Biocompatible thermoresponsive PEGMA nanoparticles crosslinked with cleavable disulfide-based crosslinker for dual drug release

Journal of Biomedical Materials Research - Part A

Volumn 103, Issue 1, 2015, Pages 243-251

  Ulasan, Mehmet ^a   Yavuz, Emine ^a,b   Bagriacik, Emin Umit ^b   Cengeloglu, Yunus ^a   Yavuz, Mustafa Selman ^a  

^a SELCUK UNIVERSITY   (Turkey)

^b GAZI UNIVERSITY   (Turkey)

Author keywords

disulfide based crosslinker; drug delivery; poly ethylene glycol methyl ether methacrylate; stimuli responsive nanoparticles; surfactant free emulsion polymerization

Indexed keywords

ALIZARIN; BIOCOMPATIBILITY; COVALENT BONDS; DRUG DELIVERY; EMULSIFICATION; EMULSION POLYMERIZATION; ETHERS; ETHYLENE; ETHYLENE GLYCOL; FUNCTIONAL POLYMERS; HYDRODYNAMICS; LIGHT SCATTERING; MOLECULES; NANOPARTICLES; POLYETHYLENE GLYCOLS; POLYOLS; SCANNING ELECTRON MICROSCOPY; SULFUR COMPOUNDS; SURFACE ACTIVE AGENTS;

CRITICAL SOLUTION TEMPERATURE; CROSSLINKER; INITIATOR CONCENTRATION; METHYL ETHERS; PARTICLE CHARACTERIZATION; POLY(ETHYLENE GLYCOL) METHYL ETHER METHACRYLATE (PEG-MMA); STIMULI-RESPONSIVE; SURFACTANT-FREE EMULSION POLYMERIZATION;

SYNTHESIS (CHEMICAL);

ALIZARIN; DIMETHYL ETHER; DISULFIDE; DITHIOTHREITOL; MACROGOL DERIVATIVE; METHACRYLIC ACID; POLY(ETHYLENE GLYCOL) METHYL ETHER METHACRYLATE; POVIDONE DERIVATIVE; RHODAMINE B; SURFACTANT; UNCLASSIFIED DRUG; BIOMATERIAL; DRUG CARRIER; METHACRYLIC ACID DERIVATIVE; NANOPARTICLE; POLYETHYLENE GLYCOL METHACRYLATE;

ARTICLE; CELL VIABILITY; CHEMICAL REACTION KINETICS; CONTROLLED DRUG RELEASE; CONTROLLED STUDY; CROSS LINKING; CYTOTOXICITY; DEGRADATION; DISULFIDE BOND; DRUG DELIVERY SYSTEM; EMULSION; HEATING; HUMAN; HUMAN CELL; HYDRODYNAMICS; LIGHT SCATTERING; PHASE TRANSITION; POLYMERIZATION; ROOM TEMPERATURE; SCANNING ELECTRON MICROSCOPY; TEMPERATURE SENSITIVITY; XTT ASSAY; CHEMISTRY;

BIOCOMPATIBLE MATERIALS; DISULFIDES; DRUG CARRIERS; METHACRYLATES; MICROSCOPY, ELECTRON, SCANNING; NANOPARTICLES; POLYETHYLENE GLYCOLS;

EID: 84912521417     PISSN: 15493296     EISSN: 15524965     Source Type: Journal    
DOI: 10.1002/jbm.a.35146     Document Type: Article

References (81)

