Water-soluble antioxidant derivative poly(triethylene glycol methyl acrylate-co-α-tocopheryl acrylate) as a potential prodrug to enable localized neuroprotection

Acta Biomaterialia

Volumn 9, Issue 1, 2013, Pages 4558-4568

  Cao, Y ^a   He, W ^a  

^a University of Tennessee Knoxville   (United States)

Author keywords

Antioxidant; Layer by layer; Neural interface; Oxidative stress; Prodrug

Indexed keywords

FREE RADICALS; GLYCOLS; HYDROGEN BONDS; MICROELECTRODES; MULTILAYERS; OXIDATIVE STRESS; PH; SOLUBILITY;

LAYER BY LAYER; LOCALISED; METHYL ACRYLATES; MICROELECTRODES ARRAYS; NEURAL INTERFACES; PRODRUGS; TANNIC ACID; TRIETHYLENE GLYCOL; VITAMIN-E; WATERSOLUBLE;

ANTIOXIDANTS;

ALPHA TOCOPHEROL DERIVATIVE; ANTIOXIDANT; ESTER DERIVATIVE; HYDROGEN; HYDROGEN PEROXIDE; POLY(TRIETHYLENE GLYCOL METHYL ACRYLATE CO ALPHA TOCOPHERYL ACRYLATE); POLYACRYLIC ACID; PRODRUG; SILICON; SILICON DIOXIDE; TANNIN; UNCLASSIFIED DRUG; WATER;

ARTICLE; ASTROCYTE; CRYSTAL STRUCTURE; DRUG SOLUBILITY; ELLIPSOMETRY; HYDROGEN BOND; HYDROLYSIS; IMPLANT; IMPLANTABLE MICROELECTRODE ARRAY; MICROELECTRODE; NEUROPROTECTION; OXIDATIVE STRESS; PH; POLYMERIZATION; PRIORITY JOURNAL;

EID: 84870251962     PISSN: 17427061     EISSN: 18787568     Source Type: Journal    
DOI: 10.1016/j.actbio.2012.08.037     Document Type: Article

References (63)

