A Novel Prosthetic Group for Site-Selective Labeling of Peptides for Positron Emission Tomography

Background: One of the challenges in positron emission tomography (PET) is labelling complex aliphatic molecules. Objective: To develop a method of metal-catalysed radiofluorination that is site-selective and works in moderate to good yields under facile conditions. Methods: We report here on the optimisation of an aliphatic C-H to C-18F bond transformation catalysed by a Mn(porphyrin) complex. Results: The successful oxidation of 11 aliphatic molecules including progesterone are reported. Radiochemical Incorporations (RCIs) up to 69% were achieved within 60 min without the need for pre-activation or specialist equipment. Conclusion: The method features mild conditions (60 °C) and promises to constitute a valuable approach to labelling of biomolecules and drug substances.

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Effect of the Prosthetic Group on the Pharmacologic Properties of18F-Labeled Rhodamine B, a Potential Myocardial Perfusion Agent for Positron Emission Tomography (PET)

Journal of Medicinal Chemistry ◽

10.1021/jm301453p ◽

2012 ◽

Vol 55 (24) ◽

pp. 11004-11012 ◽

Cited By ~ 21

Author(s):

Mark D. Bartholomä ◽

Vijay Gottumukkala ◽

Shaohui Zhang ◽

Amanda Baker ◽

Patricia Dunning ◽

...

Keyword(s):

Positron Emission Tomography ◽

Myocardial Perfusion ◽

Rhodamine B ◽

Emission Tomography ◽

Prosthetic Group ◽

Positron Emission

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Site-Selective, Late-Stage C−H 18 F-Fluorination on Unprotected Peptides for Positron Emission Tomography Imaging

Angewandte Chemie ◽

10.1002/ange.201806966 ◽

2018 ◽

Vol 130 (39) ◽

pp. 12915-12918 ◽

Cited By ~ 14

Author(s):

Zheliang Yuan ◽

Matthew B. Nodwell ◽

Hua Yang ◽

Noeen Malik ◽

Helen Merkens ◽

...

Keyword(s):

Positron Emission Tomography ◽

Late Stage ◽

Positron Emission Tomography Imaging ◽

Emission Tomography ◽

Tomography Imaging ◽

Positron Emission ◽

Site Selective

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Site-Selective, Late-Stage C−H 18 F-Fluorination on Unprotected Peptides for Positron Emission Tomography Imaging

Angewandte Chemie International Edition ◽

10.1002/anie.201806966 ◽

2018 ◽

Vol 57 (39) ◽

pp. 12733-12736 ◽

Cited By ~ 24

Author(s):

Zheliang Yuan ◽

Matthew B. Nodwell ◽

Hua Yang ◽

Noeen Malik ◽

Helen Merkens ◽

...

Keyword(s):

Positron Emission Tomography ◽

Late Stage ◽

Positron Emission Tomography Imaging ◽

Emission Tomography ◽

Tomography Imaging ◽

Positron Emission ◽

Site Selective

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Synthesis of [18F]SiFB: a prosthetic group for direct protein radiolabeling for application in positron emission tomography

Nature Protocols ◽

10.1038/nprot.2012.110 ◽

2012 ◽

Vol 7 (11) ◽

pp. 1956-1963 ◽

Cited By ~ 22

Author(s):

Alexey P Kostikov ◽

Joshua Chin ◽

Katy Orchowski ◽

Esther Schirrmacher ◽

Sabrina Niedermoser ◽

...

Keyword(s):

Positron Emission Tomography ◽

Emission Tomography ◽

Prosthetic Group ◽

Positron Emission

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An improved automated radiosynthesis of [18F]FET-βAG-TOCA

Reaction Chemistry & Engineering ◽

10.1039/c8re00279g ◽

2019 ◽

Vol 4 (3) ◽

pp. 569-574 ◽

Cited By ~ 2

Author(s):

Louis Allott ◽

Chris Barnes ◽

Diana Brickute ◽

Eric O. Aboagye

Keyword(s):

Positron Emission Tomography ◽

Click Chemistry ◽

Pet Imaging ◽

Neuroendocrine Tumours ◽

Emission Tomography ◽

Prosthetic Group ◽

Automated Radiosynthesis ◽

Positron Emission

The fluorine-18 radiolabelled octreotide [18F]FET-βAG-TOCA has been evaluated clinically for positron emission tomography (PET) imaging of neuroendocrine tumours (NETs). An improved automated radiosynthesis using “click” chemistry (CuAAC) and the 2-[18F]fluoroethylazide prosthetic group is reported and with minimal adaptation, may be used for radiolabelling other peptides.

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