesized and evaluated for hydrogenation reactions and for the corresponding para-hydrogen-induced polarization (PHIP) effects, in order to select suitable candidates for an in vivo magnetic resonance imaging (MRI) method for the assessment of glucose cellular uptake. It has been found that amidic derivatives do not yield any polarization enhancement, probably due to singlet-triplet state mixing along the reaction pathway. In contrast, ester derivatives are hydrogenated in high yield and afford enhanced (1)H and (13)C NMR spectra after para-hydrogenation. The obtained PHIP patterns are discussed and explained on the basis of the calculated spin level populations in the para-hydrogenated products. These molecules may find interesting applications in (13)C MRI as hyperpolarized probes for assessing the activity of glucose transporters in cells.
authors.affiliation: Dipartimento di Chimica IFM, University of Torino, Via P. Giuria 7, 10125 Torino, Italy.
authors.forename: Francesca
authors.initials: F
authors.lastname: Reineri
authors.forename: Daniela
authors.initials: D
authors.lastname: Santelia
authors.forename: Alessandra
authors.initials: A
authors.lastname: Viale
authors.forename: Erika
authors.initials: E
authors.lastname: Cerutti
authors.forename: Luisa
authors.initials: L
authors.lastname: Poggi
authors.forename: Tomas
authors.initials: T
authors.lastname: Tichy
authors.forename: Samuel S D
authors.initials: SS
authors.lastname: Premkumar
authors.forename: Roberto
authors.initials: R
authors.lastname: Gobetto
authors.forename: Silvio
authors.initials: S
authors.lastname: Aime
mesh_terms: D001692:Biological Transport; D002247:Carbon Isotopes; D005947:Glucose / Q000737:chemistry* / Q000378:metabolism; D006801:Humans; D006859:Hydrogen / Q000737:chemistry; D006865:Hydrogenation; D020014:K562 Cells; D008279:Magnetic Resonance Imaging / Q000379:methods*; D009682:Magnetic Resonance Spectroscopy
chemical_list: D002247:Carbon Isotopes; D006859:Hydrogen; D005947:Glucose