Multifunctional degradable nanoparticles with control over size and functionalities

• US 8,492,510 B2
• Filed: 11/23/2010
• Issued: 07/23/2013
• Est. Priority Date: 11/05/2007
• Status: Active Grant

• Current Assignee: Vanderbilt University
• Original Assignee: Vanderbilt University
• Inventors: Harth, Eva M., Van Der Ende, Alice E.
• Primary Examiner(s): Fang, Shane
• Application Number:
  US12/953,173
• Publication Number:
  US 20110257343A1
• Time in Patent Office: 973 Days
• Field of Search: 528/403, 528/421, 528/354, 528/220, 525/415
• US Class Current: 528/421
• CPC Class Codes: A61K 47/6935 the polymer being obtained otherwise than by reactions involving carbon to carbon unsaturated bonds, e.g. polyesters, polyamides or polyglycerol
• CPC Class Codes: A61K 49/0043 Fluorescein, used in vivo
• CPC Class Codes: A61K 49/0054 Macromolecular compounds, i.e. oligomers, polymers, dendrimers
• CPC Class Codes: A61K 49/0067 quantum dots, fluorescent nanocrystals
• 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: B82Y 5/00 Nanobiotechnology or nanomedicine, e.g. protein engineering or drug delivery
• CPC Class Codes: C08G 63/06 derived from hydroxycarboxylic acids
• CPC Class Codes: C08G 63/912 derived from hydroxycarboxylic acids
• CPC Class Codes: C08G 71/02 Polyureas
• CPC Class Codes: C08J 2300/16 Biodegradable polymers
• CPC Class Codes: C08J 3/12 Powdering or granulating
• CPC Class Codes: C08J 3/14 by precipitation from solutions C08J3/122 takes precedence

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 polymer 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 polymer comprising at least one monomer residue having an optionally substituted structure represented by a formula:

2. The polymer of claim 1, further comprising at least one monomer residue selected from:

a. a propargyl-functionalized monomer residue having an optionally substituted structure represented by a formula;

3. The polymer of claim 1, wherein a method of preparing the polymer comprises the step of copolymerizing a mixture of two or more of:

a. an alkene-functionalized monomer providing a residue having an optionally substituted structure represented by a formula;

4. The method of claim 3, wherein the mixture further comprises at least one monomer providing a residue having an optionally substituted structure represented by a formula:

5. The method of claim 3, wherein the alkene-functionalized monomer is present and the method further comprises the step of oxidizing the resultant polymer to provide an epoxide-functionalized monomer residue having an optionally substituted structure represented by a formula:

6. The method of claim 3, wherein the alkene-functionalized monomer is present and has an optionally substituted structure represented by a formula:

7. The method of claim 6, wherein the alkene-functionalized monomer is present and has an optionally substituted structure represented by a formula:

8. The method of claim 3, wherein the propargyl-functionalized monomer is present and has an optionally substituted structure represented by a formula:

9. The method of claim 8, wherein the propargyl-functionalized monomer is present and has an optionally substituted structure represented by a formula:

10. The method of claim 3, wherein the keto-functionalized monomer is present and has an optionally substituted structure represented by a formula:

11. The method of claim 10, wherein the keto-functionalized monomer is present and has an optionally substituted structure represented by a formula:

12. The method of claim 4, wherein the monomer providing a residue having an optionally substituted structure represented by a formula:

13. The method of claim 12, wherein the monomer providing a residue having an optionally substituted structure represented by a formula:

14. The method of claim 3, further comprising the step of reacting a functionalized monomer residue to produce a functionalized polymer.

15. The method of claim 14, wherein functionalizing comprises the step of reacting:

a. an epoxide-functionalized monomer residue having an optionally substituted structure represented by a formula;

16. The method of claim 14, wherein functionalizing comprises the step of reacting:

a. a propargyl-functionalized monomer residue having an optionally substituted structure represented by a formula;

17. The method of claim 14, wherein functionalizing comprises the steps of reacting:

a. a keto-functionalized monomer providing a residue having an optionally substituted structure represented by a formula;