Alginate derivatization: A review of chemistry, properties and applications

Biomaterials

Volumn 33, Issue 11, 2012, Pages 3279-3305

  Pawar, Siddhesh N ^a   Edgar, Kevin J ^a  

^a VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

Author keywords

Alginate; Bioartificial pancreas; Drug delivery; Drug release; Hydrogel; Polysaccharide

Indexed keywords

ANTICOAGULATION PROPERTIES; BIO-ARTIFICIAL PANCREAS; CELL-SURFACE INTERACTIONS; CHEMICAL DERIVATIZATION; CONTROLLED SYNTHESIS; DEGRADABILITY; DERIVATIZATION REACTION; DERIVATIZATIONS; DRUG RELEASE; HYDROPHOBIC-HYDROPHILIC; ISLETS OF LANGERHANS; LIVING CELL; MANNURONIC ACIDS; NUCLEATION AND GROWTH; TEMPERATURE CONDITIONS;

DRUG DELIVERY; DRUG PRODUCTS; GLUCOSE; HYDROGELS; HYDROXYAPATITE; NUCLEIC ACIDS; POLYSACCHARIDES;

ALGINATE;

2 PROPANOL; ALGINIC ACID; ALGINIC ACID DERIVATIVE; ALGINIC ACID SULFATE; ALUMINUM; BIOMATERIAL; CALCIUM; CALCIUM CARBONATE; CALCIUM CHLORIDE; CATION; DILTIAZEM; DODECYLTRIMETHYLAMMONIUM BROMIDE; EPICHLOROHYDRIN; GALACTOSE; GLUTARALDEHYDE; HEMOSTATIC AGENT; HEPARIN; HYDROXYAPATITE; HYDROXYL GROUP; ITACONIC ACID; KETOPROFEN; POLYSACCHARIDE; SILICON DERIVATIVE; SILICON DIOXIDE; SILICOTUNGSTIC ACID; SODIUM; UNCLASSIFIED DRUG; UNINDEXED DRUG; VINYL ACETATE; WATER; ZEOLITE;

ADSORPTION; ANTICOAGULATION; AQUEOUS SOLUTION; BIOCOMPATIBILITY; BIODEGRADATION; BIOENGINEERING; BLOOD CLOTTING; BROWN ALGA; CARBON NUCLEAR MAGNETIC RESONANCE; CELL ADHESION; CHEMICAL ANALYSIS; CHEMICAL BOND; CHEMICAL COMPOSITION; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; CROSS LINKING; DERIVATIZATION; DRUG ACETYLATION; DRUG DELIVERY SYSTEM; DRUG HYDROLYSIS; DRUG MANUFACTURE; DRUG RELEASE; DRUG SOLUBILITY; DRUG STABILITY; DRUG SULFATION; FRACTIONATION; GLUCONEOGENESIS; HUMAN; HYDROGEL; HYDROPHILICITY; HYDROPHOBICITY; IN VITRO STUDY; IN VIVO STUDY; IONIC STRENGTH; LIGHT SCATTERING; LIVER CELL; MOLECULAR WEIGHT; NONHUMAN; PERVAPORATION; PHOSPHORYLATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REACTION TIME; REVIEW; SIGNAL TRANSDUCTION; STEREOCHEMISTRY; SYNTHESIS;

ALGINATES; BIOCOMPATIBLE MATERIALS;

EID: 84856615725     PISSN: 01429612     EISSN: 18785905     Source Type: Journal    
DOI: 10.1016/j.biomaterials.2012.01.007     Document Type: Review

References (132)

