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Concept

Radical (chimie)

Résumé

Un radical (souvent appelé radical libre) est une espèce chimique possédant un ou plusieurs électrons non appariés sur sa couche externe. L'électron se note par un point. La présence d'un électron célibataire confère à ces molécules, la plupart du temps, une grande instabilité (elles ne respectent pas la règle de l'octet), ce qui signifie qu'elles ont la possibilité de réagir avec de nombreux composés dans des processus le plus souvent non spécifiques, et que leur durée de vie est très courte. Si un radical possède un, deux ou trois électrons célibataires, on le nomme respectivement monoradical, biradical, triradical La stabilité de ces entités chimiques décroît lorsque le nombre d'électrons célibataires augmente. Génération Les radicaux sont généralement obtenus par rupture de liaisons chimiques. Étant donné que les liaisons chimiques ont des énergies de l'ordre de centaines de kJ•mol−1, les conditions mises en jeu pour donner des radicaux sont souvent drastiques : hau

Source officielle

https://fr.wikipedia.org/wiki/Radical_(chimie)

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We collected experimental kinetic rate constants for chemical processes responsible for the development and progress of neurodegeneration, focused on the enzymatic and non-enzymatic degradation of amine neurotransmitters and their reactive and neurotoxic metabolites. A gross scheme of neurodegeneration on the molecular level is based on two pathways. Firstly, reactive species oxidise heavy atom ions, which enhances the interaction with alpha-synuclein, thus promoting its folding to the beta form and giving rise to insoluble amyloid plaques. The latter prevents the function of vesicular transport leading to gradual neuronal death. In the second pathway, radical species, OH center dot in particular, react with the methylene groups of the apolar part of the lipid bilayer of either the cell or mitochondrial wall, resulting in membrane leakage followed by dyshomeostasis, loss of resting potential and neuron death. Unlike all other central neural system (CNS)-relevant biogenic amines, dopamine and noradrenaline are capable of a non-enzymatic auto-oxidative reaction, which produces hydrogen peroxide. This reaction is not limited to the mitochondrial membrane where scavenging enzymes, such as catalase, are located. On the other hand, dopamine and its metabolites, such as dopamine-o-quinone, dopaminechrome, 5,6-dihydroxyindole and indo-5,6-quinone, also interact directly with alpha-synuclein and reversibly inhibit plaque formation. We consider the role of the heavy metal ions, selected scavengers and scavenging enzymes, and discuss the relevance of certain foods and food supplements, including curcumin, garlic, N-acetyl cysteine, caffeine and red wine, as well as the long-term administration of non-steroid anti-inflammatory drugs and occasional tobacco smoking, that could all act toward preventing neurodegeneration. The current analysis can be employed in developing strategies for the prevention and treatment of neurodegeneration, and, hopefully, aid in the building of an overall kinetic molecular model of neurodegeneration itself.

Humana Press Inc2016

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Design of High Permittivity Polysiloxane Elastomers for Dielectric Elastomer Transducers

Philip Horst Caspari

Dielectric elastomer transducers consist of a dielectric elastomer between two compliant electrodes. When the elastic capacitor is electrically charged, the dielectric elastomer elongates until a balance of elastic and electrostatic force is reached. Electrical energy is converted into mechanical work. Contrary, in the generator mode, the capacitor is stretched by an outside mechanical force. The mechanical work is converted into electrical energy due to the change of capacitance. The need of a high voltage power supply is the main obstacle for the elastomer transducer technology in various applications. Siloxane elastomers are the most frequently tested elastomers with excellent mechanical stability, processability and electrically insulating properties. It is well-known that an increase in permittivity of the silicone elastomer would allow a reduction of the driving voltage of the elastic transducer. Hence, manifold research activities have been initiated to enhance the permittivity of siloxane elastomers. In the present work, siloxane elastomers were developed that combined increased permittivity with high mechanical stability and cost-efficient processability of the siloxane materials. The synthesis of polar thiols as the first step of siloxane functionalization was studied. Serious challenges in the synthesis of polar groups that can be integrated by thiol-ene addition as side group of polysiloxanes were found. Therefore, commercially available alkylthiols were selected for the functionalization of siloxane due to their chemical stability. The alkylthiols were grafted onto the polysiloxane by thiol-ene addition and subsequently cross-linked in the well-established organotin-catalyzed condensation reaction. The impact of different types of cross-linker on the electro-mechanical properties of the polar siloxane elastomers was analyzed. A significant improvement in the performance of actuator test devices was demonstrated. In addition, the electromechanical stability of the polar siloxane elastomer was illustrated by 50.000 actuation cycles. However, solvent had to be used in the production process of the siloxane elastomers and the cross-linking reaction time was about two days. Apart from their application in thin film actuators, these polar siloxane elastomers were studied with respect to their performance in dielectric elastomer generators together with siloxane composites. Nanospring carbon nanotubes were blended as high permittivity fillers in siloxanes subsequent to cross-linking. Indeed, improved performances of the high permittivity silicone elastomers were found and a deeper understanding for the design of dielectric elastomers for generator applications was gained. The most significant result of this work was the development of polar siloxane elastomers that could be processed into thin film elastomers without any solvent within a few minutes. Two different synthetic approaches were developed based on low viscosity mixtures of cross-linkable oligo(ethylthioethyl)(methyl)siloxanes and multifunctional thiol cross-linkers. The cross-linking reaction was selectively initiated by UV-induced radical formation. These siloxane elastomers possessed an increased permittivity and showed a high electromechanical stability.