1. D. Trachootham, W.Q. Lu, M.A. Ogasawara, N.R.D. Valle, and P. Huang Redox regulation of cell survival Antioxid Redox Signal 10 2008 1343 1374
2. E.H. Sarsour, M.G. Kumar, L. Chaudhuri, A.L. Kalen, and P.C. Goswami Redox control of the cell cycle in health and disease Antioxid Redox Signal 11 2009 2985 3011
3. T. Xia, M. Kovochich, J. Brant, M. Hotze, J. Sempf, and T. Oberley Comparison of the abilities of ambient and manufactured nanoparticles to induce cellular toxicity according to an oxidative stress paradigm Nano Lett 6 2006 1794 1807
4. K. Lee, H. Lee, K.W. Lee, and T.G. Park Optical imaging of intracellular reactive oxygen species for the assessment of the cytotoxicity of nanoparticles Biomaterials 32 2011 2556 2565
5. K. Fu, D.W. Pack, A.M. Klibanov, and R. Langer Visual evidence of acidic environment within degrading poly(lactic-co-glycolic acid) (PLGA) microspheres Pharm Res 17 2000 100 106
6. J.M. Anderson, and M.S. Shive Biodegradation and biocompatibility of PLA and PLGA microspheres Adv Drug Del Rev 28 1997 5 24
7. L.R. Hochberg, M.D. Serruya, G.M. Friehs, J.A. Mukand, M. Saleh, and A.H. Caplan Neuronal ensemble control of prosthetic devices by a human with tetraplegia Nature 442 2006 164 171
8. J.K. Chapin, K.A. Moxon, R.S. Markowitz, and M.A.L. Nicolelis Real-time control of a robot arm using simultaneously recorded neurons in the motor cortex Nat Neurosci 2 1999 664 670
9. M.A. Smith, G. Perry, P.L. Richey, L.M. Sayre, V.E. Anderson, and M.F. Beal Oxidative damage in Alzheimer's Nature 382 1996 120 121
10. M.A. Smith, K. Hirai, K. Hsiao, M.A. Pappolla, P.L.R. Harris, and S.L. Siedlak Amyloid-beta deposition in Alzheimer transgenic mice is associated with oxidative stress J Neurochem 70 1998 2212 2215
11. J.N. Turner, W. Shain, D.H. Szarowski, M. Andersen, S. Martins, and M. Isaacson Cerebral astrocyte response to micromachined silicon implants Exp Neurol 156 1999 33 49
12. D.H. Szarowski, M.D. Andersen, S. Retterer, A.J. Spence, M. Isaacson, and H.G. Craighead Brain responses to micro-machined silicon devices Brain Res 983 2003 23 35
13. R. Biran, D.C. Martin, and P.A. Tresco Neuronal cell loss accompanies the brain tissue response to chronically implanted silicon microelectrode arrays Exp Neurol 195 2005 115 126
14. G.C. McConnell, T.M. Schneider, D.J. Owens, and R.V. Bellamkonda Extraction force and cortical tissue reaction of silicon microelectrode arrays implanted in the rat brain IEEE Trans Bio-Med Eng 54 2007 1097 1107
15. C.H.Y. Wong, and P.J. Crack Modulation of neuro-inflammation and vascular response by oxidative stress following cerebral ischemia-reperfusion injury Curr Med Chem 15 2008 1 14
16. A. Hald, and J. Lotharius Oxidative stress and inflammation in Parkinson's disease: is there a causal link? Exp Neurol 193 2005 279 290
17. H.Y. Lin, and J.D. Bumgardner Changes in the surface oxide composition of Co-Cr-Mo implant alloy by macrophage cells and their released reactive chemical species Biomaterials 25 2004 1233 1238
18. T.J. Krause, F.M. Robertson, and R.S. Greco Measurement of intracellular hydrogen-peroxide induced by biomaterials implanted in a rodent air pouch J Biomed Mater Res 27 1993 65 69
19. Y. Cao, and W. He Synthesis and characterization of glucocorticoid functionalized poly(N-vinyl pyrrolidone): a versatile prodrug for neural interface Biomacromolecules 11 2010 1298 1307
20. Y.H. Zhong, and R.V. Bellamkonda Controlled release of anti-inflammatory agent alpha-MSH from neural implants J Control Release 106 2005 309 318
21. Y.H. Zhong, and R.V. Bellamkonda Dexamethasone-coated neural probes elicit attenuated inflammatory response and neuronal loss compared to uncoated neural probes Brain Res 1148 2007 15 27
