US 9,176,127 B2Granted

Method for selecting a candidate drug compound

AssigneePepscan Systems B.V.

InventorsPeter Timmerman, Joris Beld, Robbert H. Meloen, Wouter C. Puijk

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Abstract

The disclosure relates to the field of candidate drug testing and drug development. A method is provided for providing a compound composed of at least one molecule attached via at least two linkages to a molecular scaffold, the method comprising providing a scaffold comprising at least a first and a second reactive group; providing at least one molecule capable of reacting with the at least first and second reactive group; contacting the scaffold with at least one molecule to form at least two linkages between the scaffold and the at least one molecule in a coupling reaction, wherein the formation of a linkage accelerates the formation of a consecutive linkage, preferably wherein the coupling reaction is performed in solution, more preferably in an aqueous solution. Furthermore, a method is provided for selecting a candidate drug compound comprising providing a library of compounds hereof and determining the binding of a target molecule to the compounds.

Claims17

Dependent claims

A method for preparing a library comprising a plurality of compounds composed of at least one peptide structure attached via at least two thioether linkages to a (hetero)aromatic molecule, the method comprising:

providing at least two compounds, each compound comprising at least one peptide structure attached via at least two thioether linkages to a (hetero)aromatic molecule using a method comprising:
providing a (hetero)aromatic molecule comprising a bis-, tris-, or tetrakis(halomethyl)-substituted (hetero)aromatic ring system;
providing at least one peptide comprising at least one amino acid having a side chain comprising an unprotected functional group selected from the group consisting of amine, guanidinium, amido, carboxylic acid, alcohol, phenol, indole, thioether, and imidazole, and at least two SH-functionalities;
and
contacting the (hetero)aromatic molecule with the at least one peptide in a buffered aqueous solution comprising at least 50% water to form, in a coupling reaction, at least two thioether linkages between the (hetero)aromatic molecule and the at least one peptide,
wherein each of the thioether linkages is formed between one of the halomethyl substituents on the (hetero)aromatic ring system and one of the SH functionalities in the peptide,
thus preparing a library comprising a plurality of compounds composed of at least one peptide structure attached via at least two thioether linkages to the (hetero)aromatic molecule.

4 more elements

Dependencies are inferred from the claim text.

Facts

Application: 14/201,523Filed 7 Mar 2014 · division
Priority: EP 0307559727 Feb 2003
Published: US 2014/0308303 A116 Oct 2014
Granted: 3 Nov 2015
Term ends: Not estimatedThe source records don’t support an estimate.

Classification7 codes

G01N 33/54306
With an insoluble carrier for immobilising immunochemicals: solid-phase reaction mechanisms
C07K 17/02
Carrier-bound or immobilised peptides ; Preparation thereof: peptides being immobilised on, or in, an organic carrier
C40B 30/04
Methods of screening libraries: by measuring the ability to specifically bind a target molecule, e.g. antibody-antigen binding, receptor-ligand…
G01N 33/54353
With an insoluble carrier for immobilising immunochemicals: with ligand attached to the carrier via a chemical coupling agent

Family

PCT/NL2004/000146Parent of this continuation · filed 26 Feb 2004
Application11/213,443Parent of this division · filed 26 Aug 2005
US 2014/0308303 A1Pre-grant publication · published 16 Oct 2014
US 8,748,105 B2Parent of this division
Application11/213,443Parent of this continuation
US 2006/0073518 A1Published application
US 9,176,127 B2This patent

From the US filing history. Foreign family members aren’t listed.