2024-03-28T10:50:20Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/1264922021-12-28T16:00:12Zcom_10261_5063com_10261_5col_10261_5066
2015-12-04T08:04:21Z
urn:hdl:10261/126492
Thioctic acid derivatives as building blocks to incorporate DNA oligonucleotides onto gold nanoparticles
Pérez-Rentero, Sonia
Grijalvo, Santiago
Peñuelas, Guillem
Fàbrega, Carme
Eritja Casadellà, Ramón
Consejo Superior de Investigaciones Científicas (España)
Cathepsins
DNA
DNA-gold nanoparticle conjugates
Stability
Surface coverage
Thioctic acid
Threoninol
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.
2015-12-04T08:04:21Z
2015-12-04T08:04:21Z
2014-07
artículo
Molecules
http://hdl.handle.net/10261/126492
10.3390/molecules190710495
http://dx.doi.org/10.13039/501100003339
25045890
eng
Publisher's version
DOI: 10.3390/molecules190710495
Sí
http://www.sherpa.ac.uk/romeo/issn/1420-3049/
openAccess
Multidisciplinary Digital Publishing Institute