Synthesis of18F-labelled biphenyls via SUZUKI cross-coupling with 4-[18F]fluoroiodobenzene

Steiniger, Björn; Wuest, Frank

doi:10.1002/jlcr.1099

Cited by 18 publications

(12 citation statements)

References 14 publications

(18 reference statements)

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“…Removal of the excess diiodobenzene byproduct can be achieved by automated solid-phase extraction. [225] The Suzuki reaction has been investigated as a method to couple together simple [ 18 F]fluoroaryl derivatives to form a series of [ 18 F]fluorobiphenyls (Scheme 49). [225] The reaction of 75 with p-tolylboronic acid was used as a model reaction to screen the effectiveness of different palladium complexes, bases, and solvents.…”

Section: Synthesis Of Pet Labelsmentioning

confidence: 99%

“…[225] The Suzuki reaction has been investigated as a method to couple together simple [ 18 F]fluoroaryl derivatives to form a series of [ 18 F]fluorobiphenyls (Scheme 49). [225] The reaction of 75 with p-tolylboronic acid was used as a model reaction to screen the effectiveness of different palladium complexes, bases, and solvents. The optimum coupling conditions to give the highest RCYs were found to be [Pd 2 -(dba) 3 ], Cs 2 CO 3 , and acetonitrile at 60 8C for 5 minutes.…”

Section: Synthesis Of Pet Labelsmentioning

confidence: 99%

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Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

et al. 2008

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Positron emission tomography (PET) is a powerful and rapidly developing area of molecular imaging that is used to study and visualize human physiology by the detection of positron-emitting radiopharmaceuticals. Information about metabolism, receptor/enzyme function, and biochemical mechanisms in living tissue can be obtained directly from PET experiments. Unlike magnetic resonance imaging (MRI) or computerized tomography (CT), which mainly provide detailed anatomical images, PET can measure chemical changes that occur before macroscopic anatomical signs of a disease are observed. PET is emerging as a revolutionary method for measuring body function and tailoring disease treatment in living subjects. The development of synthetic strategies for the synthesis of new positron-emitting molecules is, however, not trivial. This Review highlights key aspects of the synthesis of PET radiotracers with the short-lived positron-emitting radionuclides (11)C, (18)F, (15)O, and (13)N, with emphasis on the most recent strategies.

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Section: Synthesis Of Pet Labelsmentioning

confidence: 99%

Section: Synthesis Of Pet Labelsmentioning

confidence: 99%

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

et al. 2008

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“…There are only a few examples of biphenolic compounds labeled with PET isotopes and no information is available on the synthesis of potential PET radiotracers based on MH structure. Thus, the aim of this study was to prepare [ 11 C]‐labeled MH derivative (4′‐[ 11 C]methoxy‐5‐propyl‐1,1′‐biphenyl‐2‐ol or [ 11 C]MPbP) and ex vivo evaluate it on a rat model of LPS neuroinflammation.…”

Section: Figurementioning

confidence: 99%

Radiosynthesis of a Novel ¹¹C‐Labeled Derivative of 4’‐O‐Methylhonokiol and Its Preliminary Evaluation in an LPS Rat Model of Neuroinflammation

et al. 2020

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Cyclooxygenase type 2 (COX‐2) is an attractive biomarker for the visualization of neuroinflammation processes by positron emission tomography (PET). Neolignan 4’‐O‐methylhonokiol (MH) is known to have high anti‐inflammatory activity and inhibits the expression of COX‐2. We synthesized 4′‐[11C]methoxy‐5‐propyl‐1,1′‐biphenyl‐2‐ol ([11C]MPbP), a compound based on the MH structure and labeled with carbon‐11 (T1/2=20.4 min) and studied its distribution in rats treated with lipopolysaccharide (LPS). It was shown that the new ligand has significant inhibitory activity against COX‐2 (IC50=0.14 μM) and sufficient lipophilicity (logD7.4=2.46±0.12) for penetration the blood brain barrier (BBB). [11C]MPbP was obtained by 11C‐methylation using [11C]CH3I with decay‐corrected radiochemical yield of 20% based on [11C]CH3I with molar activity 10–15 GBq/μmol, high radiochemical purity (> 99%) and low level of chemical impurities (<1 μg/ml). The radioligand did not undergo any noticeable decomposition in human plasma for 40 min. The results of ex vivo biodistribution in rats demonstrated that [11C]MPbP crossed the BBB and the observed radioactivity uptake in brain of rats with LPS‐induced neuroinflammation was 4 times higher than in intact animals. Further studies of compounds with the MH scaffold are planned for their possible application in PET, including in vivo assessment in animal neuroinflammation models.

