Organic compounds -- part of the class 532-570 series – Organic compounds – Carbohydrates or derivatives
Patent
1997-05-13
2000-01-25
Wilson, James O.
Organic compounds -- part of the class 532-570 series
Organic compounds
Carbohydrates or derivatives
536 172, 536 173, 536 179, 536 182, 536 185, 536 553, 536103, 5361231, 53612313, 424 11, 424456, 424461, 424466, C07H 1510, C07H 1504, C07H 1512
Patent
active
060180331
ABSTRACT:
Polymerizable saccharide monomers are made by the reaction of a saccharose and a (meth)acrylate. Hydrophilic, hydrophobic and thermoreversible gels and foams are formed upon polymerization of the saccharide monomers. Hydrophilic sucrose monomers are synthesized by reaction of sucrose with an epoxy acrylate. Hydrophobic sucrose monomers are synthesized by reaction of sucrose with methacrylol chloride followed by acetyl chloride. Thermoreversible sucrose monomers are obtained by modifying sucrose with polymerizable substituents prepared from methacryloyl chloride and aminocarboxylic acids. The modified sucrose monomers are copolymerized with hydrophobic poly(alkyleneoxide) (meth)acrylates to produce hydrogels exhibiting inverse thermoreversible properties. The thermosensitive hydrogels are biodegradable and can be used in the area of controlled drug delivery.
REFERENCES:
patent: 3103508 (1963-09-01), Fisher et al.
patent: 3215137 (1965-11-01), Laakso
patent: 3225012 (1965-12-01), Black et al.
patent: 3356652 (1967-12-01), Ray-Chaudhuri
patent: 4042538 (1977-08-01), Lucas
patent: 4663388 (1987-05-01), Douglass et al.
patent: 5116961 (1992-05-01), Sachinvala
patent: 5149335 (1992-09-01), Kellenberger et al.
patent: 5164492 (1992-11-01), Kitazawa et al.
patent: 5173554 (1992-12-01), Kitazawa et al.
patent: 5248747 (1993-09-01), Sachinvala et al.
patent: 5580940 (1996-12-01), Oosterhoff
patent: 5693768 (1997-12-01), Bachmann et al.
Gruber, H. Hydrophile polymergele mit reaktiven gruppen, I. Herstellung und polymerisation von glucose-und saccharosemethacrylaten; Monatsch. F. Chem., 1981, 112, 273.
Patil, D.R.; Rethwisch, D.R.; Dordick, J.S.; Enzymatic synthesis of a sucrose-containing linear polyester in nearly anhydrous organic media; Biotechnology and Bioengineering, 1991, 37, 639.
Garcia-Gonzalez; Kellaway, I.W.; Blanco-Fuente, H.; Anguiano-Igea, S.; Delgado-Charro, B; Otero-Espinar, F.J.; Blanco-Mendez, J; Design and evaluation of buccoadhesive metoclopramide hydrogels composed of poly(acrylic acid) crosslinked with sucrose; Int'l. J. Pharm., 1993, 100, 65.
Lepisto, M.; Artursson, P.; Edman, P.; Laakso, T.; Sjoholm, L.; Determination of the degree of derivatization of acryloylated polysaccharides by fourier transform proton NMR spectroscopy; Anal. Biochem., 1983, 133, 123.
Laakso, T.; Stjarnkvist, P.; Sjoholm, I.; Biodegradable microspheres VI: Lysosomal release of covalently bound antiparasitic drugs from starch microparticles; J. Pharm. Sci., 1987, 76, 134.
Artursson, P; Edman, P; Laakso T.; Sjoholm, I.; Characterization of polyacryl starch microparticles as carriers for proteins and drugs; J. Pharm. Sci., 1984, 73, 1507.
Edman, P.; Ekman, B; Sjoholm, I; Immobilization of proteins in microspheres of biodegradable polyacryldextrans; J. Pharm. Sci., 1980, 69, 838.
Sachinvala, N.D., Ju. R.F., Litt, M.H., and Niemczura, W.P., Preparation of poly(methyl methacrylate) and copolymers having enhanced thermal stabilities using sucrose-based comonomers and additives., Journal of Polymer Science: Part A: Polymer Chemistry, 1995, 15-29.
Smedt, S.C.D.; Lauwers, A.; Demeester, J.; Steenbergen, M.J.V.; Hennink, W.E.; Foefs S.P.F.M.; Characterization of the network structure of dextran glycidyl methacrylate hydrogels by studying the rheological and swelling behavior; Macromolecules, 1995, 28, 5082.
Park, K.; Enzyme-digestible swelling hydrogels as platforms for long-term oral drug delivery: Synthesis and characterization; Biomaterials, 1988, 9, 435.
Shalaby, W.S.W.,; Park, K.; Biochemical and mechanical characterization of enzyme-digestible hydrogels; Pharmaceutical Research, 1990, 7, 816.
Starks, C.M.; Phase transfer catalysis. I. Heterogeneous reaction involving anion transfer by quaternary ammonium and phosphonium salts; JACS, 1971, 93, 195.
Hoppe, H.; Koppe, J.; Winkler, F.; Improved method for determining acrylamide in polyacrylamide; Plaste Kautsch, 1977, 24, 105.
Akoh, C.C.; Swanson, B.G.; One-stage synthesis of raffinoise fatty acid polyesters; J. Food Sci., 1987, 52, 1570.
Akoh, D.C.; Swanson, B.G.; Synthesis and properties of alkyl glycoside and starchyose fatty acid polyesters; J. Am. Oil Chem. Soc., 1989, 66, 1295.
