A One-Pot Three-Component Radiochemical Reaction for Rapid Assembly of 125I-labeled Molecular Probes

Ran Yan; Kerstin Sander; Eva Galante; Vineeth Rajkumar; Adam Badar; Mathew Robson; Ethaar El-Emir; Mark F. Lythgoe; R. Barbara  Pedley; Erik  Arstad

doi:10.1021/ja307926g

A One-Pot Three-Component Radiochemical Reaction for Rapid Assembly of 125I-labeled Molecular Probes

Ran Yan, Kerstin Sander, Eva Galante, Vineeth Rajkumar, Adam Badar, Mathew Robson, Ethaar El-Emir, Mark F. Lythgoe, R. Barbara Pedley, Erik Arstad

Research output: Contribution to journal › Article › peer-review

83 Citations (Scopus)

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.

Original language	English
Article number	N/A
Pages (from-to)	703−709
Number of pages	7
Journal	Journal of The American Chemistry Society
Volume	135
Issue number	2
DOIs	https://doi.org/10.1021/ja307926g
Publication status	Published - 16 Jan 2013

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title = "A One-Pot Three-Component Radiochemical Reaction for Rapid Assembly of 125I-labeled Molecular Probes",

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.",

author = "Ran Yan and Kerstin Sander and Eva Galante and Vineeth Rajkumar and Adam Badar and Mathew Robson and Ethaar El-Emir and Lythgoe, {Mark F.} and Pedley, {R. Barbara} and Erik Arstad",

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doi = "10.1021/ja307926g",

language = "English",

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journal = "Journal of The American Chemistry Society",

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T1 - A One-Pot Three-Component Radiochemical Reaction for Rapid Assembly of 125I-labeled Molecular Probes

AU - Yan, Ran

AU - Sander, Kerstin

AU - Galante, Eva

AU - Rajkumar, Vineeth

AU - Badar, Adam

AU - Robson, Mathew

AU - El-Emir, Ethaar

AU - Lythgoe, Mark F.

AU - Pedley, R. Barbara

AU - Arstad, Erik

PY - 2013/1/16

Y1 - 2013/1/16

N2 - 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.

AB - 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.

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DO - 10.1021/ja307926g

M3 - Article

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VL - 135

SP - 703−709

JO - Journal of The American Chemistry Society

JF - Journal of The American Chemistry Society

IS - 2

M1 - N/A

ER -

A One-Pot Three-Component Radiochemical Reaction for Rapid Assembly of 125I-labeled Molecular Probes

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