Novel pH-sensitive hydrogels with adjustable swelling kinetics

Biomaterials

Volumn 19, Issue 11-12, 1998, Pages 1037-1047

  Akala, Emmanuel O ^a   Kopečková, Pavla ^a   Kopeček, Jindřich ^a  

^a UNIVERSITY OF UTAH   (United States)

Author keywords

Biodegradble hydrogels; Hydrolysis; N,O diacylhydroxylamine; Swelling kinetics

Indexed keywords

AMINES; BIODEGRADATION; BIOSYNTHESIS; COMPOSITION EFFECTS; COPOLYMERIZATION; CROSSLINKING; HYDROGELS; HYDROLYSIS; MOLECULAR STRUCTURE; PH EFFECTS; REACTION KINETICS; SWELLING;

HYDROPHOBICITY;

BIOMATERIALS;

ACRYLIC ACID; ALKYL GROUP; COPOLYMER; CROSS LINKING REAGENT; HYDROXYLAMINE; POLYACRYLAMIDE; POLYMER;

ARTICLE; BIODEGRADATION; BIOPHYSICS; CHEMICAL REACTION KINETICS; ENZYME DEGRADATION; HYDROGEL; HYDROLYSIS; KINETICS; PH; POLYMERIZATION; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SYNTHESIS;

ACRYLAMIDES; ACRYLATES; AZO COMPOUNDS; BIOCOMPATIBLE MATERIALS; HYDROGELS; HYDROGEN-ION CONCENTRATION; KINETICS; METHACRYLATES; MOLECULAR WEIGHT;

EID: 0032103486     PISSN: 01429612     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0142-9612(98)00023-4     Document Type: Article

References (39)

