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Molecules 2014, 19(7), 10495-10523; doi:10.3390/molecules190710495

Thioctic Acid Derivatives as Building Blocks to Incorporate DNA Oligonucleotides onto Gold Nanoparticles

1
Institute for Advanced Chemistry of Catalonia (IQAC), Consejo Superior de Investigaciones Científicas (CSIC), Jordi Girona 18-26, E-08034 Barcelona, Spain
2
Networking Center on Bioengineering, Biomaterials and Nanomedicine (CIBER-BBN), Barcelona, 08034, Spain
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 11 June 2014 / Revised: 4 July 2014 / Accepted: 4 July 2014 / Published: 18 July 2014
(This article belongs to the Section Molecular Diversity)
View Full-Text   |   Download PDF [1382 KB, uploaded 18 July 2014]   |  

Abstract

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. View Full-Text
Keywords: thioctic acid; threoninol; DNA; DNA-gold nanoparticle conjugates; stability; surface coverage; cathepsin thioctic acid; threoninol; DNA; DNA-gold nanoparticle conjugates; stability; surface coverage; cathepsin
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This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Pérez-Rentero, S.; Grijalvo, S.; Peñuelas, G.; Fàbrega, C.; Eritja, R. Thioctic Acid Derivatives as Building Blocks to Incorporate DNA Oligonucleotides onto Gold Nanoparticles. Molecules 2014, 19, 10495-10523.

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