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The Hantzsch reaction for nitrogen-13 PET: preparation of [¹³N]nifedipine and derivatives.

ABSTRACT: Nitrogen-13 is an attractive but under-used PET radionuclide for labelling molecules of biological and pharmaceutical interest, complementing other PET radionuclides. Its short half-life (t1/2 = 9.97 min) imposes synthetic challenges, but we have expanded the hitherto limited pool of 13N labelling strategies and tracers by adapting the multicomponent Hantzsch condensation reaction to prepare a library of 13N-labelled 1,4-dihydropyridines from [13N]ammonia, including the widely-used drug nifedipine. This represents a key advance in 13N PET radiochemistry, and will serve to underpin the renewed interest in clinical opportunities offered by short-lived PET tracers.

SUBMITTER: Blower JE

PROVIDER: S-EPMC8132178 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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The Hantzsch reaction for nitrogen-13 PET: preparation of [<sup>13</sup>N]nifedipine and derivatives.

Blower Julia E JE Ma Michelle T MT Al-Salemee Fahad A I FAI Gee Antony D AD

Chemical communications (Cambridge, England) 20210501 40

Nitrogen-13 is an attractive but under-used PET radionuclide for labelling molecules of biological and pharmaceutical interest, complementing other PET radionuclides. Its short half-life (t1/2 = 9.97 min) imposes synthetic challenges, but we have expanded the hitherto limited pool of 13N labelling strategies and tracers by adapting the multicomponent Hantzsch condensation reaction to prepare a library of 13N-labelled 1,4-dihydropyridines from [13N]ammonia, including the widely-used drug nifedipi ...[more]

PMID: 33876157

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Project description:BackgroundStable isotopically labelled organisms have found wide application in life science research including plant physiology, plant stress and defense as well as metabolism related sciences. Therefore, the reproducible production of plant material enriched with stable isotopes such as 13C and 15N is of considerable interest. A high degree of enrichment (> 96 atom %) with a uniformly distributed isotope (global labelling) is accomplished by a continuous substrate supply during plant growth/cultivation. In the case of plants, 13C-labelling can be achieved by growth in 13CO2(g) atmosphere while global 15N-labelling needs 15N- containing salts in the watering/nutrient solution. Here, we present a method for the preparation of 13C and 15N-labelled plants by the use of closed growth chambers and hydroponic nutrient supply. The method is exemplified with durum wheat.ResultsIn total, 330 g of globally 13C- and 295 g of 15N-labelled Triticum durum wheat was produced during 87 cultivation days. For this, a total of 3.88 mol of 13CO2(g) and 58 mmol of 15N were consumed. The degree of enrichment was determined by LC-HRMS and ranged between 96 and 98 atom % for 13C and 95-99 atom % for 15N, respectively. Additionally, the isotopically labelled plant extracts were successfully used for metabolome-wide internal standardisation of native T.durum plants. Application of an isotope-assisted LC-HRMS workflow enabled the detection of 652 truly wheat-derived metabolites out of which 143 contain N.ConclusionA reproducible cultivation which makes use of climate chambers and hydroponics was successfully adapted to produce highly enriched, uniformly 13C- and 15N-labelled wheat. The obtained plant material is suitable to be used in all kinds of isotope-assisted research. The described technical equipment and protocol can easily be applied to other plants to produce 13C-enriched biological samples when the necessary specific adaptations e.g. temperature and light regime, as well as nutrient supply are considered. Additionally, the 15N-labelling method can also be carried out under regular glasshouse conditions without the need for customised atmosphere.

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The Hantzsch reaction for nitrogen-13 PET: preparation of [¹³N]nifedipine and derivatives.

Publications

The Hantzsch reaction for nitrogen-13 PET: preparation of [<sup>13</sup>N]nifedipine and derivatives.

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The Hantzsch reaction for nitrogen-13 PET: preparation of [13N]nifedipine and derivatives.

Publications

The Hantzsch reaction for nitrogen-13 PET: preparation of [&lt;sup&gt;13&lt;/sup&gt;N]nifedipine and derivatives.

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OmicsDI is part of the ELIXIR infrastructure

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The Hantzsch reaction for nitrogen-13 PET: preparation of [¹³N]nifedipine and derivatives.

The Hantzsch reaction for nitrogen-13 PET: preparation of [<sup>13</sup>N]nifedipine and derivatives.