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Università della Svizzera italiana

Isonitrile-based multicomponent synthesis of β-amino boronic acids as β-lactamase inhibitors

Bassini, Emanuele ; Gazzotti, Stefano ; Sannio, Filomena ; Lo Presti, Leonardo ; Sgrignani, Jacopo ; Docquier, Jean-Denis ; Grazioso, Giovanni ; Silvani, Alessandra

In: Antibiotics, 2020, vol. 9, no. 5, p. 21 p

The application of various isonitrile-based multicomponent reactions to protected (2-oxoethyl)boronic acid (as the carbonyl component) is described. The Ugi reaction, both in the four components and in the four centers–three components versions, and the van Leusen reaction, proved effective at providing small libraries of MIDA-protected β-aminoboronic acids. The corresponding free...

Université de Fribourg

Structure and dynamics of the acyl chains in the membrane trafficking and enzymatic processing of lipids

Vanni, Stefano ; Riccardi, Laura ; Palermo, Giulia ; De Vivo, Marco

In: Accounts of Chemical Research, 2019, vol. 52, no. 11, p. 3087–3096

The regulatory chemical mechanisms of lipid trafficking and degradation are involved in many pathophysiological processes, being implicated in severe pain, inflammation, and cancer. In addition, the processing of lipids is also relevant for industrial and environmental applications. However, there is poor understanding of the chemical features that control lipid membrane trafficking and allow...

Université de Fribourg

Tautomerism as primary signaling mechanism in metal sensing: the case of amide group

Deneva, Vera ; Dobrikov, Georgi ; Crochet, Aurélien ; Nedeltcheva, Daniela ; Fromm, Katharina M. ; Antonov, Liudmil

In: Beilstein Journal of Organic Chemistry, 2019, vol. 15, no. 1, p. 1898–1906

The concept for sensing systems using the tautomerism as elementary signaling process has been further developed by synthesizing a ligand containing 4- (phenyldiazenyl)naphthalene-1-ol as a tautomeric block and an amide group as metal capturing antenna. Although it has been expected that the intramolecular hydrogen bonding (between the tautomeric hydroxy group and the nitrogen atom from the...

Université de Fribourg

On the sustainability of photochemical reactions

Bochet, Christian G.

In: CHIMIA International Journal for Chemistry, 2019, vol. 73, no. 9, p. 720–723

Photochemical reactions are often presented as intrinsically environmentally friendly ('green'). This may be indeed the case, but only in particular circumstances. This short essay comments on various aspects of the greenness of photochemical reactions, both in a historical (when only mercury-based hard UV light sources were available) and a current (with the recent introduction of LED...

Université de Fribourg

Photochemical amplifier based on self-immolative dendritic spacers

Kastrati, Agonist ; Bochet, Christian G.

In: The Journal of Organic Chemistry, 2019, vol. 84, no. 12, p. 7776–7785

A self-immolative dendritic structure was synthesized. It is based on phenol derivatives with three hydroxymethyl arms at both ortho and para positions of the core unit, potentially releasing up to 27 leaving groups in a third-generation dendrimer. The triggering event is the photolysis of a photosentive ortho-nitrobenzyl group. In doing so, we expected to transform a weak chemical or...

Université de Fribourg

Carbon nanodots: Opportunities and limitations to study their biodistribution at the human lung epithelial tissue barrier

Durantie, Estelle ; Barosova, Hana ; Drasler, Barbara ; Rodriguez-Lorenzo, Laura ; Urban, Dominic A. ; Vanhecke, Dimitri ; Septiadi, Dedy ; Hirschi-Ackermann, Liliane ; Petri-Fink, Alke ; Rothen-Rutishauser, Barbara

In: Biointerphases, 2018, vol. 13, no. 6, p. 06D404

Inhalation of combustion-derived ultrafine particles (≤0.1 μm) has been found to be associated with pulmonary and cardiovascular diseases. However, correlation of the physicochemical properties of carbon-based particles such as surface charge and agglomeration state with adverse health effects has not yet been established, mainly due to limitations related to the detection of carbon...

Consortium of Swiss Academic Libraries

Selection Shapes the Robustness of Ligand-Binding Amino Acids

Bilgin, Tugce ; Kurnaz, Isil ; Wagner, Andreas

In: Journal of Molecular Evolution, 2013, vol. 76, no. 5, p. 343-349