1. Draget K.I. Alginates. Handbook of hydrocolloids 2009, 379-395. G.O. Phillips, P.A. Williams (Eds.).
2. Boateng J.S., Matthews K.H., Stevens H.N.E., Eccleston G.M. Wound healing dressings and drug delivery systems: a review. JPharm Sci 2008, 97:2892-2923.
3. Ramsey D.M., Wozniak D.J. Understanding the control of Pseudomonas aeruginosa alginate synthesis and the prospects for management of chronic infections in cystic fibrosis. Mol Microbiol 2005, 56:309-322.
4. Zimmermann H., Shirley S., Zimmermann U. Alginate-based encapsulation of cells: past, present, and future. Curr Diab Rep 2007, 7:314-320.
5. Ghidoni I., Chlapanidas T., Bucco M., Crovato F., Marazzi M., Vigo D., et al. Alginate cell encapsulation: new advances in reproduction and cartilage regenerative medicine. Cytotechnology 2008, 58:49-56.
6. Lee K.Y., Mooney D.J. Alginate: properties and biomedical applications. Prog Polym Sci 2012, 37:106-126.
7. Soonshiong P., Feldman E., Nelson R., Heintz R., Yao Q., Yao Z.W., et al. Long-term reversal of diabetes by the injection of immunoprotected islets. Proc Natl Acad Sci USA 1993, 90:5843-5847.
8. Hay I.D., Rehman Z.U., Ghafoor A., Rehm B.H.A. Bacterial biosynthesis of alginates. JChem Tech Biotechnol 2010, 85:752-759.
9. Remminghorst U., Rehm B.H. Bacterial alginates: from biosynthesis to applications. Biotechnol Lett 2006 Nov, 28:1701-1712.
10. Gacesa P. Bacterial alginate biosynthesis-recent progress and future prospects. Microbiology 1998, 144:1133-1143.
11. Rehm B.H.A., Valla S. Bacterial alginates: biosynthesis and applications. Appl Microbiol Biotechnol 1997, 48:281-288.
12. Franklin M.J., Ohman D.E. Mutant analysis and cellular localization of the AlgI, AlgJ, and AlgF proteins required for O acetylation of alginate in Pseudomonas aeruginosa. JBacteriol 2002, 184:3000-3007.
13. Franklin M.J., Douthit S.A., McClure M.A. Evidence that the algI/algJ gene cassette, required for O acetylation of Pseudomonas aeruginosa alginate, evolved by lateral gene transfer. JBacteriol 2004, 186:4759-4773.
14. Franklin M.J., Ohman D.E. Identification of algF in the alginate biosynthetic gene cluster of Pseudomonas aeruginosa which is required for alginate acetylation. JBacteriol 1993, 175:5057-5065.
15. Gimmestad M., Sletta H., Ertesvag H., Bakkevig K., Jain S., Suh S.J., et al. The Pseudomonas fluorescens AlgG protein, but not its mannuronan C-5-epimerase activity, is needed for alginate polymer formation. JBacteriol 2003, 185:3515-3523.
16. Chitnis C.E., Ohman D.E. Cloning of Pseudomonas aeruginosa algG, which controls alginate structure. JBacteriol 1990, 172:2894-2900.
17. Franklin M.J., Chitnis C.E., Gacesa P., Sonesson A., White D.C., Ohman D.E. Pseudomonas aeruginosa AlgG is a polymer level alginate C5-mannuronan epimerase. JBacteriol 1994, 176:1821-1830.
18. Zimmermann U., Klöck G., Federlin K., Hannig K., Kowalski M., Bretzel R.G., et al. Production of mitogen-contamination free alginates with variable ratios of mannuronic acid to guluronic acid by free flow electrophoresis. Electrophoresis 1992, 13:269-274.
19. Klöck G., Frank H., Houben R., Zekorn T., Horcher A., Siebers U., et al. Production of purified alginates suitable for use in immunoisolated transplantation. Appl Microbiol Biotechnol 1994, 40:638-643.
20. Haug A., Larsen B., Smidsrød O. Astudy of the constitution of alginic acid by partial hydrolysis. Acta Chem Scand 1966, 20:183-190.
21. Haug A., Larsen B., Smidsrød O. Studies on the sequence of uronic acid residues in alginic acid. Acta Chem Scand 1967, 21:691-704.
22. Painter T.J., Smidsrød O., Haug A. Acomputer study of the changes in composition-distribution occurring during random depolymerisation of a binary linear heteropolysaccharide. Acta Chem Scand 1968, 22:1637-1648.