1. Zhang J, Chen HY, Xu L, Gu YQ,. The targeted behavior of thermally responsive nanohydrogel evaluated by NIR system in mouse model. J Control Release 2008; 131: 34-40.
2. 2 ions with enhanced detection sensitivity. J Mater Chem 2010; 20: 10716-10723.
3. Berndt I, Pedersen JS, Richtering W,. Structure of multiresponsive "intelligent" core-shell microgels. J Am Chem Soc 2005; 127: 9372-9373.
4. Murthy N, Xu MC, Schuck S, Kunisawa J, Shastri N, Frechet JMJ,. A macromolecular delivery vehicle for protein-based vaccines: acid-degradable protein-loaded microgels. Proc Natl Acad Sci USA. 2003; 100: 4995-5000.
5. Na K, Bae YH,. Self-assembled hydrogel nanoparticles responsive to tumor extracellular pH from pullulan derivative/sulfonamide conjugate: characterization, aggregation, and adriamycin release in vitro. Pharm Res 2002; 19: 681-688.
6. Shi LJ, Khondee S, Linz TH, Berkland C,. Poly(N-vinylformamide) nanogels capable of pH-sensitive protein release. Macromolecules 2008; 41: 6546-6554.
7. Argentiere S, Blasi L, Morello G, Gigli G,. A novel pH-responsive nanogel for the controlled uptake and release of hydrophobic and cationic solutes. J Phys Chem C 2011; 115: 16347-16353.
8. Oh JK, Siegwart DJ, Lee HI, Sherwood G, Peteanu L, Hollinger JO, Kataoka K, Matyjaszewski K. Biodegradable nanogels prepared by atom transfer radical polymerization as potential drug delivery carriers: Synthesis, biodegradation, in vitro release, and bioconjugation. J Am Chem Soc 2007; 129: 5939-5945.
9. Oh JK, Siegwart DJ, Matyjaszewski K,. Synthesis and biodegradation of nanogels as delivery carriers for carbohydrate drugs. Biomacromolecules 2007; 8: 3326-3331.
10. Lee H, Mok H, Lee S, Oh YK, Park TG,. Target-specific intracellular delivery of siRNA using degradable hyaluronic acid nanogels. J Control Release 2007; 119: 245-252.
11. Groll J, Singh S, Albrecht K, Moeller M,. Biocompatible and degradable nanogels viaoxidation reactions of synthetic thiomers in inverse miniemulsion. J Polym Sci Part A: Polym Chem 2009; 47: 5543-5549.
12. Duracher D, Sauzedde F, Elaissari A, Perrin A, Pichot C,. Cationic aminocontaining N-isopropylacrylamide-styrene copolymer latex particles: particle size and morphology vs. polymerization process. Colloid Polym Sci 1998; 276: 219-231.
13. Duracher D, Sauzedde F, Elaissari A, Pichot C, Nabzar L,. Cationic amino containing N-isopropyl-acrylamide-styrene copolymer particles: 2-surface and colloidal characteristics. Colloid Polym Sci 1998; 276: 920-929.
14. Ferreira SA, Coutinho PJG, Gama FM,. Self-assembled nanogel made of mannan: synthesis and characterization. Langmuir 2010; 26: 11413-11420.
15. Kim BS, Qiu JM, Wang JP, Taton TA,. Magnetomicelles: composite nanostructures from magnetic nanoparticles and cross-linked amphiphilic block copolymers. Nano Lett 2005; 5: 1987-1991.
16. Park JH, von Maltzahn G, Ruoslahti E, Bhatia SN, Sailor MJ., Micellar hybrid nanoparticles for simultaneous magnetofluorescent imaging and drug delivery. Angew Chem Int Ed 2008; 47: 7284-7288.
17. 4 nanoparticles, hexa(ethyleneglycol) methyl ethermethacrylate and 2-(acetoacetoxy) ethyl methacrylate. J Magn Magn Mater 2011; 323, 557-563.
18. Raemdonck K, Demeester J, Smedt SD,. Advanced nanogel engineering for drug delivery. Soft Matter 2009; 5: 707-715.
19. Wang Y, Bansal V, Zelikin AN, Caruso F,. Templated synthesis of single-component polymer capsules and their application in drug delivery. Nano Lett 2008; 8: 1741-1745.
20. Sinha VR, Trehan A,. Biodegradable microspheres for protein delivery. J Control Release 2003; 90: 261-280.
21. Lin X, Tang D, Cui W, Cheng Y,. Controllable drug release of electrospun thermoresponsive poly(N-isopropylacrylamide)/poly(2-acrylamido-2-methylpropanesulfonic acid) nanofibers. J Biomed Mater Res Part A 2012; 100A: 1839-1845.
