C-(4-[18F]fluorophenyl)-N-phenyl nitrone: A novel 18F-labeled building block for metal free [3+2]cycloaddition

Zlatopolskiy, Boris D.; Kandler, Rene; Mottaghy, Felix M.; Neumaier, Bernd

doi:10.1016/j.apradiso.2011.09.002

Cited by 17 publications

(15 citation statements)

References 21 publications

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“…Fluorine-18 labeled C-(4-fluorophenyl)- N -phenyl nitrone reacts with various maleimides to produce corresponding isoxazolidines. [148] Similarly, these authors also investigated reaction of suitable dipolarophiles with 4- [18 F]fluorobenzonitrile oxide 177 (prepared from [18 F]FBA and oxime 176 ) and N -hydroxy-4- [18 F]fluorobenzimidoyl chloride to yield the corresponding labeled [3+2] cycloaddition product 178 (Figure 33). [149] RCCs >95% were obtained in some cases with sample small molecules.…”

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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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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“…The latest developments in metal-free 18 F-click cycloadditions have been reported by Zlatopolskiy et al [19–21] (Table 3). In a first approach, the 18 F-labeled building block C-(4-[ 18 F]fluorophenyl)-N-phenyl nitrone was developed to form 18 F-isoxazolidines via high-yielding [3+2]cycloadditions with various maleimides [19].…”

Section: New Developments In 18f-click Cycloadditionsmentioning

confidence: 99%

“…In a first approach, the 18 F-labeled building block C-(4-[ 18 F]fluorophenyl)-N-phenyl nitrone was developed to form 18 F-isoxazolidines via high-yielding [3+2]cycloadditions with various maleimides [19]. C-(4-[ 18 F]fluorophenyl)-N-phenyl nitrone was obtained from the reaction of 4-[ 18 F]fluorobenzaldehyde and N-phenylhydroxylamine in high RCY of 74% with 10 min.…”

Section: New Developments In 18f-click Cycloadditionsmentioning

confidence: 99%

“…Especially, the TTCO ligation showed promising reaction rates, which makes this click reaction concept very suitable for 18 F-labeling and also for in vivo application in living systems. Very recently, new versions of 18 F-click cycloadditions are added to the range of reactions [19–25]. In this line, the first 18 F-labeled β -lactame became available via a new radio -Kinugasa reaction [21].…”

Section: Introductionmentioning

confidence: 99%

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¹⁸F-Labeling Using Click Cycloadditions

Kettenbach

Schieferstein

Roß

2014

BioMed Research International

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Due to expanding applications of positron emission tomography (PET) there is a demand for developing new techniques to introduce fluorine-18 (t 1/2 = 109.8 min). Considering that most novel PET tracers are sensitive biomolecules and that direct introduction of fluorine-18 often needs harsh conditions, the insertion of 18F in those molecules poses an exceeding challenge. Two major challenges during 18F-labeling are a regioselective introduction and a fast and high yielding way under mild conditions. Furthermore, attention has to be paid to functionalities, which are usually present in complex structures of the target molecule. The Cu-catalyzed azide-alkyne cycloaddition (CuAAC) and several copper-free click reactions represent such methods for radiolabeling of sensitive molecules under the above-mentioned criteria. This minireview will provide a quick overview about the development of novel 18F-labeled prosthetic groups for click cycloadditions and will summarize recent trends in copper-catalyzed and copper-free click 18F-cycloadditions.

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“…Application of the Kinugasa reaction to radiochemistry could allow simple access to radiolabelled 2‐azetidinones. Herein, we describe for the first time a method for the preparation of radiofluorinated monocyclic β‐lactams through the Kinugasa reaction between the easily accessible 18 F‐labelled C ‐4‐fluorophenyl‐ N ‐phenyl nitrone ([ 18 F]‐ 1 )6b and a range of terminal alkynes. Furthermore, a model cyclic nitrone 7 was reacted with radiolabelled fluorophenylacetylenes [ 18 F]‐ 6 a , b under Kinugasa conditions to give the corresponding labelled bicyclic β‐lactams [ 18 F]‐ 8 a , b .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of ¹⁸F‐Labelled β‐Lactams by Using the Kinugasa Reaction

Zlatopolskiy

Krapf

Richarz

et al. 2014

Chemistry A European J

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Owing to their broad spectrum of biological activities and low toxicity, β-lactams are attractive lead structures for the design of novel molecular probes. However, the synthesis of positron emission tomography (PET)-isotope-labelled β-lactams has not yet been reported. Herein, we describe the simple preparation of radiofluorinated β-lactams by using the fast Kinugasa reaction between (18)F-labelled nitrone [(18)F]-1 and alkynes of different reactivity. Additionally, (18)F-labelled fused β-lactams were obtained through the reaction of a cyclic nitrone 7 with radiofluorinated alkynes [(18)F]-6 a,b. Radiochemical yields of the Kinugasa reaction products could be significantly increased by the use of different Cu(I) ligands, which additionally allowed a reduction in the amount of precursor and/or reaction time. Model radiofluorinated β-lactam-peptide and protein conjugates ([(18)F]-10 and (18)F-labelled BSA conjugate) were efficiently obtained in high yield under mild conditions (aq. MeCN, ambient temperature) within a short reaction time, demonstrating the suitability of the developed method for radiolabelling of sensitive molecules such as biopolymers.

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C-(4-[18F]fluorophenyl)-N-phenyl nitrone: A novel 18F-labeled building block for metal free [3+2]cycloaddition

Cited by 17 publications

References 21 publications

¹⁸F‐Labeling of Sensitive Biomolecules for Positron Emission Tomography

¹⁸F‐Labeling of Sensitive Biomolecules for Positron Emission Tomography

¹⁸F-Labeling Using Click Cycloadditions

Synthesis of ¹⁸F‐Labelled β‐Lactams by Using the Kinugasa Reaction

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C-(4-[18F]fluorophenyl)-N-phenyl nitrone: A novel 18F-labeled building block for metal free [3+2]cycloaddition

Cited by 17 publications

References 21 publications

18F‐Labeling of Sensitive Biomolecules for Positron Emission Tomography

18F‐Labeling of Sensitive Biomolecules for Positron Emission Tomography

18F-Labeling Using Click Cycloadditions

Synthesis of 18F‐Labelled β‐Lactams by Using the Kinugasa Reaction

Contact Info

Product

Resources

About

¹⁸F‐Labeling of Sensitive Biomolecules for Positron Emission Tomography

¹⁸F‐Labeling of Sensitive Biomolecules for Positron Emission Tomography

¹⁸F-Labeling Using Click Cycloadditions

Synthesis of ¹⁸F‐Labelled β‐Lactams by Using the Kinugasa Reaction