Journal
CHEMPHYSCHEM
Volume 22, Issue 10, Pages 960-967Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cphc.202100109
Keywords
SABRE; parahydrogen; hyperpolarization; NMR spectroscopy; isotopic labeling
Funding
- Russian Foundation for Basic Research [19-53-12013]
- Russian Ministry of Science and Higher Education [AAAA-A16-116121510087-5]
- Novosibirsk region government [19-43-540004]
- NSF [CHE-1904780]
- NIBIB [1R01EB029829]
- Russian Foundation for Basic Research
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Signal Amplification by Reversible Exchange (SABRE) technique allows for nuclear spin hyperpolarization of various compounds using parahydrogen, with potential applications in drug synthesis and scientific research. Experimental results demonstrate that the 7-hour-long activation of SABRE pre-catalyst in the presence of [N-15]dalfampridine can be resolved by the use of a pyridine co-ligand, maintaining the compound's N-15 polarization levels. Further investigations were conducted on the effects of experimental conditions on the N-15 polarization levels of [N-15]dalfampridine.
Signal Amplification by Reversible Exchange (SABRE) technique enables nuclear spin hyperpolarization of wide range of compounds using parahydrogen. Here we present the synthetic approach to prepare N-15-labeled [N-15]dalfampridine (4-amino[N-15]pyridine) utilized as a drug to reduce the symptoms of multiple sclerosis. The synthesized compound was hyperpolarized using SABRE at microtesla magnetic fields (SABRE-SHEATH technique) with up to 2.0 % N-15 polarization. The 7-hour-long activation of SABRE pre-catalyst [Ir(IMes)(COD)Cl] in the presence of [N-15]dalfampridine can be remedied by the use of pyridine co-ligand for catalyst activation while retaining the N-15 polarization levels of [N-15]dalfampridine. The effects of experimental conditions such as polarization transfer magnetic field, temperature, concentration, parahydrogen flow rate and pressure on N-15 polarization levels of free and equatorial catalyst-bound [N-15]dalfampridine were investigated. Moreover, we studied N-15 polarization build-up and decay at magnetic field of less than 0.04 mu T as well as N-15 polarization decay at the Earth's magnetic field and at 1.4 T.
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