Designing novel pH-induced chitosan-gum Odina complex coacervates for colon targeting

Industrial and Engineering Chemistry Research

Volumn 52, Issue 45, 2013, Pages 15728-15745

  Roy, Partha Sarathi ^a   Samanta, Amalesh ^a   Mukherjee, Manabendra ^b   Roy, Bappaditya ^c   Mukherjee, Abhishek ^d  

^a JADAVPUR UNIVERSITY   (India)

^b SAHA INSTITUTE OF NUCLEAR PHYSICS   (India)

^c DEPARTMENT OF MATERIALS SCIENCE   (India)

^d INDIAN INSTITUTE OF CHEMICAL BIOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BIODEGRADATION RATE; COLON TARGETING; COMPLEX COACERVATES; EXTRACELLULAR ENZYMES; GASTRIC FLUIDS; INTESTINAL FLUID; POLYELECTROLYTE COMPLEXES; POTENTIOMETRIC TITRATIONS;

BIODEGRADATION; BIOPOLYMERS; ENZYMES; MICROSPHERES; TITRATION; VOLTAMMETRY;

CHITOSAN;

EID: 84887602040     PISSN: 08885885     EISSN: 15205045     Source Type: Journal    
DOI: 10.1021/ie401681t     Document Type: Article

References (109)