EPFL2019

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New methods for developing (bi)cyclic peptides by phage display

Camille Villequey

Cyclic peptide ligands are a promising molecular format for the development of therapeutics. They combine some of the advantages of large protein therapeutics (high affinity and specificity) and of small molecule drugs (accessibility to chemical synthesis and low immunogenicity). With phage display, large combinatorial libraries of more than one billion mono- and polycyclic peptides can be developed and screened against virtually any target. During phage affinity selections, the physical link between phenotype (encoded peptide) and genotype (phage DNA) allows the identification of enriched peptide binders by sequencing of the phage vector DNA. Based on these concepts, our laboratory has established a robust chemistry in which phage displayed peptides containing two or three cysteines are cyclized or bi-cyclized with thiol-reactive linkers. This procedure has been generally applied for the isolation of potent and selective (bi)cyclic peptide ligands with therapeutic potential. The isolation of binders with optimal properties is highly dependent on the possibility to generate (bi)cyclic peptide libraries with high structural diversity and on the ability to thoroughly decode the phage selection output. In my PhD work, I developed new methods to generate large and structurally diverse libraries and to decode more efficiently phage selected peptides. In my first project, I explore the cyclization of peptides with two chemical bridges as a method to provide rapid access to phage-encoded libraries with high scaffold diversity. To this end, a range of twelve structurally diverse chemicals were tested for thiol-reactivity and phage compatibility. Subsequently, peptide libraries of the format XCXnCXnCX (X = random amino acid, C = cysteine, n = 3 or 4) were cyclized with six of these chemical linkers and panned against the protease plasma kallikrein. The selection yielded inhibitors with remarkable affinity (sub-nM KI), target selectivity (>1000-fold) and proteolytic stability (t1/2 in plasma > 3 days) despite a relatively small molecular mass (~ 1200 Da). In the second project, I developed phage-encoded libraries of small cyclic peptides in order to identify ligands that have the potential to be orally absorbed. A major challenge for the generation of such library is the usually low diversity of compounds due to the limited number of amino acids. In this work, we addressed this limitation by taking advantage of a recently discovered peptide cyclization reaction in which the thiol of a cysteine is ligated with the N-terminal amino group using a chemical reagent. We applied this strategies to two phage-encoded peptide libraries of four and five amino acids (XXXC and XXXXC) that were cyclized with eight chemical linkers yielding a collection of more than 1.3 million compounds. Panning the libraries against the two disease targets plasma kallikrein and coagulation factor XIa yielded ligands with single-digit micromolar affinity. In a third project, I developed a strategy to bypass the bacterial infection step in phage display. Bacterial infection is usually crucial for the propagation and identification of enriched clones by DNA sequencing. However, mutations or chemical modifications of the phage coat proteins, sometimes lead to decreased infection rates and therefore compromise the entire procedure. Consequently, there is an interest for developing methods in which this step could be completely omitted.

EPFL2017

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New methods for developing (bi)cyclic peptides by phage display

Camille Villequey

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Design of High Permittivity Polysiloxane Elastomers for Dielectric Elastomer Transducers

Philip Horst Caspari

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Humana Press Inc2016