Solid‐Phase Radiochemistry

Hockley, Brian G.; Scott, Peter J. H.; Kilbourn, Michael R.

doi:10.1002/9780470749043.ch22

Cited by 5 publications

(1 citation statement)

References 46 publications

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“…The electrophilic, nucleophilic and prosthetic group chemistry described throughout this review have all been adapted for SPOR, and are highlighted below as well as in recent review articles from our group [223, 224]. For example, the [ 18 F]fluoroDOPA 76 SPOR (Scheme 33), uses the same radiochemistry as employed in the corresponding solution-phase electrophilic radiosyntheses.…”

Section: Technologies For Enhancing Fluorine-18 Radiochemistrymentioning

confidence: 99%

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

Cole¹,

Stewart²,

Littich³

et al. 2014

CTMC

126

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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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Section: Technologies For Enhancing Fluorine-18 Radiochemistrymentioning

confidence: 99%

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

Cole¹,

Stewart²,

Littich³

et al. 2014

CTMC

126

View full text Add to dashboard Cite

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Solid‐Phase Organic Radiosynthesis

Hoareau

Scott

2011

Solid‐Phase Organic Synthesis

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A Resin‐Linker‐Vector Approach to Radiopharmaceuticals Containing ¹⁸F: Application in the Synthesis of O‐(2‐[¹⁸F]‐Fluoroethyl)‐L‐tyrosine

Topley¹,

Isoni²,

Logothetis³

et al. 2012

Chemistry A European J

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A Resin-linker-vector (RLV) strategy is described for the radiosynthesis of tracer molecules containing the radionuclide (18)F, which releases the labelled vector into solution upon nucleophilic substitution of a polystyrene-bound arylsulfonate linker with [(18)F]-fluoride ion. Three model linker-vector molecules 7a-c containing different alkyl spacer groups were assembled in solution from (4-chlorosulfonylphenyl)alkanoate esters, exploiting a lipase-catalysed chemoselective carboxylic ester hydrolysis in the presence of the sulfonate ester as a key step. The linker-vector systems were attached to aminomethyl polystyrene resin through amide bond formation to give RLVs 8a-c with acetate, butyrate and hexanoate spacers, which were characterised by using magic-angle spinning (MAS) NMR spectroscopy. On fluoridolysis, the RLVs 8a,b containing the longer spacers were shown to be more effective in the release of the fluorinated model vector (4-fluorobutyl)phenylcarbamic acid tert-butyl ester (9) in NMR kinetic studies and gave superior radiochemical yields (RCY≈60%) of the (18) F-labelled vector. The approach was applied to the synthesis of the radiopharmaceutical O-(2-[(18)F]-fluoroethyl)-L-tyrosine ([(18) F]-FET), delivering protected [(18) F]-FET in >90% RCY. Acid deprotection gave [(18)F]-FET in an overall RCY of 41% from the RLV.

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Solid‐Phase Radiochemistry

Cited by 5 publications

References 46 publications

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

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

Solid‐Phase Organic Radiosynthesis

A Resin‐Linker‐Vector Approach to Radiopharmaceuticals Containing ¹⁸F: Application in the Synthesis of O‐(2‐[¹⁸F]‐Fluoroethyl)‐L‐tyrosine

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Solid‐Phase Radiochemistry

Cited by 5 publications

References 46 publications

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

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

Solid‐Phase Organic Radiosynthesis

A Resin‐Linker‐Vector Approach to Radiopharmaceuticals Containing 18F: Application in the Synthesis of O‐(2‐[18F]‐Fluoroethyl)‐L‐tyrosine

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A Resin‐Linker‐Vector Approach to Radiopharmaceuticals Containing ¹⁸F: Application in the Synthesis of O‐(2‐[¹⁸F]‐Fluoroethyl)‐L‐tyrosine