22. Chen Y-C, Lo C-L, Hsiue G-H,. Multifunctional nanomicellar systems for delivering anticancer drugs. J Biomed Mater Res Part A 2013. doi: 10.1002/jbm.a.34850.
23. Bromberg I,. Intelligent polyelectrolytes and gels in oral drug delivery. Curr Pharm Biotechnol 2003; 4: 39-49.
24. Bartil T, Bounekhel M, Cedric C, Jerome R,. Swelling behavior and release properties of pH-sensitive hydrogels based on methacrylic derivatives. Acta Pharm 2007; 57: 301-314.
25. Jeong B, Gutowska A,. Lesson from nature; stimuli responsive polymers and their biomedical applications. Trends Biotechnol 2002; 20: 305-311.
26. Morishita M, Lowman AM, Takayama K, Nagai P, Peppas NA,. Elucidation of the mechanism of incorporation of insulin in controlled release system based on complexation. J Control Release 2002; 81: 25-32.
27. Peppas NA,. Devices based on intelligent biopolymers for oral protein delivery. Int J Pharm 2004; 277: 11-17.
28. Lee ES, Gao ZG, Bae YH,. Recent progress in tumor pH targeting nanotechnology. J Control Release 2008; 132: 164-170.
29. Du JZ, Sun TM, Song WJ, Wu J, Wang J,. A tumor-acidity-activated charge conversional nanogel as an intelligent vehicle for promoted tumoral-cell uptake and drug delivery. Angew Chem Int Ed 2010; 49: 3621-3626.
30. Jiang XZ, Ge ZS, Xu J, Liu H, Liu SY,. Fabrication of multiresponsive shell cross-linked micelles possessing pH-controllable core swellability and thermo-tunable corona permeability. Biomacromolecules 2007; 8: 3184-3192.
31. Wan S, Jiang M, Zhang GZ,. Dual temperature- and pH-dependent selfassembly of cellulose-based copolymer with a pair of complementary grafts. Macromolecules 2007; 40: 5552-5558.
32. Mu B, Liu P, Tang Z, Du P, Dong Y,. Temperature and pH dual-responsive cross-linked polymeric nanocapsules with controllable structures via surface-initiated atom transfer radical polymerization from templates. Nanomecidine 2011; 7: 789-796.
33. Pan Y-J, Chen Y-Y, Wang D-R, Wei C, Guo J, Lu D-R, Chu C-C, Wang C-C,. Redox/pH dual stimuli-responsive biodegradable nanohydrogels with varying responses to dithiothreitol for controlled drug release. Biomaterials 2012; 33: 6570-6579.
34. Schild HG,. Poly(N-isopropylacrylamide)-experiment, theory and application. Prog Polym Sci 1992; 17: 163-249.
35. Zhang XZ, Zhuo RX,. Dynamic properties of temperature-sensitive poly(N-isopropylacrylamide) gel cross-linked through siloxane linkage. Langmuir 2001; 17: 12-16.
36. Jean-Francois L, Holt A,. Preparation of ideal PEG analogues with a tunable thermosensitivity by controlled radical copolymerization of 2-(2-methoxyethyoxy)ethyl methacrylate and oligo (ethylene glycol) methacrylate. Macromolecules 2006; 39: 893-896.
37. Wang N, Dong A, Radosz M, Shen Y,. Thermoresponsive degradable poly(ethylene glycol) analogues. J Biomed Mater Res Part A 2008;84A:148-157.
38. Xu X-D, Wei H, Zhang X-Z, Cheng S-X, Zhuo R-X,. Fabrication and characterization of a novel composite PNIPAAm hydrogel for controlled drug release. J Biomed Mater Res Part A 2007;81:418-426.
39. Aerry S, De A, Kumar A, Saxena A, Majumdar DK, Mozumdar S,. Synthesis and characterization of thermoresponsive copolymers for drug delivery. J Biomed Mater Res Part A 2013; 101A: 2015-2026.
40. Yang Z, Xie J, Zhou W, Shi W,. Temperature sensitivity and drug encapsulation of star-shaped amphiphilic block copolymer based on dendritic poly(ether-amide). J Biomed Mater Res Part A 2009;89A:988-1000.
41. Zhang JX, Qiu LY, Jin Y,. Thermally responsive polymeric micelles self-assembled by amphiphilic polyphosphazene with poly(N-isopropylacrylamide) and ethyl glycinate as side groups: Polymer synthesis, characterization, and in vitro drug release study. J Biomed Mater Res Part A 2006;76A:773-780.
42. Alzari V, Monticelli O, Nuvoli D, Kenny J. M, Mariani A,. Stimuli responsive hydrogels prepared by frontal polymerization. Biomacromolecules 2009; 10: 2672-2677.
