journal article·2015-01

Oxaprozin/poly(2-hydroxyethyl acrylate/itaconic acid) hydrogels: morphological, thermal, swelling, drug release and antibacterial properties

Marija M. Babić, Katarina M. Antić, Jovana S. Jovašević Vuković, Bojan Đ. Božić, Sladjana Z. Davidović, Jovanka M. Filipović, Simonida Lj. Tomić

Journal of Materials Science· Volume 50· Issue 2
Publisher page

Abstract

In this study, a series of novel stimuli-sensitive hydrogels based on 2-hydroxyethyl acrylate and itaconic acid monomers were designed for the controlled release of hydrophobic drug, Oxaprozin. All samples were synthesized by the free-radical crosslinking copolymerization and characterized for structural, morphological, thermal, surface charge, swelling and antibacterial properties. In order to investigate the influence of the drug on hydrogel properties the same characterization was conducted for all Oxaprozin-loaded samples. The chemical composition of hydrogels was studied using Fourier transform infrared spectroscopy, while their morphology and thermal properties were examined by scanning electron microscopy and differential scanning calorimetry. Swelling studies, conducted in the physiological pH range from 2.20 to 8.00 and in the temperature range from 25 to 50 °C, showed that the loaded drug does not modify the pH and temperature sensitivity of the hydrogels, but reduces their swelling capacity. The in vitro drug release study conducted at pH 2.20 and 7.40 showed that all hydrogels can be tailored as colon specific drug delivery systems, and the drug release rate can be effectively controlled by IA content. In addition, the antibacterial activity of the hydrogels was determined against Escherichia coli and Staphylococcus aureus, by the zone of inhibition test. Results of our study indicate that these “smart” hydrogels, with specific morphology, surface charge, swelling capacity, drug loading efficiency and release behavior, could be designed to obtain an enhanced and site-specific controlled drug release system by simply adjusting their composition.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Hydrogels: synthesis, properties, applications · Advanced Drug Delivery Systems · Advancements in Transdermal Drug Delivery

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (61)

