Nucleic Acid Based Fluorinated Derivatives: New Tools for Biomedical Applications

Dolain, Christel; Patwa, Amit; Godeau, Guilhem; Barthélémy, Philippe

doi:10.3390/app2020245

Cited by 21 publications

(17 citation statements)

References 100 publications

(95 reference statements)

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“…[103] Fluorinated tags have also been conjugated to oligonucleotides to facilitate their internalization into cells. [100] In some cases, it is thought that fluorination leads to self-assembly prior to internalization and that larger fluorinated oligonucleotide aggregates are preferentially endocytosed rather than internalized by lipid-raft-mediated mechanisms or passive diffusion. [101,102]…”

Section: Fluorinated Lipids and Tags For Cellular Internalizationmentioning

confidence: 99%

Perfluorocarbons in Chemical Biology

Miller

Sletten

2020

ChemBioChem

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Perfluorocarbons, saturated carbon chains in which all the hydrogen atoms are replaced with fluorine, form a separate phase from both organic and aqueous solutions. Though perfluorinated compounds are not found in living systems, they can be used to modify biomolecules to confer orthogonal behavior within natural systems, such as improved stability, engineered assembly, and cell-permeability. Perfluorinated groups also provide handles for purification, mass spectrometry, and 19 F NMR studies in complex environments. Herein, we describe how the unique properties of perfluorocarbons have been employed to understand and manipulate biological systems.

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Section: Fluorinated Lipids and Tags For Cellular Internalizationmentioning

confidence: 99%

Perfluorocarbons in Chemical Biology

Miller

Sletten

2020

ChemBioChem

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“…[213] Most recently, self-assembling molecules based on nucleic acid motif are finding more applications in biology and biomedicine. [214–216]…”

Section: Supramolecular Hydrogels Made Of the Basic Biological Buimentioning

confidence: 99%

Supramolecular biofunctional materials

et al. 2017

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This review discusses supramolecular biofunctional materials, a novel class of biomaterials formed by small molecules that are held together via noncovalent interactions. The complexity of biology and relevant biomedical problems not only inspire, but also demand effective molecular design for functional materials. Supramolecular biofunctional materials offer (almost) unlimited possibilities and opportunities to address challenging biomedical problems. Rational molecular design of supramolecular biofunctional materials exploit powerful and versatile noncovalent interactions, which offer many advantages, such as responsiveness, reversibility, tunability, biomimicry, modularity, predictability, and, most importantly, adaptiveness. In this review, besides elaborating on the merits of supramolecular biofunctional materials (mainly in the form of hydrogels and/or nanoscale assemblies) resulting from noncovalent interactions, we also discuss the advantages of small peptides as a prevalent molecular platform to generate a wide range of supramolecular biofunctional materials for the applications in drug delivery, tissue engineering, immunology, cancer therapy, fluorescent imaging, and stem cell regulation. This review aims to provide a brief synopsis of recent achievements at the intersection of supramolecular chemistry and biomedical science in hope of contributing to the multidisciplinary research on supramolecular biofunctional materials for a wide range of applications. We envision that supramolecular biofunctional materials will contribute to the development of new therapies that will ultimately lead to a paradigm shift for developing next generation biomaterials for medicine.

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“…Christel Dolain and coworkers contribution [13]: Nucleic Acid Based Fluorinated Derivatives: New Tools for Biomedical Applications, reviews recent developments in the preparation of nucleic acid-based fluorinated derivatives, e.g., nucleosides or oligonucleotides connected to fabricated by coupling highly fluorinated chains or labeled with either a nucleoside or an oligonucleotides-modified with one or more fluorine atoms, have been investigated recently due to their high potential for biomedical applications. The application of nucleoside-based fluorocarbon derivatives is focused on three broad objectives: (i) construction of novel supramolecular materials and/or devices; (ii) development of new drug delivery systems; and (iii) discovery of new therapeutic molecules.…”

Section: Synthesis/applications Of Organo-fluorine Moleculesmentioning

confidence: 99%

Special Feature Organo-Fluorine Chemical Science

Hügel

Jackson

2012

Applied Sciences

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Inventing the Fluorine FutureFluorine is the 13th most abundant element and, with other fluorine containing functional groups, is a most effective element in biological substances, pharmaceuticals, agrochemicals, liquid crystals, dyes, polymers and a wide range of consumer products. This reflects its resistance to metabolic change due to the strength of the C-F bond providing biological stability and the application of its nonstick-interfacial physical characteristics. Its introduction often remains a synthetic challenge. The widespread use of organofluorines has increased the demand for the development of practical and simple reagents and experimental strategies for the incorporation of fluorine into all types of molecular structures and this was the reasoning behind this special feature on Organo-Fluorine Chemical Science.The contributed articles belong to two broad groups: (i) preparation of fluorine materials, polymers; (ii) the synthesis/applications of organo-fluorine molecules. Fluorine-Fatness-Due to Lack of FitnessTheoretical [1] and experimental observations to explain the molecular origins of fluorocarbon hydrophobicity suggest that the hydrophobicity of a fluorocarbon, whether the interaction with water is as solute or as surface, is due to its "fatness". In solution, the extra work of cavity formation to accommodate a fluorocarbon, compared to a hydrocarbon, is not offset by enhanced energetic interactions with water. The enhanced hydrophobicity of fluorinated surfaces arises because fluorocarbons pack less densely on surfaces leading to poorer van der Waals interactions with water. The interaction of water with a hydrophobic solute/surface is primarily a function of van der Waals interactions and is substantially independent of electrostatic interactions. This independence is primarily due to the strong tendency of water at room temperature to maintain its hydrogen bonding network structure at an interface lacking hydrophilic sites. OPEN ACCESS

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Nucleic Acid Based Fluorinated Derivatives: New Tools for Biomedical Applications

Cited by 21 publications

References 100 publications

Perfluorocarbons in Chemical Biology

Perfluorocarbons in Chemical Biology

Supramolecular biofunctional materials

Special Feature Organo-Fluorine Chemical Science

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