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(12) Patent Application Publication (10) Pub. No.: US 2006/025 1613 A1 Zhang Et Al US 2006025 1613A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2006/025 1613 A1 Zhang et al. (43) Pub. Date: Nov. 9, 2006 (54) BIODEGRADABLE CHITOSAN-PEG (22) Filed: May 9, 2005 COMPOSITIONS, AND METHODS OF USE Publication Classification (76) Inventors: Miqin Zhang, Bothell, WA (US); Narayan Bhattarai, Seattle, WA (US); (51) Int. Cl. Frederick A. Matsen, Seattle, WA (US) COSB 37/08 (2006.01) C08G 63/9. (2006.01) Correspondence Address: (52) U.S. Cl. ........................ 424/78.27: 525/54.2:536/20 CHRISTENSEN, O'CONNOR, JOHNSON, KINDNESS, PLLC (57) ABSTRACT 1420 FIFTHAVENUE The present invention provides compositions comprising an SUTE 28OO interpolymer of chitosan and polyethylene glycol, wherein SEATTLE, WA 98101-2347 (US) the interpolymer is a liquid below 25°C. and a gel above 35° C. The present invention also provides methods for using the (21) Appl. No.: 11/124,916 compositions to deliver drugs to a living body over time. Patent Application Publication Nov. 9, 2006 Sheet 1 of 7 US 2006/025 1613 A1 6 NHCOCH CHOH 3 4 5 o 1. HO O O 3)-2 O Hong HO H-CH CH O-(CH CHO)CH 3 A2. A 5 O 4 a 3 s 3 2 2 e 1 O O 10 20 30 40 50 60 TEMPERATURE (C) A2.2 Patent Application Publication Nov. 9, 2006 Sheet 2 of 7 US 2006/025 1613 A1 (Std) ALISOOSIA (CINOOSIS)?IWIL 000€00SZ000Z00SI000I009 (CINOOSIS)HWIL º?y 0009000?00SI000Z00SZ000€ (Std) ALISOOSIA Patent Application Publication Nov. 9, 2006 Sheet 3 of 7 US 2006/025 1613 A1 a es S > P M A24. S.75 - At 10C > , oooooooooooooooooooooooooooooooot At 37°C al O 500 1000 1500 2000 2500 3000 3500 TIME (SECOND) a Á A, 22 O O A. s O 500 1000 1500 2000 2500 3000 3500 TIME (SECOND) a 63. A p a7 3 A2,4C O O s 0 500 1000 1500 2000 2500 3000 3500 TIME (SECOND) Patent Application Publication Nov. 9, 2006 Sheet 4 of 7 US 2006/025 1613 A1 110 100 90 80 70 60 50-3 40-3 30-3, 20 0 20 40 60 80 100 120 140 TIME (h) A2.51. O 20 40 60 80 100 120 140 TIME (h) A2.2 Patent Application Publication Nov. 9, 2006 Sheet 5 of 7 US 2006/025 1613 A1 s e ed e es e e s as 52 N Wad l re er s Se (%)SSOT LHSIAA Patent Application Publication Nov. 9, 2006 Sheet 6 of 7 US 2006/025 1613 A1 5 CD s g N ?s S. s (Std) ALISOOSIA Patent Application Publication Nov. 9, 2006 Sheet 7 of 7 US 2006/025 1613 A1 100 90 80 70 60 50 40 30 20 10 O 10 20 30 40 50 TIME (DAYS) A28 100 468 OOO 20 TIME (DAYS) A2.2 US 2006/025 1613 A1 Nov. 9, 2006 BODEGRADABLE CHITOSAN-PEG SUMMARY OF THE INVENTION COMPOSITIONS, AND METHODS OF USE 0006. In accordance with the foregoing, the present STATEMENT OF GOVERNMENT LICENSE invention provides compositions comprising an interpoly RIGHTS mer of chitosan and polyethylene glycol, wherein the inter 0001. The U.S. Government has a paid-up license in this polymer is a liquid below 25°C. and a gel above 35°C. The invention and the right in limited circumstances to require interpolymer is the most abundant component in the com the patent owner to license others on reasonable terms as position, and So when the interpolymer forms a gel, the provided for by the terms of Grant No. NSF-EEC 952916.1 composition also has the consistency of a gel, although awarded by the National Science Foundation. non-gel components (e.g., drug molecules) may be present in the composition in addition to the gelled interpolymer. FIELD OF THE INVENTION The compositions of the present invention are compatible 0002 The present invention relates to biodegradable gels, with living tissue. Moreover, the compositions of the present and their use as implantable drug delivery vehicles. invention can be degraded by living tissue (i.e., are biode gradable). Thus, the compositions of the present invention BACKGROUND OF THE INVENTION can be used, for example, to deliver drugs (e.g., growth 0003. In some clinical situations it is desirable to provide factors, anti-inflammatory agents) to a living organism by a portion of a living body, such as a human body, with a drug incorporating (e.g., dissolving) the drug molecules into a over an extended time period (e.g., days, weeks, or months). liquid composition of the present invention and introducing For example, it may be desirable to provide a broken, or (e.g., injecting) the liquid composition into a living animal diseased, portion of mammalian bone with a growth factor, body having a temperature that is at, or above, the tempera that promotes new bone growth, during the process of bone ture at which the interpolymer forms a gel. The liquid healing. One way to provide the drug