23. Larsen B., Smidsrød O., Painter T.J., Haug A. Calculation of the nearest-neighbour frequencies in fragments of alginate from the yields of free monomers after partial hydrolysis. Acta Chem Scand 1970, 24:726-728.
24. Smidsrod O., Whittington S.G. Monte Carlo investigation of chemical inhomogeneity in polymers. Macromolecules 1969, 2:42-44.
25. Penman A., Sanderson G.R. Amethod for the determination of uronic acid sequence in alginates. Carbohydr Res 1972, 25:273-282.
26. Grasdalen H., Larsen B., Smidsrød O. Pmr study of the composition and sequence of uronate residues in alginates. Carbohydr Res 1979, 68:23-31.
27. Grasdalen H. High-Field, H-1-Nmr Spectroscopy of alginate - sequential structure and linkage conformations. Carbohydr Res 1983, 118:255-260.
28. Pawar S.N., Edgar K.J. Chemical modification of alginates in organic solvent systems. Biomacromolecules 2011, 12:4095-4103.
29. Sikorski P., Mo F., Skjåk-Bræk G., Stokke B.T. Evidence for egg-box-compatible interactions in calcium-alginate gels from fiber X-ray diffraction. Biomacromolecules 2007, 8:2098-2103.
30. Donati I., Holtan S., Mørch Y.A., Borgogna M., Dentini M., Skjåk-Bræk G. New hypothesis on the role of alternating sequences in calcium-alginate gels. Biomacromolecules 2005, 6:1031-1040.
31. 2+ on alginate microbeads. Biomacromolecules 2006, 7:1471-1480.
32. Skjåk-Bræk G., Grasdalen H., Smidsrød O. Inhomogeneous polysaccharide ionic gels. Carbohydr Polym 1989, 10:31-54.
33. Draget K.I., Skjåk-Bræk G., Smidsrød O. Alginic acid gels: the effect of alginate chemical composition and molecular weight. Carbohydr Polym 1994, 25:31-38.
34. Timell T.E. The acid hydrolysis of glycosides: I. General conditions and the effect of the nature of the aglycone. Can J Chem 1964, 42:1456.
35. Smidsrød O., Haug A., Larsen B. The influence of pH on the rate of hydrolysis of acidic polysaccharides. Acta Chem Scand 1966, 20:1026-1034.
36. Tsujino I., Saito T. Anew unsaturated uronide isolated from alginase hydrolysate. Nature 1961, 192:970-971.
37. Preiss J., Ashwell G. Alginic acid metabolism in bacteria. JBiol Chem 1962, 237:309-316.
38. Haug A.L., Larsen B., Smidsrød O. The degradation of alginates at different pH values. Acta Chem Scand 1963, 17:1466-1468.
39. Haug A.L., Larsen B., Smidsrød O. Alkaline degradation of alginate. Acta Chem Scand 1967, 21:2859-2870.
40. Haug A., Larsen B. Phenolic compounds in brown algae: I. The presence of reducing compounds in Ascophyllum nodosum (L.) Le Jol. Acta Chem Scand 1958, 12:650.
41. Smidsrød O., Haug A., Larsen B. The influence of reducing substances on the rate of degradation of alginates. Acta Chem Scand 1963, 17:1473-1474.
42. Smidsrød O., Haug A., Larsen B. Degradation of alginate in the presence of reducing compounds. Acta Chem Scand 1963, 17:2628-2637.
43. Leo W.J., Mcloughlin A.J., Malone D.M. Effects of sterilization treatments on some properties of alginate solutions and gels. Biotechnol Prog 1990, 6:51-53.
44. Chamberlain N.H., Cunningham G.E., Speakman J.B. Alginic acid diacetate. Nature 1946, 158:553.
45. Wassermann A. Alginic acid-acetate. JChem Soc 1948, 197.
46. Schweiger R.G. Acetylation of alginic acid. I. Preparation and viscosities of algin acetates. JOrg Chem 1962, 27:1786-1789.
47. Schweiger R.G. Acetylation of alginic acid. II. Reaction of algin acetates with calcium and other divalent ions. JOrg Chem 1962, 27:1789-1791.
48. Grasdalen H., Larsen B., Smidsrød O. C-13-Nmr studies of alginate. Carbohydr Res 1977, 56:C11-C15.
49. Grasdalen H., Larsen B., Smidsrød O. C-13-Nmr studies of monomeric composition and sequence in alginate. Carbohydr Res 1981, 89:179-191.
50. Skjåk-Bræk G., Paoletti S., Gianferrara T. Selective acetylation of mannuronic acid residues in calcium alginate gels. Carbohydr Res 1989, 185:119-129.
