Hybrid lipid oligonucleotide conjugates: synthesis, self-assemblies and biomedical applications

Patwa, Amit; Gissot, Arnaud; Bestel, Isabelle; Barthélémy, Philippe

doi:10.1039/c1cs15038c

Cited by 107 publications

(97 citation statements)

References 111 publications

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“…The majority of these approaches involve the synthesis of nucleic acids with hydrophobic modification(s) resulting in surfactant molecules that spontaneously insert into amphiphile aggregate structures. Here we will primarily consider their structures and physical properties; details of their synthesis have been reviewed elsewhere [43,44].…”

Section: Functionalisation Of Liposomes With Dnamentioning

confidence: 99%

Application of nucleic acid–lipid conjugates for the programmable organisation of liposomal modules

Beales

Vanderlick

2014

Advances in Colloid and Interface Science

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Section: Functionalisation Of Liposomes With Dnamentioning

confidence: 99%

Application of nucleic acid–lipid conjugates for the programmable organisation of liposomal modules

Beales

Vanderlick

2014

Advances in Colloid and Interface Science

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“…[16][17][18][19][20][21] The wide range of potential applications has led to considerable interest in the properties of oligonucleotides conjugated to polymers or lipophilic chains. [22][23][24][25][26][27][28][29][30] DNA conjugates often combine multiple self-assembly motifs enabling selective and orthogonal noncovalent interactions. [31][32][33][34][35][36][37] To date, little is known about materials from DNA conjugates, in which the interactions between the non-DNA parts are central for the hierarchical organization.…”

Section: Introductionmentioning

confidence: 99%

Pathway Diversity in the Self-Assembly of DNA-Derived Bioconjugates

Vyborna

Vybornyi²,

Häner

2016

Bioconjugate Chem.

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The pathway diversity of the self-assembly of amphiphilic DNA-pyrene conjugates is described.The hydrophobic pyrene units drive the self-assembly of the anionic oligomers in an aqueous environment into ribbon-shaped, DNA-grafted supramolecular polymers. Isothermal mixing of two types of sorted ribbons, each of which contains only one kind of two complementary oligonucleotides, results in the formation of tight networks. Thermal disassembly of these kinetically trapped networks and subsequent re-assembly of the liberated components leads to mixed supramolecular polymers, which now contain both types of oligonucleotides. The scrambling of the oligonucleotides prevents the interaction between ribbons and, thus, network formation. The results show that a high local density of DNA strands in linear arrays favors hybridization among sorted polymers, whereas hybridization among mixed arrays is prevented. The lack of DNA hybridization among mixed ribbons is ascribed to the electrostatic repulsion between identical, hence non-complementary, oligonucleotides. The findings highlight the importance of kinetically trapped states on the structural and functional properties of supramolecular polymers containing orthogonal self-assembly motifs.

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“…This was likely a result of the conjugated a-tocopherol interfering with the access of the ASO to the target mRNA in the nucleus by tethering the ASO to lipid membranes or other molecules within cells 27 . Lipid-conjugated siRNA, which was designed with a cleavable linker or nucleotide to release the lipid from oligonucleotides in the cells, had more potency 25,38,39 . In our previously reported case, a-tocopherol conjugated to the 5 0 terminus of the guide strand of 27/29-mer siRNA was processed by Dicer to generate 21/21-mer mature siRNA, resulting in a release of a-tocopherol moiety from the oligonucleotide in the cytoplasm 25 .…”

Section: Resultsmentioning

confidence: 99%

DNA/RNA heteroduplex oligonucleotide for highly efficient gene silencing

Yokota

2016

Clinical & Exp Neuroim

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Antisense oligonucleotides (ASOs) are recognized therapeutic agents for the modulation of specific genes at the post-transcriptional level. Similar to any medical drugs, there are opportunities to improve their efficacy and safety. Here we develop a short DNA/RNA heteroduplex oligonucleotide (HDO) with a structure different from double-stranded RNA used for short interfering RNA and single-stranded DNA used for ASO. A DNA/locked nucleotide acid gapmer duplex with an a-tocopherol-conjugated complementary RNA (Toc-HDO) is significantly more potent at reducing the expression of the targeted mRNA in liver compared with the parent single-stranded gapmer ASO. Toc-HDO also improves the phenotype in disease models more effectively. In addition, the high potency of Toc-HDO results in a reduction of liver dysfunction observed in the parent ASO at a similar silencing effect. HDO technology offers a novel concept of therapeutic oligonucleotides, and the development of this molecular design opens a new therapeutic field.

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Hybrid lipid oligonucleotide conjugates: synthesis, self-assemblies and biomedical applications

Abstract: Hybrid lipid oligonucleotide conjugates are finding more and more biotechnological applications. This short critical review highlights their synthesis, supramolecular organization as well as their applications in the field of biotechnology (111 references).

Cited by 107 publications

References 111 publications

Application of nucleic acid–lipid conjugates for the programmable organisation of liposomal modules

Application of nucleic acid–lipid conjugates for the programmable organisation of liposomal modules

Pathway Diversity in the Self-Assembly of DNA-Derived Bioconjugates

DNA/RNA heteroduplex oligonucleotide for highly efficient gene silencing

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