22. R. Wadhwa, C.F. Lagenaur, and X.T. Cui Electrochemically controlled release of dexamethasone from conducting polymer polypyrrole coated electrode J Control Release 110 2006 531 541
23. D.H. Kim, and D.C. Martin Sustained release of dexamethasone from hydrophilic matrices using PLGA nanoparticles for neural drug delivery Biomaterials 27 2006 3031 3037
24. W. Shain, L. Spataro, J. Dilgen, K. Haverstick, S. Retterer, and M. Isaacson Controlling cellular reactive responses around neural prosthetic devices using peripheral and local intervention strategies IEEE Trans Neural Syst Rehabil Eng 11 2003 186 188
25. B. Drukarch, E. Schepens, J.C. Stoof, C.H. Langeveld, and F.L. Van Muiswinkel Astrocyte-enhanced neuronal survival is mediated by scavenging of extracellular reactive oxygen species Free Radical Biol Med 25 1998 217 220
26. S. Desagher, J. Glowinski, and J. Premont Astrocytes protect neurons from hydrogen peroxide toxicity J Neurosci 16 1996 2553 2562
27. H. Kikuzaki, M. Hisamoto, K. Hirose, K. Akiyama, and H. Taniguchi Antioxidant properties of ferulic acid and its related compounds J Agric Food Chem 50 2002 2161 2168
28. O.I. Aruoma, M. Grootveld, and B. Halliwell The role of iron in ascorbate-dependent deoxyribose degradation - evidence consistent with a site-specific hydroxyl radical generation caused by iron ions bound to the deoxyribose molecule J Inorg Biochem 29 1987 289 299
29. I. Pinchuk, and D. Lichtenberg The mechanism of action of antioxidants against lipoprotein peroxidation, evaluation based on kinetic experiments Prog Lipid Res 41 2002 279 314
30. B. Halliwell Free-radicals and antioxidants - a personal view Nutr Rev 52 1994 253 265
31. E. Graf, and J.W. Eaton Antioxidant functions of phytic acid Free Radical Biol Med 8 1990 61 69
32. S. Muraoka, and T. Miura Inhibition of xanthine oxidase by phytic acid and its antioxidative action Life Sci 74 2004 1691 1700
33. V. Raboy Myo-inositol-1,2,3,4,5,6-hexakisphosphate Phytochemistry 64 2003 1033 1043
34. M.A. Schubert, M.J. Wiggins, K.M. DeFife, A. Hiltner, and J.M. Anderson Vitamin E as an antioxidant for poly(etherurethane urea): in vivo studies J Biomed Mater Res 32 1996 493 504
35. I. Baragetti, S. Furiani, S. Vettoretti, S. Raselli, F.M. Maggi, and F. Galli Role of vitamin E-coated membrane in reducing advanced glycation end products in hemodialysis patients: a pilot study Blood Purif 24 2006 369 376
36. M.G. Traber, T.D. Schiano, A.C. Steephen, H.J. Kayden, and M. Shike Efficacy of water-soluble vitamin-E in the treatment of vitamin-E malabsorption in short-bowel syndrome Am J Clin Nutr 59 1994 1270 1274
37. M.G. Traber, H.J. Kayden, J.B. Green, and M.H. Green Absorption of water-miscible forms of vitamin-E in a patient with cholestasis and in thoracic duct-cannulated rats Am J Clin Nutr 44 1986 914 923
38. G. Vanhenegouwen, H.E. Junginger, and H. Devries Hydrolysis of RRR-alpha-tocopheryl acetate (vitamin E acetate) in the skin and its UV protecting activity (an in vivo study with the rat) J Photochem Photobiol B: Biol 29 1995 45 51
39. J.Q. Pan, N.C. Liu, and W.W.Y. Lau Preparation and properties of new antioxidants with higher MW Polym Degrad Stab 62 1998 165 170
40. F. Iemma, S. Trombino, F.R. Puoci, G. Cirillo, U.G. Spizzirri, and R. Muzzalupo Synthesis and antioxidant efficiency of a new copolymer containing phosphorylated myo-inositol Macromol Biosci 5 2005 1049 1056
41. S.R. Williams, B.S. Lepene, C.D. Thatcher, and T.E. Long Synthesis and characterization of poly(ethylene glycol)-glutathione conjugate self-assembled nanoparticles for antioxidant delivery Biomacromolecules 10 2009 155 161
42. C. Fleming, A. Maldjian, D. Da Costa, A.K. Rullay, D.M. Haddleton, and J.S. John A carbohydrate-antioxidant hybrid polymer reduces oxidative damage in spermatozoa and enhances fertility Nat Chem Biol 1 2005 270 274
