- Patent Number:
12247,090
- Appl. No:
17/812354
- Application Filed:
July 13, 2022
- Abstract:
The present disclosure describes, in part, an enzyme-mediated radical initiating system and methods of using the system to produce polymers, including polymeric hydrogels, at ambient conditions.
- Inventors:
Duke University (Durham, NC, US)
- Assignees:
Duke University (Durham, NC, US)
- Claim:
1. A method for making a polymer, comprising: (a) providing a composition comprising a vinyl monomer, N-hydroxy-5-norbornene-2,3-dicarboximide (HONB), horseradish peroxidase (HRP), and hydrogen peroxide (H 2 O 2); and (b) incubating the composition to provide the polymer.
- Claim:
2. The method of claim 1 , wherein the composition comprises H 2 O 2 and HRP in a molar ratio of about 5 to about 4000.
- Claim:
3. The method of claim 1 , wherein the composition comprises HONB and H 2 O 2 in a molar ratio of about 1 to about 800.
- Claim:
4. The method of claim 1 , wherein the composition comprises HONB at a concentration of at least about 8 mM.
- Claim:
5. The method of claim 1 , wherein the composition comprises H 2 O 2 at a concentration of at least about 0.2 mM.
- Claim:
6. The method of claim 1 , wherein the composition further comprises an aqueous solution, wherein the aqueous solution has a pH of about 1 to about 8.
- Claim:
7. The method of claim 1 , wherein step (a) comprises: (i) providing a first mixture of the vinyl monomer in an aqueous solution, and (ii) adding HONB, HRP, and H 2 O 2 to the first mixture to provide the composition.
- Claim:
8. The method of claim 1 , wherein step (a) comprises: (i) providing a first mixture of HONB and H 2 O 2 , and (ii) adding HRP to the first mixture to provide the composition.
- Claim:
9. The method of claim 1 , wherein the polymer is a hydrogel.
- Claim:
10. The method of claim 1 , wherein the vinyl monomer is selected from (meth) acrylamide monomers, (meth) acrylate monomers, N-vinyl lactam monomers, and combinations thereof.
- Claim:
11. The method of claim 10 , wherein the vinyl monomer is selected from acrylamide, methacrylamide, N,N-dimethyl acrylamide, N-isopropyl acrylamide, hydroxyethyl acrylate, poly (ethylene glycol) methyl ether acrylate, poly (ethylene glycol) methyl ether methacrylate, 2-hydroxypropyl methacrylamide, 2-hydroxyethyl methacrylate, 2-methoxyethyl acrylate, methacrylic acid, 4-acryloylmorpholine, dimethyl vinylphosphonate, N-vinylcaprolactam, N-vinyl pyrrolidone, and combinations thereof.
- Claim:
12. The method of claim 1 , wherein the composition further comprises a crosslinker selected from poly (ethylene glycol) diacrylate, poly (ethylene glycol) dimethacrylate, gelatin methacryloyl, acryloylated proteins, N,N′-methylene-bisacrylamide, bisphenol A glycerolate diacrylate, multi-arm acrylate-terminated poly (ethylene glycol), and combinations thereof.
- Claim:
13. The method of claim 12 , wherein the crosslinker is 4-arm-PEG10K-acrylate.
- Claim:
14. The method of claim 1 , wherein the composition further comprises one or more water-dispersible inorganic nanomaterials selected from gold nanoparticles, silica nanoparticles, and hydroxyapatite nanoparticles.
- Claim:
15. The method of claim 1 , wherein the method is carried out at a temperature ranging from about 15° C. to about 37° C.
- Claim:
16. The method of claim 1 , wherein the method is carried out in an open reaction vessel.
- Claim:
17. The method of claim 1 , wherein the method is carried out in a closed reaction vessel.
- Claim:
18. An enzyme-mediated radical initiating system, wherein the system comprises N-hydroxy-5-norbornene-2,3-dicarboximide (HONB), horseradish peroxidase (HRP), and hydrogen peroxide (H 2 O 2).
- Claim:
19. A kit comprising: N-hydroxy-5-norbornene-2,3-dicarboximide (HONB), horseradish peroxidase (HRP), and hydrogen peroxide (H 2 O 2).
- Claim:
20. The kit of claim 19 , further comprising at least one of: a container, a vinyl monomer, a crosslinker, and instructions for carrying out a polymerization reaction.
- Patent References Cited:
10166314 January 2019 Phopase et al.
2011/0305872 December 2011 Li
2020/0230288 July 2020 Cho et al.
WO 2009/148405 December 2009
WO 2019/043547 March 2019
- Other References:
Attieh et al., Enzyme-Initiated Free-Radical Polymerization of Molecularly Impreinted Polymer Nanogels on a Solid Phase with an Immobilized Radical Source. Angew. Chem. Int. Ed. 2017; 56(12):3339-3343. cited by applicant
Bae et al., Horseradish peroxidase-catalysed in situ-forming hydrogels for tissue-engineering applications. J. Tissue Eng. Regen. Med. 2015/ 9(11):1125-1232. cited by applicant
Darabi et al., Nitroxide-Mediated Polymerization of 2-(Diethylamoino)ethyl Methacrylate (DEAEMA) in Water. Macromolecules, 2015, 48(1), 72-80. cited by applicant
Durand et al., Enzyme-mediated initiation of acrylamide polymerization: reaction mechanism. Polymer, 2000, 41(23), 8183-8192. cited by applicant
Kohri, Development of HRP-mediated enzymatic polymerization under heterogeneous conditions for the preparation of functional particles. Plym. J., 2014, 49(7), 373-380. cited by applicant
Su et al., Cardiac Stem Cell Patch Integrated with Microengineered Blood Vessels Promotes Cardiomyocyte Proliferation and Neovascularization after Acute Myocardial Infarction. ACS Appl. Mater. Interfaces, 2018, 10, 33088-33096. cited by applicant
Su et al., HRP-mediated polymerization forms tough nanocomposite hydrogels with high biocatalytic performance. Chem Commun (Camb). Sep. 21, 2013;49(73):8033-5. cited by applicant
Ullah et al., Classification, processing and application of hydrogels: A review. Mater Sci Eng C Mater Biol Appl. Dec. 1, 2015;57:414-33. cited by applicant
Zhang et al., Enzyme-Initiated Reversible Addition-Fragmentation Chain Transfer Polymerization. Macromolecules, 2015, 48, 7792-7802. cited by applicant
- Primary Examiner:
Harlan, Robert D
- Attorney, Agent or Firm:
Casimir Jones, S.C.
Reynolds, Anne M.
- Accession Number:
edspgr.12247090
Processing Request
No Comments.