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Last Updated: March 28, 2024

Claims for Patent: 9,987,369


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Summary for Patent: 9,987,369
Title:Vitamin functionalized gel-forming block copolymers for biomedical applications
Abstract: Gel-forming block copolymers were prepared comprising i) a central hydrophilic block consisting essentially of a divalent poly(ethylene oxide) chain and ii) two peripheral monocarbonate or polycarbonate hydrophobic blocks linked to the central block by linking groups bearing one or more hydrogen bond forming *--N(H)--* groups. The hydrophobic blocks comprise one or more vitamin-bearing subunits. The gel-forming block copolymers can be used to prepare various biodegradable and/or biocompatible hydrogel and organogel drug compositions, in particular antimicrobial and/or anti-tumor drug compositions. The hydrogel compositions have utility in depot injections for drug delivery. The hydrogen bonding *--N(H)--* group(s) provide longer in vivo lifetime of the hydrogel before degradation and a more prolonged and controlled release rate of a hydrophobic drug compared to similar hydrogels prepared from poly(ethylene glycol).
Inventor(s): Cheng; Wei (Singapore, SG), Fevre; Mareva B. (San Jose, CA), Hedrick; James L. (Pleasanton, CA), Ibrahim; Nor Lizawati (Singapore, SG), Lee; Ashlynn L. Z. (Singapore, SG), Ng; Victor W. L. (Singapore, SG), Ono; Robert J. (San Jose, CA), Yang; Chuan (Singapore, SG), Yang; Yi Yan (Singapore, SG)
Assignee: International Business Machines Corporation (Armonk, NY) Agency For Science, Technology And Research (Singapore, SG)
Application Number:15/340,795
Patent Claims:1. A block copolymer having the structure: ##STR00129## wherein each V' is selected from the group consisting of ##STR00130## and combinations thereof, d' is a positive number having an average value of 100 to 600, and each m' is an independent positive number having an average value between 1 and 2.

2. The block copolymer of claim 1, wherein V' is ##STR00131##

3. The block copolymer of claim 2, wherein each m' has a value in the range of 1.03 to 1.78.

4. The block copolymer of claim 2, wherein each m' has a value in the range of 1.03 to 1.3.

5. The block copolymer of claim 1, wherein d' is about 500.

6. The block copolymer of claim 1, wherein V' is ##STR00132##

7. The block copolymer of claim 6, wherein each m' has a value in the range of 1.03 to 1.78.

8. A drug composition, comprising: about 4 wt. % to about 10 wt. % of the block copolymer of claim 1; a solvent; and about 0.0001 wt. % to about 10 wt. % of a drug; wherein weight percent (wt. %) is based on total weight of the drug composition, and the drug composition is a gel, wherein the block copolymer, the solvent, and the drug are associated by noncovalent interactions.

9. The drug composition of claim 8, wherein V' is ##STR00133##

10. The drug composition of claim 8, wherein V' is ##STR00134##

11. The drug composition of claim 8, wherein the drug is an anti-tumor agent and the drug composition is suitable for treating a cancer.

12. The drug composition of claim 11, wherein the anti-tumor agent is a mono-clonal antibody.

13. The drug composition of claim 12, wherein the mono-clonal antibody is herceptin.

14. The drug composition of claim 8, wherein the solvent is water, the composition is a hydrogel, and the composition inhibits growth of cancer cells in vivo when administered by a depot injection.

15. The drug composition of claim 8, wherein the drug is an antimicrobial cationic polycarbonate.

16. The antimicrobial drug composition of claim 15, wherein the drug composition comprises a second drug that is an antimicrobial compound.

17. The antimicrobial drug composition of claim 16, wherein the antimicrobial compound is selected from the group consisting of fluconazole, doxycycline, and combinations thereof.

18. A method of treating a cancer, comprising performing an in vivo depot injection of the drug composition of claim 8 near or in contact with a cancerous tumor.

19. The method of claim 18, wherein the cancer is a breast cancer.

20. A method of preparing a block copolymer, comprising heating under vacuum with agitation at a temperature of about 50.degree. C. to about 150.degree. C. a mixture consisting of i) a cyclic carbonate monomer comprising a pendent group containing a covalently bound form of a vitamin and ii) a dinucleophilic polymeric initiator for a ring opening polymerization (ROP) of the cyclic carbonate monomer, the polymeric initiator comprising a poly(ethylene oxide) chain and two terminal *--NH.sub.2 groups, thereby forming the block copolymer.

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