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

Pérez-Rentero, Sónia; Grijalvo, Santiago; Peñuelas, Guillem; Fàbrega, Carme; Eritja, Ramón

doi:10.3390/molecules190710495

Cited by 22 publications

(12 citation statements)

References 55 publications

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“…The interesting properties of the TTF-oligonucleotides prompted us to synthesize a TTF derivative carrying a biodegradable triglycyl peptide linker between the oligonucleotide and the TTF molecule. This simple peptide sequence has been demonstrated to be hydrolyzed by cathepsin B present in endosomes [22]. During the preparation of the mentioned TTF derivative we accidentally observed the formation of gels in some solvents.…”

Section: Introductionmentioning

confidence: 88%

Synthesis, Characterization, and Self-Assembly of a Tetrathiafulvalene (TTF)–Triglycyl Derivative

et al. 2018

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In this work, we describe the synthesis, characterization, and self-assembly properties of a new tetrathiafulvalene (TTF)-triglycyl low-molecular-weight (LMW) gelator. Supramolecular organogels were obtained in various solvents via a heating-cooling cycle. Critical gelation concentrations (CGC) (range ≈ 5-50 g/L) and thermal gel-to-sol transition temperatures (T gel) (range ≈ 36-51 • C) were determined for each gel. Fourier transform infrared (FT-IR) spectroscopy suggested that the gelator is also aggregated in its solid state via a similar hydrogen-bonding pattern. The fibrillar microstructure and viscoelastic properties of selected gels were demonstrated by means of field-emission electron microscopy (FE-SEM) and rheological measurements. As expected, exposure of a model xerogel to I 2 vapor caused the oxidation of the TTF unit as confirmed by UV-vis-NIR analysis. However, FT-IR spectroscopy showed that the oxidation was accompanied with concurrent alteration of the hydrogen-bonded network.

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Section: Introductionmentioning

confidence: 88%

Synthesis, Characterization, and Self-Assembly of a Tetrathiafulvalene (TTF)–Triglycyl Derivative

et al. 2018

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“…5'-Fluorescein-CE phosphoramidite (6-FAM) was purchased from Link Technologies (Lanarkshire, Scotland). A fluorescently labeled oligodeoxynucleotide sequence (5'-FITC-CGG AGG TAC ATT CGA CTT GA-3'; FITC-ODN) 40 and a scrambled phosphorothioate oligonucleotide sequence (5'-CTG TCT GAC GTT CTT TGT-3'; Scr) were synthesized in a DNA/RNA synthesizer ABI 3400 and purified according to DMT off-based protocols with a semi-preparative HPLC. 6-FAM was automatically coupled at the 5'-termini via phosphoramidite chemistry.…”

Section: Methodsmentioning

confidence: 99%

Cationic nioplexes-in-polysaccharide-based hydrogels as versatile biodegradable hybrid materials to deliver nucleic acids

et al. 2017

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Two polysaccharide-based hydrogels made of only kcarrageenan (4%; w/v) or of a mixture of methylcellulose:kcarrageenan (2%; w/v) were used to encapsulate cationic nioplexes. These vesicular particles were made of a synthetic aminolipid and polysorbate-80 (Tween-80), as a non-ionic surfactant agent. According to oscillatory rheological measurements, the presence of nioplexes did not compromise the mechanical integrity of the gels. In vitro niosomal release experiments demonstrated the liberation of nioplexes up to 24 h, and the curves were fitted according to Higuchi, Korsmeyer-Peppas and Weibull equation models, which indicated Fickian-diffusion controlled mechanisms. Besides nioplexes, cervical cancer cells were also entrapped within the biohydrogels. Cell release confirmed that these materials did not affect the cell viability, allowing cells to spread and proliferate after 24 h. The applicability of these biocompatible hydrogels was also extended to gene delivery. In this regard, the best silencing activities were found when cationic niosomes were complexed with antisense oligonucleotides in KC hydrogels. Nioplexes were able to release through the hydrogel and promoted silencing of luciferase expression in the presence of serum without using commercially available cationic lipids. Overall, the formation of such hybrid materials by integrating cationic nioplexes within biodegradable hydrogels provides a new perspective for the delivery of macromolecular therapeutics.