1. Bungenberg de Jong, H. G.; Kruyt, H. R. Coacervation (partial miscibility in colloid systems) Proc. Koninkl. Med. Akad. Wetenschap 1929, 32, 849-856
2. Sanchez, C.; Mekhloufi, G.; Schmitt, C.; Renard, D.; Robert, P.; Lehr, C. M.; Lamprecht, A.; Hardy, J. Self-assembly of β-lactoglobulin and acacia gum in aqueous solvent: structure and phase-ordering kinetics Langmuir 2002, 18, 10323-10333
3. McNaught, A. D.; Wilkinson, A. Compendio de Terminología Química; Sintesis: Madrid, Spain, 2003; p 117.
4. Weinbreck, F.; de Vries, R.; Schrooyen, P.; de Kruif, C. G. Complex coacervation of whey proteins and gum arabic Biomacromolecules 2003, 4, 293-303
5. Kaibara, K.; Okazaki, T.; Bohidar, H. B.; Dubin, P. L. pH-induced coacervation in complexes of bovine serum albumin and cationic polyelectrolytes Biomacromolecules 2000, 1, 100-107
6. Veis, A.; Aranyi, C. Phase separation in polyelectrolyte systems. I. Complex coacervates of gelatin J. Phys. Chem. 1960, 64, 1203-1210
7. Michaels, A. S.; Miekka, R. G. Polycation-polyanion complexes: preparation and properties of poly(vinyl benzyl trimethyl ammonium) and poly(styrene sulfonate) J. Phys. Chem. 1961, 65, 1765-1773
8. Berger, J.; Reist, M.; Mayer, J. M.; Felt, O.; Gurn, R. Structure and interactions in covalently and ionically crosslinked chitosan hydrogels for biomedical applications Eur. J. Pharm. Biopharm. 2004, 57, 35-52
9. Kizilay, E.; Basak-Kayitmazer, A.; Dubin, P. L. Complexation and coacervation of polyelectrolytes with oppositely charged colloids Adv. Colloid Interface Sci. 2011, 167, 24-37
10. Kizilay, E.; Maccarrone, S.; Foun, E.; Dinsmore, A. D.; Dubin, P. L. Clustering in polyelectrolyte-micelle complex coacervation J. Phys. Chem. B 2011, 115, 7256-7263
11. Chollakup, R.; Smitthipong, W.; Eisenbach, C. D.; Tirrell, M. Phase behavior and coacervation of aqueous poly(acrylic acid)-poly(allylamine) solutions Macromolecules 2010, 43, 2518-2528
12. Kayitmazer, A. B.; Strand, S. P.; Tribet, C.; Jaeger, W.; Dubin, P. L. Effect of polyelectrolyte structure on protein-polyelectrolyte coacervates: coacervates of bovine serum albumin with poly(diallyldimethylammonium chloride) vs. chitosan Biomacromolecules 2007, 8, 3568-3577
13. Bungenberg de Jong, H. G. In Colloid Science; Kruyt, H. R., Ed.; Elsevier Publishing: Amsterdam, The Netherlands, 1949; Vol. II, Chapter X, pp 339-432.
14. Luzzi, L. A.; Gerraughty, R. J. Effects of selected variables on the extractability of oils from coacervate capsules J. Pharm. Sci. 1964, 53, 429-431
15. Wang, Q.; Mynar, J. L.; Yoshida, M.; Lee, E.; Lee, M.; Okuro, K.; Kinbara, K.; Aida, T. High-water-content mouldable hydrogels by mixing clay and a dendritic molecular binder Nature 2010, 463, 339-343
16. Tiitu, M.; Hiekkataipale, P.; Hartikainen, J.; Makela, T.; Ikkala, O. Viscoelastic and electrical transitions in gelation of electrically conducting polyaniline Macromolecules 2002, 35, 5212-5217
17. te Nijenhuis, K. Thermoreversible networks: viscoelastic properties and structure of gels Adv. Polym. Sci. 1997, 130, 1-267
18. Burchard, W.; Ross-Murphy, S. B. Physical Networks: Polymers and Gels; Elsevier Applied Science: London, UK, 1990.
19. Flory, P. J. Molecular size distribution in three dimensional polymers. I. Gelation J. Am. Chem. Soc. 1941, 63, 3083-3090
20. Stockmayer, W. H. Theory of molecular size distribution and gel formation in branched-chain polymers J. Chem. Phys. 1943, 11, 45-55
21. In Chemical and Physical Networks: Formation and Control of Properties; te Nijenhuis, K.; Mijs, W. S., Eds.; Wiley: Chichester, UK, 1998; Vol. 1.
22. Lee, S. B.; Lee, Y. M.; Song, K. W.; Park, M. H. Preparation and properties of polyelectrolyte complex sponges composed of hyaluronic acid and chitosan and their biological behaviors J. Appl. Polym. Sci. 2003, 90, 925-932
