Biodegradable photoluminescent polymers

• US 9,145,467 B2
• Filed: 08/08/2013
• Issued: 09/29/2015
• 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:
  US13/962,476
• Publication Number:
  US 20130345369A1
• Time in Patent Office: 782 Days
• US Class Current: 1/1
• 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 thermoreactive polymers, e.g. PNIPAm, C12N2539/10
• CPC Class Codes: C12N 5/0691 : Vascular smooth muscle cells; 3D culture thereof, e.g. models of blood vessels

Abstract

A composition comprises an oligomer synthesized from a multifunctional monomer, a diol, and an amino acid synthesized by reacting (i) a multifunctional monomer comprising citric acid or triethyl citrate with (ii) a diol to form a reaction product, and further reacting the reaction product with (iii) an amino acid. Examples of the diol include 1,8-octanediol, ethylene glycol, and poly(ethylene glycol). Examples of the amino acid include cysteine and serine. Further, the amino acid is linked as a side group to the oligomer backbone.

Claims

1. A composition comprising:

an oligomer synthesized by reacting (i) a multifunctional monomer comprising citric acid or triethyl citrate with (ii) a diol to form a reaction product, and further reacting the reaction product with (iii) an amino acid,

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

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

3. The composition of claim 1, wherein the amino acid comprises alanine, arginine, asparagine, aspartic acid, cysteine, glycine, glutamine, glutamic acid, histidine, isoleucine, leucine, lysine, methionine, proline, phenylalanine, serine, threonine, tyrosine, tryptophan, valine, or a combination thereof.

4. The composition of claim 1, wherein the amino acid comprises an L-amino acid, D-amino acid, D,L-amino acid, or a derivative thereof.

5. The composition of claim 1, wherein the oligomer further comprises a residue of acid anhydride or a multifunctional acid.

6. The composition of claim 5, wherein the acid anhydride or the multifunctional acid chloride comprises maleic acid, maleic anhydride, fumaric acid, fumaryl chloride, acryloylchloride, itaconic acid, or allylmalonic acid.

7. A composition comprising:

an oligomer synthesized by reacting (i) a multifunctional monomer comprising citric acid or triethyl citrate with (ii) a diol to form a reaction product, and further reacting the reaction product with (iii) an amino acid and (iv) a di-isocyanate wherein the amino acid is linked as a side group to the oligomer backbone.

8. The composition of claim 7, wherein the diol is selected from 1,8-octanediol, ethylene glycol, propylene glycol, poly(ethylene glycol), poly(propylene glycol), 1,3-propanediol, ethanediol, and cis-1,2-cyclohexanediol.

9. The composition of claim 7, wherein the amino acid comprises alanine, arginine, asparagine, aspartic acid, cysteine, glycine, glutamine, glutamic acid, histidine, isoleucine, leucine, lysine, methionine, proline, phenylalanine, serine, threonine, tyrosine, tryptophan, valine, or a combination thereof.

10. The composition of claim 7, wherein the amino acid comprises an L-amino acid, D-amino acid, D,L-amino acid, or a derivative thereof.

11. The composition of claim 7, wherein the multifunctional monomer comprises citric acid, the diol comprises 1,8-octanediol, the amino acid comprises cysteine or serine, and the di-isocyanate comprises hexamethylene-1,6-di-isocyanate or 1,4-butane-di-isocyanate.

12. A method of making a composition, the method comprising:

mixing (i) a multifunctional monomer comprising citric acid or triethyl citrate and (ii) a diol to form a mixture;

raising the temperature of the mixture to at least 80°

C.

forming an oligomer from the mixture; and

reacting an amino acid and, optionally, a di-isocyanate with the oligomer;

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

13. The method of claim 12, wherein the diol is selected from 1,8-octanediol, ethylene glycol, propylene glycol, poly(ethylene glycol), poly(propylene glycol), 1,3-propanediol, ethanediol, and cis-1,2-cyclohexanediol.

14. The method of claim 12, wherein the multifunctional monomer comprises citric acid, the diol comprises 1,8-octanediol, the amino acid comprises cysteine or serine, and the di-isocyanate comprises hexamethylene-1,6-di-isocyanate or 1,4-butane-di-isocyanate.

15. The method of claim 12 further comprising purifying the oligomer prior to reacting the amino acid with the oligomer.

16. The method of claim 12, wherein the di-isocyanate is reacted with the oligomer after the amino acid is reacted with the oligomer.

17. The method of claim 12 further comprising casting a film of the composition.

18. The method of claim 17, wherein the film is cast in a laminar airflow.