Eudragit e PO as a complementary material for designing oral drug delivery systems with controlled release properties: Comparative evaluation of new interpolyelectrolyte complexes with countercharged eudragit L100 copolymers

Molecular Pharmaceutics

Volumn 10, Issue 7, 2013, Pages 2630-2641

  Moustafine, R I ^a   Bukhovets, A V ^a   Sitenkov, A Y ^a   Kemenova, V A ^c   Rombaut, P ^b   Van Den Mooter, G ^b,d  

^a KAZAN STATE MEDICAL UNIVERSITY   (Russian Federation)

^b DEPARTMENT OF PHARMACEUTICAL AND PHARMACOLOGICAL SCIENCES   (Belgium)

^c All Russia Science Research Institute of Medicinal and Aromatic Plants   (Russian Federation)

^d UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

diclofenac sodium; Eudragit E PO; Eudragit L 100; Eudragit RL30D; FTIR; glass transition; interpolyelectrolyte complexes; MTDSC; oral drug delivery; pH dependent swelling behavior; theophylline

Indexed keywords

COPOLYMER; DICLOFENAC; EUDRAGIT; THEOPHYLLINE;

ARTICLE; CHEMICAL COMPOSITION; CONTROLLED RELEASE FORMULATION; CONTROLLED STUDY; DIFFERENTIAL SCANNING CALORIMETRY; DIFFUSION; INFRARED SPECTROSCOPY; PH; PRIORITY JOURNAL; SOLID STATE;

CALORIMETRY, DIFFERENTIAL SCANNING; DRUG DELIVERY SYSTEMS; HYDROGEN-ION CONCENTRATION; POLYMETHACRYLIC ACIDS; SPECTROSCOPY, FOURIER TRANSFORM INFRARED;

EID: 84879725847     PISSN: 15438384     EISSN: 15438392     Source Type: Journal    
DOI: 10.1021/mp4000635     Document Type: Article

References (69)

