Modern methods for the synthesis of peptide–oligonucleotide conjugates

Zubin, E. M.; Романова, Е. А.; Oretskaya, T. S.

doi:10.1070/rc2002v071n03abeh000707

Cited by 38 publications

(27 citation statements)

References 90 publications

(182 reference statements)

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“…There are numerous methods reported for synthesis of peptide–oligonucleotide conjugates [comprehensively reviewed in (27)]. We have developed previously a number of methods for such conjugation, e.g.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, cellular uptake and HIV-1 Tat-dependent trans-activation inhibition activity of oligonucleotide analogues disulphide-conjugated to cell-penetrating peptides

Turner

2005

Nucleic Acids Research

118

115

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Oligonucleotides composed of 2′-O-methyl and locked nucleic acid residues complementary to HIV-1 trans-activation responsive element TAR block Tat-dependent trans-activation in a HeLa cell assay when delivered by cationic lipids. We describe an improved procedure for synthesis and purification under highly denaturing conditions of 5′-disulphide-linked conjugates of 3′-fluorescein labelled oligonucleotides with a range of cell-penetrating peptides and investigate their abilities to enter HeLa cells and block trans-activation. Free uptake of 12mer OMe/LNA oligonucleotide conjugates to Tat (48–58), Penetratin and R9F2 was observed in cytosolic compartments of HeLa cells. Uptake of the Tat conjugate was enhanced by N-terminal addition of four Lys or Arg residues or a second Tat peptide. None of the conjugates entered the nucleus or inhibited trans-activation when freely delivered, but inhibition was obtained in the presence of cationic lipids. Nuclear exclusion was seen for free delivery of Tat (48–58), Penetratin and R9 conjugates of 16mer phosphorothioate OMe oligonucleotide. Uptake into human fibroblast cytosolic compartments was seen for Tat, Penetratin, R9F2 and Transportan conjugates. Large enhancements of HeLa cell uptake into cytosolic compartments were seen when free Tat peptide was added to Tat conjugate of 12mer OMe/LNA oligonucleotide or Penetratin peptide to Penetratin conjugate of the same oligonucleotide.

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Section: Introductionmentioning

confidence: 99%

Synthesis, cellular uptake and HIV-1 Tat-dependent trans-activation inhibition activity of oligonucleotide analogues disulphide-conjugated to cell-penetrating peptides

Turner

2005

Nucleic Acids Research

118

115

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“…[4][5][6] The assistance from Mr. Dean W. Seppala (electronics) and Mr. Jerry L. Lutz (NMR) is gratefully acknowledged. It is remarkable that no modification of the synthesizer is needed, and the only item needed for the method is a larger DNA synthesis column, which is commercially available and reasonably priced.…”

Section: Resultsmentioning

confidence: 99%

Peptide and peptide nucleic acid syntheses using a DNA/RNA synthesizer

et al. 2014

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The use of an ABI 394 DNA/RNA synthesizer for peptide and peptide nucleic acid (PNA) syntheses is described. No additional physical part or software is needed for the application. A commercially available large DNA synthesis column was used, and only about half of its volume was filled with resin when the resin was fully swollen. With additional space in the top portion of the column, agitation of reaction mixture was achieved by bubbling argon from the bottom without losing solution. Removing solutions from column was achieved by flushing argon from top to bottom. Two peptide and two PNA sequences were synthesized. Good yields were obtained in all the cases. The method is easy to follow by researchers who are familiar with DNA/RNA synthesizer.

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“…Several reviews on the synthesis of oligonucleotidepeptide conjugates (OPC) [9,[11][12][13][14] and PNA-peptide conjugates (PPC) are now available. In general there are two main synthetic strategies: a) total stepwise solid-phase synthesis and b) solution-phase or solid-phase fragment coupling of peptides with oligonucleotides that have each been prepared separately on their own solid-supports.…”

Section: Synthetic Methodologiesmentioning

confidence: 99%

Conjugates of Oligonucleotides and Analogues with Cell Penetrating Peptides as Gene Silencing Agents

Zatsepin¹,

Turner²,

Oretskaya³

et al. 2005

CPD

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The review describes key aspects of the synthesis and biological activities of conjugates of oligonucleotides and their analogues with synthetic peptides, in particular aimed towards gene silencing applications. The common methods of synthesis of oligonucleotide-peptide conjugates (OPCs) and PNA-peptide conjugates (PPCs) are described, which include both total solid-phase and fragment coupling approaches. In addition, various applications of conjugates as gene silencing agents are outlined. These include antisense and steric block applications in mammalian cells of OPCs, PPCs and phosphorodiamidate morpholinooligonucleotide (PMO)-peptide conjugates, gene silencing in bacteria, various DNA targeting applications, and recent reports of gene silencing activities of siRNA-peptide conjugates. A table listing all peptides used as oligonucleotide conjugates for gene silencing applications is also included.

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Modern methods for the synthesis of peptide–oligonucleotide conjugates

Cited by 38 publications

References 90 publications

Synthesis, cellular uptake and HIV-1 Tat-dependent trans-activation inhibition activity of oligonucleotide analogues disulphide-conjugated to cell-penetrating peptides

Synthesis, cellular uptake and HIV-1 Tat-dependent trans-activation inhibition activity of oligonucleotide analogues disulphide-conjugated to cell-penetrating peptides

Peptide and peptide nucleic acid syntheses using a DNA/RNA synthesizer

Conjugates of Oligonucleotides and Analogues with Cell Penetrating Peptides as Gene Silencing Agents

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