Carbon‐11 Radiolabelling of Organosulfur Compounds: <sup>11</sup>C Synthesis of the Progesterone Receptor Agonist Tanaproget

Haywood, Tom; Kealey, Steven; Sánchez-Cabezas, Santiago; Hall, James J.; Allott, Louis; Smith, Graham; Plisson, Christophe; Miller, Philip W.

doi:10.1002/chem.201501089

Cited by 25 publications

(23 citation statements)

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“…Therefore, PET-CT using FDG, or analogues such as 6-[ 18 F]-fluoromaltose 30 , can image a wide range of inflammatory and infectious conditions 30,31 such as granulomatous diseases and fungal infections. Other PET applications include tracking pharmaco kinetics of drugs 32,33 and musculoskeletal studies 34 with various PET tracers 35 . For further details, please see previous reviews 36,37 .…”

Section: Imaging Modalitiesmentioning

confidence: 99%

Towards clinically translatable in vivo nanodiagnostics

et al. 2017

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Nanodiagnostics as a field makes use of fundamental advances in nanobiotechnology to diagnose, characterize and manage disease at the molecular scale. As these strategies move closer to routine clinical use, a proper understanding of different imaging modalities, relevant biological systems and physical properties governing nanoscale interactions is necessary to rationally engineer next-generation bionanomaterials. In this Review, we analyse the background physics of several clinically relevant imaging modalities and their associated sensitivity and specificity, provide an overview of the materials currently used for in vivo nanodiagnostics, and assess the progress made towards clinical translation. This work provides a framework for understanding both the impressive progress made thus far in the nanodiagnostics field as well as presenting challenges that must be overcome to obtain widespread clinical adoption.

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Section: Imaging Modalitiesmentioning

confidence: 99%

Towards clinically translatable in vivo nanodiagnostics

et al. 2017

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“…Carbon disulfide, the sulfur analogue of carbon dioxide, has recently been synthesized on-line from 11 CH 3 I using either P 2 S 5 and elemental sulfur (S 8 ) at elevated temperatures in excellent yields [77, 78]. Due to the weaker C=S bond CS 2 is considered more reactive than CO 2 .…”

Section: Other Recent Advances In Carbon-11 Chemistrymentioning

confidence: 99%

New methodologies for the preparation of carbon-11 labeled radiopharmaceuticals

Dahl

Halldin

Schou

2017

Clin Transl Imaging

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PurposeThis short review aims to cover the more recent and promising developments of carbon-11 (11C) labeling radiochemistry and its utility in the production of novel radiopharmaceuticals, with special emphasis on methods that have the greatest potential to be translated for clinical positron emission tomography (PET) imaging.MethodsA survey of the literature was undertaken to identify articles focusing on methodological development in 11C chemistry and their use within novel radiopharmaceutical preparation. However, since 11C-labeling chemistry is such a narrow field of research, no systematic literature search was therefore feasible. The survey was further restricted to a specific timeframe (2000–2016) and articles in English.ResultsFrom the literature, it is clear that the majority of 11C-labeled radiopharmaceuticals prepared for clinical PET studies have been radiolabeled using the standard heteroatom methylation reaction. However, a number of methodologies have been developed in recent years, both from a technical and chemical point of view. Amongst these, two protocols may have the greatest potential to be widely adapted for the preparation of 11C-radiopharmaceuticals in a clinical setting. First, a novel method for the direct formation of 11C-labeled carbonyl groups, where organic bases are utilized as [11C]carbon dioxide-fixation agents. The second method of clinical importance is a low-pressure 11C-carbonylation technique that utilizes solvable xenon gas to effectively transfer and react [11C]carbon monoxide in a sealed reaction vessel. Both methods appear to be general and provide simple paths to 11C-labeled products.ConclusionRadiochemistry is the foundation of PET imaging which relies on the administration of a radiopharmaceutical. The demand for new radiopharmaceuticals for clinical PET imaging is increasing, and 11C-radiopharmaceuticals are especially important within clinical research and drug development. This review gives a comprehensive overview of the most noteworthy 11C-labeling methods with clinical relevance to the field of PET radiochemistry.

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“…[72] [ 11 C]CS 2 was first prepared from [ 11 C]CO 2 and H 2 Si nl ow RCY. [75] [ 11 C]CS 2 was found to react rapidly with ab road spectrum of primary amines to give 11 C-labeled thiocarbonyl thioureas,i ncluding [ 11 C]tanaproget, in high RCY and high molar activity.In2017, Haskali and Pike described anew type of 11 C-labeled agent, namely [ 11 C]CF 3 H, which was based on the fluorination of [ 11 C]CH 4 with CoF 3 (Scheme 12 C). [74] They then improved the method by switching the thionating reagent from P 2 O 5 to elemental sulfur (Scheme 12 B).…”

Section: Miscellaneous 11 Csynthons and Reagentsmentioning

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

Cited by 25 publications

References 50 publications

Towards clinically translatable in vivo nanodiagnostics

Towards clinically translatable in vivo nanodiagnostics

New methodologies for the preparation of carbon-11 labeled radiopharmaceuticals

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

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

Cited by 25 publications

References 50 publications

Towards clinically translatable in vivo nanodiagnostics

Towards clinically translatable in vivo nanodiagnostics

New methodologies for the preparation of carbon-11 labeled radiopharmaceuticals

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

Contact Info

Product

Resources

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

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