Enhancing therapeutic loading and delaying transport via molecular imprinting and living/controlled polymerization

AIChE Journal

Volumn 56, Issue 1, 2010, Pages 268-279

  Vaughan, Asa D ^a   Zhang, Jeney B ^a   Byrne, Mark E ^a  

^a AUBURN UNIVERSITY   (United States)

Author keywords

Anti inflammatory hydrogels; Controlled drug delivery; Iniferter; Living controlled polymerization; Molecular imprinting

Indexed keywords

ANTI-INFLAMMATORIES; CHAIN PROPAGATION; CONVENTIONAL FREE-RADICAL POLYMERIZATION; EXPERIMENTAL EVIDENCE; INIFERTERS; LIVING/CONTROLLED POLYMERIZATIONS; MOLECULAR IMPRINTING; ZERO-ORDER RELEASE;

BINDING ENERGY; BIOSYNTHESIS; CONTROLLED DRUG DELIVERY; DIFFUSION; FREE RADICAL POLYMERIZATION; GELS; REACTION KINETICS;

MOLECULAR MODELING;

EID: 77952739874     PISSN: 00011541     EISSN: 15475905     Source Type: Journal    
DOI: 10.1002/aic.11949     Document Type: Article

References (66)

1. Peppas NA, Bar-Howell BD. Hydrogels in Medicine and Phamacy, Vol. 1. Boca Raton: CRC Press, 1987.
2. Venkatesh S, Saha J, Pass S, Byrne ME. Transport and structural analysis of molecular imprinted hydrogels for controlled drug delivery. Eur J Pharm Biopharm. 2008; 69: 852-860.
3. Venkatesh S, Sizemore SP, Byrne ME. Biomimetic hydrogels for enhanced loading and extended release of ocular therapeutics. Biomaterials. 2007; 28: 717-724.
4. Ali M, Horikawa S, Venkatesh S, Saha J, Hong JW, Byrne ME. Zero-order therapeutic release from imprinted hydrogel contact lenses within in vitro physiological ocular tear flow. J Controlled Release. 2007; 124: 154-162.
5. Alvarez-Lorenzo C, Hiratani H, Gomez-Amoza JL, Martinez-Pacheco R, Souto C, Concheiro A. Soft contact lenses capable of sustained delivery of timolol. J Pharm Sci. 2002; 91: 2182-2192.
6. Alvarez-Lorenzo C, Yanez F, Barreiro-Iglesias R, Concheiro A. Imprinted soft contact lenses as norfloxacin delivery systems. J Controlled Release. 2006; 113: 236-244.
7. Hiratani H, Fujiwara A, Tamiya Y, Mizutani Y, Alvarez-Lorenzo C. Ocular release of timolol from molecularly imprinted soft contact lenses. Biomaterials. 2005; 26: 1293-1298.
8. Ali M, Byrne ME. Controlled release of high molecular weight hyaluronic acid from molecularly imprinted hydrogel contact lenses. Pharm Res. 2009; 26: 714-726.
9. Byrne ME, Salian V. Molecular imprinting within hydrogels. II. Progress and analysis of the field. Int J Pharm. 2008; 364: 188-212.
10. Otsu T, Yoshida M. Role of initiator-transfer agent-terminator (iniferter) in radical polymerizations: polymer design by organic disulfides as iniferters. Makromol Chem Rapid Commun. 1982; 3: 127-132.
11. Matyjaszewski K. A commentary on "role of initiator-transfer agent-terminator (Iniferter) in radical polymerizations: polymer design by organic disulfides as iniferters" by T. Otsu, M. Yoshida (Macromol. Rapid Commun. 1982, 3, 127-132). Macromol Rapid Commun. 2005; 26: 135-142.
12. Haddleton DM, Kukulj D, Duncalf DJ, Heming AM, Shooter AJ. Low-temperature living "radical" polymerization (atom transfer polymerization) of methyl methacrylate mediated by copper(I) N-alkyl-2-pyridylmethanimine complexes. Macromolecules. 1998; 31: 5201-5205.
13. Endo K, Murata K, Otsu T. Living radical polymerization of styrene with tetramethylene disulfide. Macromolecules. 1992; 25: 5554-5556.
