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Synthetic approach for unsaturated precursors for parahydrogen induced polarization of choline and its analogs.

ABSTRACT: Reported here are (i) a new synthetic approach for preparation of (ii) a new compound class, of -OH, for example, an -OH group is replaced with acetyl protecting group, protected 1,2-dehydrocholine analogs and (iii) a new synthetic route for betaine aldehyde. The C?C bond of 1,2-dehydrocholine moiety can be used for molecular addition of parahydrogen producing -OH protected hyperpolarized choline by parahydrogen-induced polarization (PHIP). The reported synthetic approach allows for incorporation of (15) N and deuterium labels, which are necessary for preparation of highly polarized PHIP contrast agents. Isotope labeling with (15) N and/or deuterium was conducted. Hyperpolarized (15) N-choline enabled by the reported synthetic approach can be potentially used as an imaging biomarker of cancer similar to choline positron emission tomography tracers.

SUBMITTER: Shchepin RV

PROVIDER: S-EPMC4159776 | biostudies-literature | 2013 Nov

REPOSITORIES: biostudies-literature

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Synthetic approach for unsaturated precursors for parahydrogen induced polarization of choline and its analogs.

Shchepin Roman V RV Chekmenev Eduard Y EY

Journal of labelled compounds & radiopharmaceuticals 20130715 13

Reported here are (i) a new synthetic approach for preparation of (ii) a new compound class, of -OH, for example, an -OH group is replaced with acetyl protecting group, protected 1,2-dehydrocholine analogs and (iii) a new synthetic route for betaine aldehyde. The CC bond of 1,2-dehydrocholine moiety can be used for molecular addition of parahydrogen producing -OH protected hyperpolarized choline by parahydrogen-induced polarization (PHIP). The reported synthetic approach allows for incorporatio ...[more]

PMID: 25196027

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