51. Skjåk-Bræk G., Zanetti F., Paoletti S. Effect of acetylation on some solution and gelling properties of alginates. Carbohydr Res 1989, 185:131-138.
52. Köhler S., Heinze T. New solvents for cellulose: dimethyl sulfoxide/ammonium fluorides. Macromol Biosci 2007, 7:307-314.
53. Sun H., DiMagno S.G. Anhydrous tetrabutylammonium fluoride. JAm Chem Soc 2005, 127:2050-2051.
54. Coleman R.J., Lawrie G., Lambert L.K., Whittaker M., Jack K.S., Grøndahl L. Phosphorylation of alginate: synthesis, characterization, and evaluation of invitro mineralization capacity. Biomacromolecules 2011, 12:889-897.
55. Alban S., Schauerte A., Franz G. Anticoagulant sulfated polysaccharides: part I. Synthesis and structure-activity relationships of new pullulan sulfates. Carbohydr Polym 2002, 47:267-276.
56. Linhardt R.J., Claude S. Hudson Award address in carbohydrate chemistry. Heparin: structure and activity. JMed Chem 2003, 46:2551-2564.
57. Ronghua H., Yumin D., Jianhong Y. Preparation and invitro anticoagulant activities of alginate sulfate and its quaterized derivatives. Carbohydr Polym 2003, 52:19-24.
58. Freeman I., Kedem A., Cohen S. The effect of sulfation of alginate hydrogels on the specific binding and controlled release of heparin-binding proteins. Biomaterials 2008, 29:3260-3268.
59. Fan L., Jiang L., Xu Y., Zhou Y., Shen Y., Xie W., et al. Synthesis and anticoagulant activity of sodium alginate sulfates. Carbohydr Polym 2011, 83:1797-1803.
60. Gama C.I., Tully S.E., Sotogaku N., Clark P.M., Rawat M., Vaidehi N., et al. Sulfation patterns of glycosaminoglycans encode molecular recognition and activity. Nat Chem Biol 2006, 2:467-473.
61. Rogers C.J., Clark P.M., Tully S.E., Abrol R., Garcia K.C., Goddard W.A., et al. Elucidating glycosaminoglycan-protein-protein interactions using carbohydrate microarray and computational approaches. Proc Natl Acad Sci USA 2011, 108:9747-9752.
62. Carré M.-C., Delestre C., Hubert P., Dellacherie E. Covalent coupling of a short polyether on sodium alginate: synthesis and characterization of the resulting amphiphilic derivative. Carbohyd Polym 1991, 16:367-379.
63. Scott J.E., Tigwell M.J., Phelps C.F., Nieduszynski I.A. Mechanism of scission of alginate chains by periodate. Carbohydr Res 1976, 47:105-117.
64. Bouhadir K.H., Lee K.Y., Alsberg E., Damm K.L., Anderson K.W., Mooney D.J. Degradation of partially oxidized alginate and its potential application for tissue engineering. Biotechnol Prog 2001, 17:945-950.
65. Marc Duval J., Delestre C., Carré M.-C., Hubert P., Dellacherie E. Synthesis and characterization of some covalent dextran-polyoxyethyleneglycol derivatives. Carbohydr Polym 1991, 15:233-242.
66. Sinquin A., Hubert P., Dellacherie E. Amphiphilic derivatives of alginate: evidence for intra- and intermolecular hydrophobic associations in aqueous solution. Langmuir 1993, 9:3334-3337.
67. Maestro A., Gonzalez C., Gutierrez J.M. Rheological behavior of hydrophobically modified hydroxyethyl cellulose solutions: a linear viscoelastic model. JRheol 2002, 46:127-143.
68. Sinquin A., Hubert P., Dellacherie E. Intermolecular associations in hydrophobically modified derivatives of propyleneglycol alginate. Polymer 1994, 35:3557-3560.
69. Sinquin A., Houzelle M.C., Hubert P., Choplin L., Viriot M.L., Dellacherie E. Amphiphilic derivatives of propylene glycol alginate: a revisit of their physicochemical behavior in dilute aqueous solution. Langmuir 1996, 12:3779-3782.
70. Sinquin A., Hubert P., Marchal P., Choplin L., Dellacherie E. Rheological properties of semi-dilute aqueous solutions of hydrophobically modified propylene glycol alginate derivatives. Colloids Surf A Physicochem Eng Asp 1996, 112:193-200.
