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Principles Of Fluorescence Spectroscopy

In this review, we describe the recent advances in supramolecular helical assemblies formed from chiral and achiral small molecules, oligomers (foldamers), and helical and nonhelical polymers from the viewpoints of their formations with unique chiral phenomena, such as amplification of chirality during the dynamic helically assembled processes, properties, and specific functionalities, some of which have not been observed in or achieved by biological systems. In addition, a brief historical overview of the helical assemblies of small molecules and remarkable progress in the synthesis of single-stranded and multistranded helical foldamers and polymers, their properties, structures, and functions, mainly since 2009, will also be described.

Supramolecular Helical Systems: Helical Assemblies of Small Molecules, Foldamers, and Polymers with Chiral Amplification and Their Functions

This review describes a multidimensional treatment of molecular recognition phenomena involving aromatic rings in chemical and biological systems. It summarizes new results reported since the appearance of an earlier review in 2003 in host-guest chemistry, biological affinity assays and biostructural analysis, data base mining in the Cambridge Structural Database (CSD) and the Protein Data Bank (PDB), and advanced computational studies. Topics addressed are arene-arene, perfluoroarene-arene, S⋅⋅⋅aromatic, cation-π, and anion-π interactions, as well as hydrogen bonding to π systems. The generated knowledge benefits, in particular, structure-based hit-to-lead development and lead optimization both in the pharmaceutical and in the crop protection industry. It equally facilitates the development of new advanced materials and supramolecular systems, and should inspire further utilization of interactions with aromatic rings to control the stereochemical outcome of synthetic transformations.

Aromatic rings in chemical and biological recognition: energetics and structures.

We show that the Raman scattering technique can give complete structural information for one-dimensional systems, such as carbon nanotubes. Resonant confocal micro-Raman spectroscopy of an (n,m) individual single-wall nanotube makes it possible to assign its chirality uniquely by measuring one radial breathing mode frequency omega(RBM) and using the theory of resonant transitions. A unique chirality assignment can be made for both metallic and semiconducting nanotubes of diameter d(t), using the parameters gamma(0) = 2.9 eV and omega(RBM) = 248/d(t). For example, the strong RBM intensity observed at 156 cm(-1) for 785 nm laser excitation is assigned to the (13,10) metallic chiral nanotube on a Si/SiO2 surface.

Structural (n,m) determination of isolated single wall carbon nanotubes by resonant Raman scattering

Applications of Supramolecular Anion Recognition

Attractive in theory and confirmed to exist, anion–π interactions have never really been seen at work. To catch them in action, we prepared a collection of monomeric, cyclic and rod-shaped naphthalenediimide transporters. Their ability to exert anion–π interactions was demonstrated by electrospray tandem mass spectrometry in combination with theoretical calculations. To relate this structural evidence to transport activity in bilayer membranes, affinity and selectivity sequences were recorded. π-acidification and active-site decrowding increased binding, transport and chloride > bromide > iodide selectivity, and supramolecular organization inverted acetate > nitrate to nitrate > acetate selectivity. We conclude that anion–π interactions on monomeric surfaces are ideal for chloride recognition, whereas their supramolecular enhancement by π,π-interactions appears perfect to target nitrate. Chloride transporters are relevant to treat channelopathies, and nitrate sensors to monitor cellular signaling and cardiovascular diseases. A big impact on organocatalysis can be expected from the stabilization of anionic transition states on chiral π-acidic surfaces.

/pdf/experimental-evidence-for-the-functional-relevance-of-anion-sncewng0go.pdf

Experimental evidence for the functional relevance of anion– π interactions

This critical review covers progress with synthetic transport systems, particularly ion channels and pores, between January 2006 and December 2009 in a comprehensive manner. This is the third part of a series launched in the year 2000, covering a rich collection of structural and functional motifs that should appeal to a broad audience of non-specialists, including to organic, biological, supramolecular and polymer chemists. Impressive breakthroughs have been achieved over the past four years in part because of a fruitful expansion toward new types of interactions, including metal–organic, π–π, aromatic electron donor–acceptor, anion–π or anion–macrodipole interactions as well as dynamic covalent bonds (169 references).

/pdf/recent-synthetic-transport-systems-58eo0yk78w.pdf

Recent synthetic transport systems

The lipid bilayer membranes are Nature’s dynamic structural motifs that individualize cells and keep ions, proteins, biopolymers and metabolites confined in the appropriate location. The compartmentalization and isolation of these molecules from the external media facilitate the sophisticated functions and connections between the different biological processes accomplished by living organisms. However, cells require assistance from minimal energy shortcuts for the transport of molecules across membranes so that they can interact with the exterior and regulate their internal environments.Ion channels and pores stand out from all other possible transport mechanisms due to their high selectivity and efficiency in discriminating and transporting ions or molecules across membrane barriers. Nevertheless, the complexity of these smart “membrane holes” has driven researchers to develop simpler artificial structures with comparable performance to the natural systems. As a broad range of supramolecular interactions...

/pdf/ion-channel-models-based-on-self-assembling-cyclic-peptide-4mi1u56sbd.pdf

Ion channel models based on self-assembling cyclic peptide nanotubes.

The delivery of nucleic acids with transient activity for genetic engineering is a promising methodology with potential applications in the treatment of diseases ranging from cancer and infectious diseases to heritable disorders Restoring the expression of a missing protein, correcting defective splicing of transcripts and silencing or modulating the expression of genes are powerful approaches that could have substantial benefits in biological research and medicine Impressive progress in improving gene delivery has been made in the past decade, and several products have reached the market However, translating the results of in vitro and preclinical studies into functional therapies is hindered by the suboptimal performance of gene delivery vehicles in capturing, protecting and delivering nucleic acid cargoes safely and efficaciously Chemistry has a key role in the development of innovative synthetic materials to overcome the challenges of producing next-generation gene delivery therapies and protocols In this Review, we discuss the latest chemical advances in the production of materials for the delivery of nucleic acids to cells and for gene therapy Non-viral vehicles for the delivery of nucleic acids have potential applications for the treatment of diseases by, for example, restoring, correcting or silencing the expression of genes In this Review, the authors discuss the latest developments in synthetic materials used for gene delivery and the challenges that must be overcome to transfer these innovations into the clinic

/pdf/synthetic-materials-at-the-forefront-of-gene-delivery-3m2rylpby7.pdf

Synthetic materials at the forefront of gene delivery

https://archive-ouverte.unige.ch/unige:73238/ATTACHMENT02

Javier Montenegro

Papers

Experimental evidence for the functional relevance of anion– π interactions

Recent synthetic transport systems

Ion channel models based on self-assembling cyclic peptide nanotubes.

Synthetic materials at the forefront of gene delivery

Cellular uptake: lessons from supramolecular organic chemistry