43. Cimen EK, Rzaev ZMO, Piskin E,. Bioengineering functional copolymers: V. Synthesis, LCST, and thermal behavior of poly(N-isopropyl acrylamide-co-p-vinylphenylboronic acid). J Appl Polym Sci 2005; 95: 573-582.
44. Eke I, Elmas B, Tuncel M, Tuncel A,. A new, highly stable cationic-thermosensitive microgel: uniform isopropylacrylamide-dimethylaminopropylmethacrylamide copolymer particles. Colloids Surf A 2006; 279: 247-253.
45. Kim JH, Lee TR,. Hydrogel templated growth of Au nanoparticles: synthesis of thermally responsive hydrogel-nanoparticle composite. Langmuir 2007; 23: 6504-6509.
46. Naha PC, Bhattacharya K, Tenuta T, Dawson KA, Lynch I, Gracia A, Lyng FM, Byrne HJ,. Intracellular localisation, geno- and cytotoxic response of poly N-isopropylacrylamide (PNIPAM) nanoparticles to human keratinocyte (HaCaT) and colon cells (SW 480). Toxicol Lett 2010; 198: 134-143.
47. Lutz JF, Andrieu J, Uzgun S, Rudolph C, Agarwal S,. Biocompatible, thermoresponsive, and biodegradable: simple preparation of "All-in-One" biorelevant polymers. Macromolecules 2007; 40: 8540-8543.
48. Lutz JF, Weichenhan K, Akdemir O, Hoth A,. About the phase transitions in aqueous solutions of thermoresponsive copolymers and hydrogels based on 2-(2-methoxyethoxy)ethyl methacrylate and oligo(ethylene glycol) methacrylate. Macromolecules 2007; 40: 2503-2508.
49. Beamish JA, Zhu J, Kottke-Marchant K, Marchant RE,. The effects of monoacrylated poly(ethylene glycol) on the properties of poly(ethylene glycol) diacrylate hydrogels used for tissue engineering. J Biomed Mater Res Part A 2010;92A:441-450.
50. Yavuz MS, Buyukserin F, Zengin Z, Camli ST,. Thermoresponsive oligo (ethylene glycol) methacrylate colloids with antifouling surface properties. J Polym Sci Part A: Polym Chem 2011; 49: 4800-4808.
51. Buyukserin F, Camli ST, Yavuz MS, Budak GG,. Novel antifouling oligo (ethylene glycol) methacrylate particles via surfactant-free emulsion polymerization. J Colloid Interface Sci 2011; 355: 76-80.
52. Park K, Shalaby WSW, Park H, editors. Biodegradable Hydrogels for Drug Delivery. Basel: Technomic; 1993.
53. Schafer FQ, Buettner GR,. Redox environment of the cell as viewed through the redox state of the glutathione disulfide/glutathione couple. Free Radic Biol Med 2001; 30: 1191-1212.
54. Hao Y, Lin C-C,. Degradable thiol-acrylate hydrogels as tunable matrices for three-dimensional hepatic culture. J Biomed Mater Res Part A. 2013; doi: 10.1002/jbm.a.35044.
55. Stabenfeldt SE, García AJ, LaPlaca MC,. Thermoreversible laminin-functionalized hydrogel for neural tissue engineering. J Biomed Mater Res Part A 2006; 77A: 718-725.
56. Liu Y, Shu XZ, Gra, SD, and, Prestwich GD,. Disulfide-crosslinked hyaluronan-gelatin sponge: growth of fibrous tissue in vivo. J Biomed Mater Res Part A 2004; 68A: 142-149.
57. Quirk S,. Triggered release of small molecules from proteinoid microspheres. J Biomed Mater Res Part A 2009; 91: 391-399.
58. Volkmann G, Liu X-Q,. Intein lacking conserved C-terminal motif G retains controllable N-cleavage activity. FEBS J. 2011; 278: 3431-3446.
59. Pan Y-J, Chen Y-Y, Wang D-R, Wei C, Guo J, Lu D-R, Chu C-C, Wang C-C,. Redox/pH dual stimuli-responsive biodegradable nanohydrogels with varying responses to dithiothreitol and glutathione for controlled drug release. Biomaterials 2012; 33: 6570-6579.
60. Park H, Park K,. Biocompatibility issues of implantable drug delivery systems. Pharmacol Res 1996; 13: 1770-1776.
61. Smetana K,. Cell biology of hydrogels. Biomaterials 1993; 14: 1046-1050.
62. Anderson JM, Langone JJ,. Issues and perspectives on the biocompatibility and immunotoxicity evaluation of implanted controlled release systems. J Control Release 1999; 57: 107-113.
63. Anderson JM,. In vivo biocompatibility of implantable delivery systems and biomaterials. Eur J Pharm Biopharm 1994; 40: 1-8.