71. Babak V.G., Skotnikova E.A., Lukina I.G., Pelletier S., Hubert P., Dellacherie E. Hydrophobically associating alginate derivatives: surface tension properties of their mixed aqueous solutions with oppositely charged surfactants. JColloid Interface Sci 2000, 225:505-510.
72. Pelletier S., Hubert P., Lapicque F., Payan E., Dellacherie E. Amphiphilic derivatives of sodium alginate and hyaluronate: synthesis and physico-chemical properties of aqueous dilute solutions. Carbohyd Polym 2000, 43:343-349.
73. Leonard M., Rastello de Boisseson M., Hubert P., Dellacherie E. Production of microspheres based on hydrophobically associating alginate derivatives by dispersion/gelation in aqueous sodium chloride solutions. JBiomed Mater Res A 2004, 68A:335-342.
74. Galant C., Kjoniksen A.L., Nguyen G.T.M., Knudsen K.D., Nystrom B. Altering associations in aqueous solutions of a hydrophobically modified alginate in the presence of beta-cyclodextrin monomers. JPhys Chem B 2006, 110:190-195.
75. Burckbuchler V., Kjoniksen A.L., Galant C., Lund R., Amiel C., Knudsen K.D., et al. Rheological and structural characterization of the interactions between cyclodextrin compounds and hydrophobically modified alginate. Biomacromolecules 2006, 7:1871-1878.
76. Augst A.D., Kong H.J., Mooney D.J. Alginate hydrogels as biomaterials. Macromol Biosci 2006, 6:623-633.
77. Shapiro L., Cohen S. Novel alginate sponges for cell culture and transplantation. Biomaterials 1997, 18:583-590.
78. Donati I., Vetere A., Gamini A., Coslovi A., Campa C., Paoletti S. Galactose-substituted alginate 1: Preliminary characterization and study of gelling properties. Biomacromolecules 2003, 4:624-631.
79. Donati I., Coslovi A., Gamini A., Vetere A., Campa C., Paoletti S. Galactose-substituted alginate 2: conformational aspects. Biomacromolecules 2004, 5:186-196.
80. Donati I., Draget K.I., Borgogna M., Paoletti S., Skjåk-Bræk G. Tailor-made alginate bearing galactose moieties on mannuronic residues: selective modification achieved by a chemoenzymatic strategy. Biomacromolecules 2005, 6:88-98.
81. Yang J., Goto M., Ise H., Cho C.-S., Akaike T. Galactosylated alginate as a scaffold for hepatocytes entrapment. Biomaterials 2002, 23:471-479.
82. Irwin M.A. The liver: biology and pathobiology 2009, 5th ed.
83. Rowley J.A., Madlambayan G., Mooney D.J. Alginate hydrogels as synthetic extracellular matrix materials. Biomaterials 1999, 20:45-53.
84. Rowley J.A., Mooney D.J. Alginate type and RGD density control myoblast phenotype. JBiomed Mater Res 2002, 60:217-223.
85. Draget K.I., Smidsrød O., Skjåk-Bræk G. Alginates from algae. Polysaccharides and polyamides in the food industry: properties, production, and patents 2005, 1-30. A. Steinbüchel, S.K. Rhee (Eds.).
86. Thu B., Bruheim P., Espevik T., Smidsrød O., SoonShiong P., Skjåk-Bræk G. Alginate polycation microcapsules 2. Some functional properties. Biomaterials 1996, 17:1069-1079.
87. Grasselli M., Diaz L.E., Cascone O. Beaded matrices from cross-linked alginate for affinity and ion exchange chromatography of proteins. Biotechnol Tech 1993, 7:707-712.
88. Chang C., Zhang L., Zhou J., Zhang L., Kennedy J.F. Structure and properties of hydrogels prepared from cellulose in NaOH/urea aqueous solutions. Carbohydr Polym 2010, 82:122-127.
89. Zhou J., Chang C., Zhang R., Zhang L. Hydrogels prepared from unsubstituted cellulose in NaOH/urea aqueous solution. Macromol Biosci 2007, 7:804-809.
90. Kartha K.P.R., Srivastava H. Reaction of epichlorohydrin with carbohydrate polymers. II. Starch reaction mechanism and physicochemical properties of modified starch. Starch/Stärke 1985, 37:297-306.
91. Moe S.T., Skjåk-Bræk G., Smidsrød O. Covalently cross-linked sodium alginate beads. Food Hydrocolloid 1991, 5:119-123.
92. Moe S.T., Skjåk-Bræk G., Elgsaeter A., Smidsrød O. Swelling of covalently crosslinked alginate gels: influence of ionic solutes and nonpolar solvents. Macromolecules 1993, 26:3589-3597.