Show source-provided references
1. Jaiswai M, Koul V (2013) Assessment of multicomponent hydrogel scaffolds of poly(acrylic acid-2-hydroxy ethyl methacrylate)/gelatin for tissue engineering applications. J Biomater Appl 27:848–86110.1177/0885328211428524 ↗
2. Yin W, Su R, Qi W, He Z (2012) A casein-polysaccharide hybrid hydrogel cross-linked by transglutaminase for drug delivery. J Mater Sci 47:2045–2055. doi: 10.1007/s10853-011-6005-710.1007/s10853-011-6005-7 ↗
3. Saraydin D, Karadag E, Sahiner N, Guven O (2002) Incorporation of maleic acid into acrylamide hydrogel by radiation technique and its effect on swelling behavior. J Mater Sci 37:3217–3223. doi: 10.1023/A:101617063075010.1023/A:1016170630750 ↗
4. Peppas NA, Bures P, Leobandung W, Ichikawa H (2000) Hydrogels in pharmaceutical formulations. Eur J Pharm Biopharm 50:27–4610.1016/S0939-6411(00)00090-4 ↗
5. Park K, Shalaby WSW, Park H (1991) Biodegradable hydrogels for drug delivery, Technomic Publishing Company Inc, Lancaster
6. Lee KY, Mooney DJ (2001) Hydrogels for tissue engineering. Chem Rev 101:1869–187910.1021/cr000108x ↗
7. Kashyap N, Kumar N, Kumar MN (2005) Hydrogels for pharmaceutical and biomedical applications. Crit Rev Ther Drug 22:107–14910.1615/CritRevTherDrugCarrierSyst.v22.i2.10 ↗
8. Khademhosseini A, Langer R (2007) Review: microengineered hydrogels for tissue engineering. Biomaterials 28:5087–509210.1016/j.biomaterials.2007.07.021 ↗
9. Koh MY, Ohtsuki C, Miyazaki T (2011) Modification of polyglutamic acid with silanol groups and calcium salts to induce calcification in a simulated body fluid. J Biomater Appl 25:581–59410.1177/0885328209357111 ↗
10. Jaiswal M, Gupta A, Dinda AK, Koul V (2010) Polycaprolactone diacrylate (PCL-DAr) crosslinked biodegradable semi-interpenetrating networks (semi-IPNs) of polyacrylamide and gelatin for controlled drug delivery. Biomed Mater 5:06501410.1088/1748-6041/5/6/065014 ↗
11. He H, Cao X, Lee LJ (2004) Design of a novel hydrogel-based intelligent system for controlled drug release. J Control Release 95:391–40210.1016/j.jconrel.2003.12.004 ↗
12. Vihola H, Laukkanen A, Hirvonen J, Tenhu H (2002) Binding and release of drugs into and from thermosensitive poly(N-vinyl caprolactam) nanoparticles. Eur J Pharm Sci 16:69–7410.1016/S0928-0987(02)00076-3 ↗
13. Young KC, Seo YJ, Young HK (1992) A glucose-triggered solubilizable polymer gel matrix for an insulin delivery system. Int J Pharm 80:9–1610.1016/0378-5173(92)90257-3 ↗
14. Shamunga Sudar S, Sangeetha D (2012) Investigation on sulphonated PEEK beads for drug delivery, bioactivity and tissue engineering applications. J Mater Sci 47:2736–2742. doi: 10.1007/s10853-011-6100-910.1007/s10853-011-6100-9 ↗
15. Liu C, Yu J, Jiang G, Liu X, Li Z, Gao G, Liu F (2013) Thermosensitive poly(N-isopropylacrylamide)hydrophobic associated hydrogels: optical, swelling/deswelling, and mechanical properties. J Mater Sci 48:774–784. doi: 10.1007/s10853-012-6794-310.1007/s10853-012-6794-3 ↗
16. Burugapalli K, Bhatia D, Koul V, Choudhary V (2010) Interpenetrating polymer networks based on poly(acrylic acid) and gelatin I: swelling and thermal behavior. J Appl Polym Sci 82:217–22710.1002/app.1841 ↗
17. Bajpai AK, Shukla SK, Bhanu S, Kankane S (2008) Responsive polymers in controlled drug delivery. Prog Polym Sci 33:1088–111810.1016/j.progpolymsci.2008.07.005 ↗
18. Mohamed R, Choudhary V, Koul V (2009) Synthesis and characterization of biodegradable interpenetrating polymer networks based on gelatin and divinyl ester synthesized from poly(caprolactone diol). J Appl Poly Sci 111:1478–148710.1002/app.28907 ↗
19. Ekici S (2011) Intelligent poly(N-isopropylacrylamide)-carboxymethyl cellulose full interpenetrating polymeric networks for protein adsorption studies. J Mater Sci 46:2843–2850. doi: 10.1007/s10853-010-5158-010.1007/s10853-010-5158-0 ↗
20. Kim JK, Kim HJ, Chung JY, Lee JH, Young SB, Kim YH (2013) Natural and synthetic biomaterials for controlled drug delivery. Arch Pharm Res 37:60–6810.1007/s12272-013-0280-6 ↗