is to implant a drug interpolymer gels in the animal body, and is thereafter delivery composition at the desired location in the living gradually degraded by the Surrounding tissues so that the body. Some drug delivery compositions are biodegradable, drug molecules are released over time. Optionally, the exist as a gel at the temperature of the living body, but exist polyethylene glycol/chitosan interpolymer molecules can be as a liquid below the temperature of the living body. Drug covalently cross-linked to each other to increase the lifetime molecules can be incorporated into these compositions in of the gel in a living body (i.e., reduce the rate of degradation their liquid form, and the compositions can thereafter be of the gel by the tissues of the body). introduced into a living body where they form a gel that is degraded by the body over time, thereby releasing the drug 0007 Accordingly, in one aspect the present invention molecules. provides compositions comprising an interpolymer of chi tosan and polyethylene glycol, wherein the interpolymer is 0004 Synthetic polymers such as polyethylene glycol, a liquid below 25° C. and is a gel above 35° C. The poly(lactic acid) (PLA), and PEG-PLGA-PEG have been polyethylene glycol may be present in the interpolymer in an used as thermoreversible drug delivery systems (Jeong, B. et amount of from 30% by weight to 65% by weight based on al., Nature 388:860 (1997); Jeong, B., et al., Macromol the total weight of the interpolymer. ecules 32:7064 (1999); Jeong, B., et al., J. Biomed. Mater. Res. 50:171 (2000)). Natural polymers are typically more 0008. In another aspect the present invention provides desirable than synthetic polymers for biomedical applica methods for delivering a drug to a living body. The methods tions because of their biocompatibility and biodegradability. of this aspect of the invention include the step of delivering (Jeong, B., and A. Gutowska, Trends Biotechnol. 20:360 a composition comprising a drug to a portion of a living (2002); Chenite, A., et al., Biomaterials 21:2155 (2000)). body, wherein: (a) the composition comprises an interpoly For example, Chenite et al. (Biomaterials 21:2155 (2000)) mer of chitosan and polyethylene glycol, wherein the inter developed a thermoreversible gel, composed of chitosan and polymer is a liquid below 25°C. and a gel above 35° C.; (b) glycerol-2-phosphate salts, that gels at a temperature of the interpolymer forms a gel after it is delivered to the living about 37°C., or above, depending on the amount of the salts body; and (c) the composition comprises a drug that is present in the composition. In the practice of the Chenite et released from the gel into the living body. al. technology, the chitosan Solution had to be prepared in dilute acid in order to dissolve the chitosan. Consequently, 0009. In a further aspect the present invention provides the chitosan Solution had an acidic pH that is irritating to methods of promoting the growth of bone in a living body. living tissue. Additionally, excess sodium glycerol phos The methods of this aspect of the invention include the step phate (B-GP) salt was required to gel the chitosan Solution. of introducing a composition comprising a growth factor The excess f-GP salt may be harmful if it is absorbed by into a bone, wherein: living tissue. 0010 (a) the composition comprises an interpolymer of 0005. A need remains, therefore, for drug delivery com chitosan and polyethylene glycol, wherein the interpolymer positions, made from biocompatible natural, or synthetic, is a liquid below 25° C. and a gel above 35° C.; (b) the polymers, that are biodegradable and that exist as a liquid interpolymer forms a gel after it is delivered to the bone; and below the temperature of a recipient living body, and as a gel (c) the gel comprises a growth factor that promotes the at the temperature of the recipient living body. The liquid growth of bone and that is released from the gel into the phase of the compositions can be loaded with drug mol bone. The gel may optionally further comprise living osteo ecules, and thereafter be introduced into a living body where blasts, which are cells that make bone. The methods of this they form a gel that is degraded and releases the drug over aspect of the invention are useful, for example, for treating time. osteoporosis. US 2006/025 1613 A1 Nov. 9, 2006 BRIEF DESCRIPTION OF THE DRAWINGS Concentration of genipin was 0.5 mM. Triplicates for each gel were analyzed and each data point represents the mean 0011.
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