Document Detail


A one-pot three-component radiochemical reaction for rapid assembly of 125I-labeled molecular probes.
MedLine Citation:
PMID:  23194416     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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 [(125)I]iodide to yield 5-[(125)I]iodo-1,2,3-triazoles. Using a selection of azides and alkynes in a combinatorial approach, we have synthesized a library of structurally diverse (125)I-labeled triazoles functionalized with bioconjugation groups, fluorescent dyes, and biomolecules. Our preliminary biological evaluation suggests that 5-[(125)I]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.
Authors:
Ran Yan; Kerstin Sander; Eva Galante; Vineeth Rajkumar; Adam Badar; Mathew Robson; Ethaar El-Emir; Mark F Lythgoe; R Barbara Pedley; Erik Årstad
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2013-01-07
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  135     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2013 Jan 
Date Detail:
Created Date:  2013-01-16     Completed Date:  2013-06-19     Revised Date:  2014-02-20    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  703-9     Citation Subset:  IM    
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MeSH Terms
Descriptor/Qualifier:
Iodine Radioisotopes / chemistry*
Molecular Probes / chemical synthesis,  chemistry*
Molecular Structure
Radiochemistry
Time Factors
Triazoles / chemical synthesis,  chemistry*
Grant Support
ID/Acronym/Agency:
G1001497//Medical Research Council; //Cancer Research UK; //Department of Health; //Medical Research Council
Chemical
Reg. No./Substance:
0/Iodine Radioisotopes; 0/Molecular Probes; 0/Triazoles

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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