title: 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.
authors.affiliation: Department of Radiology, Vanderbilt University Institute of Imaging Science (VUIIS), Nashville, TN, 37232, USA.
authors.forename: Roman V
authors.initials: RV
authors.lastname: Shchepin
authors.forename: Eduard Y
authors.initials: EY
authors.lastname: Chekmenev
mesh_terms: D002794:Choline / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry*; D003287:Contrast Media / Q000138:chemical synthesis* / Q000737:chemistry; D003903:Deuterium / Q000737:chemistry; D006859:Hydrogen / Q000737:chemistry*; D009587:Nitrogen Isotopes / Q000737:chemistry
chemical_list: D003287:Contrast Media; D009587:Nitrogen Isotopes; D006859:Hydrogen; D003903:Deuterium; D002794:Choline
keywords: 15N; MRI; NMR; PASADENA; PHIP; choline; contrast agent; hyperpolarization; parahydrogen