Wehrli, F.W. and Wirthlin, T. Interpretation of C-13 NMR spectra, Heyden and Sons Inc.; New York, NY, 1976, 225.
Shalaby, W.S.W.; Blevins, W.E.; Park, K.; In vitro and in vivo studies of enzyme-digestible hydrogels for oral drug delivery; Journal of Controlled Release, 1992, 19, 131.
Huglin, M; Zakaria, M., Observations of the homogeneity of crosslinked copolymers prepared by y-irradiation; Polymer, 1984, 25, 797.
Davis, T; Huglin, M.; Some mechanical properties of poly(2-hydroxyethyl methacrylate) gels swollen in water/1,4-dioxane mixtures; Makromol Chem. Rapid Commun., 1988, 9, 39.
Garcia, O; Trigo, R.M.; Blanco, M.D.; Teijon, J.M.; Influence of degree of crosslinking on 5-fluorouracil release from poly(2-hydroxyethyl methacrylate) hydrogels; Biomaterials, 1994, 15, 689.
Jin, X.; Carfagna, C; Nicolais, L.; Lanzetta. R.; Synthesis, characterization, and in vitro degradation of a novel thermotropic ternary copolyester based on p-hydroxybenzoic acid, glycolic acid, and p-hydroxycinnamic acid; Macromolecules, 1995, 28, 4785.
Dubrovskii, S.A.; Afaneseva, M.V.; Lagutina, M.A.; Kazanskii, K.S.; Measurement of swelling in weakly crosslinked hydrogels; Polymer Science U.S.S.R., 1990, 32, 166.
Hartley, F.D.; Cross, M.M.; Lord, F.W.; The mechanism of polyurethane foam formation; In Advances in Polyurethane Technology; J. M. Buist and H. Gudgeon, Eds,; John Wiley and Sons Inc.; New York, NY, 1968, 139.
Tomlinson, E.; Burger, J.J.; Incorporation of water-soluble drugs in albumin microspheres; In Methods in Enzymology; K. J. Widder and R. Green, Eds.; Academic press, Inc.; 1985, 112, 35.
Straathof, A.J.J.; Vrijenhoef, J.P.; Sprangers, E.P.A.T.; Bekkum, H.V.; Kieboom, A.P.G.; Enzymic formation of .beta.-D-fructofuranosides from sucrose: activity and selectivity of invertase in mixtures of water and alcohol; J. Carbohydrate Chemistry, 1988, 7, 223.
Hickmott, P.W.; Reaction of .alpha..beta.-unsaturated acid chlorides with alcohols in the presence of tertiary amines; J. Chem. Soc., 1964, 883.
Strumia, M.C.; Zamora, M.N.; Bertorello, H.E.; Hydrogels from acrylic sucrose. Synthesis and characterization; J. Appl. Poly. Sci., Applied Polymer Symposium 49, 9-14, 1991.
Jeong, S.Y.; Kim, S.W.; Eenink, M. J. D.; Feijen, J. Self-regulating insulin delivery systems. I. Synthesis and characterization of glycosylated insulin; J. Cont. Rel., 1984,1, 57.
Horbett, T.A.; Ratner, B.D.; Kost, J.; Singh, M. A bioresponsive membrane for insulin delivery; Plenum Press: New York, 1984, 209.
Yoshida, R.; Sakai, K.; Okano, T.; Sakurai, Y. Pulsatile drug delivery systems using hydrogels; Adv. Drug Delivery Reviews, 1993, 11, 85.
Hoffman, A.S., Afrassiabi, A. and Dong, L.C., Thermally reversible hydrogels: II. Delivery and selective removal of substances from aqueous solutions., J. Cont. Rel., 1986, 4, 213-222.
Dong, L.C. and Hoffman, A.S., Thermally reversible hydrogels: III. Immobilization of enzymes for feedback reaction control, J. Cont. Rel., 1986, 4, 223-227.
Shalaby, S. W. Thermoreversible gels; In Water-solution polymers; Synthesis, solution properties, and applications; S.W. Shalaby, C.L. McCormick and G.B. Butler, Eds.; American Chemical Society; Washington D.C., 1991, 467, 502.
Bae, Y.H., Okano, T. and Kim, S.W., Makromolek. Chem., Rapid Commun., (1988) 9, 185.
Yoshida, M., Asano, M. and Kumakura, M., A new temperature-sensitve hydrogel with .alpha.-amino acid group as side chain of polymer., Eur. Polym. J., (1989) 25, 1197-1202.
Yoshida, M., Suzuki, Y., Tamada, M., Kumakura, M. and Katakai, R., External stimulus-responsive poly(methacryloyldipeptides) having sequences of L-amino acyl-L-alanine ethyl esters as pendent groups., Eur. Polym. J. (1991) 27, 493-499.
Bae, Y.H., Okano, T., Hsu, R. and Kim, S.W., Makromolek. Chem., Rapid Commun., (1987) 8, 481.
Patil, D.R., Rethwisch, D.G., and Dordick, J.S., Enzymatic synthesis of a sucrose-containing linear polyester in nearly anhydrous organic media., Bio
BongJo Seong
Chen Jun
Park Kinam
Purdue Research Foundation
Wilson James O.
LandOfFree
Hydrophilic, hydrophobic, and thermoreversible saccharide gels a does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Hydrophilic, hydrophobic, and thermoreversible saccharide gels a, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Hydrophilic, hydrophobic, and thermoreversible saccharide gels a will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-2316717