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Concept

Rotaxane

Related publications (27)

Large Libraries of Structurally Diverse Macrocycles Suitable for Membrane Permeation

Christian Heinis, Alessandro Angelini, Alexander Lund Nielsen, Mischa Schüttel, Manuel Leonardo Merz, Xinjian Ji, Anne Sofie Luise Zarda, Ganesh Kumar Mothukuri, Zsolt Bognár, Edward Jeffrey Will

Macrocycles offer an attractive format for drug development due to their good binding properties and potential to cross cell membranes. To efficiently identify macrocyclic ligands for new targets, methods for the synthesis and screening of large combinator ...

Wiley-VCH Verlag GmbH2024

Design of Customized Mouthguards with Superior Protection Using Digital-Based Technologies and Impact Tests

Dominique Pioletti, Naser Nasrollahzadeh Mamaghani, Martin Broome

Background In contact sports, an impact on the jaw can generate destructive stress on the tooth-bone system. Mouthguards can be beneficial in reducing the injury risk by changing the dynamics of the trauma. The material properties of mouthguards and their ...

Springer2024

Synthesis and direct assay of large macrocycle diversities by combinatorial late-stage modification at picomole scale

Christian Heinis, Gerardo Turcatti, Alessandro Angelini, Jonathan Patrice Vesin, Julien Bortoli Chapalay, Manuel Leonardo Merz, Sevan Mleh Habeshian, Mischa Schüttel, Ganesh Kumar Mothukuri, Gontran Sangouard, Cristina Diaz Perlas, Zsolt Bognár

Macrocycles have excellent potential as therapeutics due to their ability to bind challenging targets. However, generating macrocycles against new targets is hindered by a lack of large macrocycle libraries for high-throughput screening. To overcome this, ...

Nature Research2022

Generating macrocyclic inhibitors of protein-protein interactions

Gontran Sangouard

Protein-protein interactions (PPIs) play important roles in many diseases and their modulation is an attractive strategy for developing new therapeutics. However, the relatively large and often flat binding surfaces of PPIs makes the development of inhibit ...

EPFL2022

Dissociative Sticking Probability of Methane on Pt(110)-(2×1)

Rainer Beck, Ana Gutiérrez González

In this work, we revisit the dissociative sticking of methane on Pt(110)-(2×1) using quasi-classical trajectory (QCT) calculations and supersonic molecular beam (SMB) experiments. Experimentally, we apply the King and Wells method and the reflection absorp ...

2021

A precise polyrotaxane synthesizer

Bo Song, Cristian Pezzato

Mechanically interlocked molecules are likely candidates for the design and synthesis of artificial molecular machines. Although polyrotaxanes have already found niche applications in exotic materials with specialized mechanical properties, efficient synth ...

American Association for the Advancement of Science2020

Macrocycle synthesis strategy based on step-wise “adding and reacting” three components enables screening of large combinatorial libraries

Christian Heinis, Gerardo Turcatti, Alessandro Angelini, Alessandro Zorzi, Jonathan Patrice Vesin, Kaycie Marie Butler, Julien Bortoli Chapalay, Sangram Shivdas Kale, Ganesh Kumar Mothukuri, Carl Leonard Stenbratt

Macrocycles provide an attractive modality for drug development, but generating ligands for new targets is hampered by the limited availability of large macrocycle libraries. We have established a solution-phase macrocycle synthesis strategy in which three ...

2020

Non-equilibrium kinetics and trajectory thermodynamics of synthetic molecular pumps

Cristian Pezzato

A major goal in the design of synthetic molecular machines is the creation of pumps that can use the input of energy to transport material from a reservoir at low chemical potential to a different reservoir at higher chemical potential, thereby forming and ...

ROYAL SOC CHEMISTRY2020

A Molecular Dual Pump

Cristian Pezzato

Artificial molecular machines (AMMs) built from mechanically interlocked molecules (MIMs) can use energy ratchets to control the unidirectional motion of their component parts. These energy ratchets are operated by the alteration of kinetic barriers and th ...

