Radioiodination of polymer‐supported organotrifluoroborates

Li, Yong; Yao, Min‐Liang; Hall, Kelly; Green, James F.; Kabalka, George W.

doi:10.1002/jlcr.1837

Cited by 12 publications

(5 citation statements)

References 18 publications

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“…As an additional test of the labeling method, 5‐iodo‐2'‐deoxyuridine (IUdR)‐ 13b , an agent currently undergoing investigation as therapeutic radiopharmaceutical, was also produced using the chloramine‐T approach, where the isolated yield was 57% ± 3%. In general, the isolated yields obtained using chloramine‐T are comparable or higher than those previously reported for other solid‐phase radioiodination methods . It should also be noted that the coated material was evaluated over 2 months after storage at 4 ° C, where there was no significant change in radiochemical yield or purity.…”

Section: Resultssupporting

confidence: 73%

A hybrid solid‐fluorous phase radioiodination and purification platform

Dzandzi

Beckford-Vera

Valliant

2014

Labelled Comp Radiopharmac

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A new class of fluorous materials was developed to create a hybrid solid-solution phase strategy for the expedient preparation and HPLC-free purification of (125) I-labeled compounds. The system is referred to as a hybrid platform in that it combines solution phase labeling and fluorous solid-phase purification in one step as opposed to two separate individual processes. Treatment of fluorous arylstannanes coated on fluorous silica with [(125) I]NaI and the appropriate oxidant made it possible to produce and selectively isolate the nonfluorous radiolabeled products in high purity (>98%) free from excess starting material and unreacted radioiodine. Examples included simple aryl and heterocyclic (click) derivatives, known radiopharmaceuticals including meta-iodobenzylguanidine (MIBG) and iododeoxyuridine (IUdR), and a new agent with high affinity for prostate-specific membrane antigen. The coated fluorous silica kits are simple to prepare, and reactions can be performed at room temperature using different oxidants generating products in minutes in biocompatible solutions.

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Section: Resultssupporting

confidence: 73%

A hybrid solid‐fluorous phase radioiodination and purification platform

Dzandzi

Beckford-Vera

Valliant

2014

Labelled Comp Radiopharmac

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“…These include polymer-supported [12][13][14][15][16] and fluorous labeling [17][18][19][20] methods that allow for expedited "HPLC-free" preparation of iodine-based radiopharmaceuticals. Although a great deal of emphasis has been placed on creating new labeling constructs, the nature of the oxidants used for iodination reactions has remained unchanged for some time.…”

Section: Introductionmentioning

confidence: 99%

“…Addressing these issues, new synthetic methods for rapid introduction of iodine and in situ purification have recently been reported. These include polymer-supported − and fluorous labeling − methods that allow for expedited “HPLC-free” preparation of iodine-based radiopharmaceuticals. Although a great deal of emphasis has been placed on creating new labeling constructs, the nature of the oxidants used for iodination reactions has remained unchanged for some time .…”

Section: Introductionmentioning

confidence: 99%

Fluorous Analogue of Chloramine-T: Preparation, X-ray Structure Determination, and Use as an Oxidant for Radioiodination and s-Tetrazine Synthesis

Dzandzi¹,

Beckford-Vera²,

Genady

et al. 2015

J. Org. Chem.

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A fluorous oxidant that can be used to introduce radioiodine into small molecules and proteins and generate iodinated tetrazines for bioorthogonal chemistry has been developed. The oxidant was prepared in 87% overall yield by combining a fluorous amine with tosyl chloride, followed by chlorination using aqueous sodium hypochlorite. A crystal structure of the oxidant, which is a fluorous analogue of chloramine-T, was obtained. The compound was shown to be stable for 7 days in EtOH and for longer than three months as a solid. The oxidant was effective at promoting the labeling of arylstannanes using [(125)I]NaI, where products were isolated in high specific activity in yields ranging from 46% to 86%. Similarly, iodinated biologically active proteins (e.g., thrombin) were successfully produced, as well as a radioiodinated tetrazine, through a concomitant oxidation-halodemetalation reaction. Because of its fluorous nature, unreacted oxidant and associated reaction byproducts can be removed quantitatively from reaction mixtures by passing solutions through fluorous solid phase extraction cartridges. This feature enables rapid and facile purification, which is critical when working with radionuclides and is similarly beneficial for general synthetic applications.

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“…We successfully established methods for the synthesis and characterization of Dowex-supported organotrifluoroborates. 5 The application of the Dowex-supported organotrifluoroborates in radioiodination 6 greatly simplified the purification procedure in the preparation of certain radiotracers (Scheme 1). However, most likely due to the insolubility of the Dowex-supported organotrifluoroborates in THF-H 2 O system, the radiolabelling yields were slightly lower when compared to the yields in the corresponding reactions carried out in solution.…”

Section: Introductionmentioning

confidence: 99%