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“…Steiniger and Wuest coupled 4-[ 18 F]fluoroiodobenzene and 4-tolylboronic acid 50 with a variety of Pd(0) and Pd(II) catalysts, bases, and solvent conditions (Scheme 27b) [202]. They determined that Pd 2 (dba) 3 with Cs 2 CO 3 in MeCN were the ideal conditions to further investigate the cross-coupling of 4-[ 18 F]fluoroiodobenzene with various aryl boronic acids.…”

Section: Other Strategies For Radiolabeling With Fluorine-18mentioning

confidence: 99%

Radiosyntheses using Fluorine-18: The Art and Science of Late Stage Fluorination

Cole¹,

Stewart²,

Littich³

et al. 2014

CTMC

127

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Positron (β+) emission tomography (PE) is a powerful, noninvasive tool for the in vivo, three-dimensional imaging of physiological structures and biochemical pathways. The continued growth of PET imaging relies on a corresponding increase in access to radiopharmaceuticals (biologically active molecules labeled with short-lived radionuclides such as fluorine-18). This unique need to incorporate the short-lived fluorine-18 atom (t1/2 = 109.77 min) as late in the synthetic pathway as possible has made development of methodologies that enable rapid and efficient late stage fluorination an area of research within its own right. In this review we describe strategies for radiolabeling with fluorine-18, including classical fluorine-18 radiochemistry and emerging techniques for late stage fluorination reactions, as well as labeling technologies such as microfluidics and solid-phase radiochemistry. The utility of fluorine-18 labeled radiopharmaceuticals is showcased through recent applications of PET imaging in the healthcare, personalized medicine and drug discovery settings.

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Synthesis of18F-labelled biphenyls via SUZUKI cross-coupling with 4-[18F]fluoroiodobenzene

Abstract: SummaryThe The reaction proceeded in excellent radiochemical yields of up to 94% within 5 min while showing good compatibility to many functional groups.

Cited by 18 publications

References 14 publications

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

Radiosynthesis of a Novel ¹¹C‐Labeled Derivative of 4’‐O‐Methylhonokiol and Its Preliminary Evaluation in an LPS Rat Model of Neuroinflammation

Radiosyntheses using Fluorine-18: The Art and Science of Late Stage Fluorination

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Synthesis of18F-labelled biphenyls via SUZUKI cross-coupling with 4-[18F]fluoroiodobenzene

Abstract: SummaryThe The reaction proceeded in excellent radiochemical yields of up to 94% within 5 min while showing good compatibility to many functional groups.

Cited by 18 publications

References 14 publications

Synthesis of 11C, 18F, 15O, and 13N Radiolabels for Positron Emission Tomography

Synthesis of 11C, 18F, 15O, and 13N Radiolabels for Positron Emission Tomography

Radiosynthesis of a Novel 11C‐Labeled Derivative of 4’‐O‐Methylhonokiol and Its Preliminary Evaluation in an LPS Rat Model of Neuroinflammation

Radiosyntheses using Fluorine-18: The Art and Science of Late Stage Fluorination

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Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

Synthesis of ¹¹C, ¹⁸F, ¹⁵O, and ¹³N Radiolabels for Positron Emission Tomography

Radiosynthesis of a Novel ¹¹C‐Labeled Derivative of 4’‐O‐Methylhonokiol and Its Preliminary Evaluation in an LPS Rat Model of Neuroinflammation