Perfluoroalkylchain conjugation as a new tactic for enhancing cell permeability of peptide nucleic acids (PNAs) via reducing the nanoparticle size

Ellipilli, Satheesh; Murthy, Raghavendra Vasudeva; Ganesh, Krishna N.

doi:10.1039/c5cc05342k

Cited by 26 publications

(25 citation statements)

References 42 publications

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“…These thiols were used in combination with 1H,1H,2H,2H-perfluoro-1-decanethiol (HF8) or 1H,1H,2H,2H-perfluoro-1-octanethiol (HF6) as the fluorinated components. The uptake by HeLa cells and the cytotoxicity of these charged H-/F-mixed monolayer AuNPs were compared to those of charge neutral NPs obtained by using the thiols N-1-{2-[2-(2-methoxyethoxy)ethoxy]ethyl}-8-sulfanyloctanamide (HC8TEG) and 2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9-hexadecafluoro-10-(methoxy-PEG550)decan-1-thiol (HF8PEG), Figure 1B. The synthesis of the thiols HMDDS, HMDA, and HTMDA is reported in the Supporting Information (SI).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…4,5 Soft NPs made of peptide nucleic acid (PNA) conjugated to perfluoroundecanoyl chains display a 3-fold higher cellular uptake by HeLa cells with respect to undecanoyl PNA. 6 Soft NPs obtained by complexation of polyampholites with perfluorododecanoic acid were found to hinder the formation of amyloid fibrils, while hydrogenated analogues were not effective. 7,8 Furthermore, in a thermodynamic analysis of water-soluble fluorinated AuNPs as putative drug delivery systems, we found that nanoparticles displaying fluorinated ligands on their surface interact with drug-like guests with higher affinity than hydrogenated NPs of similar structure.…”

Section: ■ Introductionmentioning

confidence: 97%

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Fluorinated and Charged Hydrogenated Alkanethiolates Grafted on Gold: Expanding the Diversity of Mixed-Monolayer Nanoparticles for Biological Applications

et al. 2016

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Low intrinsic toxicity, high solubility, and stability are important and necessary features of gold nanoparticles to be used in the biomedical field. In this context, charged nanoparticles proved to be very versatile, and among them charged mixed-monolayer gold nanoparticles, displaying monolayers with well-defined morphologies, represent a paradigm. By using mixtures of hydrogenated and fluorinated thiols, the formation of monolayer domains may be brought to an extreme because of the immiscibility of fluorinated and hydrogenated chains. Following this rationale, mixed monolayer gold nanoparticles featuring ammonium, sulfonate, or carboxylic groups on their surface were prepared by using amphiphilic hydrogenated thiols and 1H,1H,2H,2H-perfluoro-alkanethiols. The toxicity of these systems was assessed in HeLa cells and was found to be, in general, low even for the cationic nanoparticles which usually show a high cytotoxicity and is comparable to that of homoligand gold nanoparticles displaying amphiphiliccharge neutralhydrogenated or fluorinated thiolates in their monolayer. These properties make the mixed ligand monolayer gold nanoparticles an interesting new candidate for medical application.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 97%

Fluorinated and Charged Hydrogenated Alkanethiolates Grafted on Gold: Expanding the Diversity of Mixed-Monolayer Nanoparticles for Biological Applications

et al. 2016

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“…There are reports that the cells can uptake 0.5–8 µm particles by phagocytosis [ 23 ]. Particles around 500 nm can also enter the cytosol via cellular permeability [ 24 ]. It is known that particles bigger than 200 nm are usually filtered by the liver, while smaller particles can be quickly cleared by the kidney or through extravasation [ 25 ].…”

Section: Resultsmentioning

confidence: 99%

Modified Nanoemulsions with Iron Oxide for Magnetic Resonance Imaging

et al. 2016

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A nanoemulsion (NE) is a surfactant-based, oil-in-water, nanoscale, high-energy emulsion with a mean droplet diameter of 400–600 nm. When mixed with antigen and applied nasally, a NE acts as a mucosal adjuvant and induces mucosal immune responses. One possible mechanism for the adjuvant effect of this material is that it augments antigen uptake and distribution to lymphoid tissues, where the immune response is generated. Biocompatible iron oxide nanoparticles have been used as a unique imaging approach to study the dynamics of cells or molecular migration. To study the uptake of NEs and track them in vivo, iron oxide nanoparticles were synthesized and dispersed in soybean oil to make iron oxide-modified NEs. Our results show that iron oxide nanoparticles can be stabilized in the oil phase of the nanoemulsion at a concentration of 30 µg/μL and the iron oxide-modified NEs have a mean diameter of 521 nm. In vitro experiments demonstrated that iron oxide-modified NEs can affect uptake by TC-1 cells (a murine epithelial cell line) and reduce the intensity of magnetic resonance (MR) images by shortening the T2 time. Most importantly, in vivo studies demonstrated that iron oxide-modified NE could be detected in mouse nasal septum by both transmission electron microscopy and MR imaging. Altogether these experiments demonstrate that iron oxide-modified NE is a unique tool that can be used to study uptake and distribution of NEs after nasal application.

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“…Conjugation of ASOs to molecules that can bind to certain ligands in the cell can improve their cell uptake and internalization. Small hydrophobic molecules, such as cholesterol [83], lipids [84], or fluorinated chains [85,86] may increase ASOs stability and their membrane permeation. Multivalent N-acetylgalactosamine (GalNAc) conjugation is another important way for ASOs delivery to hepatocytes [87].…”

Section: Strategies To Improve Asos Cell Targeting and Overcome Toxicitymentioning

confidence: 99%

Progress in the Use of Antisense Oligonucleotides for Vaccine Improvement

et al. 2020

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Antisense oligonucleotides (ASOs) are synthetically prepared short single-stranded deoxynucleotide sequences that have been validated as therapeutic agents and as a valuable tool in molecular driving biology. ASOs can block the expression of specific target genes via complementary hybridization to mRNA. Due to their high specificity and well-known mechanism of action, there has been a growing interest in using them for improving vaccine efficacy. Several studies have shown that ASOs can improve the efficacy of vaccines either by inducing antigen modification such as enhanced expression of immunogenic molecules or by targeting certain components of the host immune system to achieve the desired immune response. However, despite their extended use, some problems such as insufficient stability and low cellular delivery have not been sufficiently resolved to achieve effective and safe ASO-based vaccines. In this review, we analyze the molecular bases and the research that has been conducted to demonstrate the potential use of ASOs in vaccines.

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Perfluoroalkylchain conjugation as a new tactic for enhancing cell permeability of peptide nucleic acids (PNAs) via reducing the nanoparticle size

Cited by 26 publications

References 42 publications

Fluorinated and Charged Hydrogenated Alkanethiolates Grafted on Gold: Expanding the Diversity of Mixed-Monolayer Nanoparticles for Biological Applications

Fluorinated and Charged Hydrogenated Alkanethiolates Grafted on Gold: Expanding the Diversity of Mixed-Monolayer Nanoparticles for Biological Applications

Modified Nanoemulsions with Iron Oxide for Magnetic Resonance Imaging

Progress in the Use of Antisense Oligonucleotides for Vaccine Improvement

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