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(12) Patent Application Publication (10) Pub. No.: US 2010/0028434 A1 Chenite Et Al

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(12) Patent Application Publication (10) Pub. No.: US 2010/0028434 A1 Chenite Et Al US 20100028434A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2010/0028434 A1 Chenite et al. (43) Pub. Date: Feb. 4, 2010 (54) TEMPERATURE CONTROLLED AND PH Publication Classification DEPENDENT SELF GELLING (51) Int. Cl. BIOPOLYMERICAQUEOUS SOLUTION A6II 35/12 (2006.01) A6II 47/26 (2006.01) (75) Inventors: Abdellatif Chenite, Kirkland (CA); A6II 47/08 (2006.01) Cyril Chaput, Montreal (CA); A6IR 9/00 (2006.01) DongWang, Montreal (CA); A6II 35/32 (2006.01) Amine Selmani, Laval (CA) A6II 35/34 (2006.01) A6II 35/36 (2006.01) Correspondence Address: A6II 35/56 (2006.01) DAVID S. RESNICK A6II 35/66 (2006.01) NIXON PEABODY LLP, 100 SUMMER STREET A636/00 (2006.01) BOSTON, MA 02110-2131 (US) (52) U.S. Cl. ........ 424/485; 514/777: 514/774; 424/93.1; (73) Assignee: BIOSYNTECH CANADA, INC., 424.793.7 Laval (CA) (57) ABSTRACT (21) Appl. No.: 12/576,354 The present invention relates a biopolymeric liquid aqueous composition for producing self-gelling systems and gels, (22) Filed: Oct. 9, 2009 which comprises: an acidic water-based medium, 0.1 to 10% by weight of a pH-gelling acid-soluble biopolymer; and 0.1 to Related U.S. Application Data 10% by weight of a water-soluble molecule having a basic character and a pKa between 6.0 and 8.4, or a water-soluble (63) Continuation of application No. 10/130,316, filed on residue or sequence of the molecule having a basic character Aug. 27, 2002, now abandoned, filed as application and a pKa between 6.0 and 8.4. The liquid composition has a No. PCT/CA00/01341 on Nov. 10, 2000. final pH ranging from 5.8 and 7.4, and forms a stable solid and homogeneous gel within a temperature range from 10 to 70° (60) Provisional application No. 60/165,641, filed on Nov. C. The present invention also relates to a method for preparing 15, 1999. the composition and uses thereof. Patent Application Publication Feb. 4, 2010 Sheet 1 of 4 US 2010/0028434 A1 Heating O 2O 40 6O 8O 1OO Temperature (OC) trial s Heating O 2O 40 60 8O 1OO Temperature OC First F. Patent Application Publication Feb. 4, 2010 Sheet 2 of 4 US 2010/0028434 A1 7OOO 6OOO O SSssa Cooling a. pigo356-35Ceeeeese SS a) Sea s 5000 2. 4OOO s 3OOO 2OOO 1OOO 40 60 8O 1OO Temperature (OC) Frag F 5OOO 3OOO s 2OOO 1OOO - Heating O O 2O 40 60 8O 1 OO Temperature OC Fras 4. Patent Application Publication Feb. 4, 2010 Sheet 3 of 4 US 2010/0028434 A1 Heating O O 2O 40 60 8O 100 Temperature OC Fre F5 1OOO - o pH = 7.2 . " 800 .."' O . H . Ut 600 - s 5 400 - o Os H 2OO - e pH = 5.4 O 8 is a ?h ................ A. A. A A A. A A. A. A - O 1O 2O 3O 4O 50 6O Time, (mn) Eza F. E. Patent Application Publication Feb. 4, 2010 Sheet 4 of 4 US 2010/0028434 A1 NB2% + BES2% at room temperature 450 4OO BES 2% 350 ...' pH=7.2 3OO 250 2OO 150 BES O% 1OO pH=5.4 5O a A A a A A a A. A. A. A. A. A ka A a a A A A A. A. A. A A a k A. A A. A. A. A O - O 5O 1 OO 150 200 25O 3OO 350 4OO 45O 500 Time (min) Fras - 7 1200 - 1 OOO .4 OAyo Bis-TrisD •' pH=7 35 8OO - 600 - 2% Bis-Tris pH=6.98 400 3% BS-Tris i H=723 200 f O 1723.N. o o O O 4, ::::... v w w w w v. O 1OO 2OO 3OO 400 Time (min) tra FE US 2010/0028434 A1 Feb. 4, 2010 TEMPERATURE CONTROLLED AND PH 0013. A further aim of the present invention is to provide DEPENDENT SELF GELLING gels that would retain its solid or gel State at the physiological BIOPOLYMERICAQUEOUS SOLUTION temperature or 37° C. 0014 Still one aim of the present invention is to provide a BACKGROUND OF THE INVENTION method for the preparation of Such gels. 0001 (a) Field of the Invention 0015. In accordance with the present invention, there is 0002 The present invention relates to the composition of provided a biopolymeric liquid aqueous composition for pro molecular assemblies in liquid Solution that enables tempera ducing self-gelling systems and gels, which comprises: ture-controlled pH-dependant formation of biopolymeric 0016 a) an acidic water-based medium; and gels, such as polysaccharide-based, and methods of prepara 0017 b) 0.1 to 10% by weight of a pH-gelling acid tion thereof. soluble biopolymer; and 0003) (b) Description of Prior Art (0.018 c) 0.1 to 10% by weight of a water-soluble mol 0004 Biopolymers and macromolecules are attractive ecule having a basic character and a pKa between 6.0 materials for the preparation and design of self-gelling and/or and 8.4, or a water-soluble residue or sequence of the auto-assembling systems. Numerous attempts tend to molecule having a basic character and a pKa between develop such systems on the basis of polysaccharides and 6.0 and 8.4: polypeptides. wherein the liquid composition has a final pH ranging from 0005. In