Biodegradable photoluminescent polymers

• US 8,530,611 B2
• Filed: 06/18/2009
• Issued: 09/10/2013
• Est. Priority Date: 06/20/2008
• Status: Active Grant

• Current Assignee: Board of Regents of the University of Texas System (University of Texas System)
• Original Assignee: Board of Regents of the University of Texas System (University of Texas System)
• Inventors: Yang, Jian, Gautam, Santosh
• Primary Examiner(s): Choi, Ling
• Assistant Examiner(s): Mesh, Gennadiy
• Application Number:
  US13/000,327
• Publication Number:
  US 20110183435A1
• Time in Patent Office: 1,545 Days
• Field of Search: 528/289, 528/292, 528/296, 528/310, 525/418, 525/450
• US Class Current: 528/289
• CPC Class Codes: A61L 27/18 obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: A61L 27/3891 as distinct cell layers
• CPC Class Codes: A61L 27/50 Materials characterised by their function or physical properties , e.g. injectable or lubricating compositions, shape-memory materials, surface modified materials
• CPC Class Codes: A61L 27/507 for artificial blood vessels apparatus for applying cells on a blood vessel prosthesis A61F2/062
• CPC Class Codes: C08F 283/00 Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
• CPC Class Codes: C08F 283/006 on to polymers provided for in C08G18/00 C08F283/004 takes precedence
• CPC Class Codes: C08F 289/00 Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds not provided for in groups C08F251/00 - C08F287/00
• CPC Class Codes: C08F 290/00 Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
• CPC Class Codes: C08G 18/4236 containing only aliphatic groups
• CPC Class Codes: C08G 18/4283 Hydroxycarboxylic acid or ester
• CPC Class Codes: C08G 18/4646 containing one nitrogen atom in the ring
• CPC Class Codes: C08G 18/4676 containing sulfur
• CPC Class Codes: C08G 18/73 acyclic
• CPC Class Codes: C08G 2230/00 Compositions for preparing biodegradable polymers
• CPC Class Codes: C08G 63/6854 derived from polycarboxylic acids and polyhydroxy compounds
• CPC Class Codes: C08G 63/6858 Polycarboxylic acids and polyhydroxy compounds in which at least one of the two components contains aliphatic unsaturation
• CPC Class Codes: C08G 63/914 derived from polycarboxylic acids and polyhydroxy compounds
• CPC Class Codes: C08J 2367/04 Polyesters derived from hydroxy carboxylic acids, e.g. lactones C08J2367/06 takes precedence
• CPC Class Codes: C08J 5/18 Manufacture of films or sheets
• CPC Class Codes: C12N 2533/30 Synthetic polymers
• CPC Class Codes: C12N 5/0691 : Vascular smooth muscle cells; 3D culture thereof, e.g. models of blood vessels

Abstract

In one aspect, the present invention describes biodegradable photoluminescent polymer (BPLP) compositions. In some embodiments, an aliphatic biodegradable photoluminescent polymer (BPLP) composition comprises a degradable oligomer, wherein the oligomer is synthesized from a diol, an amino acid, and a biocompatible multifunctional carboxylic acid comprising a hydroxyl group. The amino acid is linked as a side group to the degradable oligomer backbone, and fluorescence emanates from a 6-membered ring formed by a carboxylic acid group of the amino acid, an alpha carbon of the amino acid, an amide linkage formed by an amino group of the amino acid, and a central carbon of the multifunctional carboxylic acid via an esterification reaction of the carboxylic acid group of the amino acid and the hydroxyl group of the multifunctional carboxylic acid.

Claims

1. An aliphatic biodegradable photoluminescent polymer (BPLP) composition comprising:

a degradable oligomer, wherein the oligomer is synthesized from a biocompatible multifunctional carboxylic acid comprising a hydroxyl group, a diol, and an amino acid;

wherein the amino acid is linked as a side group to the degradable oligomer backbone;

wherein fluorescence emanates from a 6-membered ring formed by a carboxylic acid group of the amino acid, an alpha carbon of the amino acid, an amide linkage formed by an amino group of the amino acid, and a central carbon of the multifunctional carboxylic acid via an esterification reaction of the carboxylic acid group of the amino acid and the hydroxyl group of the multifunctional carboxylic acid.

2. The composition of claim 1, wherein the biocompatible multifunctional carboxylic acid comprises citric acid, the diol comprises 1,8-octanediol, and the amino acid comprises cysteine or serine.

3. The composition of claim 1, wherein the diol comprises a saturated aliphatic diol, C3-C12 diol, hydrophilic diol, hydrophobic diol or any combination thereof.

4. The composition of claim 1, wherein the diol is selected from a 1,8-octanediol, ethylene glycol, propylene glycol, poly(ethylene glycol), poly(propylene glycol), 1,3-propanediol, ethanediol, and cis-1,2-cyclohexanediol.

5. The composition of claim 1, wherein the BPLP is crosslinked.

6. The composition of claim 5, wherein the crosslinking is achieved by radical polymerization initiated by photoinitiators or redox initiators.

7. The composition of claim 5, wherein the crosslinking is achieved by a condensation reaction.

8. The composition of claim 1, wherein an acid anhydride or a multifunctional acid chloride is used in addition to the multifunctional carboxylic acid.