Multifunctional degradable nanoparticles with control over size and functionalities

• US 10,442,890 B2
• Filed: 08/21/2017
• Issued: 10/15/2019
• Est. Priority Date: 11/05/2007
• Status: Active Grant

• Current Assignee: Vanderbilt University
• Original Assignee: Vanderbilt University
• Inventors: Harth, Eva M., Calkins, David J., Van Der Ende, Alice E.
• Primary Examiner(s): Fang, Shane
• Application Number:
  US15/682,278
• Publication Number:
  US 20180142061A1
• Time in Patent Office: 785 Days
• Field of Search: 528403, 528421, 528354, 528220, 525415
• 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 47/59 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. polyureas or polyurethanes
• CPC Class Codes: A61K 47/593 Polyesters, e.g. PLGA or polylactide-co-glycolide
• CPC Class Codes: A61K 47/595 Polyamides, e.g. nylon polyamino acids A61K47/62
• CPC Class Codes: A61K 49/0041 Xanthene dyes, used in vivo, e.g. administered to a mice, e.g. rhodamines, rose Bengal in vivo G01N
• CPC Class Codes: A61K 49/0056 Peptides, proteins, polyamino acids
• 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 9/0048 Eye, e.g. artificial tears
• CPC Class Codes: A61K 9/5153 Polyesters, e.g. poly(lactide-co-glycolide)
• CPC Class Codes: C08G 63/08 Lactones or lactides
• CPC Class Codes: C08G 63/78 Preparation processes
• CPC Class Codes: C08G 63/912 derived from hydroxycarboxylic acids

Abstract

In one aspect, the invention relates to polymers, crosslinked polymers, functionalized polymers, nanoparticles, and functionalized nanoparticles and methods of making and using same. In one aspect, the invention relates to degradable polymers and degradable nanoparticles. In one aspect, the invention relates to methods of preparing degradable nanoparticles and, more specifically, methods of controlling particle size during the preparation of degradable nanoparticles. In one aspect, the degradable nanoparticles are useful for complexing, delivering, and releasing payloads, including pharmaceutically active payloads. This abstract is intended as a scanning tool for purposes of searching in the particular art and is not intended to be limiting of the present invention.

Claims

1. A composition comprising a crosslinked degradable polyester particle including polymer backbones comprising δ

-valerolactone monomer residues, the crosslinked degradable polyester particle comprising one or more crosslinks comprising a structure selected from;

(a)

2. The composition of claim 1, further comprising:

at least one of a biologically active agent, a pharmaceutically active agent, or an imaging agent.

3. The composition of claim 2, wherein the composition is produced by a nucleophilic substitution reaction between a nucleophile including at least one of the biologically active agent, the pharmaceutically active agent, or the imaging agent and the polymer backbones.

4. The composition of claim 3, wherein at least one of the biologically active agent, the pharmaceutically active agent, or the imaging agent are attached to an optionally substituted organic radical comprising 1 to 24 carbon atoms.

5. The composition of claim 4, wherein the biologically active agent, the pharmaceutically active agent, or the imaging agent is covalently bonded to the optionally substituted organic radical comprising 1 to 24 carbon atoms.

6. The composition of claim 4, wherein the optionally substituted organic radical comprising 1 to 24 carbon atoms includes substituted or unsubstituted monovalent organic radicals selected from the group consisting of ethyl, propyl, butyl, pentyl, hexyl, heptyl, octyl, decyl, dodecyl, hexadecyl, higher cyclic or acyclic alkyl, and alkoxylene.

7. The composition of claim 2, wherein the at least one of a biologically active agent, a pharmaceutically active agent, or an imaging agent are encapsulated within the a crosslinked degradable polyester particle.

8. The composition of claim 1, wherein the crosslinked degradable polyester particle is a copolymer and/or a nanoparticle.