1. [1] Friend DR, editor. Oral colon-specific drug delivery. Boca Raton, FL: CRC Press, 1992.
2. [2] Ikesue K, Kopečková P, Kopeček J. Degradation of proteins by guinea pig intestinal enzymes. Int J Pharm 1993:95:171-9.
3. [3] MacFarlane GT, Cummings JH, Allison C. Protein degradation by human intestinal bacteria. J Gen Microbiol 1986:132:1647-56.
4. [4] Lee VHL, Yamamoto A. Penetration and enzymatic barrier to peptide and protein absorption. Adv Drug Del Rev 1990; 4:171-207.
5. [5] Mrsny RJ. The colon as a site of drug delivery. J Control Rel 1992;22:15-34.
6. [6] Rubinstein A. Approaches and opportunities in colon-specific drug delivery. Crit Rev Ther Drug Carrier Syst 1995;12:101-49.
7. [7] Woodley JF. Enzymatic barriers for GI peptide and protein delivery. Crit Rev Ther Drug Carrier Syst 1994;11:61-95.
8. [8] Saffran M, Kumar GS, Savarier C, Burnham JC, Williams F, Neckers DC. A new approach to the oral administration of insulin and other peptide drugs. Science 1986;233:1081-4.
9. [9] Přádný M, Kopeček J. Hydrogels for site-specific oral delivery. Poly(acrylic acid-co-butyl acrylate) cross-linked with 4,4′-bis(methacryloylamino)azobenzene. Makromol Chem 1990; 191:1887-97.
10. [10] Brøndsted H, Kopeček J. Hydrogels for site-specific oral drug delivery: synthesis and characterization. Biomaterials 1991; 12:584-92.
11. [11] Yeh PY, Kopečková P, Kopeček J. Biodegradable and pH-sensitive hydrogels: synthesis by cross-linking of N,N-dimethylacrylamide copolymer precursors. J Polym Sci: Part A: Polym Chem 1994;32:1627-37.
12. [12] Yeh P-Y, Kopečková P, Kopeček J. Degradability of hydrogels containing azoaromatic cross-links. Macromol Chem Phys 1995;196:2183-202.
13. [13] Yeh P-Y, Berenson MM, Samowitz WS, Kopečková P, Kopeček, J. Site-specific drug delivery and penetration enhancement in the gastrointestinal tract. J Control Rel 1995;36:109-24.
14. [14] Ghandehari H, Kopečková P, Yeh P-Y, Kopeček J. Biodegradable and pH sensitive hydrogels: synthesis by a polymer-polymer reaction. Macromol Chem Phys 1996;197:965-80.
15. [15] Ghandehari H, Kopečková P, Kopeček J. In vitro degradation of pH sensitive hydrogels containing aromatic azo bonds. Biomaterials 1997,18:861-72.
16. [16] Ulbrich K, Strohalm J, Kopeček J. Polymers containing enzymatically degradable bonds. 6. Hydrophilic gels cleavable by chymotrypsin. Biomaterials 1982;3:150-4.
17. [17] Šubr V, Duncan R, Kopeček J. Release of macromolecules and daunomycin from hydrophilic gels containing enzymatically degradable bonds. J Biomater Sci Polym Ed 1990;4:261-78.
18. [18] Ulbrich K, Šubr V, Seymour LW, Duncan R. Novel biodegradable hydrogels prepared using divinylic cross-linking agent N,O-dimethacryloylhydroxylamine. 1. Synthesis and characterization of rates of gel degradation and rate of release of model drugs in vitro and in vivo. J Control Rel 1993;24:181-90.
19. [19] Ulbrich K, Šubr V, Podpěrová P, Burešová M. Synthesis of novel hydrolytically degradable hydrogels for controlled drug release. J Control Rel 1995;34:155-65.
20. [20] Yale HL. The hydroxamic acids. Chem Rev 1943;33:209-56.
21. [21] Bauer L, Exner O. The chemistry of hydroxamic acids and N-hydroxyimides. Angew Chem Internatl Edit 1974;13:376-84.
22. [22] Fishbein WN, Daly J, Streeter CL. Preparation and some properties of stable and carbon-14 and tritium-labeled short-chain aliphatic hydroxamic acids. Anal Biochem 1969;28:13-24.
23. [23] Kimura Y, Makita Y, Kumagai T, Yamane H, Kitao T, Sasatani, H, Kim SI. Degradation of azo-containing polyurethane by the action of intestinal flora: its mechanism and application as a drug delivery system. Polymer 1992;33:5294-9.
24. [24] Van den Mooter G, Samyn C, Kinget R. Azo polymers for colon-specific delivery. Int J Pharmaceutics 1992;87:37-46.
25. [25] Cheng C-L, Gehrke SH, Ritschel WA. Development of an azopolymer based colonic release capsule for delivering proteins/ macromolecules. Meth Find Exp Clin Pharmacol 1994;16:271-8.
26. [26] Bragger J, Lloyd AW, Marriott C, Bloomfield SF, Martin GP, Phillips J. Bacterial cleavage of novel azo polymer cross-linking compounds to free amines. J Pharm Pharmacol 1995;47(12B): 1122.
27. [27] Hovgaard L, Brøndsted H. Current applications of polysaccharides in colon targeting. Crit Rev Ther Drug Carrier Syst 1996;13:185-223.
28. [28] Rubinstein A, Friend DR. Specific delivery to the gastrointestinal tract. In: Domb AJ, editor. Polymeric site-specific pharmacotherapy. Chichester: Wiley, 1994:267-313.
29. [29] Brøndsted H, Kopeček J. pH-sensitive hydrogels: characteristics and potential in drug delivery. In: Harland R, Prudhomme R, editors. Polyelectrolyte gels. ACS Symp Series 480, 1992: 285-304.
30. [30] Peppas NA, Khare AR. Preparation, structure and diffusional behavior of hydrogels in controlled release. Adv Drug Del Rev 1993;11:1-33.
31. [31] Khare AR, Peppas NA. Swelling/deswelling of anionic copolymer gels. Biomaterials 1995;16:550-69.
32. [32] Kopeček J, Jokl J, Lím D. Mechanism of three-dimensional polymerization of glycol methacrylates. J Polym Sci 1968;C16: 3877-89 (in German).
33. [33] Kopeček J, Lím D. Mechanism of three-dimensional polymerization of glycol methacrylates. II. The system glycol monomethacrylate-glycol dimethacrylates-solvents. J Polym Sci A-1 1971;9:2801-15.
34. [34] Kou JH, Amidon GL, Lee PI. pH-dependent swelling and solute diffusion characteristics of poly(hydroxyethylmethacrylate-comethacrylic acid) hydrogels. Pharm Res 1988;5:592-7.
35. [35] Ilavský M, Dušek K, Vacík J, Kopeček J. Deformational, swelling and potentiometric behavior of ionized gels of 2-hydroxyethyl methacrylate-methacrylic acid copolymers. J Appl Polym Sci 1979;23:2073-82.
36. [36] Firestone BA, Siegel RA. Dynamic pH-dependent swelling properties of a hydrophobic polyelectrolyte gel. Polym Commun 1988;29:204-8.
37. [37] Schott H. Kinetics of swelling of polymers and gels. J Pharm Sci 1992;81:467-70.
38. [38] Hörpel D, Klesse W, Ringsdorf H, Schmidt B. Micellforming co-and blockcopolymers for sustained drug release. Proc. IUPAC Int. Symp. on Macromolecules. Amherst, MA, 1982:346.
39. [39] Morawetz H, Westhead EW. Acid-base catalysis in polyelectrolyte solutions. J Polym Sci 1955;16:273-81.