1. Dittgen, M.; Durrani, M.; Lehmann, K. Acrylic polymers. A review of pharmaceutical applications STP Pharm. Sci. 1997, 7, 403-437
2. Skalsky, B.; Petereit, H.-U. Chemistry and application properties of polymethacrylate systems. In Aqueous polymeric coatings for pharmaceutical dosage forms, 3 d ed.; McGinity, J. W.; Felton, L. A., Eds.; Informa Healthcare: New York, 2008; pp 237-279.
3. Siepmann, F.; Siepmann, J.; Walther, M.; MacRae, R. J.; Bodmeier, R. Polymer blends for controlled release coatings J. Controlled Release 2008, 125, 1-15
4. Gallardo, D.; Skalsky, B.; Kleinebudde, P. Controlled release solid dosage forms using combinations of (meth)acrylate copolymer Pharm. Dev. Technol. 2008, 13 (5) 413-423
5. Mustafin (Moustafine), R. I. Interpolymer combinations of chemically complementary grades of Eudragit copolymers: A new direction in the design of peroral solid dosage forms of drug delivery systems with controlled release (review) Pharm. Chem. J. 2011, 45 (5) 285-295
6. Zezin, A. B.; Rogacheva, V. B. Polyelectrolyte complexes. In Achievements of the Physics and Chemistry of Polymers (in Russian); Khimiya: Moscow, Russia, 1973; pp 3-30.
7. Tsuchida, E. Formation of polyelectrolyte complexes and their structures J. Macromol. Sci. Pure Appl. Chem. 1994, A31, 1-15
8. Thünemann, A. F.; Müller, M.; Dautzenberg, H.; Joanny, J.-F.; Löwen, H. Polyelectrolyte complexes Adv. Polym. Sci. 2004, 166, 113-171
9. Moustafine, R. I.; Zaharov, I. M.; Kemenova, V. A. Physicochemical characterization and drug release properties of Eudragit E PO/Eudragit L100-55 interpolyelectrolyte complexes Eur. J. Pharm. Biopharm. 2006, 63 (1) 26-36
10. Kemenova, V. A.; Moustafine, R. I.; Alekseyev, K. V.; Scorodinskaya, A. M.; Zezin, A. B.; Tenchova, A. I.; Kabanov, V. A. Applying interpolymer complexes in pharmacy Pharmacya 1991, 60 (1) 67-72
11. Hartig, M. S.; Greene, R. R.; Dikov, M. M.; Prokop, A.; Davidson, J. M. Multifunctional nanoparticulate polyelectrolyte complexes Pharm. Res. 2007, 24 (12) 2353-2369
12. Khutoryanskiy, V. V. Hydrogen-bounded interpolymer complexes as materials for pharmaceutical applications Int. J. Pharmaceutics 2007, 334, 15-26
13. Khutoryanskiy, V. V. Pharmaceutical applications of interpolymer complexes. In Hydrogen-bonded interpolymer complexes. Formation, structure and applications; Khutoryanskiy, V. V.; Staikos, G., Eds.; World Scientific Publishing Co. Pte. Ltd.: Singapore, 2009; pp 235-258.
14. Lankalapalli, S.; Kolapalli, V. R. M. Polyelectrolyte complexes: A review of their applicability in drug delivery technology Ind. J. Pharm. Sci. 2009, 71, 481-487
15. Sauer, D.; McGinity, J. W. Properties of theophylline tablets dry powder coated with Eudragit E PO and Eudragit L 100-55 Pharm. Dev. Technol. 2009, 16 (6) 632-641
16. Obeidat, W. M.; Abu Znait, A. H.; Sallam, A. A. Novel combination of anionic and cationic polymethacrylate polymers for sustained release tablet preparation Drug Dev. Ind. Pharm. 2008, 34 (6) 650-660
17. Obeidat, W. M.; Abu Znait, A. H.; Sallam, A. A. Sustained release tablets containing soluble polymethacrylates: Comparison with tableted polymethacrylate IPEC polymers AAPS PharmSciTech 2010, 11 (1) 54-63
18. Bani-Jaber, A. H.; Alkawareek, M. J.; Al-Gousous, J. J.; Abu Helwa, A. Y. Floating and sustained-release characteristics of efferverscent tablets prepared with a mixed matrix of Eudragit L-100-55 and Eudragit E PO Chem. Pharm. Bull. 2011, 59 (2) 155-160
19. Mustafin (Moustafine), R. I.; Kabanova, T. V. Synthesis and characterization of an interpolyelectrolyte complex based on Eudragit E100 and L100 copolymers Pharm. Chem. J. 2004, 38 (11) 625-627
20. Mustafin (Moustafine), R. I.; Kabanova, T. V. Diffusion transport properties of polymeric complex matrix systems based on Eudragit E100 and L100 copolymers Pharm. Chem. J. 2005, 39 (2) 89-93
