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Thioctic acid derivatives as building blocks to incorporate DNA oligonucleotides onto gold nanoparticles

AuthorsPérez-Rentero, Sonia; Grijalvo, Santiago ; Peñuelas, Guillem; Fàbrega, Carme ; Eritja Casadellà, Ramón
DNA-gold nanoparticle conjugates
Surface coverage
Thioctic acid
Issue DateJul-2014
PublisherMultidisciplinary Digital Publishing Institute
AbstractOligonucleotide gold nanoparticle conjugates are being used as diagnostic tools and gene silencing experiments. Thiol-chemistry is mostly used to functionalize gold nanoparticles with oligonucleotides and to incorporate DNA or RNA molecules onto gold surfaces. However, the stability of such nucleic acid-gold nanoparticle conjugates in certain conditions may be a limitation due to premature break of the thiol-gold bonds followed by aggregation processes. Here, we describe a straightforward synthesis of oligonucleotides carrying thioctic acid moiety based on the use of several thioctic acid-L- Threoninol derivatives containing different spacers, including triglycine, short polyethyleneglycol, or aliphatic spacers. The novel thioctic-oligonucleotides were used for the functionalization of gold nanoparticles and the surface coverage and stability of the resulting thioctic-oligonucleotide gold nanoparticles were assessed. In all cases gold nanoparticles functionalized with thioctic-oligonucleotides had higher loadings and higher stability in the presence of thiols than gold nanoparticles prepared with commercially available thiol-oligonucleotides. Furthermore, the thioctic derivative carrying the triglycine linker is sensitive to cathepsin B present in endosomes. In this way this derivative may be interesting for the cellular delivery of therapeutic oligonucleotides as these results provides the basis for a potential endosomal escape.
Publisher version (URL)DOI: 10.3390/molecules190710495
Appears in Collections:(IQAC) Artículos
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