Synthesis and characterization of oligonucleotide conjugates bearing electroactive labels

Oxime bond formation has been applied to the preparation of oligonucleotides labeled with electrochemical ferrocene and viologen labels. Aminooxy functionalized ferrocene and viologen derivatives were prepared by a straightforward route and efficiently conjugated with aldehyde containing oligonucleo...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2013-02, Vol.23 (4), p.955-958
Main Authors: Moreau, Julie, Dendane, Nabil, Schöllhorn, Bernd, Spinelli, Nicolas, Fave, Claire, Defrancq, Eric
Format: Article
Language:English
Subjects:
Chemical Sciences
Conjugation
disulfide bonds
Electrochemical Techniques - methods
electrochemistry
Ferrocene
Ferrous Compounds - chemistry
genetic conjugation
Metallocenes
Oligonucleotides
Oligonucleotides - chemical synthesis
Oligonucleotides - chemistry
Oxime
Oximes - chemical synthesis
Oximes - chemistry
Viologen
Viologens - chemistry
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Summary:Oxime bond formation has been applied to the preparation of oligonucleotides labeled with electrochemical ferrocene and viologen labels. Aminooxy functionalized ferrocene and viologen derivatives were prepared by a straightforward route and efficiently conjugated with aldehyde containing oligonucleotides either at 3′ or 5′ end. Both labels were found to not disturb the recognition properties of the oligonucleotide. The versatility of the method was further demonstrated by preparing bi-functionalized conjugates with a disulfide at 3′ end and an electrochemical label at 5′ end.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2012.12.057