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Last Updated: July 13, 2020

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Claims for Patent: 10,052,307

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Summary for Patent: 10,052,307
Title:Micellar nanocomplex
Abstract: The present invention relates to micellar nanocomplexes and a method of forming the same. The micellar nanocomplex comprises a micelle and an agent encapsulated within said micelle, where the micelle comprises a polymer-flavonoid conjugate, wherein said polymer is bonded to the B ring of said flavonoid. The micellar nanocomplex may have useful applications as a drug-delivery system.
Inventor(s): Kurisawa; Motoichi (Singapore, SG), Nunnarpas; Yongvongsoontorn (Singapore, SG), Ying; Jackie Y (Singapore, SG), Chung; Joo Eun (Singapore, SG), Bae; Ki Hyun (Singspore, SG), Tan; Min-han (Singapore, SG), Lee; Esther (Singapore, SG)
Assignee: Agency for Science, Technology and Research (Singapore, SG)
Application Number:15/309,675
Patent Claims:1. A micellar nanocomplex comprising a micelle and an agent encapsulated within said micelle, said micelle comprising a polymer-flavonoid conjugate, wherein said polymer is bonded to the B ring of said flavonoid.

2. The micellar nanocomplex of claim 1, wherein at least one flavonoid is bonded to said polymer.

3. The micellar nanocomplex of claim 1, wherein said polymer is bonded to said flavonoid via a linker.

4. The micellar nanocomplex of claim 3, wherein said linker is selected from the group consisting of a thioether, imine, amine, azo and 1,2,3-triazole group.

5. The micellar nanocomplex of claim 1, wherein said flavonoid is a monomeric flavonoid or a dimeric flavonoid.

6. The micellar nanocomplex of claim 2, wherein when more than one flavonoid is present in said conjugate, at least one of the flavonoid is bonded to said polymer via the B ring.

7. The micellar nanocomplex of claim 6, wherein the other of said at least one flavonoid is bonded to said polymer via the A ring.

8. The micellar nanocomplex of claim 1, wherein said polymer is a hydrophilic polymer.

9. The micellar nanocomplex of claim 8, wherein said hydrophilic polymer comprises monomers selected from the group consisting of acrylamides, alkyls, oxazolines, alkenyls, imines, acrylic acids, methacrylates, diols, oxiranes, alcohols, amines, anhydrides, esters, lactones, carbonates, carboxylic acids, acrylates, hydroxyls, phosphates, terephthalate, amides and ethers.

10. The micellar nanocomplex of claim 8, wherein said hydrophilic polymer is selected from the group consisting of polyacrylamide, poly(N-isopropylacrylamide), poly(oxazoline), polyethylenimine, poly(acrylic acid), polymethacrylate, poly(ethylene glycol), poly(ethylene oxide), poly(vinyl alcohol), poly(vinylpyrrolidinone), polyethers, poly(allylamine), polyanhydrides, poly(.beta.-amino ester), poly(butylene succinate), polycaprolactone, polycarbonate, polydioxanone, poly(glycerol), polyglycolic acid, poly(3-hydroxypropionic acid), poly(-hydroxyethyl methacrylate), poly(N-(2-hydroxypropyl)methacrylamide), polylactic acid, poly(lactic-co-glycolic acid), poly(ortho esters), poly(-oxazoline), poly(sebacic acid), poly(terephthalate-co-phosphate) and copolymers thereof.

11. The micellar nanocomplex of claim 8, wherein said hydrophilic polymer is a polysaccharide.

12. The micellar nanocomplex of claim 8, wherein said hydrophilic polymer is a polysaccharide selected from the group consisting of hyaluronic acid, dextran, pullulan, chitosan, cellulose, amylose, starch, gelatin, carrageenan, cyclodextrin, dextran sulfate, Ficoll, gellan, guar gum, pectin, polysucrose, pullulan, scleroglucan, xanthan, xyloglucan and alginate.

13. The micellar nanocomplex of claim 1, wherein said flavonoid is selected from the group consisting of flavones, isoflavones, flavans, proanthocyanidins and anthocyanidins.

14. The micellar nanocomplex of claim 13, wherein said flavans is selected from the group consisting of (-)-epicatechin, (+)-epicatechin, (-)-catechin, (+)-catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, Fisetinidol, Gallocatechin, Gallocatechin gallate, Mesquitol and Robinetinidol, ellagitannin, gallotannin, oolongtheanin, phlorotannin, tannin, theacitrin, theadibenzotropolone, theaflavin, theanaphthoquinone, thearubigins, theasinensin and mixtures thereof.

15. The micellar nanocomplex of claim 1, wherein said agent is a therapeutic agent.

16. The micellar complex of claim 15, wherein said therapeutic agent is a chemotherapeutic agent selected from the group consisting of alkylating agents, anthracyclines, cytoskeletal disruptors, epothilones, histone deacetylase inhibitors, topoisomerase I inhibitors, topoisomerase II inhibitors, kinase inhibitors, monoclonal antibodies, antibody-drug conjugates, nucleotide analogs, precursor analogs, peptide antibiotics, platinum-based agents, retinoids, vinca alkaloids, cytokines, anti-metabolites, and vinca alkaloids derivatives, and other cytotoxics.

