In Vivo Chemistry for Pretargeted Tumor Imaging in Live Mice

Rossin, Raffaella; Verkerk, Pascal Renart; Bosch, Sandra M. van den; Vulders, Roland C. M.; Verel, Iris; Lub, Johan; Robillard, Marc S.

doi:10.1002/ange.200906294

Cited by 176 publications

(207 citation statements)

References 11 publications

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“…3 Fluorine-18 ( 18 F) is the most widely used PET isotope in nuclear medicine with half-life of 109.8 min. The advantages of 18 F include the ease of production with high yield and high specific activity. Furthermore, it has a low positron energy, which contributes to improved resolution and high quality of the PET image.…”

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confidence: 99%

“…Recently, 64 Cu and 111 In labeled tetrazines have been successfully used in pretargeted in vivo imaging of tumor specific monoclonal antibodies. 13,14,18 Despite the recent great progress in the synthetic development of new IEDDA ligands for PET imaging, no successful 18 F-labeled IEDDA ligands for pretargeted imaging in vivo have been reported so far.…”

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confidence: 99%

“…Instead, radiolabeled tetrazine derivatives have been shown to maintain their reactivity also in vivo. 12,14 When clinical applications of pretargeted PET imaging are considered, 18 F would be the ideal isotope due to its general availability and optimal physical properties. 9,21,22 However, due to the instability of the tetrazine moiety under conditions typically used in direct 18 Ffluorination, no 18 F-tetrazine was synthesized until very recently.…”

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confidence: 99%

“…12,14 When clinical applications of pretargeted PET imaging are considered, 18 F would be the ideal isotope due to its general availability and optimal physical properties. 9,21,22 However, due to the instability of the tetrazine moiety under conditions typically used in direct 18 Ffluorination, no 18 F-tetrazine was synthesized until very recently. 23−25 A recently reported 18 F propyl tetrazine was synthesized via a direct 18 F-fluorination only in low radiochemical yields (4−18% decay corrected yield), but favorable pharmacokinetics in vivo.…”

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confidence: 99%

“…9,21,22 However, due to the instability of the tetrazine moiety under conditions typically used in direct 18 Ffluorination, no 18 F-tetrazine was synthesized until very recently. 23−25 A recently reported 18 F propyl tetrazine was synthesized via a direct 18 F-fluorination only in low radiochemical yields (4−18% decay corrected yield), but favorable pharmacokinetics in vivo. 23 Successful and more efficient synthesis of 18 F-labeled tetrazine derivative was very recently published by using a [ 18 F]SiFA−OH building block, but influence of the relatively lipophilic alkylated organosilicon moiety on pharmacokinetics of the compound was not reported.…”

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confidence: 99%

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A New Highly Reactive and Low Lipophilicity Fluorine-18 Labeled Tetrazine Derivative for Pretargeted PET Imaging

Keinänen

Chenna

et al. 2015

ACS Med. Chem. Lett.

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A new 18 F-labeled tetrazine derivative was developed aiming at optimal radiochemistry, fast reaction kinetics in inverse electron-demand Diels−Alder cycloaddition (IEDDA), and favorable pharmacokinetics for in vivo bioorthogonal chemistry. The radiolabeling of the tetrazine was achieved in high yield, purity, and specific activity under mild reaction conditions via conjugation with 5-[ 18 F]fluoro-5-deoxyribose, providing a glycosylated tetrazine derivative with low lipophilicity. The 18 F-tetrazine showed fast reaction kinetics toward the most commonly used dienophiles in IEDDA reactions. It exhibited excellent chemical and enzymatic stability in mouse plasma and in phosphate-buffered saline (pH 7.41). Biodistribution in mice revealed favorable pharmacokinetics with major elimination via urinary excretion. The results indicate that the glycosylated 18 F-labeled tetrazine is an excellent candidate for in vivo bioorthogonal chemistry applications in pretargeted PET imaging approaches.

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A New Highly Reactive and Low Lipophilicity Fluorine-18 Labeled Tetrazine Derivative for Pretargeted PET Imaging

Keinänen

Chenna

et al. 2015

ACS Med. Chem. Lett.

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Superbase‐Catalyzed [4+2] Cycloaddition of Acetylenes to 3,6‐Di(pyrrol‐2‐yl)‐1,2,4,5‐tetrazine: A Facile Synthesis of 3,6‐Di(pyrrol‐2‐yl)pyridazines

et al. 2013

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Acetylenes undergo the [4 + 2] cycloaddition to 3,6-di(pyrrol-2-yl)-1,2,4,5-tetrazine in the potassium hydroxide/dimethyl sulfoxide or potassium tert-butoxide/dimethyl sulfoxide systems (80 8C, 2.5-4 h) to afford (after extrusion of the nitrogen molecule from the intermediate) 3,6-di(pyrrol-2-yl)pyridazines in up to 73% yield, while under non-catalytic conditions this reaction does not take place. This unusual result substantially extends the scope of synthetic application and mechanistic diversity of the Diels-Alder reaction. The step-wise mechanisms involving the formation of [OH/tetrazine] À or [t-BuO/tetrazine] À anionic intermediate complexes or cycloaddition of tetrazine to the acetylide anion are considered.

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Chemical Reactions in Living Systems

Schauenburg,

Weil

2023

Advanced Science

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The term “in vivo (“in the living”) chemistry” refers to chemical reactions that take place in a complex living system such as cells, tissue, body liquids, or even in an entire organism. In contrast, reactions that occur generally outside living organisms in an artificial environment (e.g., in a test tube) are referred to as in vitro. Over the past decades, significant contributions have been made in this rapidly growing field of in vivo chemistry, but it is still not fully understood, which transformations proceed efficiently without the formation of by‐products or how product formation in such complex environments can be characterized. Potential applications can be imagined that synthesize drug molecules directly within the cell or confer new cellular functions through controlled chemical transformations that will improve the understanding of living systems and develop new therapeutic strategies. The guiding principles of this contribution are twofold: 1) Which chemical reactions can be translated from the laboratory to the living system? 2) Which characterization methods are suitable for studying reactions and structure formation in complex living environments?

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In Vivo Chemistry for Pretargeted Tumor Imaging in Live Mice

Cited by 176 publications

References 11 publications

A New Highly Reactive and Low Lipophilicity Fluorine-18 Labeled Tetrazine Derivative for Pretargeted PET Imaging

A New Highly Reactive and Low Lipophilicity Fluorine-18 Labeled Tetrazine Derivative for Pretargeted PET Imaging

Superbase‐Catalyzed [4+2] Cycloaddition of Acetylenes to 3,6‐Di(pyrrol‐2‐yl)‐1,2,4,5‐tetrazine: A Facile Synthesis of 3,6‐Di(pyrrol‐2‐yl)pyridazines

Chemical Reactions in Living Systems

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