A Highly Efficient Copper‐Mediated Radioiodination Approach Using Aryl Boronic Acids

Zhang, Pu; Zhuang, Rongqiang; Guo, Zhide; X, Su; Chen, Xiaoyuan; Zhang, Xianzhong

doi:10.1002/chem.201604105

Cited by 62 publications

(68 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Identification of the product was confirmed by HPLC, with co‐elution of a sample of unlabelled MIBG. These results compared favourably with other approaches for the preparation of radiolabelled MIBG, which demonstrates the potential of this methodology for widespread use in generating radioiodine‐labelled tracers ,…”

Section: Resultsmentioning

confidence: 65%

Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes

Webster

O’Rourke

Fletcher

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

Radiopharmaceuticals that incorporate radioactive iodine in combination with single‐photon emission computed tomography imaging play a key role in nuclear medicine, with applications in drug development and disease diagnosis. Despite this importance, there are relatively few general methods for the incorporation of radioiodine into small molecules. This work reports a rapid air‐ and moisture‐stable ipso‐iododeboronation procedure that uses NIS in the non‐toxic, green solvent dimethyl carbonate. The fast reaction and mild conditions of the gold‐catalysed method led to the development of a highly efficient process for the radiolabelling of arenes, which constitutes the first example of an application of homogenous gold catalysis to selective radiosynthesis. This was exemplified by the efficient synthesis of radiolabelled meta‐[125I]iodobenzylguanidine, a radiopharmaceutical that is used for the imaging and therapy of human norepinephrine transporter‐expressing tumours.

show abstract

Section: Resultsmentioning

confidence: 65%

Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes

Webster

O’Rourke

Fletcher

et al. 2017

Chemistry A European J

View full text Add to dashboard Cite

show abstract

“…The reaction conditions and precursors required to obtain optimal RCYs differed for radioiodination and astatination, highlighting the particular behavior of heavy halogenides with aryliodonium salts. Besides the excellent reactivity of these precursors, their separation from the radiolabeled prosthetic groups of interest was performed efficiently and rapidly using silica cartridges which greatly contributed to the overall radiosynthesis yield in comparison with the conventional arylstannane chemistry or the recently reported copper catalyzed arylboron chemistry 14,15 that require lengthy HPLC purification and thus leading to additional loss of radiolabeled product. Overall these precursors and the methods developed herein appear particularly attractive for the development of radioiodinated and astatinated proteins for preclinical applications and potentially for clinical applications, especially since toxicity concern are reduced and an HPLC step is not required, thus allowing easy transfer to fully automated synthesis.…”

Section: Discussionmentioning

confidence: 99%

“…13 Most recent literature shows an interest in developing nucleophilic radioiodination approaches for these reasons, with for instance recent reports on the use of arylboron precursors. 14,15 …”

Section: Introductionmentioning

confidence: 99%

Bifunctional aryliodonium salts for highly efficient radioiodination and astatination of antibodies

Guérard

Navarro

Lee

et al. 2017

Bioorganic & Medicinal Chemistry

View full text Add to dashboard Cite

In this report we describe the development of an alternative approach to arylstannane chemistry for radiolabeling antibodies with radioiodine or astatine based on aryliodonium salts precursors. Bifunctional aryliodonium salts were designed and tested for the synthesis of 125I and 211At labeled prosthetic groups for bioconjugation. The nature of the electron rich aryl group was varied and its impact on the regioselectivity of radiohalogenation was evaluated. Unexpectedly, whereas the 2-thienyl group provided the best regioselectivity towards the radioiodination of the aryl moiety of interest (98:2), it was less selective for astatination (87:13); the anisyl group providing the best regioselectivity of astatination (94:6). Under optimized conditions, both radioiodination and astatination could be performed very efficiently in mild conditions (radiochemical yields > 85%). The ionic nature of the precursors was exploited to develop an efficient purification approach: the HPLC step that is usually necessary in conventionnal approaches to optimize removal of organotin toxic precursors and side products was replaced by a filtration through a silica cartridge with a significantly reduced loss of radiolabeled product. The purified radioiodinated and astatinated prosthetic groups were then conjugated efficiently to an anti-CD138 monoclonal antibody (75–80% conjugation yield). By using this novel and simple radiohalogenation procedure, higher overall radiochemical yields of astatination were obtained in comparison with the use of an arylstannane precursor and procedures of the litterature for labeling the same antibody. Overall, due to their simplicity of use and high robustness, these new precursors should simplify the labeling of proteins of interest with iodine and astatine radioisotopes for imaging and therapeutic applications.

show abstract

“…1C). Moreover, Zhang et al 34 and Wilson et al 35 disclosed aromatic 131 I/ 123 I-iodination reactions involving copper catalysts and boronic acids/esters (Fig. 1C).…”

mentioning

confidence: 91%

[¹¹C]Cyanation of arylboronic acids in aqueous solutions

Placzek

Hooker

et al. 2017

Chem. Commun.

View full text Add to dashboard Cite

show abstract

A Highly Efficient Copper‐Mediated Radioiodination Approach Using Aryl Boronic Acids

Cited by 62 publications

References 28 publications

Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes

Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes

Bifunctional aryliodonium salts for highly efficient radioiodination and astatination of antibodies

[¹¹C]Cyanation of arylboronic acids in aqueous solutions

Contact Info

Product

Resources

About

A Highly Efficient Copper‐Mediated Radioiodination Approach Using Aryl Boronic Acids

Cited by 62 publications

References 28 publications

Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes

Rapid Iododeboronation with and without Gold Catalysis: Application to Radiolabelling of Arenes

Bifunctional aryliodonium salts for highly efficient radioiodination and astatination of antibodies

[11C]Cyanation of arylboronic acids in aqueous solutions

Contact Info

Product

Resources

About

[¹¹C]Cyanation of arylboronic acids in aqueous solutions