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“…Among the possible 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 Submitted to 9 causes stated above, our CFS analysis indicates that increasing the yield of the DNA ink formation is an important factor. Therefore, the use of cyclic disulfides such as lipoic acid derivatives [13] reported to increase binding of oligonucleotides to gold surfaces combined with increased DNA ink that can bind per each OGNP, [21] would provide improved yields to our DNA origami stamp method for gold nanoparticle alignment. Figure S8 shows examples of OGNP of each class obtained in CFS runs.…”

Section: Revised Manuscriptmentioning

confidence: 99%

DNA‐Origami‐Driven Lithography for Patterning on Gold Surfaces with Sub‐10 nm Resolution

et al. 2017

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The programmability [1] and self-assembly properties of DNA provides means of precise organization of matter at the nanoscale. [2] DNA origami allows the folding of DNA into twodimensional [3] and three-dimensional [4] structures, and has been used to organize biomolecules, [2b, e, 5] nanophotonic [2a, c, f, 6] and electronic [7] components with a resolution of 6 nm / pixel. [8] Two-dimensional DNA origami has been also used as a platform to organize other chemical [9] species that can then be placed on technologically relevant substrates. [2c, 10] Nevertheless, these approaches have only used the DNA nanostructure to hold the chemical species on the surface and, to the best of our knowledge, have never been utilized to immobilize nucleic acids patterns on surfaces with sub-10 nm resolution providing an enable 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 59 60 61 62 63 64 65 Submitted to 2 platform for potential applications such as multiplexed biochemical assays. [11] to the creation of metasurfaces [12] with potentially reconfigurable features. Revised ManuscriptHerein we report on the use of a two-dimensional DNA origami as a template to covalently attach DNA with a pre-programmed pattern on a surface (see Scheme 1). The method utilizes the incorporation of modified staple strands in programmed positions of the DNA origami (DNA origami stamp), acting as DNA ink. Once the DNA origami is immobilized on the surface, the modified staples can react with the surface creating a defined DNA pattern (Stamping step). The pattern can then be exposed upon denaturation of the DNA origami stamp (Unmasking step), allowing the non-bound staples to be rinsed off of the surface. As a proof-of-principle of this methodology, we have created a linear pattern of thiolmodified DNA ink on gold surfaces. The formation of the linear pattern was revealed by the successful formation of bead-on-a-string-like structures (here named "chains" for simplicity) composed of gold nanoparticles conjugated with thiol-oligonucleotides (OGNP) that are hybridized to the DNA ink pattern (Development step). The linear pattern provided a direct evidence of the stamping process and was chosen as a simple geometry that can be statistically analysed in our experimental setup. Montecarlo Simulations have been used for better understanding of our statistical results and to determine key elements governing the process that can be used for future optimization of pattern information transfer with DNA origami stamp methodology. Furthermore, we have studied the development of more complex patterns using Montecarlo Simulations.We demonstrate that our approach can be employed to form DNA patterns with sub-10 nm resolution to flat gold surfaces, an unsolved goal to date. This methodology can thus be extended to other surfaces utilizing different covalent strategies. [10b, 13] M...

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

Cited by 22 publications

References 55 publications

Synthesis, Characterization, and Self-Assembly of a Tetrathiafulvalene (TTF)–Triglycyl Derivative

Synthesis, Characterization, and Self-Assembly of a Tetrathiafulvalene (TTF)–Triglycyl Derivative

Cationic nioplexes-in-polysaccharide-based hydrogels as versatile biodegradable hybrid materials to deliver nucleic acids

DNA‐Origami‐Driven Lithography for Patterning on Gold Surfaces with Sub‐10 nm Resolution

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