Star polymer nanoshells and methods of preparation thereof

• US 8,945,513 B2
• Filed: 03/18/2011
• Issued: 02/03/2015
• Est. Priority Date: 03/18/2011
• Status: Expired due to Fees

• Current Assignee: International Business Machines Corporation, San José State University Research Foundation
• Original Assignee: International Business Machines Corporation, San José State University Research Foundation
• Inventors: Lee, Victor Yee-Way, Miller, Robert Dennis, Sly, Joseph, Tjio, Melia
• Primary Examiner(s): Hartley, Michael G
• Assistant Examiner(s): YOUNG, MICAH PAUL
• Application Number:
  US13/051,083
• Publication Number:
  US 20120237447A1
• Time in Patent Office: 1,418 Days
• Field of Search: 424/426, 424/427, 424/490, 424/489, 424/9.6, 424/9.1, 424/9.322
• US Class Current: 424/9.322
• CPC Class Codes: A61K 47/58 obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. poly[meth]acrylate, polyacrylamide, polystyrene, polyvinylpyrrolidone, polyvinylalcohol or polystyrene sulfonic acid resin
• CPC Class Codes: A61K 47/6929 the form being a nanoparticle, e.g. an immuno-nanoparticle
• CPC Class Codes: A61K 49/0036 Porphyrins used in photodynamic therapy A61K41/0071 or A61K41/0076; used as targeting group or modifying agent for targeting a therapeutic compound A61K47/546
• CPC Class Codes: A61K 49/0054 Macromolecular compounds, i.e. oligomers, polymers, dendrimers
• CPC Class Codes: A61K 49/0065 the luminescent/fluorescent agent having itself a special physical form, e.g. gold nanoparticle
• CPC Class Codes: A61K 49/0093 Nanoparticle, nanocapsule, nanobubble, nanosphere, nanobead, i.e. having a size or diameter smaller than 1 micrometer, e.g. polymeric nanoparticle
• CPC Class Codes: A61K 49/0097 Cells, viruses, ghosts, red blood cells, viral vectors, used for imaging or diagnosis in vivo
• CPC Class Codes: A61K 49/0423 Nanoparticles, nanobeads, nanospheres, nanocapsules, i.e. having a size or diameter smaller than 1 micrometer
• CPC Class Codes: A61K 49/1818 particles, e.g. uncoated or non-functionalised microparticles or nanoparticles
• CPC Class Codes: A61K 9/5115 Inorganic compounds
• CPC Class Codes: A61K 9/5138 obtained by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyvinyl pyrrolidone, poly(meth)acrylates
• CPC Class Codes: A61K 9/5192 Processes
• CPC Class Codes: A61P 43/00 Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
• CPC Class Codes: B01J 13/02 Making microcapsules or microballoons for medical preparations A61K9/50
• CPC Class Codes: B82Y 30/00 Nanotechnology for materials or surface science, e.g. nanocomposites
• CPC Class Codes: B82Y 5/00 Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
• CPC Class Codes: C09B 47/00 Porphines; Azaporphines non-dyeing compounds C07D487/22
• CPC Class Codes: C09B 67/0005 the pigments being nanoparticles
• CPC Class Codes: C09B 67/0032 Treatment of phthalocyanine pigments C09B67/0016, C09B67/0019 take precedence
• CPC Class Codes: C09B 67/0097 Dye preparations of special physical nature; Tablets, films, extrusion, microcapsules, sheets, pads, bags with dyes
• CPC Class Codes: C09B 68/41 : Polymers attached to the pigment surface C09B68/444, C09B68/446 take precedence
• CPC Class Codes: C09B 68/444 : Polyether
• CPC Class Codes: C09B 68/446 : Amines or polyamines, e.g. aminopropyl, 1,3,4,-triamino-pentyl or polyethylene imine
• CPC Class Codes: G01N 33/587 : Nanoparticles
• CPC Class Codes: Y10T 428/249953 : Composite having voids in a component [e.g., porous, cellular, etc.]
• CPC Class Codes: Y10T 428/2993 : Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
• CPC Class Codes: Y10T 428/2998 : including synthetic resin or polymer

Abstract

A nanoshell is disclosed, comprising a star polymer occlusion complex comprising i) an amphiphilic unimolecular star polymer having a crosslinked core covalently linked to 6 or more independent polymer arms, and ii) a cargo material occluded in the star polymer; and a shell comprising an inorganic material in contact with a peripheral surface of the star polymer occlusion complex.

