A broadly applicable [18F]trifluoromethylation of aryl and heteroaryl iodides for PET imaging

Huiban, Mickaël; Tredwell, Matthew; Mizuta, Satoshi; Wan, Zhimin; Zhang, Xiaomin; Collier, Thomas Lee; Gouverneur, Véronique; Passchier, Jan

doi:10.1038/nchem.1756

Cited by 183 publications

(160 citation statements)

References 36 publications

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“…The growing importance of PET as ar outine imaging methodh as led to an associated demand for new tracers and more facile production techniques of existing tracers.T his demandh as to be met with innovative new radiolabelling chemistry and technology.R ecently there has been an umber of important advances in the field of rapid late-stage 18 Fr adiolabellingu sing transition-metal reagents, [6][7][8][9][10] fluoride acceptors, [11,12] click chemistry [13,14] and enzymatic reactions. [15,16] CO. [24,25] Recently,o ur group reported ar apid and high yielding route to an ew 11 Cl abelling synthon, 11 Cc arbon disulfide [26] that has many of the desirable characteristics for PET labelling, including ease of synthesis, ease of handling, high reactivity and the potential to radiolabel aw ide range of compounds.…”

Section: Synthesis Of the Progesterone Receptor Agonist Tanaprogetmentioning

confidence: 99%

Carbon‐11 Radiolabelling of Organosulfur Compounds: ¹¹C Synthesis of the Progesterone Receptor Agonist Tanaproget

Haywood

Kealey

Sánchez-Cabezas

et al. 2015

Chemistry A European J

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Herein a new (11) C radiolabelling strategy for the fast and efficient synthesis of thioureas and related derivatives using the novel synthon, (11) CS2 , is reported. This approach has enabled the facile labelling of a potent progesterone receptor (PR) agonist, [(11) C]Tanaproget, by the intramolecular reaction of the acyclic aminohydroxyl precursor with (11) CS2 , which has potential applications as a positron emission tomography radioligand for cancer imaging.

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Section: Synthesis Of the Progesterone Receptor Agonist Tanaprogetmentioning

confidence: 99%

Carbon‐11 Radiolabelling of Organosulfur Compounds: ¹¹C Synthesis of the Progesterone Receptor Agonist Tanaproget

Haywood

Kealey

Sánchez-Cabezas

et al. 2015

Chemistry A European J

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“…6 The high sensitivity of the PET technique also makes it suitable for addressing questions fundamental to drug development for oncology, cardiology, neurosciences, and inflammatory diseases. 7 PET is a powerful clinical imaging technique that is widely used for diagnostic applications in clinical oncology, owing to its unrivalled sensitivity and quantitative accuracy. C (t ½ 20 minutes), and 64 Cu (t ½ 12.7 hours).…”

Section: Introductionmentioning

confidence: 99%

Nano-graphene oxide composite for in vivo imaging

Jang¹,

Kang²,

Lee³

et al. 2018

IJN

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Introduction Positron emission tomography (PET) tracers has the potential to revolutionize cancer imaging and diagnosis. PET tracers offer non-invasive quantitative imaging in biotechnology and biomedical applications, but it requires radioisotopes as radioactive imaging tracers or radiopharmaceuticals. Method This paper reports the synthesis of 18 F-nGO-PEG by covalently functionalizing PEG with nano-graphene oxide, and its excellent stability in physiological solutions. Using a green synthesis route, nGO is then functionalized with a biocompatible PEG polymer to acquire high stability in PBS and DMEM. Results and discussion The radiochemical safety of 18 F-nGO-PEG was measured by a reactive oxygen species and cell viability test. The biodistribution of 18 F-nGO-PEG could be observed easily by PET, which suggested the significantly high sensitivity tumor uptake of 18 F-nGO-PEG and in a tumor bearing CT-26 mouse compared to the control. 18 F-nGO-PEG was applied successfully as an efficient radiotracer or drug agent in vivo using PET imaging. This article is expected to assist many researchers in the fabrication of 18 F-labeled graphene-based bio-conjugates with high reproducibility for applications in the biomedicine field.

