Stepwise synthesis of oligonucleotide-peptide conjugates containing guanidinium and lipophilic groups in their 3'-termini.
Two 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.
Grijalvo
Santiago
S
Institute for Research in Biomedicine, Networking Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Barcelona, Spain.
Terrazas
Montserrat
M
Aviñó
Anna
A
Eritja
Ramón
R
D000818:Animals; D001483:Base Sequence; D002460:Cell Line; D020868:Gene Silencing; D019791:Guanidine / Q000138:chemical synthesis / Q000737:chemistry*; D008156:Luciferases / Q000235:genetics / Q000378:metabolism; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry*; D016376:Oligonucleotides, Antisense / Q000138:chemical synthesis / Q000737:chemistry / Q000235:genetics; D010455:Peptides / Q000138:chemical synthesis / Q000737:chemistry*; D054735:Phosphorothioate Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D048790:Renilla / Q000201:enzymology
D009841:Oligonucleotides; D016376:Oligonucleotides, Antisense; D010455:Peptides; D054735:Phosphorothioate Oligonucleotides; D008156:Luciferases; D019791:Guanidine