situ formed gels were also proposed with ionic 5.8 and 7.4, and forms a stable solid and homogeneous gel polysaccharides. A composition can be used as a medical within a temperature range from 10 to 70° C. device for drug delivery, the application of a diagnostic agent, 0019. The composition can be prepared from organic and/ or the prevention of post-operative adhesions, and is com or inorganic acids, such as hydrochloric acid, citric acid, posed of an aqueous liquid vehicle which is capable of being ascorbic acid, lactic acid, lactobionic acid, acetic acid, Sali gelled in situ. It includes at least one ionic polysaccharide, at cylic acid, formic acid, glutamic acid, phosphoric acid, ortho least one film forming polymer, and a medicament or phar phosphoric acid, or glycerophosphoric acid, or a mixture maceutical agent, water, and optionally, a counter-ion capable thereof. of gelating the ionic polysaccharide. However, the gelation is 0020. The biopolymer preferably comprises a pH-gelling reached by interaction between the ionic polysaccharide and acid-soluble polysaccharide, polypeptidic or poly(amino the film-forming polymer, or by counter-ion induced cross acids), or synthetic polymer, such as a solution of chitosan, linking of the ionic polysaccharide. Other in situ forming gels modified chitosan or chitosan derivative, the solution of chi are based upon polyoxyalkylene composition or polyoxy tosan being cationic and bearing amino groups. alkylene/polysaccharide mixture or alginate/cation mixture 0021. The molecule, residue or sequence may be an in situ. organic salt selected from the group consisting of mono 0006. It would be highly desirable to be provided with a phosphate salt, mono-Sulfonate salt, mono-sulfate Salt and biopolymeric gel that is formed while excluding any organic mono-carboxylate salt. Solvent, any organic monomers, any ionic or covalent cross 0022. Alternatively, the molecule, residue or sequence linking that may be potentially toxic or induce a reduced may be a salt of polyol selected from the group consisting of biological compatibility. mono-phosphate dibasic salt, mono-Sulfonate salt, mono-sul 0007. It would be highly desirable to be provided with a fate salt and mono-carboxylate salt of polyol, said polyol biopolymeric gel that is formed by stimulus-induced free being selected from the group consisting of glycerol, histidi interactions between biologically acceptable and well-recog nol, acetol, diethylstil-bestrol, indole-glycerol, sorbitol, ribi nized molecules. tol. Xylitol, arabinitol, erythritol, inositol, mannitol, glucitol, 0008. It would be highly desirable to be provided with, a palmitoyl-glycerol, linoleoyl-glycerol, oleoyl-glycerol, and temperature-controlled pH-dependant formed biopolymeric arachidonoyl-glycerol, or a mixture thereof. gels that could be used to encapsulate cells and cellular mate 0023 The glycerol may also be selected from the group rial while retaining their biological activity. consisting of glycerol-2-phosphate, sn-glycerol 3-phosphate 0009. It would be highly desirable to be provided with Such gels, which would retain its Solid or gel state at the and L-glycerol-3-phosphate salt, or a mixture thereof. physiological temperature or 37°C. 0024. In a further embodiment, the molecule, residue or sequence is a salt of a Sugar selected from the group consist ing of mono-phosphate dibasic salt, mono-Sulfonate salt, SUMMARY OF THE INVENTION mono-Sulfate salt and mono-carboxylate salt of a Sugar, said 0010. One aim of the present invention is to provide a way Sugar being selected from the group consisting of fructose, allowing the preparation of a neutral clear liquid solution of a galactose, ribose, glucose, Xylose, rhamnulose, Sorbose, pH-controlled acid-soluble biopolymer while avoiding any erythrulose, deoxy-ribose, ketose, mannose, arabinose, fucu unwanted precipitation or heterogeneous gelation. lose, fructopyranose, ketoglucose, Sedoheptulose, trehalose, 0011. A second major aim of the present invention is to tagatose. Sucrose, allose, threose, Xylulose, hexose, meth provide a neutral clear liquid solution of a pH-controlled ylthio-ribose, and methylthio-deoxy-ribulose, or a mixture acid-soluble biopolymer that will thermally form solid homo thereof. geneous gels at a temperature close to the physiological tem 0025. The molecule, residue or sequence may be selected perature. from the group consisting of sodium, magnesium or iron salt 0012 Another aim is to provide temperature-controlled of glycerol-2-phosphate, sn-glycerol-3-phosphate and pH-dependant formed gels, which could be used to encapsu L-glycerol-3-phosphate, glucose-1-phosphate, glucose-6- late cells and cellular material while retaining their biological phosphate, fructose-1-phosphate and fructose-6-phosphate, activity.
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