A Facile Radiolabeling of [<sup>18</sup>F]FDPA via Spirocyclic Iodonium Ylides: Preliminary PET Imaging Studies in Preclinical Models of Neuroinflammation

Wang, Lu; Cheng, Ran; Fujinaga, Masayuki; Yang, Jian; Zhang, Yiding; Hatori, Akiko; Kumata, Katsushi; Yang, Jing; Vasdev, Neil; Du, Yunfei; Ran, Chongzhao; Zhang, Ming-Rong; Liang, Steven H.

doi:10.1021/acs.jmedchem.7b00432

Cited by 48 publications

(57 citation statements)

References 36 publications

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“…The corresponding spirocyclic iodonium ylide (SCIDY) 70 precursor 17 for 18 F-labeling was obtained from the oxidation of iodinated compound 12 , followed by ligand exchange with SPIAd 71 in 56% yield (Scheme 2B). The labeled compound 18 ([ 18 F] 8) was obtained in 28% RCY, using our SCIDY method 70–75 and 19 ([ carbonyl - 11 C] 8) was generated in 13% RCY using analogous [ 11 C]COCl 2 protocol 46 (Scheme 2B). Despite the fact that compound 19 exhibited high brain permeability ( ca.…”

Section: Resultsmentioning

confidence: 99%

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In Vitro and in Vivo Evaluation of ¹¹C-Labeled Azetidinecarboxylates for Imaging Monoacylglycerol Lipase by PET Imaging Studies

Cheng

Mori

et al. 2018

J. Med. Chem.

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Monoacylglycerol lipase (MAGL) is the principle enzyme for metabolizing endogenous cannabinoid ligand, 2-arachidonoyglycerol (2-AG). Blockade of MAGL increases 2-AG levels, resulting in subsequent activation of the endocannabinoid system, and has emerged as a novel therapeutic strategy to treat drug addiction, inflammation and neurodegenerative diseases. Herein we report a new series of MAGL inhibitors, which were radiolabeled by site-specific labeling technologies, including 11C-carbonylation and spirocyclic iodonium ylide (SCIDY) radiofluorination. The lead compound [11C]10 (MAGL-0519) demonstrated high specific binding and selectivity in vitro and in vivo. We also observed unexpected washout kinetics with these irreversible radiotracers, in which in vivo evidence for turnover of the covalent residue was unveiled between MAGL and azetidine carboxylates. This work may lead to new directions for drug discovery and PET tracer development based on azetidine carboxylate inhibitor scaffold.

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Section: Resultsmentioning

confidence: 99%

“…70–73, 75 The aryl iodide 12 could be oxidized in chloroform. 70 Without further purification, the resulted intermediate could couple the spirocyclic auxiliaries (SPIAd) 71 directly to afford the desired ylide precursor 17 .…”

Section: Methodsmentioning

confidence: 99%

In Vitro and in Vivo Evaluation of ¹¹C-Labeled Azetidinecarboxylates for Imaging Monoacylglycerol Lipase by PET Imaging Studies

Cheng

Mori

et al. 2018

J. Med. Chem.

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“…A spiroadamantyl aryliodonium ylide has also been used to prepare another radiotracer for TSPO 18 kDa, namely, [ 18 F]FDPA . The choice of base for use in the radiofluorination reaction was found to be critical.…”

Section: Discussionmentioning

confidence: 99%

Hypervalent aryliodine compounds as precursors for radiofluorination

Pike

2018

Labelled Comp Radiopharmac

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Over the last 2 decades or so, hypervalent iodine compounds, such as diaryliodonium salts and aryliodonium ylides, have emerged as useful precursors for labeling homoarenes and heteroarenes with no-carrier-added cyclotron-produced [ F]fluoride ion (t = 109.8 min). They permit rapid and effective radiofluorination at electron-rich as well as electron-deficient aryl rings, and often with unrestricted choice of ring position. Consequently, hypervalent aryliodine compounds have found special utility as precursors to various small-molecule F-labeling synthons and to many radiotracers for biomedical imaging with positron emission tomography. This review summarizes this advance in radiofluorination chemistry, with emphasis on precursor synthesis, radiofluorination mechanism, method scope, and method application.