23. Sankalia, M. G.; Mashru, R. C.; Sankalia, J. M.; Sutariya, V. B. Reversed chitosan-alginate polyelectrolyte complex for stability improvement of α-amylase: optimization and physicochemical characterization Eur. J. Pharm. Biopharm. 2007, 65, 215-232
24. Werle, M.; Takeuchi, H.; Bernkop-Schnurch, A. Modified chitosans for oral drug delivery J. Pharm. Sci. 2009, 98, 1643-1656
25. Sionkowska, A. Current research on the blends of natural and synthetic polymers as new biomaterials: review Prog. Polym. Sci. 2011, 36, 1254-1276
26. Naidu, V. G. M.; Madhusudhana, K.; Sashidhar, R. B.; Ramakrishna, S.; Khar, R. K.; Ahmed, F. J.; Diwan, P. V. Polyelectrolyte complexes of gum kondagogu and chitosan, as diclofenac carriers Carbohydr. Polym. 2009, 76, 464-471
27. Chauhan, N. S. Medicinal and Aromatic Plants of Himachal Pradesh; Indus Publishing: Delhi, India, 1999.
28. Aspinall, G. O. Gums and mucilages Adv. Carbohydr. Chem. Biochem. 1969, 24, 333-379
29. Bhattacharya, A. K.; Rao, C. V. N. Gum Jeol: the structure of the degraded gum derived from it Can. J. Chem. 1964, 42, 107-112
30. Bhattacharyya, A. K.; Mukherjee, A. K. Structural studies of the gum Jeol polysaccharide Bull. Chem. Soc. Jpn. 1964, 37, 1425-1429
31. Mukherjee, B.; Samanta, A.; Dinda, S. C. Gum Odina-a new tablet binder Trends. Appl. Sci. Res. 2006, 1, 309-316
32. Dinda, S. C.; Mukherjee, B.; Samanta, A. Gum Odina: a novel matrix forming material for sustained drug delivery Orient. Pharm. Exp. Med. 2011, 11, 131-136
33. Sinha, V. R.; Al-Azaki, A. A.; Kumar, R. V. Novel Lannea Woodier gum matrices for controlled release of drugs Carbohydr. Polym. 2011, 83, 1492-1498
34. Okamoto, Y.; Nose, M.; Miyatake, K.; Sekine, J.; Oura, R.; Shigemasa, Y. Physical changes of chitin and chitosan in canine gastrointestinal tract Carbohydr. Polym. 2001, 44, 211-215
35. Weecharangsan, W.; Opanasopit, P.; Ngawhirunpat, T.; Apirakaramwong, A.; Rojanarata, T.; Ruktanonchai, U.; Lee, R. J. Evaluation of chitosan salts as non-viral gene vectors in CHO-K1 cells Int. J. Pharm. 2008, 348, 161-168
36. Recillas, M.; Silva, L. L.; Peniche, C.; Goycoolea, F. M.; Rinaudo, M.; Argüelles-Monal, W. M. Thermoresponsive behavior of chitosan-g- N -isopropylacrylamide copolymer solutions Biomacromolecules 2009, 10, 1633-1641
37. Biological Evaluation of Medical Devices. Part 5. Tests for Cytotoxicity: In Vitro Methods; ISO 10993-5; Association for the Advancement of Medical Instrumentation: Arlington, VA, 2009.
38. Faneca, H.; Faustino, A.; Pedroso de Lima, M. C. J. Controlled Release 2008, 126, 175-184
39. Biological Evaluation of Medical Devices. Part 9: Degradation of Materials Related to Biological Testing; Technical Information Report 10993; Association for the Advancement of Medical Instrumentation: Arlington, VA, 1995; pp 141-221.
40. Hovgaard, L.; Brondsted, H. Current applications of polysaccharides in colon targeting Crit. Rev. Ther. Drug. Carrier Syst. 1996, 8, 185-223
41. Salyer, A. A. Energy sources of major intestinal fermentative anaerobes Am. J. Clin. Nutr. 1979, 32, 158-163
42. Hawksworth, G.; Drasar, B. S.; Hill, M. J. Intestinal bacteria and hydrolysis of glycosidic bonds J. Med. Microbiol. 1971, 4, 451-459
43. Prizont, R.; Konigsberg, N. Identification of bacterial glycosidases in rat cecal contents Dig. Dis. Sci. 1981, 26, 773-777
44. Mason, V. C. Some observations on the distribution and origin of nitrogen in sheep feces J. Agric. Sci. 1969, 73, 99-111
45. Salyers, A. A.; Palmer, J. K.; Wilkins, T. D. Degradation of polysaccharides by intestinal bacterial enzymes Am. J. Clin. Nutr. 1978, 31, S128-S130
