Modular PET Agent Construction Strategy through Strain-Promoted Double-Click Reagent with Efficient Photoclick Step

Li, Manshu; Ma, Xingcong; Molnar, Christopher J; Wang, Shuli; Wu, Zhanhong; Popik, Vladimir V.; Li, Zibo

doi:10.1021/acs.bioconjchem.2c00427

Cited by 5 publications

(4 citation statements)

References 54 publications

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“…Just last year, Li et al reported on the use of a particularly elegant photoactivated variant of the SPAAC reaction for radiosynthesis . This strategy relies on a unique monocyclopropenone-caged dibenzocyclooctadiyne (MC-DIBOD) that contains one normal strained alkyne as well as a second triple bond masked as a cyclopropenone (Figure ).…”

Section: The Strain-promoted Azide–alkyne Cycloadditionmentioning

confidence: 99%

“…114 Just last year, Li et al reported on the use of a particularly elegant photoactivated variant of the SPAAC reaction for radiosynthesis. 118 This strategy relies on a unique mono- cyclopropenone-caged dibenzocyclooctadiyne (MC-DIBOD) that contains one normal strained alkyne as well as a second triple bond masked as a cyclopropenone (Figure 12). The investigators demonstrated that this cross-linking reagent can undergo an initial SPAAC ligation with a radiofluorinated azide and then�after the second strained alkyne is unmasked by UV irradiation�a second strain-promoted cycloaddition with an azide-tagged biomolecule.…”

Section: Cycloadditionmentioning

confidence: 99%

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Click Chemistry and Radiochemistry: An Update

Bauer,

Cornejo,

Hoang

et al. 2023

Bioconjugate Chem.

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The term "click chemistry" describes a class of organic transformations that were developed to make chemical synthesis simpler and easier, in essence allowing chemists to combine molecular subunits as if they were puzzle pieces. Over the last 25 years, the click chemistry toolbox has swelled from the canonical copper-catalyzed azide−alkyne cycloaddition to encompass an array of ligations, including bioorthogonal variants, such as the strain-promoted azide−alkyne cycloaddition and the inverse electron-demand Diels−Alder reaction. Without question, the rise of click chemistry has impacted all areas of chemical and biological science. Yet the unique traits of radiopharmaceutical chemistry have made it particularly fertile ground for this technology. In this update, we seek to provide a comprehensive guide to recent developments at the intersection of click chemistry and radiopharmaceutical chemistry and to illuminate several exciting trends in the field, including the use of emergent click transformations in radiosynthesis, the clinical translation of novel probes synthesized using click chemistry, and the advent of click-based in vivo pretargeting.

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Section: The Strain-promoted Azide–alkyne Cycloadditionmentioning

confidence: 99%

Section: Cycloadditionmentioning

confidence: 99%

Click Chemistry and Radiochemistry: An Update

Bauer,

Cornejo,

Hoang

et al. 2023

Bioconjugate Chem.

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“…The crucial role of SPAAC is determined by the unique properties of the azido group, [16] fast SPAAC kinetics, and a wide range of available cycloalkyne‐based reagents [17–27] …”

Section: Introductionmentioning

confidence: 99%

“…[12][13][14][15] The crucial role of SPAAC is determined by the unique properties of the azido group, [16] fast SPAAC kinetics, and a wide range of available cycloalkyne-based reagents. [17][18][19][20][21][22][23][24][25][26][27] Nevertheless, to use SPAAC to visualize modified biomolecules, a cycloalkyne reagent should be preconjugated with a fluorescent dye which introduces an additional synthetic, structural, and functional load. [28] In this regard, the design and synthesis of cycloalkynes which give fluorescent triazoles, would enable the avoidance of additional synthetic steps and undesirable structural complexity.…”

Section: Introductionmentioning

confidence: 99%

Development of Fluorescent Isocoumarin‐Fused Oxacyclononyne – 1,2,3‐Triazole Pairs

Vidyakina

Shtyrov

Ryazantsev

et al. 2023

Chemistry A European J

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Fluorescent isocoumarin‐fused cycloalkynes, which are reactive in SPAAC and give fluorescent triazoles regardless of the azide nature, have been developed. The key structural feature that converts the non‐fluorescent cycloalkyne/triazole pair to its fluorescent counterpart is the pi‐acceptor group (COOMe, CN) at the C6 position of the isocoumarin ring. The design of the fluorescent cycloalkyne/triazole pairs is based on the theoretical study of the S1 state deactivation mechanism of the non‐fluorescent isocoumarin‐fused cycloalkyne IC9O using multi‐configurational ab initio and DFT methodologies. The calculations revealed that deactivation proceeds through the electrocyclic ring opening of the α‐pyrone cycle and is accompanied by a redistribution of electron density in the fused benzene ring. We proposed that the S1 excited state deactivation barrier could be increased by introducing a pi‐acceptor group into a position that is in direct conjugation with the formed C=O group and has a reduced electron density in the transition state. As a proof of concept, we designed and synthesized two fluorescent isocoumarin‐fused cycloalkynes IC9O‐COOMe and IC9O‐CN bearing pi‐acceptors at the C6 position. The importance of the nature of a pi‐acceptor group was shown by the example of much less fluorescent CF3‐substituted cycloalkyne IC9O‐CF3.

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Chelator boosted tumor-retention and pharmacokinetic properties: development of 64Cu labeled radiopharmaceuticals targeting neurotensin receptor

Zhang,

Ma,

et al. 2024

Eur J Nucl Med Mol Imaging

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Modular PET Agent Construction Strategy through Strain-Promoted Double-Click Reagent with Efficient Photoclick Step

Cited by 5 publications

References 54 publications

Click Chemistry and Radiochemistry: An Update

Click Chemistry and Radiochemistry: An Update

Development of Fluorescent Isocoumarin‐Fused Oxacyclononyne – 1,2,3‐Triazole Pairs

Chelator boosted tumor-retention and pharmacokinetic properties: development of 64Cu labeled radiopharmaceuticals targeting neurotensin receptor

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