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Título: | Thioctic acid derivatives as building blocks to incorporate DNA oligonucleotides onto gold nanoparticles |
Autor: | Pérez-Rentero, Sonia CSIC ORCID; Grijalvo, Santiago CSIC ORCID; Peñuelas, Guillem; Fàbrega, Carme CSIC ORCID; Eritja Casadellà, Ramón CSIC ORCID | Palabras clave: | Cathepsins DNA DNA-gold nanoparticle conjugates Stability Surface coverage Thioctic acid Threoninol |
Fecha de publicación: | jul-2014 | Editor: | Multidisciplinary Digital Publishing Institute | Citación: | Molecules | Resumen: | Oligonucleotide 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. | Versión del editor: | DOI: 10.3390/molecules190710495 | URI: | http://hdl.handle.net/10261/126492 | DOI: | 10.3390/molecules190710495 |
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molecules-19-10495thiooctic.pdf | Artículo principal | 1,38 MB | Adobe PDF | Visualizar/Abrir |
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