Synthesis and characterization of tritium-labelled substances

Filer, Crist N.

doi:10.1016/j.apradiso.2018.02.029

Cited by 10 publications

(7 citation statements)

References 153 publications

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“…In previous work, the anti-inflammatory drug etodolac was labeled with tritium through the reduction and hydrogenolysis of aketone-based precursor. [21] In contrast, within our PdNp catalyzed HIE, deuterium incorporation was directly achieved at the drug target etodolac on both methylene carbons attached to the indole scaffold (Figure 4, compound 12). Additionally,I buprofen was successfully deuterated with high selectivity for its benzylic positions giving satisfying isotopic enrichments (Figure 4, compound 13).…”

Section: Methodsmentioning

confidence: 83%

Palladium Nanoparticles for the Deuteration and Tritiation of Benzylic Positions on Complex Molecules

Pfeifer

Zeltner²,

Fackler

et al. 2021

Angewandte Chemie

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Palladium nanoparticles (PdNp) were revealed as an efficient hydrogen isotope exchange catalyst for the deuterium and tritium labeling of benzylic positions of complex molecules.Apractical waytoobtain small palladium nanoparticles and to apply them as acatalyst for hydrogen isotope exchange (HIE) is presented. Several model compounds and popular bioactive molecules were submitted to HIE reactions catalyzed by the PdNp.B enzylic positions situated far away from heteroatoms were labeled with high isotopic enrichments.T he observed non-directed HIE gave rise to regioselectivities complementary to those obtained with other methods,w hich typically require specific directing groups.F or this reason, the successful deuteration of abroad variety of benzylic positions created ahelpful tool to produce internal LC-MS standards of complex drugs.F urthermore,t his nanocatalyst paved the way for the radiolabeling of drug molecules with high specific activities by using low pressures of tritium gas.

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Section: Methodsmentioning

confidence: 83%

Palladium Nanoparticles for the Deuteration and Tritiation of Benzylic Positions on Complex Molecules

Pfeifer

Zeltner²,

Fackler

et al. 2021

Angewandte Chemie

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“…In the proton-coupled 3 H NMR spectrum of [ 3 H]-spiperone, a triplet with a coupling constant J = 7.6 Hz was observed, which suggested the location of the installed tritium at the phenyl p-position. [94] with the permission of Elsevier F I G U R E 6 3 Tritium proton decoupled NMR spectrum of [ 3 H] dihydroergocryptine recorded in CD 3 OD at 320 MHz. Reproduced with minor editing privilege from Egan et al [92] with the permission of Springer Nature shows a proton decoupled 3 H NMR spectrum of this higher specific activity [ 3 H]-spiperone.…”

Section: Recent and Most Recent Resultsmentioning

confidence: 99%

“…The recent review by Filer, [ 94 ] dealing with synthesis and characterization of the tritium‐labeled biologically active compounds, contains an interesting example of the tritium NMR spectrum of [propionate‐2,3‐ 3 H] N ‐succinimidyl propionate (known as “[ 3 H] NSP”), which reveals its tritiation sites; see Figure 64. Based on those data, it was supposed that the most likely nucleophiles acylated by [ 3 H] NSP were the amines of peptide or protein lysine residues.…”

Section: Recent and Most Recent Resultsmentioning

confidence: 99%

Tritium NMR: A compilation of data and a practical guide

Krivdin

2023

Magnetic Reson in Chemistry

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The present review is focused on experimental methods and structural applications of tritium NMR. It consists of five parts covering accordingly, introduction, brief overview, early (based on the papers appearing before 2000), more recent (based on the papers appeared in the interim of 2000 to 2015), and recent (based on the papers that appeared after 2015) reports. A special interest in this review is focused on practical aspects of tritium NMR spectroscopy, which is thoroughly illustrated by its numerous applications in chemistry and biochemistry.

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“…Hundreds of tritiated compounds have been prepared by this approach. 19,20 Moreover, the corresponding deuterium labelling procedure has also been utilised for many years, [21][22][23] either using conventional hydrogenation with deuterium gas or by transfer-hydrogenation with various deuterium donors. 24,25 The dehalogenation of chloroaromatics, however, generally gives low atom% abundance 26 due to competing isotopic scrambling reactions which introduce protium instead of deuterium or tritium at the labelling site.…”

Section: Introductionmentioning

confidence: 99%

“…Indeed, the procedure has been widely employed in industrial research organisations and is currently offered by all the main radiolabelling contract laboratories. Hundreds of tritiated compounds have been prepared by this approach 19,20 . Moreover, the corresponding deuterium labelling procedure has also been utilised for many years, 21–23 either using conventional hydrogenation with deuterium gas or by transfer‐hydrogenation with various deuterium donors 24,25 …”

Section: Introductionmentioning

confidence: 99%

Studies of hydrogen isotope scrambling during the dehalogenation of aromatic chloro‐compounds with deuterium gas over palladium catalysts

Lockley

Venanzi

Crane

2020

Labelled Comp Radiopharmac

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Catalytic dehalogenation of aromatic halides using isotopic hydrogen gas is an important strategy for labelling pharmaceuticals, biochemicals, environmental agents and so forth. To extend, improve and further understand this process, studies have been carried out on the scrambling of deuterium isotope with protium during the catalytic deuterodehalogenation of model aryl chlorides using deuterium gas and a palladium on carbon catalyst in tetrahydrofuran solution. The degree of scrambling was greatest with electron‐rich chloroarene rings. The tetrahydrofuran solvent and the triethylamine base were not the source of the undesired protium; instead, it arose, substantially, from the water content of the catalyst, though other sources of protium may also be present on the catalyst. Replacement of the Pd/C catalyst with one prepared in situ by reduction of palladium trifluoroacetate with deuterium gas and dispersed upon micronised polytetrafluoroethylene led to much reduced scrambling (typically 0–6% compared with up to 40% for palladium on carbon) and to high atom% abundance, regiospecific labelling. The improved catalytic system now enables efficient polydeuteration via the dehalogenation of polyhalogenated precursors, making the procedure viable for the preparation of MS internal standards and, potentially, for high specific activity tritium labelling.

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Synthesis and characterization of tritium-labelled substances

Cited by 10 publications

References 153 publications

Palladium Nanoparticles for the Deuteration and Tritiation of Benzylic Positions on Complex Molecules

Palladium Nanoparticles for the Deuteration and Tritiation of Benzylic Positions on Complex Molecules

Tritium NMR: A compilation of data and a practical guide

Studies of hydrogen isotope scrambling during the dehalogenation of aromatic chloro‐compounds with deuterium gas over palladium catalysts

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