GABAergic radioligands labelled with tritium

Filer, Crist N.

doi:10.1002/jlcr.1737

Cited by 8 publications

(7 citation statements)

References 145 publications

(125 reference statements)

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“…Various methods for the incorporation of deuterium were reported previously, and the topic was recently reviewed . In addition, tritiated compounds are of increasing importance for radiolabeling of bioactive compounds in medicinal chemistry applications. , Hence, facile, fast, and efficient protocols for the deuteration and tritiation , of indole and pyridine derivatives are of great value. A novel method to conduct such transformations is reported in this contribution.…”

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confidence: 99%

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Selective Ru(0)-Catalyzed Deuteration of Electron-Rich and Electron-Poor Nitrogen-Containing Heterocycles

2012

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A highly selective Ru(3)(CO)(12)-catalyzed deuteration method using t-BuOD as deuterium source is reported. Electron-rich and electron-poor N-heteroarenes such as indoles, azaindoles, deazapurines, benzimidazole, quinolines, isoquinolines, and pyridines were efficiently deuterated at specific positions with high selectivity; in most cases, deuterium incorporation was close to the theoretically possible values. To further increase deuteration degrees, several cycles of the reaction protocol can be carried out which gave superior deuteration degrees employing a much lower excess of deuterating agent compared to established protocols. It was proved that the same protocol can in principle be applied to tritiation reactions important for radioactive labeling of bioactive molecules.

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confidence: 99%

“…Finally, we investigated the possibility of using the presented methodology for tritiation reactions based on the high importance of radiolabeled compounds for medicinal applications. , For that purpose, it is necessary to enable access to t -BuOT. According to literature reports, CF 3 COOT was employed in the synthesis of chiral methyl groups .…”

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confidence: 99%

Selective Ru(0)-Catalyzed Deuteration of Electron-Rich and Electron-Poor Nitrogen-Containing Heterocycles

2012

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“…So many receptor studies of these types are carried out that only a brief summary and some leading references will be given here. A typical example, and one that has been recently reviewed, is the interaction of small gamma‐aminobutyric acid (GABA)ergic ligands with the various pharmacologically distinct GABA receptor systems …”

Section: Discussionmentioning

confidence: 99%

Tritium: a coming of age for drug discovery and development ADME studies

Lockley

McEwen

Cooke

2012

Labelled Comp Radiopharmac

115

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Owing to recent developments in tritium chemistry and analysis, high‐quality tritium‐labelled drugs can now be prepared simply, cheaply and in timescales commensurate with those needed for rapid drug discovery in adsorption, distribution, metabolism and excretion (ADME) projects. Such 3H‐labelled drugs are enabling high‐quality decision‐making at key points in the drug discovery process, thus ensuring more effective research projects, a key issue in commercial success. In addition, tritium‐labelled compounds continue to play a significant role in ADME studies later in the pharmaceutical development process. This is especially so for highly potent and hence low‐dose agents, for drugs with complex structures and for those compounds that undergo molecular fragmentation as a result of metabolism.

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“…Reduction of the triple bond in ATA and its derivatives with tritium has provided a convenient route to the preparation of GABA labelled to high specific activity due to the incorporation of four tritium atoms [17][18][19][20]. An improved synthesis of ATA has been reported [21].…”

Section: -Aminotetrolic Acidmentioning

confidence: 98%

Unsaturated Analogues of the Neurotransmitter GABA: trans-4-Aminocrotonic, cis-4-Aminocrotonic and 4-Aminotetrolic Acids

Johnston

2015

Neurochem Res

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Analogues of the neurotransmitter GABA containing unsaturated bonds are restricted in the conformations they can attain. This review traces three such analogues from their synthesis to their use as neurochemicals. trans-4-Aminocrotonic acid was the first conformationally restricted analogue to be extensively studied. It acts like GABA across a range of macromolecules from receptors to transporters. It acts similarly to GABA on ionotropic receptors. cis-4-Aminocrotonic acid selectively activates bicuculline-insensitive GABAC receptors. 4-Aminotetrolic acid, containing a triple bond, activates bicuculline-sensitive GABAA receptors. These findings indicate that GABA activates GABAA receptors in extended conformations and GABAC receptors in folded conformations. These and related analogues are important for the molecular modelling of ionotropic GABA receptors and to the development of new agents acting selectively on these receptors.

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GABAergic radioligands labelled with tritium

Abstract: The synthesis and applications of GABAergic radioligands labelled with tritium are reviewed.

Cited by 8 publications

References 145 publications

Selective Ru(0)-Catalyzed Deuteration of Electron-Rich and Electron-Poor Nitrogen-Containing Heterocycles

Selective Ru(0)-Catalyzed Deuteration of Electron-Rich and Electron-Poor Nitrogen-Containing Heterocycles

Tritium: a coming of age for drug discovery and development ADME studies

Unsaturated Analogues of the Neurotransmitter GABA: trans-4-Aminocrotonic, cis-4-Aminocrotonic and 4-Aminotetrolic Acids

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