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“…Researchers are developing methods to access [ 18 F]CF3-substituted molecules for the application in pharmaceutical discovery programmes (Figure 86). [300].…”

Section: Imaging Agentsmentioning

confidence: 99%

Squaryl Molecular Metaphors – Application to Rational Drug Design and Imaging Agents

Kitson¹

2017

J Diagn Imaging Ther

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Molecular Metaphors is the application of squaryl building blocks towards creative functional group chemistry to produce lead compounds and imaging agents. This strategy is applied to rational drug design and to various imaging agents that would normally contain conventional functional group chemistry. These, include carboxylic acids, α-amino acids, peptide bonds and phosphonates. Moreover, the squaryl metaphor is a precursor to complex organic molecules involving functional group interchange (FGI) and rearrangements. This article discusses the application of these metaphors in the area of neurochemistry, especially NMDA receptors. An important area of drug design is the inhibition of angiotensin II enzyme by the use of losartan. This commercial drug contains a tetrazole moiety that can be modified using the squaryl group to give a semisquarate derivative. These concepts can extend to the semisquarate of ibuprofen. Moreover, a discussion on peptidomimetics regarding the substitution of the peptide bond for squaramide allows for a change in the biological properties due to modification at the peptide bond. Furthermore, the topic on how squaryl metaphors can be exploited primarily by the central 1,3-hydroxyamide sequence to the generation of a novel class of HIV protease inhibitors. Also, squaryl metaphors can be used to develop potential inhibitors of glutathione and novel anti-migraine drugs. The discussion continues on the design of anticancer drugs: in particular, a novel class of metalloproteases, including phosphonates for semisquaramides, leading to squaryl nucleosides. This review concludes with the application of squaryl metaphors in the design of positron emission tomography (PET) and magnetic resonance imaging (MRI) agents towards theranostics. describe the ability of individual functional chemical groups to mimic other moieties [2,3]. KeywordsErlenmeyer rationalised these concepts and categorised isosteres into atoms, ions and molecules based on the valence level of electrons [4]. A further understanding by Friedman led to the term bioisosterism to include all atoms and molecules that fit the broadest definition of isosteres [5]. This approach was independent of whether the drug was an agonist or an antagonist towards biological activity.Moreover, Thornber applied the term bioisosterism to include subunits, groups or molecules that possess physicochemical properties of similar biological effects [6]. Finally, in 1991 Burger widened the definition of bioisosteres to include compounds or groups that possess similar molecular shapes and volumes independent of agonists or antagonists [7]. REVIEW ARTICLE Squaryl KitsonThese bioisosteres would require approximately the same distribution of electrons and give a high probability of generating comparable physical properties such as hydrophobicity [8]. Currently, bioisosterism is one of the most useful tools to the medicinal chemist in rational drug design and in particular regarding the carboxylic acid bioisosteres [9]. The carboxylic acid functional ...

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A broadly applicable [18F]trifluoromethylation of aryl and heteroaryl iodides for PET imaging

Cited by 183 publications

References 36 publications

Carbon‐11 Radiolabelling of Organosulfur Compounds: ¹¹C Synthesis of the Progesterone Receptor Agonist Tanaproget

Carbon‐11 Radiolabelling of Organosulfur Compounds: ¹¹C Synthesis of the Progesterone Receptor Agonist Tanaproget

Nano-graphene oxide composite for in vivo imaging

Squaryl Molecular Metaphors – Application to Rational Drug Design and Imaging Agents

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A broadly applicable [18F]trifluoromethylation of aryl and heteroaryl iodides for PET imaging

Cited by 183 publications

References 36 publications

Carbon‐11 Radiolabelling of Organosulfur Compounds: 11C Synthesis of the Progesterone Receptor Agonist Tanaproget

Carbon‐11 Radiolabelling of Organosulfur Compounds: 11C Synthesis of the Progesterone Receptor Agonist Tanaproget

Nano-graphene oxide composite for in vivo imaging

Squaryl Molecular Metaphors – Application to Rational Drug Design and Imaging Agents

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Product

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Carbon‐11 Radiolabelling of Organosulfur Compounds: ¹¹C Synthesis of the Progesterone Receptor Agonist Tanaproget

Carbon‐11 Radiolabelling of Organosulfur Compounds: ¹¹C Synthesis of the Progesterone Receptor Agonist Tanaproget