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“…[81,132,133,[135][136][137][138][139][140][141][142][143] It is noteworthy that [ 18 F]FPEB synthesized by the SCIDYm ethod was fully automated, thereby resulting in asubstantial improvement (3-10 fold) in the RCY and molar activity compared with the traditional S N Ar method. [81,132,133,[135][136][137][138][139][140][141][142][143] It is noteworthy that [ 18 F]FPEB synthesized by the SCIDYm ethod was fully automated, thereby resulting in asubstantial improvement (3-10 fold) in the RCY and molar activity compared with the traditional S N Ar method.…”

Section: Angewandte Chemiementioning

confidence: 99%

Chemistry for Positron Emission Tomography: Recent Advances in ¹¹C‐, ¹⁸F‐, ¹³N‐, and ¹⁵O‐Labeling Reactions

et al. 2019

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Positron emission tomography (PET) is a molecular imaging technology that provides quantitative information about function and metabolism in biological processes in vivo for disease diagnosis and therapy assessment. The broad application and rapid advances of PET has led to an increased demand for new radiochemical methods to synthesize highly specific molecules bearing positron-emitting radionuclides. This article provides an overview of commonly-used labeling chemistry in the examples of clinically relevant PET tracers, and highlights most recent development and breakthroughs over the past decade with focus on 11C, 18F, 13N, and 15O.

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A Facile Radiolabeling of [¹⁸F]FDPA via Spirocyclic Iodonium Ylides: Preliminary PET Imaging Studies in Preclinical Models of Neuroinflammation

Cited by 48 publications

References 36 publications

In Vitro and in Vivo Evaluation of ¹¹C-Labeled Azetidinecarboxylates for Imaging Monoacylglycerol Lipase by PET Imaging Studies

In Vitro and in Vivo Evaluation of ¹¹C-Labeled Azetidinecarboxylates for Imaging Monoacylglycerol Lipase by PET Imaging Studies

Hypervalent aryliodine compounds as precursors for radiofluorination

Chemistry for Positron Emission Tomography: Recent Advances in ¹¹C‐, ¹⁸F‐, ¹³N‐, and ¹⁵O‐Labeling Reactions

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A Facile Radiolabeling of [18F]FDPA via Spirocyclic Iodonium Ylides: Preliminary PET Imaging Studies in Preclinical Models of Neuroinflammation

Cited by 48 publications

References 36 publications

In Vitro and in Vivo Evaluation of 11C-Labeled Azetidinecarboxylates for Imaging Monoacylglycerol Lipase by PET Imaging Studies

In Vitro and in Vivo Evaluation of 11C-Labeled Azetidinecarboxylates for Imaging Monoacylglycerol Lipase by PET Imaging Studies

Hypervalent aryliodine compounds as precursors for radiofluorination

Chemistry for Positron Emission Tomography: Recent Advances in 11C‐, 18F‐, 13N‐, and 15O‐Labeling Reactions

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Product

Resources

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A Facile Radiolabeling of [¹⁸F]FDPA via Spirocyclic Iodonium Ylides: Preliminary PET Imaging Studies in Preclinical Models of Neuroinflammation

In Vitro and in Vivo Evaluation of ¹¹C-Labeled Azetidinecarboxylates for Imaging Monoacylglycerol Lipase by PET Imaging Studies

In Vitro and in Vivo Evaluation of ¹¹C-Labeled Azetidinecarboxylates for Imaging Monoacylglycerol Lipase by PET Imaging Studies

Chemistry for Positron Emission Tomography: Recent Advances in ¹¹C‐, ¹⁸F‐, ¹³N‐, and ¹⁵O‐Labeling Reactions