A One-Pot Three-Component Radiochemical Reaction for Rapid Assembly of125I-Labeled Molecular Probes

Article


Yan, Ran, Sander, Kerstin, Galante, E., Rajkumar, Vineeth, Badar, Adam, Robson, Mathew, El-Emir, Ethaar, Lythgoe, Mark F., Pedley, R. Barbara and Årstad, Erik 2012. A One-Pot Three-Component Radiochemical Reaction for Rapid Assembly of125I-Labeled Molecular Probes. Journal of the American Chemical Society. 135 (2), pp. 703-709.
AuthorsYan, Ran, Sander, Kerstin, Galante, E., Rajkumar, Vineeth, Badar, Adam, Robson, Mathew, El-Emir, Ethaar, Lythgoe, Mark F., Pedley, R. Barbara and Årstad, Erik
Abstract

Nuclear imaging in conjunction with radioactive tracers enables noninvasive measurements of biochemical events in vivo. However, access to tracers remains limited due to the lack of methods for rapid assembly of radiolabeled molecules with the prerequisite biological activity. Herein, we report a one-pot, three-component, copper(II)-mediated reaction of azides, alkynes, and [125I]iodide to yield 5-[125I]iodo-1,2,3-triazoles. Using a selection of azides and alkynes in a combinatorial approach, we have synthesized a library of structurally diverse 125I-labeled triazoles functionalized with bioconjugation groups, fluorescent dyes, and biomolecules. Our preliminary biological evaluation suggests that 5-[125I]iodo-1,2,3-triazoles are resistant to deiodination in vivo, both as small molecular probes and as antibody conjugates. The ability to incorporate radioactive iodide into triazoles directly from the parent azides and alkynes makes the method broadly applicable and offers the potential to rapidly assemble molecular probes from an array of structurally diverse, and readily available, building blocks.

JournalJournal of the American Chemical Society
Journal citation135 (2), pp. 703-709
ISSN0002-7863
Year2012
PublisherAmerican Chemical Society
Digital Object Identifier (DOI)doi:10.1021/ja307926g
Web address (URL)https://doi.org/10.1021/ja307926g
Publication dates
Print29 Nov 2012
Publication process dates
Deposited18 Aug 2017
Accepted01 Nov 2012
Copyright information© ACS 2013
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