17. The micellar complex of claim 16, wherein said chemotherapeutic agent is selected from the group consisting of Actinomycin, Afatinib, All-trans retinoic acid, Axitinib, Azacitidine, Azathioprine, Bevacizumab, Bleomycin, Bosutinib, Bortezomib, Carboplatin, Capecitabine, Cetuximab, Cisplatin, Chlorambucil, Crizotinib, Cyclophosphamide, Cytarabine, Dasatinib, Daunorubicin, Docetaxel, Doxifluridine, Doxorubicin, Epirubicin, Epothilone A (C26H39NO6S), Epothilone B (C27H41NO6S), Epothilone C (C26H39NO5S), Epothilone D (C27H41NO5S), Epothilone E (C26H39NO7S), Epothilone F (C27H41NO7S), Erlotinib, Etoposide, Fluorouracil, Fostamatinib, Gefitinib, Gemcitabine, Hydroxyurea, Idarubicin, Imatinib, Irinotecan, Lapatinib, Lenvatinib, Mechlorethamine, Mercaptopurine, Methotrexate, Mitoxantrone, Nilotinib, Oxaliplatin, Paclitaxel, Panitumumab, Pazopanib, Pegaptanib, Pemetrexed, Ranibizumab, Regorafenib, Ruxolitinib, Sorafenib, Sunitinib, Trastuzumab, Teniposide, Tioguanine, Tofacitinib, Topotecan, Valrubicin, Vemurafenib, Vinblastine, Vincristine, Vindesine, Vinorelbine.

18. The micellar nanocomplex of claim 1, wherein said micellar nanocomplex has a size in the range of 30 to 300 nm, 50 to 300 nm, 100 to 300 nm, 30 to 50 nm, 30 to 100 nm, 30 to 150 nm, 150 to 300 nm, 200 to 300 nm, 250 to 300 nm, 100 to 150 nm, 100 to 200 nm, 100 to 250 nm, 130 to 180 nm, or 130 to 250 nm.

19. The micellar nanocomplex of claim 1, wherein the loading efficiency of said agent present within said micelle is more than 30%, more than 35%, more than 40%, more than 45%, more than 50%, more than 55%, more than 60%, more than 65%, more than 70%, more than 75%, or 80%.

20. The micellar nanocomplex of claim 1, wherein the loading content of said agent present within said micelle is in the range of 1 to 10 w/w %, 5 to 25 w/w %, 20 to 45 w/w %, 30 to 50 w/w %, 35 to 50 w/w %, 40 to 50 w/w %, 45 to 50 w/w %, 30 to 35 w/w %, 30 to 40 w/w % or 30 to 45 w/w %.

21. A method for forming a micellar nanocomplex comprising a micelle and an agent encapsulated within said micelle, the method comprising the steps of: a. adding said agent in a suitable solvent to a polymer-flavonoid conjugate, wherein said polymer is bonded to the B ring of said flavonoid; and b. allowing the self-assembly of a micelle comprising said polymer-flavonoid conjugate and encapsulation of said agent within said micelle to thereby form said micellar nanocomplex.

22. The method of claim 21, wherein step (a) further comprises the steps of: a. removing said solvent to form a dry film of said agent and said polymer-flavonoid conjugate; and b. hydrating said dry film with an aqueous solvent.

23. The method of claim 21, further comprising the step of isolating the formed micellar nanocomplex by filtration.

24. The method of claim 21, wherein step (a) further comprises the step of dialysing the agent in a suitable solvent.

25. The micellar nanocomplex of claim 1 for treating a tumor.

Summary for Patent:   Start Trial

Foriegn Application Priority Data
Foreign Country Foreign Patent Number Foreign Patent Date
Singapore10201402244SMay 9, 2014
PCT Information
PCT FiledMay 08, 2015PCT Application Number:PCT/SG2015/050104
PCT Publication Date:November 12, 2015PCT Publication Number:WO2015/171079

Details for Patent 10,052,307

Applicant Tradename Biologic Ingredient Dosage Form BLA Number Approval Date Patent No. Assignee Estimated Patent Expiration Status Orphan Source
Genentech HERCEPTIN trastuzumab VIAL; INTRAVENOUS 103792 001 1998-09-25   Start Trial Agency for Science, Technology and Research (Singapore, SG) 2034-05-09 RX Orphan search
Imclone ERBITUX cetuximab VIAL; INTRAVENOUS 125084 001 2004-06-18   Start Trial Agency for Science, Technology and Research (Singapore, SG) 2034-05-09 RX Orphan search
Genentech AVASTIN bevacizumab VIAL; INTRAVENOUS 125085 001 2004-02-26   Start Trial Agency for Science, Technology and Research (Singapore, SG) 2034-05-09 RX Orphan search
Genentech AVASTIN bevacizumab VIAL; INTRAVENOUS 125085 002 2004-02-26   Start Trial Agency for Science, Technology and Research (Singapore, SG) 2034-05-09 RX Orphan search
>Applicant >Tradename >Biologic Ingredient >Dosage Form >BLA >Number >Approval Date >Patent No. >Assignee >Estimated Patent Expiration >Status >Orphan >Source

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