Para-hydrogenated glucose derivatives as potential 13c- hyperpolarized probes for magnetic resonance imaging
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 1H and 13C 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 13C MRI as hyperpolarized probes for assessing the activity of glucose transporters in cells.
Reineri, Francesca,Santelia, Daniela,Viale, Alessandra,Cerutti, Erika,Poggi, Luisa,Tichy, Tomas,Premkumar, Samuel S. D.,Gobetto, Roberto,Aime, Silvio
Method for the synthesis of alkyl, cycloalkyl or alcenyl aldosides or polyaldosides
The process comprises the action of a saturated aliphatic or cycloaliphatic alcohol or an aliphatic or cycloaliphatic alcohol comprising a double ethylenic bound not situated in alpha of the hydroxyl group with an aldose, aldoside or polyaldoside in the solvent and reactant formed by the hydrogen fluoride. Application to the synthesis of surfactants or as additives for rigidifying polyurethane foams.
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(2008/06/13)
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