14. Ward JH, Peppas NA. Kinetic gelation modeling of controlled radical polymerizations. Macromolecules. 2000; 33: 5137-5142.
15. Matyjaszewski K, Jo SM, Paik HJ, Gaynor SG. Synthesis of well-defined polyacrylonitrile by atom transfer radical polymerization. Macromolecules. 1997; 30: 6398-6400.
16. High K, Meng Y, Washabaugh MW, Zhao Q. Determination of picomolar equilibrium dissociation constants in solution by enzyme-linked immunosorbent assay with fluorescence detection. Anal Biochem. 2005; 347: 159-161.
17. Qin DQ, Qin SH, Qiu KY. A reverse ATRP process with a hexasubstituted ethane thermal iniferter diethyl 2, 3-dicyano-2, 3-di(p-tolyl)succinate as the initiator. Macromolecules. 2000; 33: 6987-6992.
18. Qin L, He X-W, Li W-Y, Zhang Y-K. Molecularly imprinted polymer prepared with bonded β-cyclodextrin and acrylamide on functionalized silica gel for selective recognition of tryptophan in aqueous media. J Chromatogr A. 2008; 1187: 94-102.
19. Baek SH, Kim BS, Kim BK. Hydrogels based on polyurethane-polyacrylic acid multiblock copolymers via macroiniferter technique. Prog Org Coat. 2004; 49: 353-357.
20. Chen H, Peng C, Ye Z, Liu H, Hu Y, Jiang J. Recognition of multiblock copolymers on nanopatterned surfaces: insight from molecular simulations. Langmuir. 2007; 23: 2430-2436.
21. Cheng Z, Zhu X, Fu GD, Kang ET, Neoh KG. Dual-brush-type amphiphilic triblock copolymer with intact epoxide functional groups from consecutive RAFT polymerizations and ATRP. Macromolecules. 2005; 38: 7187-7192.
22. Gabashvili A, Medina DD, Gedanken A, Mastai Y. Templating mesoporous silica with chiral block copolymers and its application for enantioselective separation. J Phys Chem B. 2007; 111: 11105-11110.
23. Kwon IK, Matsuda T. Photo-iniferter-based thermoresponsive block copolymers composed of poly(ethylene glycol) and poly(N-isopropylacrylamide) and chondrocyte immobilization. Biomaterials. 2006; 27: 986-995.
24. Qin Y, Sukul V, Pagakos D, Cui C, Jakle F. Preparation of organoboron block copolymers via ATRP of silicon and boron-functionalized monomers. Macromolecules. 2005; 38: 8987-8990.
25. de Boer B, Simon HK, Werts MPL, van der Vegte EW, Hadziioannou G. "Living" free radical photopolymerization initiated from surface-grafted iniferter monolayers. Macromolecules. 2000; 33: 349-356.
26. Francis R, Ajayaghosh A. Minimization of homopolymer formation and control of dispersity in free radical induced graft polymerization using xanthate derived macro-photoinitiators. Macromolecules. 2000; 33: 4699-4704.
27. Lee HJ, Nakayama Y, Matsuda T. Spatio-resolved, macromolecular architectural surface: highly branched graft polymer via photochemically driven quasiliving polymerization technique. Macromolecules. 1999; 32: 6989-6995.
28. Liu P, Liu Y, Su Z. Modification of poly(hydroethyl acrylate)-grafted cross-linked poly(vinyl chloride) particles via surface-initiated atom-transfer radical polymerization (SI-ATRP). Competitive adsorption of some heavy metal ions on modified polymers. Ind Eng Chem Res. 2006; 45: 2255-2260.
29. Matsuda T, Ohya S. Photoiniferter-based thermoresponsive graft architecture with albumin covalently fixed at growing graft chain end. Langmuir. 2005; 21: 9660-9665.
