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Title

Stepwise synthesis of oligonucleotide–peptide conjugates containing guanidinium and lipophilic groups in their 3′-termini

AuthorsGrijalvo, Santiago ; Terrazas, Montserrat ; Aviñó, Anna ; Eritja Casadellà, Ramón
KeywordsODN–peptide conjugates
Dickerson–Drew dodecamer
Luciferase
Postsynthetic guanidinylation reaction
Ureas
Antisense oligonucleotide
Phosphorothioates
Issue Date1-Apr-2010
PublisherElsevier
CitationBioorganic and Medicinal Chemistry Letters 20(7): 2144–2147 (2010)
AbstractTwo different series of oligonucleotide–peptide conjugates have been efficiently synthesized by stepwise solid-phase synthesis. First, oligonucleotides and oligonucleotide phosphorothioates containing polar groups at the 3′-termini, such as amine and guanidinium groups were prepared. ODNs conjugates carrying several lysine residues were obtained directly from Fmoc deprotection whereas ODN conjugates with guanidinium groups were obtained by post-synthetic guanidinylation. The second family contains different urea moieties that were achieved by standard protocols. All products were fully characterized by reversed phase HPLC and MALDI-TOF mass spectrometry yielding satisfactory results. Oligonucleotide–phosphorothioate conjugates were evaluated as potential antisense oligonucleotides in the inhibition of the luciferase gene.
Publisher version (URL)http://dx.doi.org/10.1016/j.bmcl.2010.02.049
URIhttp://hdl.handle.net/10261/47084
DOI10.1016/j.bmcl.2010.02.049
ISSN0960-894X
E-ISSN1464-3405
Appears in Collections:(IQAC) Artículos
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