Fullerene compositions

Patent metadata

Field	Value
Publication number	US-10029020-B2
Application number	US-201615567338-A
Country	US
Kind code	B2
Filing date	Apr 22, 2016
Priority date	Apr 23, 2015
Publication date	Jul 24, 2018
Grant date	Jul 24, 2018

Abstract

Provided herein are fullerene compositions, and methods of preparing fullerene compositions. More particularly, the fullerene compositions include a fullerene-polymer complex having a fullerene and a non-conjugated hydrophilic or amphiphilic polymer. The non-conjugated polymer is substituted with a substituent having a functional group capable of forming intermolecular interactions with the fullerene via pi-stacking.

First claim

What is claimed is:

1. A composition comprising a fullerene-polymer complex comprising one or more fullerenes and a non-conjugated hydrophilic or amphiphilic polymer, said non-conjugated polymer being substituted with at least one substituent comprising a functional group comprising a carbon-carbon pi-bond which interacts with said one or more fullerenes via pi-stacking.

2. The composition according to claim 1 , wherein said functional group is selected from the group consisting of allyl, propargyl, phenyl, naphthyl, pyrenyl, vinyl, ethynyl, benzyl, anthryl, indolyl, imidazolyl, thienyl, pyrazinyl, pyrimidinyl, piridazinyl, and triazolyl.

3. The composition according to claim 1 , wherein said non-conjugated polymer is a linear polymer wherein at least one chain end of said linear polymer is provided with said functional group.

4. The composition according to claim 1 , wherein said non-conjugated polymer is selected from the group consisting of polyvinylpyrrolidone (PVP), poly(ethylene glycol) (PEG), a polymer produced from a cyclic imino ether, polyvinyl alcohol (PVA), a dextran, polyglutamic acid (PGA), a poly(oligoethylene glycol acrylate) (POEGA), a poly(oligoethylene glycol methacrylate) (POEGMA), poly[N-( 2 -hydroxypropyl)methacrylamide (PHPMA), and copolymers thereof.

5. The composition according claim 1 wherein said non-conjugated polymer further comprises an amide bond.

6. The composition according to claim 1 , wherein said fullerene-polymer complex is provided as particles having an average size between 25 nm and 100 nm as measured via dynamic light scattering.

7. The composition according to claim 1 wherein said fullerene-polymer complex is suspended in an aqueous solvent, and wherein said composition comprises at least 1 wt % of said one or more fullerenes.

8. The composition according to claim 1 , wherein said one or more fullerenes comprise at least 90 wt % C 60 .

9. A medicament comprising the composition according to claim 1 .

10. A method for the treatment of an oxidative damage-related diseases or disorder comprising administering a composition according to claim 1 to a patient in need thereof.

11. An antioxidant composition comprising a composition according to claim 1 .

12. A method for the preparation of the composition according to claims 1 , comprising:
(a) providing one or more fullerenes and a non-conjugated hydrophilic or amphiphilic polymer, said non-conjugated polymer being substituted with at least one substituent comprising a functional group comprising a carbon-carbon pi-bond capable of interacting with said fullerene via pi-stacking; and
(b) mechanochemically treating said fullerene and said non-conjugated polymer, thereby obtaining a fullerene-polymer complex.

13. The method according to claim 12 , wherein step (b) comprises milling said fullerene and said non-conjugated polymer.

14. The method according to claim 12 , wherein said functional group is selected from the list consisting of allyl, propargyl, phenyl, naphthyl, and pyrenyl.

15. The method according to claim 12 , wherein step (b) is performed in the absence of solvents.

16. A method for increasing the solubility of fullerenes in water, comprising forming a complex between a fullerene and a non-conjugated polymer, wherein said non-conjugated polymer is substituted with at least one substituent comprising a functional group comprising a carbon-carbon pi-bond capable of interacting with said fullerene via pi-stacking.

17. The method of claim 10 , wherein the oxidative damage-related disease or disorder is selected from the group consisting of Parkinson's disease, Alzheimer's disease, cardiovascular diseases, and cancer.

18. The method of claim 13 , wherein the milling is performed using High Speed Vibration Milling.

Assignees

• Univ Gent

Inventors

• Hoogenboom Richard
• Van Guyse Joachim
• Retamero De La Rosa Victor

Classifications

• A61P9/00

  Drugs for disorders of the cardiovascular system · CPC title

• A61P35/00

  Antineoplastic agents · CPC title

• A61P25/28

  for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia · CPC title

• A61P25/16

  Anti-Parkinson drugs · CPC title

• C01B32/154

  Preparation · CPC title