64. Shabna A, Saranya V, Malathi J, Shenbagarathai R, Madhavan HN,. 2013. Indigenously produced polyhydroxyalkanoate based co-polymer as cellular supportive biomaterial. J Biomed Mater Res Part A 2013. doi: 10.1002/jbm.a.35029.
65. Sheikh FA, Ju HW, Moon BM, Park HJ, Kim J-H, Lee OJ, Park CH,. 2013. Facile and highly efficient approach for the fabrication of multifunctional silk nanofibers containing hydroxyapatite and silver nanoparticles. J Biomed Mater Res Part A 2013. doi: 10.1002/jbm.a.35024.
66. Peng C-L, Yang L-Y, Luo T-Y, Lai P-S, Yang S-J, Lin W-J, Shieh M-J,. Development of pH sensitive 2-(diisopropylamino)ethyl methacrylate based nanoparticles for photodynamic therapy. Nanotechnology 2010; 21: 155103.
67. 2 and CaO rich calcium silicate systems via sol-gel process: Bioactivity, biocompatibility, and drug delivery tests. J Biomed Mater Res Part A 2013. Doi: 10.1002/jbm.a.34978.
68. Yang X, Bakaic E, Hoare T, Cranston ED,. Injectable polysaccharide hydrogels reinforced with cellulose nanocrystals: morphology, rheology, degradation, and cytotoxicity. Biomacromolecules. 2013; 14: 4447-4455.
69. Yavuz MS, Buyukserin F, Zengin Z, Camli ST,. Thermoresponsive oligo(ethylene glycol) methacrylate colloids with antifouling surface properties. J Polym Sci Part A: Polym Chem 2011; 49: 4800-4808.
70. Zhang L, Liu W, Lin L, Chen D, Stenzel MH,. Degradable disulfide core-cross-linked micelles as a drug delivery system prepared from vinyl functionalized nucleosides via the RAFT process. Biomacromolecules 2008; 9: 3321-3331.
71. Tuncel A,. Emulsion copolymerization of styrene and poly(ethylene glycol) ethyl ether methacrylate. Polymer 2000; 41: 1257-1267.
72. Guven G, Piskin E,. Optimization of monosize/cationic nanoparticle synthesis and their interaction with genomic DNA. Polym Adv Tech 2006; 17: 850-854.
73. Camli ST, Büyükserin F, Yavuz MS, Budak GG,. Fine-tuning of poly(methylmethacrylate) nanoparticle size at the sub-100 nm scale using surfactant-free emulsion polymerization. Colloids Surf A Physicochem Eng Aspects 2010; 366: 141-146.
74. dosSantos AM, McKenna TF, Gulliot J,. Emulsion copolymerization of styrene and n-butyl acrylate in presence of acrylic and methacrylic acids: effect of pH on kinetics and carboxyl group distribution. J Appl Polym Sci 1997; 65: 2343-2355.
75. Elmas B, Tuncel M, Senel S, Patir S, Tuncel A,. Hydroxyl functionalized thermosensitive microgels with quadratic crosslinking density distribution. J Colloid Interface Sci 2007; 313: 174.
76. Duracher D, Elaissari A, Pichot C,. Preparation of poly(N-isopropylmethacrylamide) latexes kinetic studies and characterization. J Polym Sci Part A: Polym Chem 1999; 37: 1823-1837.
77. Goldshtein J, Margel S,. Synthesis and characterization of new UV absorbing microspheres of narrow size distribution by dispersion polymerization of 2-(2'-hydroxy-5'-methacryloxyethylphenyl)-2H-benzotriazole. Polymer 2009; 50: 3422-3430.
78. Van de Wetering P, Cherng J, Talsma H, Crommelin DJA, Hennink WE,. 2-(dimethylamino)ethyl methacrylate based (co)polymers as gene transfer agents. J Control Release 1998; 53: 145-153.
79. Uzgun S, Akdemir O, Hasenpusch G, Maucksch C, Galos MM, Sander B, Stark H, Imker R, Lutz JF, Rudolph C,. Characterization of tailor-made copolymers of oligo(ethylene glycol) methyl ether methacrylate and N,N-dimethylaminoethyl methacrylate as nonviral gene transfer agents: influence of macromolecular structure on gene vector particle properties and transfection efficiency. Biomacromolecules 2010; 11: 39-50.
80. Wu YJ, Zhang YH,. An efficient one-pot synthesis of 3-substituted-5-amino 1,2,4-thiadiazoles from isothiocyanates and amidines. Tetrahedron Lett 2008; 49: 2869-2871.
81. Granik VG,. Achievements in the chemistry of amidines. Usp Khim 1983; 52: 669-703.