Revealing cooperative binding of polycationic cyclodextrins with DNA oligomers by capillary electrophoresis coupled to mass spectrometry

Przybylski, Cédric; Benito, Juan M.; Bonnet, Véronique; Mellet, Carmen Ortiz; Fernández, José Manuel Garcı́a

doi:10.1016/j.aca.2017.11.034

Cited by 17 publications

(11 citation statements)

References 64 publications

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“…KCE entails separation of compounds, biomolecules and ligands, that engage in noncovalent interactions inside the capillary during electrophoresis. KCE‐MS was employed to study the molecular association of cyclodextrins to DNA and determine the stoichiometry of the complexes, the dissociation constants, and Gibbs free energy data [153]. This work validated how CE‐MS can be a useful tool for the high‐throughput screening of gene delivery carriers namely carbohydrate‐based scaffolds where techniques such as dynamic light scattering and isothermal titration calorimetry cannot be used owing to the low amount of sample available.…”

Section: Separation Of Nucleic Acidsmentioning

confidence: 82%

Recent developments in the characterization of nucleic acids by liquid chromatography, capillary electrophoresis, ion mobility, and mass spectrometry (2010–2020)

Santos

Brodbelt

2020

J of Separation Science

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The development of new strategies for the analysis of nucleic acids has gained momentum due to the increased interest in using these biomolecules as drugs or drug targets. The application of new mass spectrometry ion activation techniques and the optimization of separation methods including liquid chromatography, capillary electrophoresis, and ion mobility have allowed more detailed characterization of nucleic acids and oligonucleotide therapeutics including confirmation of sequence, localization of modifications and interaction sites, and structural analysis as well as identification of failed sequences and degradation products. This review will cover tandem mass spectrometry methods as well as the recent developments in liquid chromatography, capillary electrophoresis, and ion mobility coupled to mass spectrometry for the analysis of nucleic acids and oligonucleotides.

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Section: Separation Of Nucleic Acidsmentioning

confidence: 82%

Recent developments in the characterization of nucleic acids by liquid chromatography, capillary electrophoresis, ion mobility, and mass spectrometry (2010–2020)

Santos

Brodbelt

2020

J of Separation Science

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“…These conformational and architectural dissimilarities further condition the inclusion properties: 4 -dimer can host the adamantane carboxylate guest to form a 4 -dimer:AC stable ternary species whereas the same AC guest triggers 5 -dimer disruption. Interestingly, the synthetic approach is compatible with the incorporation of functional elements at the primary positions of the cyclooligosaccharide, e.g., cationic centers to modulate the reactivity of guests confined in the CD cavity (Wei et al, 2018; Yi et al, 2018) or to mediate nucleic acid condensation (Aranda et al, 2013; Martínez et al, 2013; Jiménez Blanco et al, 2016; Martínez-Negro et al, 2017; Przybylski et al, 2018). The possibility of implementing different supramolecular organization levels (e.g., clusterization and/or inclusion and/or spatiotemporal controlled dissociation) with aromatic clips offers then a valuable tool to program the behavior of monodisperse CD-based devices in biological environments for (bio)molecular encapsulation and controlled release.…”

Section: Resultsmentioning

confidence: 99%

Dynamic Control of the Self-Assembling Properties of Cyclodextrins by the Interplay of Aromatic and Host-Guest Interactions

et al. 2019

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The presence of a doubly-linked naphthylene clip at the O -2 I and O -3 II positions in the secondary ring of β-cyclodextrin (βCD) derivatives promoted their self-assembly into head-to-head supramolecular dimers in which the aromatic modules act either as cavity extension walls (if the naphthalene moiety is 1,8-disubstituted) or as folding screens that separate the individual βCD units (if 2,3-disubstituted). Dimer architecture is governed by the conformational properties of the monomer constituents, as determined by NMR, fluorescence, circular dichroism, and computational techniques. In a second supramolecular organization level, the topology of the assembly directs host-guest interactions and, reciprocally, guest inclusion impacts the stability of the supramolecular edifice. Thus, inclusion of adamantane carboxylate, a well-known βCD cavity-fitting guest, was found to either preserve the dimeric arrangement, leading to multicomponent species, or elicit dimer disruption. The ensemble of results highlights the potential of the approach to program self-organization and external stimuli responsiveness of CD devices in a controlled manner while keeping full diastereomeric purity.

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“…In the last decade, however, multivalent polycations based on molecular systems emerged as a promising alternative [86][87][88][89][90][91][92][93][94][95][96]. Polycationic cyclodextrins have become the iconic representatives in this category [5,[97][98][99][100][101][102][103][104]. The efficiency in compacting nucleic acids into nanocomplexes (so-called CDplexes) capable of mediating cell entry and subsequent expression of the nucleic acid anticipated activity (transfection) was significantly enhanced for prototypes that can additionally establish cyclodextrin-cyclodextrin interactions through either hydrophobic , host-guest [79,134] or aromatic-aromatic contacts [135][136][137][138][139][140][141][142][143][144][145][146].…”

Section: Biomacromolecule-templated Formation Of Functional Glycocd Nmentioning

confidence: 99%

Cyclodextrin-Based Functional Glyconanomaterials

2020

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Cyclodextrins (CDs) have long occupied a prominent position in most pharmaceutical laboratories as “off-the-shelve” tools to manipulate the pharmacokinetics of a broad range of active principles, due to their unique combination of biocompatibility and inclusion abilities. The development of precision chemical methods for their selective functionalization, in combination with “click” multiconjugation procedures, have further leveraged the nanoscaffold nature of these oligosaccharides, creating a direct link between the glyco and the nano worlds. CDs have greatly contributed to understand and exploit the interactions between multivalent glycodisplays and carbohydrate-binding proteins (lectins) and to improve the drug-loading and functional properties of nanomaterials through host–guest strategies. The whole range of capabilities can be enabled through self-assembly, template-assisted assembly or covalent connection of CD/glycan building blocks. This review discusses the advancements made in this field during the last decade and the amazing variety of functional glyconanomaterials empowered by the versatility of the CD component.

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Revealing cooperative binding of polycationic cyclodextrins with DNA oligomers by capillary electrophoresis coupled to mass spectrometry

Cited by 17 publications

References 64 publications

Recent developments in the characterization of nucleic acids by liquid chromatography, capillary electrophoresis, ion mobility, and mass spectrometry (2010–2020)

Recent developments in the characterization of nucleic acids by liquid chromatography, capillary electrophoresis, ion mobility, and mass spectrometry (2010–2020)

Dynamic Control of the Self-Assembling Properties of Cyclodextrins by the Interplay of Aromatic and Host-Guest Interactions

Cyclodextrin-Based Functional Glyconanomaterials

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