21. Moustafine, R. I.; Kabanova, T. V.; Kemenova, V. A.; Van den Mooter, G. Characteristics of interpolyelectrolyte complexes of Eudragit E100 with Eudragit L100 J. Controlled Release 2005, 103, 191-198
22. Moustafine, R. I.; Bobyleva, O. L. Design of new polymer carriers based of Eudragit EPO/Eudragit L100-55 interpolyelectrolyte complexes using swelliability measurements J. Controlled Release 2006, 116 (2) e35-e36
23. Mustafin (Moustafine), R. I.; Bobyleva, O. L.; Bobyleva, V. L.; Van den Mooter, G.; Kemenova, V. A. Potential carriers for controlled drugs delivery based on interpolyelectrolyte complexes using Eudragit types EPO and L100-55. I. Synthesis and comparative physicochemical evaluation Pharm. Chem. J. 2010, 44 (6) 319-323
24. Mustafin (Moustafine), R. I.; Bobyleva, V. L.; Kemenova, V. A. Potential carriers for controlled drugs delivery based on Eudragit EPO/L100-55 interpolyelectrolyte complexes. 2. Comparative evaluation of diffusion transport properties Pharm. Chem. J. 2010, 44 (7) 391-395
25. Moustafine, R. I.; Bobyleva, V. L.; Bukhovets, A. V.; Garipova, V. R.; Kabanova, T. V.; Kemenova, V. A.; Van den Mooter, G. Structural transformations during swelling of polycomplex matrices based on countercharged (meth)acrylate copolymers (Eudragit E PO/Eudragit L 100-55) J. Pharm. Sci. 2011, 100 (3) 874-885
26. Mustafin (Moustafine), R. I.; Bukhovets, A. V.; Sitenkov, A. Yu.; Garipova, V. R.; Kemenova, V. A.; Rombaut, P.; Van den Mooter, G. Synthesis and characterization of a new carrier based on Eudragit EPO/S100 interpolyelectrolyte complex for controlled colon-specific drug delivery Pharm. Chem. J. 2011, 45 (9) 568-574
27. Menjoge, A. R.; Kulkarni, M. G. Mechanistic investigations of phase behavior in Eudragit E blends Int. J. Pharmaceutics 2007, 343, 106-121
28. Gallardo, D.; Skalsky, B.; Kleinebudde, P. Characterization of combinations between anionic-cationic poly(methyl methacrylate) copolymers Pharm. Ind. 2011, 73 (10) 1875-1884
29. Kabanova, T. V.; Zdanova, E. R.; Moustafine, R. I. Characterization of Eudragit E 100/Carbomer 940P interpolyelectrolyte complexes using swellability measurements J. Controlled Release 2006, 116 (2) e33-e35
30. Mustafin (Moustafine), R. I.; Kabanova, T. V.; Zhdanova, E. R.; Bukhovets, A. V.; Garipova, V. R.; Nasibullin, Sh. F.; Kemenova, V. A. Synthesis and physicochemical evaluation of a new carrier based on an interpolyelectrolyte complex formed by Eudragit EPO and Carbomer 940 Pharm. Chem. J. 2010, 44 (5) 271-273
31. Mustafin (Moustafine), R. I.; Kabanova, T. V.; Zhdanova, E. R.; Bukhovets, A. V.; Garipova, V. R.; Nasibullin, Sh. F.; Kemenova, V. A. Diffusion-transport properties of a polycomplex matrix system based on Eudragit EPO and Carbomer 940 Pharm. Chem. J. 2010, 44 (3) 147-150
32. Mustafin (Moustafine), R. I.; Kabanova, T. V.; Semina, I. I.; Bukhovets, A. V.; Garipova, V. R.; Shilovskaya, E. V.; Nasibullin, Sh. F.; Sitenkov, A. Yu.; Kazakova, R. R.; Kemenova, V. A. Biopharmaceutical assessment of a polycomplex matrix system based on Carbomer 940 and Eudragit EPO for colon-specific drug delivery Pharm. Chem. J. 2011, 45 (8) 491-494
33. Quinteros, D. A.; Manzo, R. H.; Allemandi, D. A. Design of a colonic delivery system based on cationic polymethacrylate (Eudragit E100)-mesalamine complexes Drug Del. 2011, 17 (4) 208-213
34. Quinteros, D. A.; Manzo, R. H.; Allemandi, D. A. Interaction between Eudragit E100 and anionic drugs: Addition of anionic polyelectrolytes and their influence on drug release performance J. Pharm. Sci. 2011, 100 (11) 4664-4673
35. Moustafine, R. I.; Kemenova, V. A.; Van den Mooter, G. Characteristics of interpolyelectrolyte complexes of Eudragit E100 with sodium alginate Int. J. Pharmaceutics 2005, 294, 113-120