AMER CHEMICAL SOC2019

Fixed DNA Molecule Arrays for High-Throughput Single DNA-Protein Interaction Studies

Vytautas Navikas

The DNA Curtains assay is a recently developed experimental platform for protein-DNA interaction studies at the single-molecule level that is based on anchoring and alignment of DNA fragments. The DNA Curtains so far have been made by using chromium barrie ...

AMER CHEMICAL SOC2019

Improving the binding affinity of in-vitro-evolved cyclic peptides by inserting atoms into the macrocycle backbone

Christian Heinis, Jonas Alfred Karl Wilbs, Simon Jan Middendorp

Cyclic peptides binding to targets of interest can be generated efficiently with powerful in vitro display techniques, such as phage display or mRNA display. The cyclic peptide libraries screened with these methods are generated by altering in a combinator ...

2016

Crystalline and Soft Materials Based on Dative Boron-Nitrogen Bonds

Nicolas Luisier

The thesis describes the utilization of dative boron-nitrogen bond is used for the construction of new materials. In chapter 2.1, the synthesis of new organogels based on bisimidazolyl ligands and diboronate esters is described. Gels with a critical gel co ...

EPFL2016

Facile synthesis of oligoyne amphiphiles and their rotaxanes

Holger Frauenrath, Stephen Schrettl, Tobias Hoheisel, Martin Fritzsche

Carbon-rich organic compounds containing a series of conjugated triple bonds (oligoynes) are relevant synthetic targets, but an improved access to oligoynes bearing functional groups would be desirable. Here, we report the straightforward synthesis of two ...

Royal Soc Chemistry2015

Functionalized imidazoliniums from the three-component domino reaction of N-formylmethylcarboxamides with amines and isocyanides

Jieping Zhu

In the presence of Zn(OTf)2, the three-component domino reaction of N formylmethyl-substituted tertiary amides and enamides with amines and isocyanides in acetonitrile at room temperature produced functionalized imidazoliniums in good to excellent yields. ...

2014

Synthesis of borasiloxane-based macrocycles by multicomponent condensation reactions in solution or in a ball mill

Rosario Scopelliti, Kay Severin, Albert Ruggi, Mirela Pascu

Large macrocycles containing imine and borasiloxane links are obtained in polycondensation reactions of 4-formylbenzeneboronic acid, t-Bu2Si(OH)2, and diamines. The multicomponent reactions can be performed in solution or – advantageously – by mechanochemi ...

Royal Soc Chemistry2013

Molecular Borophosphate Cages

Rosario Scopelliti, Kay Severin, Justus Tönnemann

A synthetic procedure for the synthesis of two molecular borophosphate cages is described. Heating of ethyl phosphate with phenylboronic or 4-formylboronic acid in toluene gives [6+6] condensation products of the general formula EtOPO3BAr. Crystallogr ...

Wiley-Blackwell2013

Self-Assembly of Arylboronate Esters with Pyridyl Side Chains

Rosario Scopelliti, Kay Severin, Erin Sheepwash, Kai Zhou

Boronate esters that contain N-donor groups are self-complementary structures, which can assemble by means of dative boron–nitrogen bonds to form macrocycles or polymers. Herein, we describe the synthesis of dioxaborinanes and benzodioxaboroles containing ...

Wiley-Blackwell2013

Interfacial Self-Assembly as Catalytic Platform for Multielectron Redox Reactions

Astrid Johana Olaya Avendano

In Nature, many vital biological processes take place across the interface formed between two dielectric media. For instance, photosynthesis and aerobic respiration involve a series of redox reactions occurring across energy-transducing membranes, in charg ...

EPFL2013

Multicomponent Assembly of Boronic Acid-Based Macrocycles, Cages, and Polymers

Burçak Içli

This work describes the synthesis and characterization of boronic acid-based supramolecular structures. Different reversible interactions such as boronate ester formation, imine condensation and dative B–N bond formation are used to assemble macrocycles, c ...

EPFL2012

Boronic Acids as Building Blocks for Molecular Nanostructures and Polymeric Materials

Kay Severin

Boronic acids are versatile building blocks for the construction of complex molecular architectures. Using reversible condensation reactions, it is possible to obtain macrocycles, cages, dendritic structures, and rotaxanes, as well as 1-, 2-, and 3-dimensi ...

2009