Cationic polymers with d-fructose substituents

Patent metadata

Field	Value
Publication number	US-2020407502-A1
Application number	US-201816495676-A
Country	US
Kind code	A1
Filing date	Mar 23, 2018
Priority date	Mar 23, 2017
Publication date	Dec 31, 2020
Grant date	—

Abstract

The invention relates to new cationic polymers conjugated with D-fructose, as a result of which they can selectively interact with specific structure elements on cell surfaces. The problem was that of creating novel, biocompatible, easy-to-produce, D-fructose-conjugated cationic polymers that have a higher selectivity with respect to certain cell types. To solve this problem, the invention proposes cationic polymers with covalently bonded D-fructose of general formula (I) with the following components: a) cationic polymer: macromolecular compounds of n repeat units with one or more positive charges; b) linker: a unit that links the cationic polymer with D-fructose or derivatives of D-fructose by means of any alkyl or aryl group, any alkenyl or alkinyl group, an ether, thioether or amine, an ester, amide or other carboxylic acid derivative, a heterocycle (e.g. triazole or m maleimide), a disulphide, an imine or an imide; c) D-fructose: one or more D-fructoses or D-fructose derivatives in an open-chain, furanoid or pyranoid structure, not glycosidically linked via one of the five possible carbon atoms (1, 3, 4, 5, 6).

First claim

1 . Cationic polymers with covalently bonded D-fructose of general formula (I) with the components:
a) cationic polymer: macromolecular compounds of n repeating units having one or more positive charges; b) linker: a unit linking the cationic polymer to D-fructose or to derivatives of D-fructose by any alkyl or aryl radical, any alkenyl or alkynyl radical, an ether, thioether or amine, an ester, Amide or another carboxylic acid derivative, a heterocycle (e.g. triazole or maleimide), a disulfide, an imine or an imide; c) D-fructose: one or more D-fructose or D-fructose derivatives in open-chain, furanoid or pyranoid structure, non-glycosidically linked via one of the five possible carbon atoms (1, 3, 4, 5, 6).

2 . Cationic polymers with covalently bonded D-fructose according to claim 1 , characterized in that they have functional groups which have positive charges under appropriate conditions.

3 . Cationic polymers with covalently bonded D-fructose according to at least one of claims 1 to 2 , characterized in that they contain functional groups which can carry positive charges at different positions once or several times in the polymer.

4 . Cationic polymers with covalently bonded D-fructose according to at least one of claims 1 to 3 , characterized in that they can be described both as a homopolymer or as a copolymer (random and/or block and/or gradient).

5 . Cationic polymers with covalently bonded D-fructose according to at least one of claims 1 to 4 , characterized in that they are linear or branched, wherein the latter form includes, for example, stars (dendrimers), brushes, combs, etc.

6 . Cationic polymers with covalently bonded D-fructose according to at least one of claims 1 to 5 , characterized in that one or more D-fructose residues are bonded to individual, a plurality of or all repeating units of the cationic polymer via linkers according to claim 1 .

7 . Cationic polymers with covalently bonded D-fructose according to at least one of claims 1 to 6 , characterized in that the D-fructose can contain next to free OH groups further substituents on the carbon atoms 1, 2, 3, 4, 5 and/or 6.

8 . Cationic polymers with covalently bonded D-fructose according to at least one of claims 1 to 7 , characterized in that a biologically active material from the group of nucleic acids is bonded electrostatically and/or covalently.

9 . Cationic polymers with covalently bonded D-fructose according to claim 8 , characterized in that the bonded nucleic acid is from the group of DNA, RNA, a ribosome and/or a DNA-RNA hybrid and is double-stranded and/or single-stranded.

10 . Use of the cationic polymer with covalently bonded D-fructose according to any one of claims 1 to 9 for the transport and delivery of a biologically active material into a living cell.

11 . The use of the cationic polymers with covalently bonded D-fructose according to any one of claims 1 to 9 for the selective killing of certain cell types.

Assignees

• Univ Jena Friedrich Schiller

Inventors

• Gottschaldt Michael
• Proehl Michael
• Englert Christoph
• Schubert Ulrich Sigmar

Classifications

• C08G73/0226

  Quaternisation of polyalkylene(poly)amines · CPC title

• A61K47/6455

  Polycationic oligopeptides, polypeptides or polyamino acids, e.g. for complexing nucleic acids · CPC title

• C07H3/02

  Monosaccharides · CPC title

• A61K47/543

  Lipids, e.g. triglycerides; Polyamines, e.g. spermine or spermidine · CPC title

• C08G69/48 Primary

  Polymers modified by chemical after-treatment · CPC title