The traceless Staudinger ligation for indirect<sup>18</sup>F-radiolabelling

Carroll, Laurence; Boldon, Sophie; Béjot, Romain; Moore, Jane E.; Declerck, Jérôme; Gouverneur, Véronique

doi:10.1039/c0ob00564a

Cited by 41 publications

(29 citation statements)

References 33 publications

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“…169 This process is attractive, since it results in a native amide bond without inclusion of the phosphine oxide in the final product and can be used to introduce a [ 18 F]-fluoroethylamide under catalyst-free conditions in short reaction times and with high radiochemical yields.…”

Section: Perspectivementioning

confidence: 99%

Applications of Fluorine in Medicinal Chemistry

et al. 2015

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The role of fluorine in drug design and development is expanding rapidly as we learn more about the unique properties associated with this unusual element and how to deploy it with greater sophistication. The judicious introduction of fluorine into a molecule can productively influence conformation, pKa, intrinsic potency, membrane permeability, metabolic pathways, and pharmacokinetic properties. In addition, (18)F has been established as a useful positron emitting isotope for use with in vivo imaging technology that potentially has extensive application in drug discovery and development, often limited only by convenient synthetic accessibility to labeled compounds. The wide ranging applications of fluorine in drug design are providing a strong stimulus for the development of new synthetic methodologies that allow more facile access to a wide range of fluorinated compounds. In this review, we provide an update on the effects of the strategic incorporation of fluorine in drug molecules and applications in positron emission tomography.

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Section: Perspectivementioning

confidence: 99%

Applications of Fluorine in Medicinal Chemistry

et al. 2015

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“…[7][8][9] Due to the mild reaction conditions and the formation of an amide (peptide) bond, 10 this Staudinger approach has found various applications, e.g. the labeling of bioactive molecules with fluorescence dyes 11 as well as radionuclides, [12][13][14] the chemoselective modification of peptides 5,15,16 and proteins, 17,18 the modification of polymers, 19 the preparation of special lactams, 20,21 or the synthesis of glycosyl amides. 22,23 The absence of cytotoxic copper salts makes the Staudinger approach interesting for potential in vitro and in vivo applications in contrast to other ligation reactions like the 1,3-dipolar Huisgen cycloaddition.…”

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confidence: 99%

Preparation of 4-Halobenzoate-Containing Phosphane-Based Building Blocks for Labeling Reactions Using the Traceless Staudinger Ligation

Mamat

Köckerling

2014

Synthesis

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Functionalized phosphane-containing key building blocks were synthesized that are suitable for the labeling of biologically active molecules by the traceless Staudinger ligation. Thus, a 2-(diphenylphosphanyl)phenyl 4-stannylbenzoate building block was converted into the 4-iodobenzoate by the introduction of iodine. The traceless Staudinger ligation was used to introduce the resulting 4-iodobenzoate moiety into selected molecules of pharmacological interest. Furthermore, the labeling procedure was used to insert the 4-iodobenzoate moiety into a peptide on solid support. Finally, a convenient recovery procedure of the key phosphane building block 2-(diphenylphosphanyl)phenol from 2-(diphenylphosphoryl)phenol was evaluated.

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“…al. [130] Several amino acid derivatives were functionalized with diarylphosphine based thioesters 150 and the corresponding radiotracers 151 and 152 were obtained in >95% RCC, based on conversion from [18 F]FEA (Figure 26). While the Staudinger ligation does not require a metal catalyst and resulting radiotracers can be purified with ease, its major limitation is the relatively slow kinetics (2.0 × 10 −3 M −1 s −1 ) [131] of the reaction, which is often accelerated by high reaction temperature.…”

Section: Indirect Methods For 18f-radiolabeling Of Biomoleculesmentioning

confidence: 99%

¹⁸F‐Labeling of Sensitive Biomolecules for Positron Emission Tomography

Krishnan

Vasdev

et al. 2017

Chemistry A European J

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Positron emission tomography (PET) imaging study of fluorine-18 labeled biomolecules is an emerging and rapidly growing area for preclinical and clinical research. The present review focuses on recent advances in radiochemical methods for incorporating fluorine-18 into biomolecules via ‘direct’ or ‘indirect’ bioconjugation. Recently developed prosthetic groups and pre-targeting strategies, as well as representative examples in 18F-labeling of biomolecules in PET imaging research studies are highlighted.

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The traceless Staudinger ligation for indirect¹⁸F-radiolabelling

Abstract: The Staudinger ligation of phosphine-substituted thioesters with (18)F-fluoroethylazide has been successfully applied to access (18)F-labelled molecules in radiochemical yields superior to 95%; the first fluorous variant of a Staudinger radio-ligation has been validated.

Cited by 41 publications

References 33 publications

Applications of Fluorine in Medicinal Chemistry

Applications of Fluorine in Medicinal Chemistry

Preparation of 4-Halobenzoate-Containing Phosphane-Based Building Blocks for Labeling Reactions Using the Traceless Staudinger Ligation

¹⁸F‐Labeling of Sensitive Biomolecules for Positron Emission Tomography

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The traceless Staudinger ligation for indirect18F-radiolabelling

Abstract: The Staudinger ligation of phosphine-substituted thioesters with (18)F-fluoroethylazide has been successfully applied to access (18)F-labelled molecules in radiochemical yields superior to 95%; the first fluorous variant of a Staudinger radio-ligation has been validated.

Cited by 41 publications

References 33 publications

Applications of Fluorine in Medicinal Chemistry

Applications of Fluorine in Medicinal Chemistry

Preparation of 4-Halobenzoate-Containing Phosphane-Based Building Blocks for Labeling Reactions Using the Traceless Staudinger Ligation

18F‐Labeling of Sensitive Biomolecules for Positron Emission Tomography

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The traceless Staudinger ligation for indirect¹⁸F-radiolabelling

¹⁸F‐Labeling of Sensitive Biomolecules for Positron Emission Tomography