30. Nakayama Y, Sudo M, Uchida K, Matsuda T. Spatio-resolved hyperbranched graft polymerized surfaces by iniferter-based photograft copolymerization. Langmuir. 2002; 18: 2601-2606.
31. Hutchison JB, Lindquist AS, Anseth KS. Experimental characterization of structural features during radical chain homopolymerization of multifunctional monomers prior to macroscopic gelation. Macromolecules. 2004; 37: 3823-3831.
32. Kannurpatti AR, Anderson KJ, Anseth JW, Bowman CN. Use of "living" radical polymerizations to study the structural evolution and properties of highly crosslinked polymer networks. J Polym Sci Part B: Polym Phys. 1997; 35: 2297-2307.
33. Smith D, Pentzer EB, Nguyen ST. Bioactive and therapeutic ROMP polymers. Polym Rev. 2007; 47: 419-459.
34. Ding S, Xing Y, Radosz M, Shen Y. Magnetic nanoparticle supported catalyst for atom transfer radical polymerization. Macromolecules. 2006; 39: 6399-6405.
35. Yang J, Ding S, Radosz M, Shen Y. Reversible catalyst supporting via hydrogen-bonding-mediated self-assembly for atom transfer radical polymerization of MMA. Macromolecules. 2004; 37: 1728-1734.
36. Chen XP, Qiu KY. Synthesis of well-defined poly(methyl methacrylate) by radical polymerization with a new initiation system TPED/FeCl3/PPh3. Macromolecules. 1999; 32: 8711-8715.
37. Sugihara Y, Kagawa Y, Yamago S, Okubo M. Organotellurium-mediated living radical polymerization in miniemulsion. Macromolecules. 2007; 40: 9208-9211.
38. Hawker CJ, Bosman AW, Harth E. New polymer synthesis by nitroxide mediated living radical polymerizations. Chem Rev. 2001; 101: 3661-3688.
39. Kannurpatti AR, Lu S, Bunker GM, Bowman CN. Kinetic and mechanistic studies of iniferter photopolymerizations. Macromolecules. 1996; 29: 7310-7315.
40. Vaughan AD, Byrne ME. Optimizing recognition characteristics of biomimetic polymer gels via polymerization reaction and crosslinking density analysis. ACS PMSE Preprints. 2006; 94: 762-763.
41. Boonpangrak S, Whitcombe MJ, Prachayasittikul V, Mosbach K, Yei L. Preparation of molecularly imprinted polymers using nitroxide-mediated living radical polymerization. Biosens Bioelectron. 2006; 22: 349-354.
42. Vaughan AD, Sizemore SP, Byrne ME. Enhancing molecularly imprinted polymer binding properties via controlled/living radical polymerization and reaction analysis. Polymer. 2007; 48: 74-81.
43. Rueckert B, Hall AJ, Sellergren B. Molecularly imprinted composite materials via iniferter-modified supports. J Mater Chem. 2002; 12: 2275-2280.
44. Wei X, Li X, Husson SM. Surface molecular imprinting by atom transfer radical polyemrization. Biomacromolecules. 2005; 6: 1113-1121.
45. Hägerström H, Paulsson M, Edsman K. Evaluation of mucoadhesion for two polyelectrolyte gels in simulated physiological conditions using a rheological method. Eur J Pharm Sci. 2000; 9: 301-309.
46. Crank J. The Mathematics of Diffusion. New York: Oxford University Press, 1975.
47. Sperling LH. Introduction to Physical Polymer Science, 4th ed. Hoboken: Wiley, 2005.
48. Flory PJ. Principles of Polymer Chemistry, 1st ed. Ithaca: Cornell University Press, 1953: 663.
49. Brazel CS, Peppas NA. Synthesis and characterization of thermo- and chemomechanically responsive poly(N-isopropylacrylamide-co-methacrylic acid) hydrogels. Macromolecules. 1995; 28: 8016-8020.