36. Moustafine, R. I.; Salachova, A. R.; Frolova, E. S.; Kemenova, V. A.; Van den Mooter, G. Interpolyelectrolyte complexes of Eudragit EPO with sodium alginate as potential carriers for colonic drug delivery: monitoring of structural transformation and composition changes during swellability and release evaluating Drug Dev. Ind. Pharm. 2009, 35 (12) 1439-1451
37. Sonavane, G. S.; Devarajan, P. V. Preparation of alginate nanoparticles using Eudragit E100 as a new complexing agent: Development, in vitro, and in vivo evaluation J. Biomed. Nanotechnol. 2007, 3 (2) 160-169
38. Prado, H. J.; Matulewicz, M. C.; Bonelli, P.; Cukierman, A. L. Preparation and characterization of controlled release matrices based on novel seaweed interpolyelectrolyte complexes Int. J. Pharmaceutics 2012, 429, 12-21
39. Prado, H. J.; Matulewicz, M. C.; Bonelli, P.; Cukierman, A. L. Basic butylated methacrylate copolymer/kappa-carrageenan interpolyelectrolyte complex: Preparation, characterization and drug release behavior Eur. J. Pharm. Biopharm. 2008, 70 (1) 171-178
40. Bani-Jaber, A. H.; Al-Aani, L.; Alkhatib, H.; Al-Khalidi, B. Prolonged intragastric drug delivery mediated by Eudragit E-carrageenan polyelectrolyte matrix tablets AAPS PharmSciTech 2011, 12 (1) 354-361
41. Farag, Y.; Leopold, C. S. Development of shellac-coated sustained release pellet formulations Eur. J. Pharm. Sci. 2011, 42, 400-405
42. Ausar, S. F.; Bianco, I. D.; Castagna, L. F.; Alansino, R. V.; Beltramo, D. M. Interaction of a cationic acrylate polymer with caseins: Biphasic effect of Eudragit 100 on the stability of casein micelles J. Agric. Food Chem. 2003, 51, 4417-4423
43. Lorenzo-Lamoza, M. L.; Remuňán-Lopez, C.; Vila-Jato, J. L.; Alonso, M. J. Design of microencapsulated chitosan microspheres for colonic drug delivery J. Controlled Release 1998, 52, 109-118
44. Mustafin (Moustafine), R. I.; Protasova, A. A.; Van den Mooter, G.; Kemenova, V. A. Diffusion transport in interpolyelectrolyte matrix systems based on chitosan and Eudragit L100 Pharm. Chem. J. 2005, 39 (12) 663-666
45. Mustafin (Moustafine), R. I.; Protasova, A. A.; Van den Mooter, G.; Kemenova, V. A. Modification of chitosan by inclusion into interpolyelectrolyte complex with Eudragit L Pharm. Chem. J. 2006, 40 (6) 325-328
46. Moustafine, R. I.; Margulis, E. B.; Sibgatullina, L. F.; Kemenova, V. A.; Van den Mooter, G. Comparative evaluation of interpolyelectrolyte complexes of chitosan with Eudragit L100 and Eudragit L100-55 for oral controlled drug delivery Eur. J. Pharm. Biopharm. 2008, 70 (1) 215-225
47. Li, M. G.; Lu, W. L.; Wang, J. C.; Zhang, X.; Zhang, H.; Wang, X. Q.; Wu, C. S.; Zhang, Q. Preparation and characterization of insulin nanoparticles employing chitosan and poly(methylmethacrylate/methylmethacrylic acid) copolymer J. Nanosci. Nanotechnol. 2006, 6, 2874-2886
48. Jelvehgari, M.; Zakeri-Milani, P.; Siahi-Shadbad, M. R.; Loveymi, B. D.; Nokhodchi, A.; Azari, Z.; Valizadeh, H. Development of pH-sensitive insulin nanoparticles using Eudragit L100-55 and chitosan with different molecular weights AAPS PharmSciTech 2010, 11, 1237-1242
49. Palena, M. C.; Manzo, R. H.; Jimenez-Kalruz, A. F. Self-organized nanoparticles based on drug-interpolyelectrolyte complexes as drug carries J. Nanopart. Res. 2012, 14, 867-878
50. Alhnan, M. A.; Basit, A. W. Engineering polymer blend microparticles: An investigation into the influence of polymer blend distribution and interaction Eur. J. Pharm. Sci. 2011, 42, 30-36
51. Lamprecht, A.; Yamamoto, H.; Takeuchi, H.; Kawachima, Y. Microsphere design for colonic delivery of 5-fluorouracil J. Controlled Release 2003, 90, 313-322
52. Ali Said, A. E.-H. Radiation synthesis of interpolymer polyelectrolyte complex and its application as a carrier for colon-specific drug delivery system Biomaterials 2005, 26 (15) 2733-2739