93. Yeom C.K., Lee K.-H. Characterization of sodium alginate membrane crosslinked with glutaraldehyde in pervaporation separation. JAppl Polym Sci 1998, 67:209-219.
94. Yeom C.K., Jegal J.G., Lee K.H. Characterization of relaxation phenomena and permeation behaviors in sodium alginate membrane during pervaporation separation of ethanol-water mixture. JAppl Polym Sci 1996, 62:1561-1576.
95. Patil M.B., Veerapur R.S., Bhat S.D., Madhusoodana C.D., Aminabhavi T.M. Hybrid composite membranes of sodium alginate for pervaporation dehydration of 1,4-dioxane and tetrahydrofuran. Desalination Water Treat 2009, 3:11-20.
96. Adoor S.G., Manjeshwar L.S., Bhat S.D., Aminabhavi T.M. Aluminum-rich zeolite beta incorporated sodium alginate mixed matrix membranes for pervaporation dehydration and esterification of ethanol and acetic acid. JMemb Sci 2008, 318:233-246.
97. 40) incorporated novel sodium alginate hybrid composite membranes for pervaporation dehydration of acetic acid. Sep Purif Technol 2007, 54:178-186.
98. Patil M.B., Veerapur R.S., Patil S.A., Madhusoodana C.D., Aminabhavi T.M. Preparation and characterization of filled matrix membranes of sodium alginate incorporated with aluminum-containing mesoporous silica for pervaporation dehydration of alcohols. Sep Purif Technol 2007, 54:34-43.
99. 4-5) molecular sieve-loaded novel sodium alginate composite membranes for pervaporation dehydration of aqueous-organic mixtures near their azeotropic compositions. JMemb Sci 2006, 282:473-483.
100. Kim Y.-J., Yoon K.-J., Ko S.-W. Preparation and properties of alginate superabsorbent filament fibers crosslinked with glutaraldehyde. JAppl Polym Sci 2000, 78:1797-1804.
101. Kim J.H., Jegal J., Kim J.H., Lee K.H., Lee Y. Enantioselective permeation of alpha-amino acid optical isomers through crosslinked sodium alginate membranes. JAppl Polym Sci 2003, 89:3046-3051.
102. Riyajan S.-A., Sakdapipanich J. Development of a controlled release neem capsule with a sodium alginate matrix, crosslinked by glutaraldehyde and coated with natural rubber. Polym Bull 2009, 63:609-622.
103. Kulkarni A.R., Soppimath K.S., Aminabhavi T.M., Dave A.M., Mehta M.H. Glutaraldehyde crosslinked sodium alginate beads containing liquid pesticide for soil application. JControl Release 2000, 63:97-105.
104. Chan A.W., Whitney R.A., Neufeld R.J. Kinetic controlled synthesis of pH-responsive network alginate. Biomacromolecules 2008, 9:2536-2545.
105. Chan A.W., Whitney R.A., Neufeld R.J. Semisynthesis of a controlled stimuli-responsive alginate hydrogel. Biomacromolecules 2009, 10:609-616.
106. Leone G., Torricelli P., Chiumiento A., Facchini A., Barbucci R. Amidic alginate hydrogel for nucleus pulposus replacement. JBiomed Mater Res-A 2008, 84A:391-401.
107. Xu J.B., Bartley J.P., Johnson R.A. Preparation and characterization of alginate hydrogel membranes crosslinked using a water-soluble carbodiimide. JAppl Polym Sci 2003, 90:747-753.
108. Bouhadir K.H., Hausman D.S., Mooney D.J. Synthesis of cross-linked poly(aldehyde guluronate) hydrogels. Polymer 1999, 40:3575-3584.
109. Shah S.B., Patel C.P., Trivedi H.C. Ceric-induced grafting of acrylate monomers onto sodium alginate. Carbohydr Polym 1995, 26:61-67.
110. Shah S.B., Patel C.P., Trivedi H.C. Fenton's reagent-initiated graft copolymerization of acrylonitrile onto sodium alginate. JAppl Polym Sci 1994, 51:1421-1426.
111. Shah S.B., Patel C.P., Trivedi H.C. Kinetics and reaction mechanism of Fenton's-reagent-initiated graft copolymerization of acrylonitrile onto sodium alginate. JAppl Polym Sci 1994, 52:857-860.
112. Tripathy T., Pandey S.R., Karmakar N.C., Bhagat R.P., Singh R.P. Novel flocculating agent based on sodium alginate and acrylamide. Eur Polym J 1999, 35:2057-2072.