43. G. Decher Fuzzy nanoassemblies: toward layered polymeric multicomposites Science 277 1997 1232 1237
44. E. Kharlampieva, and S.A. Sukhishvili Hydrogen-bonded layer-by-layer polymer films Polym Rev 46 2006 377 395
45. F.J. Hua, X.G. Jiang, D.J. Li, and B. Zhao Well-defined thermosensitive, water-soluble polyacrylates and polystyrenics with short pendant oligo (ethylene glycol) groups synthesized by nitroxide-mediated radical polymerization J Polym Sci A: Polym Chem 44 2006 2454 2467
46. N.X. Jin, H. Zhang, S. Jin, M.D. Dadmun, and B. Zhao Shifting sol-gel phase diagram of a doubly thermosensitive hydrophilic diblock copolymer poly(methoxytri(ethylene glycol) acrylate-co-acrylic acid)-b- poly(ethoxydi(ethylene glycol) acrylate-co-acrylic acid) in aqueous solution Macromolecules 45 2012 4790 4800
47. C. Sanchez-Moreno, J.A. Larrauri, and F. Saura-Calixto A procedure to measure the antiradical efficiency of polyphenols J Sci Food Agric 76 1998 270 276
48. P.K. Campbell, K.E. Jones, R.J. Huber, K.W. Horch, and R.A. Normann A silicon-based, 3-dimensional neural interface - manufacturing processes for an intracortical electrode array IEEE Trans Bio-Med Eng 38 1991 758 768
49. K.D. Wise Silicon microsystems for neuroscience and neural prostheses IEEE Eng Med Biol Mag 24 2005 22 29
50. K.A. Marx Quartz crystal microbalance. A useful tool for studying thin polymer films and complex biomolecular systems at the solution-surface interface Biomacromolecules 4 2003 1099 1120
51. C. Ortiz, B. Vazquez, and J.S. Roman Synthesis, characterization and properties of polyacrylic systems derived from vitamin E Polymer 39 1998 4107 4114
52. M.D. Dubbs, and R.B. Gupta Solubility of vitamin E (alpha-tocopherol) and vitamin K-3 (menadione) in ethanol-water mixture J Chem Eng Data 43 1998 590 591
53. I. Erel-Unal, and S.A. Sukhishvili Hydrogen-bonded multilayers of a neutral polymer and a polyphenol Macromolecules 41 2008 3962 3970
54. Kim B-S, Lee H-i, Min Y, Poon Z, Hammond PT. Hydrogen-bonded multilayer of pH-responsive polymeric micelles with tannic acid for surface drug delivery. Chem Commun 2009;45:4194-6.
55. I. Erel-Unal, and S.A. Sukhishvili Hydrogen-bonded hybrid multilayers: film architecture controls release of macromolecules Macromolecules 41 2008 8737 8744
56. M. Akagawa, and K. Suyama Amine oxidase-like activity of polyphenols - mechanism and properties Eur J Biochem 268 2001 1953 1963
57. M. Mazlan, S.M. Then, G.M. Top, and W.Z.W. Ngah Comparative effects of alpha-tocopherol and gamma-tocotrienol against hydrogen peroxide induced apoptosis on primary-cultured astrocytes J Neurol Sci 243 2006 5 12
58. T. Finkel, and N.J. Holbrook Oxidants, oxidative stress and the biology of ageing Nature 408 2000 239 247
59. B. Halliwell, M.V. Clement, and L.H. Long Hydrogen peroxide in the human body FEBS Lett 486 2000 10 13
60. M.G. Traber, C.A. Thellman, M.J. Rindler, and H.J. Kayden Uptake of intact TPGS (d-alpha-tocopheryl polyethylene glycol-1000 succinate) a water-miscible form of vitamin-e by human-cells in vitro Am J Clin Nutr 48 1988 605 611
61. P.P. Wattamwar, Y.Q. Mo, R. Wan, R. Palli, Q.W. Zhang, and T.D. Dziubla Antioxidant activity of degradable polymer poly(trolox ester) to suppress oxidative stress injury in the cells Adv Funct Mater 20 2010 147 154
62. M. Ignatova, N. Manolova, I. Rashkov, M. Sepulchre, and N. Spassky Water-soluble polymers bearing biologically-active residues, 3. Hydrolysis of polyethers and poly(ether-ester)s bearing 1-naphthylacetyl groups Macromol Chem Phys 196 1995 1663 1669
63. R. Xu, and M.L. Go Structure-hydrolyzability relationships in a series of piperidinyl and tropinyl esters with antimuscarinic activity Chem Pharm Bull (Tokyo) 45 1997 476 481