50. Kavimandan NJ, Losi E, Peppas NA. Novel delivery system based on complexation hydrogels as delivery vehicles for insulin-transferrin conjugates. Biomaterials. 2006; 27: 3846-3854.
51. Berger J, Reist M, Mayer JM, Felt O, Peppas NA, Gurny R. Structure and interactions in covalently and ionically crosslinked chitosan hydrogels for biomedical applications. Eur J Pharm Biopharm. 2004; 57: 19-34.
52. Hariharan D, Peppas NA. Characterization, dynamic swelling behaviour and solute transport in cationic networks with applications to the development of swelling-controlled release systems. Polymer. 1996; 37: 149-161.
53. Lowman AM, Dziubla TD, Bures P, Peppas NA. Structural and dynamic response of neutral and intelligent networks in biomedical environments. In: NA Peppas and MV Sefton, Eds. Molecular and Cellular Foundations of Biomaterials, Vol. 29. New York: Academic Press, 2004: 75-130.
54. Anseth KS, Kline LM, Walker TA, Anderson KJ, Bowman CN. Reaction kinetics and volume relaxation during polymerizations of multiethylene glycol dimethacrylates. Macromolecules. 1995; 28: 2491-2499.
55. Anseth KS, Wang CM, Bowman CN. Reaction behaviour and kinetic constants for photopolymerizations of multi(meth)acrylate monomers. Polymer. 1994; 35: 3243-3250.
56. Odian G. Principles of Polymerization, 2nd ed. New York: Wiley, 1981.
57. Smith DA, Wallwork ML, Zhang J, Kirkham J, Robinson C, Marsh A, Wong M. The effect of electrolyte concentration on the chemical force titration behavior of ω-functionalized SAMs: evidence for the formation of strong ionic hydrogen bonds. J Phys Chem B. 2000; 104: 8862-8870.
58. Srinivasan R, Feenstra JS, Park ST, Xu S, Zewail AH. Direct determination of hydrogen-bonded structures in resonant and tautomeric reactions using ultrafast electron diffraction. J Am Chem Soc. 2004; 126: 2266-2267.
59. Noss KR, Vaughan AD, Byrne ME. Tailored binding and transport parameters of molecularly imprinted films via macromolecular structure: the rational design of recognitive polymers. J Appl Polym Sci. 2008; 107: 3435-3441.
60. Bell CL, Peppas NA. Water, solute and protein diffusion in physiologically responsive hydrogels of poly(methacrylic acid-g-ethylene glycol). Biomaterials. 1996; 17: 1203-1218.
61. Spizzirri UG, Peppas NA. Structural analysis and diffusional behavior of molecularly imprinted polymer networks for cholesterol recognition. Chem Mater. 2005; 17: 6719-6727.
62. Vega J, Michaelian K, Garzón IL, Beltrán MR, Hernández L. Isomers of adenine. J Mol Struct: THEOCHEM. 1999; 493: 275-285.
63. Maitani Y, Kugo M, Nakagaki M, Nagai T. Ionic size and behavior of diclofenac salts in water and ethanol/water mixtures by conductivity at 25°C. J Pharm Sci. 1993; 82: 1245-1249.
64. Mandal R, Gangopadhyay J, Lahiri SC. Studies on hydrophobic interaction from the conductometric studies of medicinal compounds (as salts). Z Phys Chem. 2005; 219: 795-805.
65. Khudyakov IV, Legg JC, Purvis MB, Overton BJ. Kinetics of photopolymerization of acrylates with functionality of 1-6. Ind Eng Chem Res. 1999; 38: 3353-3359.
66. Sigwalt P, Moreau M. Carbocationic polymerization: mechanisms and kinetics of propagation reactions. Prog Polym Sci. 2006; 31: 44-120.