113. Tripathy T., Singh R.P. Characterization of polyacrylamide-grafted sodium alginate: a novel polymeric flocculant. JAppl Polym Sci 2001, 81:3296-3308.
114. Biswal D.R., Singh R.P. The flocculation and rheological characteristics of hydrolyzed and unhydrolyzed grafted sodium alginate in aqueous solutions. JAppl Polym Sci 2004, 94:1480-1488.
115. 2+ ion cross-linked interpenetrating network matrix tablets of polyacrylamide-grafted-sodium alginate and sodium alginate for sustained release of diltiazem hydrochloride. Carbohydr Polym 2010, 82:867-873.
116. Toti U.S., Aminabhavi T.M. Synthesis and characterization of polyacrylamide grafted sodium alginate membranes for pervaporation separation of water plus isopropanol mixtures. JAppl Polym Sci 2004, 92:2030-2037.
117. Kurkuri M.D., Kumbar S.G., Aminabhavi T.M. Synthesis and characterization of polyacrylamide-grafted sodium alginate copolymeric membranes and their use in pervaporation separation of water and tetrahydrofuran mixtures. JAppl Polym Sci 2002, 86:272-281.
118. Yang W., Zhang L., Wu L., Li J., Wang J., Jiang H., et al. Synthesis and characterization of MMA-NaAlg/hydroxyapatite composite and the interface analyse with molecular dynamics. Carbohydr Polym 2009, 77:331-337.
119. Mollah M.Z.I., Khan M.A., Hoque M.A., Aziz A. Studies of physico-mechanical properties of photo-cured sodium alginate with silane monomer. Carbohydr Polym 2008, 72:349-355.
120. Kulkarni R.V., Setty C.M., Sa B. Polyacrylamide-g-alginate-based electrically responsive hydrogel for drug delivery application: synthesis, characterization, and formulation development. JAppl Polym Sci 2010, 115:1180-1188.
121. Yang S., Liu G., Cheng Y., Zheng Y. Electroresponsive behavior of sodium alginate-g-poly (acrylic acid) hydrogel under DC electric field. JMacromol Sci Part A 2009, 46:1078-1082.
122. Kulkarni R.V., Sa B. Novel pH-sensitive interpenetrating network hydrogel beads of carboxymethylcellulose - (polyacrylamide-grafted-alginate) for controlled release of ketoprofen: preparation and characterization. Curr Drug Deliv 2008, 5:256-264.
123. Sen G., Singh R.P., Pal S. Microwave-initiated synthesis of polyacrylamide grafted sodium alginate: synthesis and characterization. JAppl Polym Sci 2010, 115:63-71.
124. Liu Y., Yang L., Li J., Shi Z. Grafting of methyl methacrylate onto sodium alginate initiated by potassium ditelluratoargentate(III). JAppl Polym Sci 2005, 97:1688-1694.
125. Işiklan N., Kurşun F., Inal M. Graft copolymerization of itaconic acid onto sodium alginate using ceric ammonium nitrate as initiator. JAppl Polym Sci 2009, 114:40-48.
126. Işiklan N., Kurşun F., Inal M. Graft copolymerization of itaconic acid onto sodium alginate using benzoyl peroxide. Carbohydr Polym 2010, 79:665-672.
127. Ma P., Xiao C., Li L., Shi H., Zhu M. Facile preparation of ferromagnetic alginate-g-poly(vinyl alcohol) microparticles. Eur Polym J 2008, 44:3886-3889.
128. Omagari Y., Kaneko Y., Kadokawa J.-I. Chemoenzymatic synthesis of amylose-grafted alginate and its formation of enzymatic disintegratable beads. Carbohydr Polym 2010, 82:394-400.
129. Kim J.H., Lee S.B., Kim S.J., Lee Y.M. Rapid temperature/pH response of porous alginate-g-poly(N-isopropylacrylamide) hydrogels. Polymer 2002, 43:7549-7558.
130. Gao C., Liu M., Chen S., Jin S., Chen J. Preparation of oxidized sodium alginate-graft-poly((2-dimethylamino) ethyl methacrylate) gel beads and invitro controlled release behavior of BSA. Int J Pharm 2009, 371:16-24.
131. Morch Y.A., Donati I., Strand B.L., Skjåk-Bræk G. Molecular engineering as an approach to design new functional properties of alginate. Biomacromolecules 2007, 8:2809-2814.
132. Fox S.C., Li B., Xu D., Edgar K.J. Regioselective esterification and etherification of cellulose - a review. Biomacromolecules 2011, 12:1956-1972.