Claims

1. A nanoshell, comprising:

a star polymer occlusion complex comprising i) an amphiphilic unimolecular star polymer having a crosslinked polymer core covalently linked to 6 or more independent polymer arms, and ii) a cargo material occluded in the star polymer; and

a shell comprising gold exterior to and in contact with a peripheral surface of the star polymer occlusion complex;

wherein the crosslinked polymer core is a product of a vinyl polymerization and/or a ring opening polymerization.

2. The nanoshell of claim 1, wherein i) the core is hydrophobic, ii) the cargo material is hydrophobic, and iii) each of the 6 or more polymer arms comprises a) a hydrophobic chain segment covalently linked to the core and b) a peripheral hydrophilic chain segment linked to the hydrophobic chain segment.

3. The nanoshell of claim 1, wherein the shell comprises one or more shell layers.

4. The nanoshell of claim 3, wherein the one or more shell layers are porous.

5. The nanoshell of claim 1, wherein the nanoshell has an average diameter of about 15 nm to about 300 nm.

6. The nanoshell of claim 1, wherein the cargo material is an imaging agent.

7. The nanoshell of claim 1, wherein the cargo material is a biologically active compound.

8. The nanoshell of claim 1, further comprising an organic surface group covalently linked to the shell, the organic surface group comprising a chemical moiety selected from the group consisting of dyes, poly(alkylene oxide) chain segments, poly(alkylene imine) chain segments, biologically active moieties, and combinations thereof.

9. The nanoshell of claim 1, wherein an aqueous mixture of the nanoshell is suitable for diagnostic imaging.

18. The composition of claim 1, wherein the crosslinked polymer core consists essentially of a crosslinked poly(styrene).

19. The composition of claim 1, wherein each of the polymer arms comprises a poly(styrene) chain segment linked to the core.

20. The composition of claim 1, wherein each of the polymer arms comprises a hydrophobic chain segment linked to the core, the chain segment comprising a backbone carbonate repeat unit and/or a backbone ester repeat unit.

21. The composition of claim 1, wherein each of the polymer arms comprises a peripheral hydrophilic chain segment comprising a poly(ethylene oxide) backbone.

22. The composition of claim 1, wherein the core comprises a crosslinked polyester.

23. The composition of claim 1, wherein each of the polymer arms comprises a peripheral hydrophilic chain segment that includes a repeat unit having a side chain tertiary amine group.

24. The composition of claim 1, wherein each of the polymer arms comprises a peripheral hydrophilic chain segment that includes a repeat unit having a structure:

25. The composition of claim 1, wherein the cargo material is a porphyrinoid compound.

26. The composition of claim 1, wherein the cargo material has a structure selected from the group consisting of

27. The composition of claim 1, wherein the nanoshell comprises one macromolecule of the star polymer.

10. A method, comprising:

treating a star polymer occlusion complex with gold seeds, thereby forming a seeded occlusion complex, wherein the star polymer occlusion complex comprises an amphiphilic unimolecular star polymer and a cargo material occluded therein, the star polymer having a crosslinked polymer core covalently linked to 6 or more independent polymer arms; and

depositing gold by electroless deposition on the seeded occlusion complex, thereby forming a nanoshell, wherein the nanoshell comprises a shell comprising gold exterior to and in contact with a peripheral surface of the star polymer occlusion complex;

wherein the crosslinked polymer core is a product of a vinyl polymerization and/or a ring opening polymerization.

11. The method of claim 10, wherein i) the core is hydrophobic, ii) the cargo material is hydrophobic, and iii) each of the 6 or more polymer arms comprises a) a hydrophobic chain segment covalently linked to the core and b) a peripheral hydrophilic chain segment linked to the hydrophobic chain segment.

12. The method of claim 10, further comprising treating the nanoshell with an organic tagging agent, thereby forming a tagged nanoshell comprising an organic surface group covalently linked to the shell, the organic surface group comprising a chemical moiety selected from the group consisting of dyes, poly(alkylene oxide) chain segments, poly(alkylene imine) chain segments, biologically active moieties, and combinations thereof.

13. The method of claim 10, wherein the star polymer is formed by organocatalyzed ring opening polymerization.

14. The method of claim 13, wherein the star polymer comprises a polycarbonate chain segment, a polyester chain segment, or a combination thereof.

15. The method of claim 10, wherein the cargo material is an imaging agent.

16. The method of claim 10, wherein the cargo material is a biologically active compound.

17. The method of claim 10, wherein the nanoshell has an average diameter of about 15 nm to about 300 nm.