46. Goldstein, J.; Newbury, D.; Joy, D.; Lyman, C.; Echlin, P.; Lifshin, E. Scanning Electron Microscopy and X-ray Microanalysis, 3 rd ed.; Kluwer Academic: New York, 2003.
47. Pereira, J. L. G. C.; Pais, A. A. C. C.; Redinha, J. S. Maximum likelihood estimation with nonlinear regression in polarographic and potentiometric studies Anal. Chim. Acta 2001, 433, 135-143
48. Ikeda, S.; Kumagai, H.; Sakiyama, T.; Chu, C.; Nakamura, K. Method for analyzing pH-sensitive swelling of amphoteric hydrogels-application to a polyelectrolyte complex gel prepared from xanthan and chitosan Biosci., Biotechnol., Biochem. 1995, 59, 1422-1427
49. Mekhloufi, G.; Sanchez, C.; Renard, D.; Guillemin, S.; Hardy, J. pH-induced structural transitions during complexation and coacervation of β-lactoglobulin and acacia gum Langmuir 2005, 21, 386-394
50. Weinbreck, F.; Nieuwenhuijse, H.; Robijn, G. W.; de Kruif, C. G. Complexation of whey proteins with carrageenan J. Agric. Food Chem. 2004, 52, 3550-3555
51. Tolstoguzov, V. B. Some thermodynamic considerations in food formulation Food Hydrocolloids 2003, 17, 1-23
52. Claesson, P. M.; Ninhami, B. W. pH-dependent interactions between adsorbed chitosan layers Langmuir 1992, 8, 1406-1412
53. Basu, S.; Dasgupta, P. C.; Sircar, A. K. Studies in polyelectrolytes. II. Gum arabate J. Colloid Sci. 1951, 6, 539-549
54. Daniel, C.; Dammer, C.; Guenet, J. M. On the definition of thermoreversible gels: the case of syndiotactic polystyrene Polymer 1994, 35, 4243-4246
55. Molecular Gels: Materials with Self-Assembled Fibrillar Networks; Weiss, R. G.; Terech, P., Eds.; Springer: Dordrecht, The Netherlands, 2006.
56. Garai, A.; Nandi, A. K. Rheology of polyaniline-dinonylnaphthalene disulfonic acid (DNNDSA) montmorillonite clay nanocomposites in the sol state: shear thinning versus pseudo-solid behavior J. Nanosci. Nanotechnol. 2008, 8, 1842-1851
57. Johnson, S. B.; Dustan, D. E.; Franks, G. V. A novel thermally-activated crosslinking agent for chitosan in aqueous solution: a rheological investigation Colloid Polym. Sci. 2004, 282, 602-612
58. Vachoud, L.; Zydowicz, N.; Domard, A. Physicochemical behaviour of chitin gels Carbohydr. Res. 2000, 326, 295-304
59. Laneuville, S. I.; Turgeon, S. L.; Sanchez, C.; Paquin, P. Gelation of native β-lactoglobulin induced by electrostatic attractive interaction with xanthan gum Langmuir 2006, 22, 7351-7357
60. Bohidar, H.; Dubin, P. L.; Majhi, P. R.; Tribet, C.; Jaeger, W. Effects of protein-polyelectrolyte affinity and polyelectrolyte molecular weight on dynamic properties of bovine serum albumin-poly(diallylmethylammonium chloride) coacervates Biomacromolecules 2005, 6, 1573-1585
61. Wang, X.; Lee, J.; Wang, Y.-W.; Huang, Q. Composition and rheological properties of β-lactoglobulin/pectin coacervates: effects of salt concentration and initial protein/polysaccharide ratio Biomacromolecules 2007, 8, 992-997
62. Marudova, M.; McDougall, A. J.; Ring, S. G. Physicochemical studies of pectin/poly- l -lysine gelation Carbohydr. Res. 2004, 339, 209-216
63. Kaminska, A.; Sionkowska, A. Effect of UV radiation on the infrared spectra of collagen Polym. Degrad. Stab. 1996, 51, 19-26
64. Paluszkiewicz, C.; Stodolak, E.; Hasik, M.; Blazewicz, M. FT-IR study of montmorillonite-chitosan nanocomposite materials Spectrochim Acta Part A 2011, 79, 784-788
65. Oudadesse, H.; Bui, X. V.; Le Gal, Y.; Mostafa, A.; Cathelineau, G. Chitosan effects on bioactive glass for application as biocomposite biomaterial Int. J. Biol. Biomed. Eng. 2011, 5, 49-56
66. Hsu, S. L.; Moore, W. H.; Krimm, S. Vibrational spectrum of the unordered polypeptide chain: a Raman study of feather keratin Biopolymers 1976, 15, 1513-1528
67. Williams, W. H.; Flemming, I. Spectroscopic Methods in Organic Chemistry, 4 th ed., revised; McGraw-Hill Book: England, 1989.
