Molecular recognition of nucleotides by a new bis(guanidinium)tetrakis(β-cyclodextrin) tetrapod

Menuel, S.; Duval, Raphaël E.; Cuc, Diana; Mutzenhardt, Pierre; Marsura, Alain

doi:10.1039/b613312f

Cited by 25 publications

(33 citation statements)

References 36 publications

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“…[625] Relatively strong complexes of native di-and tripeptides with monoamino-b-CDs are observed only in the presence of lipophilic amino acid residues, which, according to NMR analysis, dip into the cavity. [627] 10. [626] The association constants of nucleotides with aminocyclodextrins can exceed K = 10 6 m À1 , with complexes stabilized largely by salt bridges with heptaamino-b-CD, for example.…”

Section: Angewandte Chemiementioning

confidence: 99%

Binding Mechanisms in Supramolecular Complexes

2009

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Supramolecular chemistry has expanded dramatically in recent years both in terms of potential applications and in its relevance to analogous biological systems. The formation and function of supramolecular complexes occur through a multiplicity of often difficult to differentiate noncovalent forces. The aim of this Review is to describe the crucial interaction mechanisms in context, and thus classify the entire subject. In most cases, organic host-guest complexes have been selected as examples, but biologically relevant problems are also considered. An understanding and quantification of intermolecular interactions is of importance both for the rational planning of new supramolecular systems, including intelligent materials, as well as for developing new biologically active agents.

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Section: Angewandte Chemiementioning

confidence: 99%

Binding Mechanisms in Supramolecular Complexes

2009

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“…4. Toxicity studies clearly demonstrate the cellular harmlessness of the tetrapod at a high concentration [18].…”

Section: Strategies For Nucleic-acids Cell-transfer By Cyclodextrinsmentioning

confidence: 95%

“…On the light of literature results, we have chosen to investigate in 2007 a new concept of nonpolymeric CyD oligomer ''bottom-up'' synthesis (summarized in Fig. 3) having CyD cavities regularly distributed around a simple central backbone and including a pre-defined and adequate number of cationic guanidinium centres [18]. The structure was designed to induce three types of non-covalent interactions between the host (CyD) and the guest (nucleotide): electrostatic, hydrogen bonding and hydrophobic inclusion in CyD cavity.…”

Section: Strategies For Nucleic-acids Cell-transfer By Cyclodextrinsmentioning

confidence: 99%

“…As a preliminary work was investigated in order to verify the three types of interaction reality are working with our model. Firstly, we find our ''phosphine imide'' strategy was an efficient easy way to obtain designed CyDs water soluble multipod in large scale, allowing a full control on the number of cationic centres and of CyDs cavities introduced in the final molecular skeleton [18]. Secondly, it was established that the tetrapod model was able to recognize the nucleotides AMP, ADP and ATP at a supramolecular level, combining host-guest hydrophobic inclusion of both ribose and nucleobase moieties into CyDs and strong electrostatic interactions between guanidinium sites and phosphate anions.…”

Section: Strategies For Nucleic-acids Cell-transfer By Cyclodextrinsmentioning

confidence: 99%

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Interest of designed cyclodextrin-tools in gene delivery

Duval¹,

Clarot²,

Dumarçay-Charbonnier³

et al. 2012

Annales Pharmaceutiques Françaises

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Cyclodextrins (CyDs) currently displays even today the image of a natural macrocyclic compound largely dominant in the formation of inclusion complexes with small hydrophobic molecules. During the past 10years, advances in this field allowed to achieve more and more sophisticated CyDs derivatives opening a simple access in scale-up quantities to original and better CyD-based gene delivery systems. In addition, possibility to combine covalent and supramolecular approaches offers new venues for the design of tailor-made CyD-based nanovehicles to improve their transfection ability and gene transfer in cells. In this account, we describe our recent progress in the construction of a novel CyD-based G0 (generation number) core dendrimer, scalable to CyD oligomers by a strategy using protonable guanidine tethers and whose concept can be generalized for the assembly of CyD pre-coated dendrimers. The synthetic strategy based on an original Staudinger-Aza-Wittig tandem coupling reaction. We present an outline of the different analytical strategies to characterize CyD-ODN (cyclodextrin-oligodeoxynucleotide) complexes. Among them, Capillary electrophoresis (CE) was used to perfectly characterize our CyD-siRNA and CyD-DNA complexes and shown to be a very attractive method with advantages of low sample consumption, rapid analysis speed, and high efficiency that make this technology a major tool for association constant measurement. Finally, we present the different biological methods that can be used, in vitro, to study gene delivery, and more precisely ones we have performed to evaluate the capability of our original model bis-guanidinium-tetrakis-β-cyclodextrin dendrimeric tetrapod, to deliver efficiently DNA or siRNA in eukaryotic cells.

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“…Marsura et al. linked two guanidinium moieties to four cyclodextrins and thus achieved K values of 2×10 6 M −1 (pH 6.5, D 2 O) 6c. The most successful approach to guanidinium‐based construction of nucleotide hosts has been achieved by Kunitake et al.…”

Section: Introductionmentioning

confidence: 99%

Nucleotide Recognition in Water by a Guanidinium‐Based Artificial Tweezer Receptor

Kuchelmeister

Schmuck

2011

Chemistry A European J

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The water-soluble tweezer receptor 1 with two symmetric peptidic arms, which are connected by an aromatic scaffold and contain lysine, phenylalanine, and a guanidinium-based anion-binding site as headgroup, has been synthesized. UV/Vis-derived Job plots show that the receptor forms 1:1 complexes with nucleotides and phosphate in buffered water at neutral pH. Binding constants have been determined by fluorescence and UV/Vis spectroscopy. All nucleotides tested were bound very efficiently, even in pure water, with binding constants between 10(4) and 10(5) M(-1) . Interestingly, all mononucleotides were bound much stronger than phosphate by a factor of at least 5 to 10. Furthermore 1 favors the binding of adenosine monophosphate (AMP) over adenosine diphosphate (ADP) and adenosine triphosphate (ATP), which is unprecedented for artificial nucleotide receptors reported so far. According to NMR spectroscopy and molecular modeling studies, the efficient binding is a result of strong electrostatic contacts supported by π-π interactions with the nucleobase within the cavity-shaped receptor.

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Molecular recognition of nucleotides by a new bis(guanidinium)tetrakis(β-cyclodextrin) tetrapod

Cited by 25 publications

References 36 publications

Binding Mechanisms in Supramolecular Complexes

Binding Mechanisms in Supramolecular Complexes

Interest of designed cyclodextrin-tools in gene delivery

Nucleotide Recognition in Water by a Guanidinium‐Based Artificial Tweezer Receptor

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