Sequence-defined antibody-recruiting macromolecules

Aksakal, Resat; Tonneaux, Corentin; Uvyn, Annemiek; Fossépré, Mathieu; Turgut, Hatice; Badi, Nezha; Surin, Mathieu; Geest, Bruno G. De; Prez, Filip Du

doi:10.1039/d3sc01507f

Cited by 6 publications

(2 citation statements)

References 38 publications

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“…Interestingly, a relevant design of the abiotic polymer structure enables the editing of encoded information by the light trigger . Besides data storage, such macromolecules have been used in catalysis, , drug delivery, − sensing, ,− selective binding, , molecular transport, , or as peptidomimetic foldamers. , The biological environment, where natural macromolecules perform sophisticated functions, is chiral. Therefore, the stereochemistry of macromolecules should be an essential parameter for their function.…”

Section: Introductionmentioning

confidence: 99%

Revealing the Effect of Stereocontrol on Intermolecular Interactions between Abiotic, Sequence-Defined Polyurethanes and a Ligand

Szatko,

Forysiak,

Kozub

et al. 2024

ACS Biomater. Sci. Eng.

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The development of precision polymer synthesis has facilitated access to a diverse library of abiotic structures wherein chiral monomers are positioned at specific locations within macromolecular chains. These structures are anticipated to exhibit folding characteristics similar to those of biotic macromolecules and possess comparable functionalities. However, the extensive sequence space and numerous variables make selecting a sequence with the desired function challenging. Therefore, revealing sequence− function dependencies and developing practical tools are necessary to analyze their conformations and molecular interactions. In this study, we investigate the effect of stereochemistry, which dictates the spatial location of backbone and pendant groups, on the interaction between sequence-defined oligourethanes and bisphenol A ligands. Various methods are explored to analyze the receptor-like properties of model oligomers and the ligand. The accuracy of molecular dynamics simulations and experimental techniques is assessed to uncover the impact of discrete changes in stereochemical arrangements on the structures of the resulting complexes and their binding strengths. Detailed computational investigations providing atomistic details show that the formed complexes demonstrate significant structural diversity depending on the sequence of stereocenters, thus affecting the oligomer−ligand binding strength. Among the tested techniques, the fluorescence spectroscopy data, fitted to the Stern−Volmer equation, are consistently aligned with the calculations, thus validating the developed simulation methodology. The developed methodology opens a way to engineer the structure of sequence-defined oligomers with receptor-like functionality to explore their practical applications, e.g., as sensory materials.

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Section: Introductionmentioning

confidence: 99%

Revealing the Effect of Stereocontrol on Intermolecular Interactions between Abiotic, Sequence-Defined Polyurethanes and a Ligand

Szatko,

Forysiak,

Kozub

et al. 2024

ACS Biomater. Sci. Eng.

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“…In a single modification, the heterocyclic carbonyl undergoes chemo- and regioselective amidation, while in the additional presence of a Michael acceptor (e.g., maleimide), a double modification takes place (ring opening, followed by a thiol–X reaction). , The unique reactivity of TLs can be introduced through the commercially available homocysteine thiolactone (HCTL), which can be easily modified through the amine in the α-position (Figure ). Hence, it has been extensively used for postpolymerization modifications, − toward sequence-defined and functional polymers, − surfaces, , hydrogels, , and bioconjugate materials. − …”

Section: Introductionmentioning

confidence: 99%

γ-Functional Iminiumthiolactones for the Single and Double Modification of Peptides

Mommer,

Warner,

Lienert

2023

Bioconjugate Chem.

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Sequence of Monomers and Position of Stereocenters Matter for Thermal Properties of Stereocontrolled Oligourethanes

Forysiak,

Lizak,

Szweda

2024

ChemPhysChem

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Polyurethanes are commodity materials used for multiple applications. In recent years, a new category of polyurethane material has emerged, characterized by the lack of polymer molar mass distribution, control of the monomer arrangement in the chain, and even full stereocontrol. Various multistep synthesis strategies have been developed to fabricate sequence‐defined polyurethanes. However, synthesizing stereocontrolled polyurethanes with a controlled sequence is still a challenge. Polyurethanes with structural precision, as represented by biopolymers, i.e. proteins or nucleic acids, have opened new application directions for these groups of materials. It has been shown that polyurethanes can be used as biomimetics, information carriers, molecular tags, and materials with strictly controlled properties. Precise synthesis of macromolecules allows us to fine‐tune the properties of polymers to specific needs. Therefore, it is essential to collect information on the sequence‐structure relationship of polymers. In our work, we present synthetic pathways to make sequence and stereo‐defined oligourethanes. We demonstrate that structural details, i.e., the monomer sequences and position of the stereocenter, have a tremendous effect on the thermal properties of model oligourethanes. We show that the introduction of chirality by constitutional isomerization can be used to program the thermal characteristics of polymers, which are key features for material applications.

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Sequence-defined antibody-recruiting macromolecules

Abstract: Antibody-recruiting molecules represent a novel class of therapeutic agents that mediate the recruitment of endogenous antibodies to target cells, leading to their elimination by the immune system. Compared to single-ligand...

Cited by 6 publications

References 38 publications

Revealing the Effect of Stereocontrol on Intermolecular Interactions between Abiotic, Sequence-Defined Polyurethanes and a Ligand

Revealing the Effect of Stereocontrol on Intermolecular Interactions between Abiotic, Sequence-Defined Polyurethanes and a Ligand

γ-Functional Iminiumthiolactones for the Single and Double Modification of Peptides

Sequence of Monomers and Position of Stereocenters Matter for Thermal Properties of Stereocontrolled Oligourethanes

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