68. Lin-Vien, D.; Colthup, N. B.; Fateley, W. G.; Grasselli, J. G. The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules; Academic Press: San Diego, CA, USA, 1991.
69. de Vasconcelos, C. L.; Bezerril, P. M.; dos Santos, D. E.; Dantas, T. N.; Pereira, M. R.; Fonseca, J. L. Effect of molecular weight and ionic strength on the formation of polyelectrolyte complexes based on poly(methacrylic acid) and chitosan Biomacromolecules 2006, 7, 1245-1252
70. Colthup, N. B.; Daly, L. H.; Wiberley, S. E. Introduction to infrared and Raman Spectroscopy, 3 rd ed.; Academic Press: San Diego, CA, USA, 1990; p 319.
71. Qian, F.; Cui, F.; Ding, J.; Tang, C.; Yin, C. Chitosan graft copolymer nanoparticles for oral protein drug delivery: preparation and characterization Biomacromolecules 2006, 7, 2722-2727
72. Finar, I. L. Organic Chemistry: Stereochemistry of Natural Products; Longmans: London, UK, 1975; Vol. 2.
73. Shevchenko, L. L. Infrared spectra of salts and complexes of carboxylic acids and some of their derivatives Russ. Chem. Rev. 1963, 32, 201-207
74. Kaèuráková, M.; Capek, P.; Sasinková, V.; Wellner, N.; Ebringerová, A. FT-IR study of plant cell wall model compounds: pectic polysaccharides and hemicelluloses Carbohydr. Polym. 2000, 43, 195-203
75. Renard, D.; Lavenant-Gourgeon, L.; Christine Ralet, M. C.; Christian Sanchez, C. Acacia senegal gum: continuum of molecular species differing by their protein to sugar ratio, molecular weight, and charges Biomacromolecules 2006, 7, 2637-2649
76. Simsek-Ege, F. A.; Bond, G. M.; Stringer, J. Polyelectrolyte complex formation between alginate and chitosan as a function of pH J. Appl. Polym. Sci. 2003, 88, 346-351
77. 2 system for membrane coat application J. Pharm. Sci. 2001, 90, 1134-1142
78. Briggs, D. In Practical Surface Analysis; Briggs, D.; Seah, M. P., Eds.; Wiley: Chichester, UK, 1990; Vol. 1, p 437.
79. Beamson, G. D. B. High Resolution XPS of Organic Polymers; Wiley: Chichester, UK, 1992.
80. Ratner, B. D.; Caster, D. G. In Surface Analysis-The Principal Techniques; Vickerman, J. C., Ed.; Wiley: Chichester, UK, 1997; p 43.
81. Amaral, I. F.; Granja, P. L.; Barbosa, M. A. Chemical modification of chitosan by phosphorylation: an XPS, FT-IR and SEM study J. Biomater. Sci., Polym. Ed. 2005, 16, 1575-1593
82. Fleutot, S.; Dupin, J. C.; Baraille, I.; Forano, C.; Renaudin, G.; Leroux, F.; Gonbeaua, D.; Martinez, H. A new route for local probing of inner interactions within a layered double hydroxide/benzene derivative hybrid material Phys. Chem. Chem. Phys. 2009, 11, 3554-3565
83. Lee, J. W.; Kim, S. Y.; Kim, S. S.; Lee, Y. M.; Lee, K. H.; Kim, S. J. Synthesis and characteristics of interpenetrating polymer network hydrogel composed of chitosan and poly (acrylic acid) J. Appl. Polym. Sci. 1999, 73, 113-120
84. Tavares, I. S.; Caroni, A. L. P. F.; Neto, A. A. D.; Pereira, M. R.; Fonseca, J. L. C. Surface charging and dimensions of chitosan coacervated nanoparticles Colloids Surf., B 2012, 90, 254-258
85. Dung, P. I.; Milas, M.; Rinaudo, M.; Desbrires, J. Water soluble derivatives obtained by controlled chemical modifications of chitosan Carbohydr. Polym. 1994, 24, 209-214
86. Wan, Y.; Creber, K. A. M.; Peppley, B.; Bui, V. T. Ionic conductivity of chitosan membranes Polymer 2003, 44, 1057-1065
87. Wan, Y.; Katherine, A. M.; Creber, B. P.; TamBui, V. Chitosan-based solid electrolyte composite membranes. I. Preparation and characterization J. Membr. Sci. 2006, 280, 666-674
88. Vinod, V. T. P.; Sashidhar, R. B.; Suresh, K. I.; Rama Rao, B.; Vijaya Saradhi, U. V. R.; Prabhakar Rao, T. Morphological, physico-chemical and structural characterization of gum kondagogu (Cochlospermum gossypium): a tree gum from India Food Hydrocolloids 2008, 22, 899-915
