Patents

9. Methods for proximity mediated coupling of a first agent to a second agent

Alex Manicardi, Annemieke Madder

The present invention relates to a method for covalently binding a first agent and a second agent, the first agent comprising a first recognition element, wherein the first recognition element comprises an 1,4-dioxo moiety having a structure of Formula IA, IB or IC, wherein R12 is C1-30oalkyl, C2-30alkenyl, C6-15aryl, or C5-15heteroaryl, wherein the C1-30alkyl, C2-30alkenyl, C6-15aryl, or C5-15heteroaryl group are optionally substituted with an C1-6alkyl, C3-6cycloalkyl, halogen, amine, hydroxyl, sulfhydryl, carboxyl, or C1-6alkoxy; and R13, if present, is hydrogen, C1-30alkyl or C2-30alkenyl; the second agent comprising a second recognition element, wherein the second recognition element comprises a nucleophilic moiety selected from a hydrazine moiety, an aminooxy moiety, an aminosulfanyl moiety or a hydroxylamine moiety; wherein: (A) the first recognition element and the second recognition element are capable of non-covalently binding to each other such that the 1,4-dioxo moiety and the nucleophilic moiety are brought in proximity; the method comprising contacting the first agent with the second agent, thereby covalently binding the 1,4-dioxo moiety and the nucleophilic moiety; or (B) the first recognition element and the second recognition element are capable of non-covalently binding to a third recognition element such that the 1,4-dioxo moiety and the nucleophilic moiety are brought in proximity; the method comprising contacting the first agent with the second agent and the third recognition element, thereby covalently binding the 1,4-dioxo moiety and the nucleophilic moiety; wherein the first recognition element is a peptide nucleic acid (PNA), a peptide, a peptidomimetic, an oligonucleotide, an oligonucleotide mimic, or a combination thereof; the second recognition element is a PNA, a peptide, a peptidomimetic, an oligonucleotide, an oligonucleotide mimic, or a combination thereof; and the third recognition element is a nucleic acid, an oligonucleotide, an oligonucleotide mimic, a PNA, a protein, a peptide, a cyclodextrin, a cucurbituril, a cyclophane, or a combination thereof. The invention further provides related products including kits of parts.

WO2022079127A1  

8. Bioconjugation reagent and methods

Annemieke Madder, Ewout De Geyter, Eirini Antonatou, Sabina Smolen, Dimitris Kalaitzakis, Georgios Vassilikogiannakis
The present invention in general relates to the field of bioconjugation. More in particular, the invention relates to novel bioconjugation reactants based on an α,β unsaturated γ-hydroxylactam structure, amongst others allowing a higher degree of functionalization compared to classical bioconjugation reactants such as maleimide. The present invention also provides methods of preparing the novel bioconjugation reactants, as well as uses thereof in human and/or veterinary medicine; and conjugation processes.

7. 2-Hydroxypyrrolidin-5-ones for bioconjugation  and methods for their production

Inventors: Annemieke Madder, Ewout De Geyter, Eirini Antonatou, Sabine Smolen, Dimitris Kalaitzakis, Georgios Vassilikogiannakis.

The present invention in general relates to the field of bioconjugation. More in particular, the invention relates to novel bioconjugation reactants based on an α,β unsaturated γ- hydroxylactam structure, amongst others allowing a higher degree of functionalization compared to classical bioconjugation reactants such as maleimide. The present invention also provides methods of preparing the novel bioconjugation reactants, as well as uses thereof in human and/or veterinary medicine; and conjugation processes.

WO2020174086A2 

6. Synthetic receptors for ionophoric compounds.

Inventors: Vincent Ornelis, Annemieke Madder, Sarah De Saeger, Andreja Rajkovic, Benedikt Sas

The present invention relates to synthetic receptors for ionophoric compounds, such as ionophoric toxins. Hence, the invention provides synthetic molecules capable of binding different ionophoric compounds, thereby being suitable for use in the detection, isolation and detoxification of such ionophoric compounds. The present invention further provides the use of such synthetic receptors in human and veterinary medicine, such as in the diagnosis, prevention and/or treatment of disorders caused by such ionophoric compounds. Finally, the invention provides methods of preparing such synthetic receptors for ionophoric compounds.

WO2019166475 

5. Hydrogel-forming composition for controlled release.

Inventors: Charlotte Martin, Richard Hoogenboom, Annemieke Madder and Steven Ballet.

The present invention provides peptide hydrogelators capable of forming hydrogels as carriers of active ingredients and acting as sustained or controlled release drug delivery systems.

WO2017140792 

4. Methods for covalently binding a cell surface protein and a ligand.

Inventors: Annemieke Madder, Willem Vannecke, Christophe Ampe en Marleen van Troys.

The present invention relates to a method for covalently binding a cell surface protein and a ligand, the ligand being capable of specifically binding to the cell surface protein, the method consisting essentially of contacting the living cells expressing the cell surface protein with the ligand comprising at least one furan moiety, thereby covalently binding the cell surface protein and the ligand.

WO2017148979A1 

3. Hydrogel forming peptides.

Inventors: Richard Hoogenboom, Annemieke Madder, Steven Ballet and Jeroen Mangelschots.

Provided are hydrogel-forming peptides that comprise at least one dyad of hydrophobic amino acid residues in which one is a β 3 - or β 2 -homo amino acid residue. The hydrogels derived from these peptides can be loaded with biological materials and can be used in physiological conditions.

WO2017009358A1 

2. Methods for the site-selective coupling of a first agent to a second agent.

Inventors: Annemieke Madder, Eirini Antonatou and Kurt Hoogewijs.

The present invention relates to a method for site-selective coupling of a first agent to a second agent, comprising the steps of: contacting a first agent comprising at least one furan moiety with an activation signal and with a second agent comprising at least one hydrazine moiety or at least one hydroxylamine moiety, thereby activating said furan moiety to an activated furan moiety; and reacting said activated furan moiety with the hydrazine moiety or the hydroxylamine moiety, thereby site-selectively coupling said first agent to said second agent.

WO2017001204A1  

1. Method for cross-linking peptides.

Inventors: Annemieke Madder, Kurt Hoogewijs, Annelies Deceuninck , Lieselot Carrette

The present invention relates to a method for cross-linking peptides using an activated furan-moiety. In particular, the present invention provides a method for cross-linking peptides comprising the steps of: a) providing a composition comprising furan-peptides, said furan-peptides comprising at least one amino acid comprising a furan-moiety; b) contacting said composition comprising furan-peptides with second peptides, thereby obtaining a mixture comprising furan-peptides and second peptides; c) adding an activation signal to said mixture of step b), thereby activating said furan-peptides to activated furan-peptides, and d) reacting said activated furan-peptides with said second peptides, thereby cross-linking said activated furan-peptides with said second peptides.

WO2012085279A2