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Concept

Macrocycle

Publications associées (25)

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

Methods for high-throughput synthesis and screening of peptide libraries

Zsolt Bognár

Macrocycles provide an attractive modality for drug development but the identification of ligands to targets of interest is hindered by the lack of large macrocyclic compound libraries for high-throughput screening. A strategy to efficiently synthesize lar ...

EPFL2024

Development of methods for the synthesis of large combinatorial libraries of macrocyclic compounds

Mischa Schüttel

Macrocycles have raised much interest in the pharmaceutical industry due to their ability to bind challenging targets while often still being able to cross membranes to reach intracellular proteins. However, the development of macrocyclic ligands to new di ...

EPFL2023

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

Macrocyclization of omega-Isocyanoaldehydes and Towards the Total Synthesis of Jamaicensamide A

Teerawat Songsichan

In the first chapter of this thesis, the macrocyclization of a new type of bifunctional substrates, omega-isocyanoaldehyde derivatives, is described. Ten different omega-isocyanoaldehydes in terms of different ring sizes and functional groups were prepared ...

EPFL2021

Methods for the generation of large combinatorial macrocycle libraries

Sevan Mleh Habeshian

Macrocycles are an attractive class of molecules due to their good binding properties and yet rather small size that allows, in many cases, crossing membranes to reach intracellular targets. In comparison to classical small molecule drugs, macrocycles are ...

EPFL2021

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

Phthalocyanines for dye-sensitized solar cells

Mohammad Khaja Nazeeruddin, Tom Theodorus Antonius Lummen

Phthalocyanines (Pcs) are robust and intensely colored macrocycles (blue pigments) with high chemical, thermal and light stability, properties that are of paramount importance for realistic photovoltaic applications. In particular, Pcs have played a very i ...

2019

Thiol-to-amine cyclization reaction enables screening of large libraries of macrocyclic compounds and the generation of sub-kilodalton ligands

Christian Heinis, Gerardo Turcatti, Yu Wu, Xudong Kong, Jonathan Patrice Vesin, Patrick Andreas Gonschorek, Van Manh Pham, Julien Bortoli Chapalay, Sangram Shivdas Kale, Milan Bergeron-Brlek, João Miguel Franco Machado

Macrocyclic compounds are an attractive modality for drug development, but the limited availability of large, structurally diverse macrocyclic libraries hampers the discovery of leads. Here, we describe the discovery of efficient macrocyclization reactions ...

2019

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

Molecularly Defined Nanostructures Based on a Novel AAA-DDD Triple Hydrogen Bonding Motif

Kay Severin, Konstantin Zhurov, Marcus Papmeyer

A facile and flexible method for the synthesis of a new AAA–DDD triple hydrogen-bonding motif is described. Polytopic supramolecular building blocks with precisely oriented AAA and DDD groups are thus accessible in few steps. These building blocks were use ...

Wiley-VCH Verlag GmbH2016

Platinum-Catalyzed Domino Reactionwith Benziodoxole Reagents for Accessing Benzene-Alkynylated Indoles

Jérôme Waser, Yifan Li

Indoles are omnipresent in natural products, bioactive molecules, and organic materials. Consequently, their synthesis or functionalization are important fields of research in organic chemistry. Most works focus on installation or modification of the pyrro ...

Wiley-Blackwell2015

Lanthanide coordination chemistry: from old concepts to coordination polymers

Jean-Claude Bünzli

Because of their remarkable and unmatched optical and magnetic properties, the lanthanides are under the limelight when it comes to high technology. These elements are used in strategic applications such as optical glasses and lasers, telecommunications, l ...

Taylor & Francis2014

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

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

Investigation of the Release of Bioactive Volatiles from Amphiphilic Multiarm Star-Block Copolymers by Thermogravimetry and Dynamic Headspace Analysis

Jan-Anders Edvin Maansson, Harm-Anton Klok, John Christopher Plummer, Céline Ternat

Amphiphilic multiarm star-block copolymers with a hydrophobic inner and a hydrophilic outer shell have been used to encapsulate hydrophobic bioactive volatiles in aqueous media under realistic application conditions. The release rates of the bioactive comp ...

American Chemical Society2008

Efficient synthesis of cyclic glycolipids analogues

Sandrine Gerber, Gérald Coste

A straightforward approach to macrocyclic structures containing deoxysugar subunits was developed through the functionalization of a bishemiketal. The choice of the length and the nature of the linkers can provide macrocycles with diverse rigidities and po ...

2007