89. Prabaharan, M.; Gong, S. Novel thiolated carboxymethyl chitosan-g-β-cyclodextrin as mucoadhesive hydrophobic drug delivery carriers Carbohydr. Polym. 2008, 73, 117-125
90. Muzzarelli, C.; Stanic, V.; Gobbi, L.; Tosi, G.; Muzzarelli, R. A. A. Spray-drying of solutions containing chitosan together with polyuronans and characterization of the microspheres Carbohydr. Polym. 2004, 57, 73-82
91. Kim, C. H.; Choi, K. S. Synthesis and properties of carboxyalkyl chitosan derivatives J. Ind. Eng. Chem. 1998, 4, 19-25
92. Cui, Z. M.; Liu, C. P.; Lu, T. H.; Xing, W. J. Polyelectrolyte complexes of chitosan and phosphotungstic acid as proton-conducting membranes for direct methanol fuel cells J. Power Sources 2007, 167, 94-99
93. Aparicio, M.; Mosa, J.; Etienne, M.; Duran, A. Proton-conducting methacrylate-silica sol-gel membranes containing tungstophosphoric acid J. Power Sources 2005, 145, 231-236
94. Neto, C. G. T.; Giacometti, J. A.; Jobb, A. E.; Ferreira, F. C.; Fonseca, J. L. C.; Pereira, M. R. Thermal analysis of chitosan based networks Carbohydr. Polym. 2005, 62, 97-103
95. Zohuriaan, M. J.; Shokrolahi, F. Thermal studies on natural and modified gums Polym. Test. 2004, 23, 575-579
96. Maciel, J. S.; Silva, D. A.; Paula, H. C. B.; Paula, R. C. M. Chitosan carboxymethyl cashew gum polyelectrolyte complex: synthesis and thermal stability Eur. Polym. J. 2005, 41, 2726-2733
97. Denuziere, A.; Ferrief, D.; Domard, A. Chitosan-chondroitin sulfate and chitosan-hyaluronate polyelectrolyte complexes. Physico-chemical aspects Carbohydr. Polym. 1996, 29, 317-323
98. Ghaffari, A.; Navaee, K.; Oskoui, M.; Bayati, K.; Rafiee-Tehrani, M. Preparation and characterization of free mixed-film of pectin/chitosan/Eudragit RS intended for sigmoidal drug delivery Eur. J. Pharm. Biopharm. 2007, 67, 175-186
99. Zhang, C.; Ping, Q.; Zhang, H.; Shen, J. Synthesis and characterization of water-soluble O-succinyl-chitosan Eur. Polym. J. 2003, 39, 1629-1634
100. Bemiller, J. N.; Whistler, R. L. Carbohydrates. In Food Chemisstry, 3 rd ed.; Fennema, O. R., Ed.; Dekker: New York, 1996; p 17.
101. Phillips, G. O.; Takigami, S.; Takigami, M. Hydration characteristics of the gum exudate from Acacia Senegal Food Hydrocolloids 1996, 10, 11-19
102. Shanta, K. L.; Harding, D. R. K. Synthesis and characterization of chemically modified chitosan microspheres Carbohydr. Polym. 2002, 48, 247-253
103. Nugraha, E.; Suyatma, N. E.; Tighzert, L.; Copinet, A. Effects of hydrophilic plasticizers on mechanical, thermal, and surface properties of chitosan films J. Agric. Food Chem. 2005, 53, 3950-3957
104. Smitha, B.; Sridhar, S.; Khan, A. A. Polyelectrolyte complexes of chitosan and poly(acrylic acid) as proton exchange membranes for fuel cells Macromolecules 2004, 37, 2233-2239
105. Cerrai, P.; Guerra, G.; Tricoli, M. Polyelectrolyte complexes obtained by radical polymerization in the presence of chitosan Macromol. Chem. Phys. 1996, 197, 3567-3579
106. Park, W. Insoluble polyelectrolyte complex formed from chitosan and α-keratose: conformational change of α-keratose Macromol. Chem. Phys. 1996, 197, 2175-2183
107. Taravel, M.; Domard, A. Collagen and its interaction with chitosan. II. Influence of the physicochemical characteristics of collagen Biomaterials 1995, 16, 865-871
108. Salyers, A. A.; Vercellotti, J. R.; West, S. E. H.; Wilkins, T. D. Fermentation of mucin and plant polysaccharides by strains of bacteroides from the human colon Appl. Environ. Microbiol. 1977, 33, 319-322
109. Salyers, A. A.; Leedle, J. A. Carbohydrate metabolism in the human colon. In Human Intestinal Microflora in Health and Disease; Hentge, D. J., Ed.; Academic Press: New York, 1983; pp 129-46.