53. Zhang, Y.; Hu, L.; Min, Y.; Zhai, M.; Wang, J.; Ha, H. Radiation synthesis of poly[(dimethylaminoethyl methacrylate)- co -(diallyl dimethyl ammonium chloride)] hydrogels and its application as a carrier for notoginsenoside delivery Eur. Polym. J. 2006, 42 (11) 2959-2967
54. ® E prepared by hot-melt extrusion using thermal, microthermal and spectroscopic analysis Int. J. Pharmaceutics 2008, 354, 158-167
55. Albers, J.; Alles, R.; Matthée, K.; Knop, K.; Nahrup, J. S.; Kleinebudde, P. Mechanism of drug release from polymethacrylate-based extrudates and milled strands prepared by hot-melt extrusion Eur. J. Pharm. Biopharm. 2009, 71 (2) 387-394
56. Kwei, T. K.; Pearce, E. M.; Pennacchia, J. R. Correlation between the glass transition temperatures of polymer mixtures and intermolecular force parameters Macromolecules 1987, 20 (4) 1174-1176
57. Gordon, S.; Taylor, J. S. Ideal copolymers and the second-order transitions of synthetic rubbers. I. Non-crystalline copolymers J. Appl. Chem. 1952, 2, 493-500
58. Simha, R.; Boyer, R. F. On a general relation involving the glass temperatures and coefficient of expansion of polymers J. Chem. Phys. 1962, 37, 1003-1017
59. Gao, C.; Liu, M.; Chen, J.; Chen, C. Physicochemical characterization and drug release properties of PDMAEMA/OSA semi-IPN hydrogels with microporous structure Polym. Adv. Technol. 2012, 23, 389-297
60. Luo, X.; Goh, S. H.; Lee, S. Y.; Tan, K. L. Interpolymer complexation between poly(N -methyl-4-piperidinyl methacrylate) and acidic polymers Macromolecules 1998, 31, 3251-3254
61. Huang, X.-D.; Goh, S. H.; Lee, S. Y.; Zhao, Z. D.; Wong, M. W. Miscibility and interactions in blends and complexes of poly[2-(dimethylamino) ethyl methacrylate] with poly(p -vinylphenol) Macromolecules 1999, 32, 4327-4331
62. Hadj-Hamou, A. S.; Djadoun, S. Interpolymer-specific interactions and miscibility in poly(styrene- co -acrylic acid)/poly(styrene- co-N, N -dimethylacrylamide) blends J. Appl. Polym. Sci. 2007, 103, 1011-1024
63. Hadj-Hamou, A. S.; Djadoun, S. Interpolymer interactions and miscibility in poly (n -butyl methacrylate- co -methacrylic acid)/poly(styrene- co-N, N -dimethyl acrylamide) blends J. Appl. Polym. Sci. 2006, 102, 2717-2724
64. Abdellaoui, N.; Djadoun, S. Miscibility and complexation behavior in poly(ethyl methacrylate)/poly(styrene- co -methacrylic acid), poly[2-(N, N -dimethylamino) ethyl methacrylate]/poly(styrene- co -methacrylic acid), and poly{styrene- co -[2-(N, N -dimethyl amino) ethyl methacrylate]}/poly(styrene- co -methacrylic acid) systems J. Appl. Polym. Sci. 2005, 98, 658-664
65. Abdellaoui-Arous, N.; Djadoun, S. Poly[2-(N, N -dimethylamino) ethyl methacrylate]/poly(styrene- co -methacrylic acid) interpolymer complexes Macromol. Symp. 2011, 303, 123-133
66. Zhang, G.; Jiang, M.; Zhu, L.; Wu, C. Intermacromolecular complexation because of specific interactions 11. Ionic interaction complexation and its comparison with hydrogen-bonding complexation Polymer 2001, 42 (1) 151-159
67. Feldstein, M. M.; Kiseleva, T. I.; Bondarenko, G. N.; Kostina, J. V.; Singh, P.; Cleary, G. W. Mechanisms of molecular interactions in polybase-polyacid complex formed by copolymers of N,N - dimethylaminoethylmethacrylate with alkylmethacrylates and methacrylic acid with ethylacrylate J. Appl. Polym. Sci. 2009, 112 (3) 1142-1165
68. Korsmeyer, R. W.; Gurny, R.; Docler, E.; Buri, P.; Peppas, N. A. Mechanisms of solute release from porous hydrophilic polymers Int. J. Pharmaceutics 1983, 15, 25-35
69. Takayama, K.; Hirata, M.; Machida, Y.; Masada, T.; Sannan, T.; Nagai, T. Effect of interpolymer complex formation on bioadhesive property and drug release phenomenon of compressed tablet consisting of chitosan and sodium hyaloronate Chem. Pharm. Bull. 1990, 38 (7) 1993-1997