21. Khutoryanskaya OV, Mayeva ZA, Mun GA, Khutoryanskiy VV (2008) Designing temperature-responsive biocompatible copolymers and hydrogels based on 2-hydroxyethyl(meth)acrylates. Biomacromolecules 9:3353–336110.1021/bm8006242 ↗
22. Chan Y, Wong T, Byrne F, Kavallaris M, Bulmus V (2008) Acid-labile core cross-linked micelles for pH-triggered release of antitumor drugs. Biomacromolecules 9:1826–183610.1021/bm800043n ↗
23. Arun A, Reddy BSR (2005) In vitro drug release studies from the polzmeric hydrogels based on HEA and HPMA using 4-{(E)-[(3Z)-3-(4-(acryloxy)benzylidene)-2-hexylidene]methyl}phenyl acrylate as a crosslinker. Biomaterials 26:1185–119310.1016/j.biomaterials.2004.04.023 ↗
24. Luck M, Paulke BR, Schroder W, Blunk T, Muller RH (1998) Analysis of plasma protein adsorption on polzmeric nanoparticles with different surface characteristics. J Biomed Mater Res 39:478–48510.1002/(SICI)1097-4636(19980305)39:3<478::AID-JBM19>3.0.CO;2-6 ↗
25. McAllister K, Sazani P, Adam M, Cho MJ, Rubinstein M, Samulski RJ, DeSimone JM (2002) Polzmeric nanogels produced via inverse microemulsion polymerization as potential gene and antisense delivery agents. J Am Chem Soc 124:15198–1520710.1021/ja027759q ↗
26. Ramos CM, Lainez S, Sancho F, Esparza MAG, Planells-Cases R, Verdugo JMG, Ribelles JLG, Sanchez MS, Pradas MM, Barcia JA, Soria JM (2008) Differentiation of postnatal neural stem cells into glia and functional neurons on laminin-coated polymeric substrates. Tissue Eng A 14:1365–137510.1089/ten.tea.2007.0295 ↗
27. Lluch AV, Fernandez AC, Ferrer GG, Pradas MM (2009) Bioactive scaffolds mimicking natural dentin structure. J Biomed Mater Res B 90:182–19410.1002/jbm.b.31272 ↗
28. Hoogenboom R, Popescu D, Steinhauer W, Keul H, Moller M (2009) Nitroxide-mediated copolymerization of 2-hydroxyethyl acrylate and 2-hydroxypropyl acrylate: copolymerization kinetics and thermoresponsive properties. Marcromol Rap Commun 30:2042–204810.1002/marc.200900507 ↗
29. Krezović BD, Dimitrijević SI, Filipović JM, Nikolić RR, Tomić SLj (2013) Antimicrobial P(HEMA/IA)PVP semi-interpenetrating network hydrogels. Polym Bull 70:809–81910.1007/s00289-012-0830-y ↗
30. Dobić SN, Filipović JM, Tomić SLj (2012) Synthesis and characterization of poly(2-hydroxyethyl methacrylate/itaconic acid/poly(ethylene glycol)dimethacrylate)hydrogels. Chem Eng J 179:372–38010.1016/j.cej.2011.10.083 ↗
31. Rainsford KD, Omar H, Ashraf A, Hewson AT, Bunning RAD, Rishiraj R, Shepherd R, Seabrook W (2002) Recent pharmacodynamics and pharmacokinetic findings on oxaprozin. InflammoPharmalogy 10:185–23910.1163/156856002321168204 ↗
32. Henry DA (1988) Side effects of non-steroidal anti-inflammatory drugs. Bailliere Clin Rheum 2:425–45410.1016/S0950-3579(88)80021-9 ↗
33. Mau S, Lovely G, Prakash KS, Punit K, Sujata S, Tej PS (2013) Current perspectives in NSAID-induced gastropathy. Mediat Inflamm. doi: 10.1155/20137258209
34. Yazdanian M, Briggs K, Jankovsky C, Hawi A (2004) The high solubility definition of the current FDA guidance on biopharmaceutical classification system may be too strict for acidic drugs. Pharmacol Res 21:293–29910.1023/B:PHAM.0000016242.48642.71 ↗
35. Brown K (1971) Oxazoles, US patent 3,578,67110.1136/bmj.3.5774.578 ↗
36. Božić B, Rogan J, Poleti D, Božić B, Ušćumlić G (2012) Synthesis, characterization and antiproliferative activity of transition metal complexes with 3-(4,5-diphenyl-1,3-oxazol-2-yl)propanoic acid (oxaprozin). Chem Pharm Bull 60:865–86910.1248/cpb.c12-00185 ↗
37. Mall ID, Srivastava VC, Kumar GVA, Mishra IM (2006) Characterization and utilization of mesoporous fertilizer plant waste carbon for adsorptive removal of dyes from aqueous solution. Colloid Surface A 278:175–18710.1016/j.colsurfa.2005.12.017 ↗
38. Bell CL, Peppas NA (1995) Measurement of swelling force in ionic polymer networks. III. Swelling force of interpolymer complexes. J Control Release 37:277–28010.1016/0168-3659(95)00085-2 ↗
39. Peppas NA (1985) Analysis of Fickian and non-Fickian drug release from polymer. Pharm Acta Helv 60:110–111
40. Elechiguerra JL, Burt JL, Morones JR, Camacho-Brabado A, Gao X, Lara HH, Yacaman MJ (2005) Interaction of silver nanoparticles with HIV-1. J Nanobiotechnol 3:1–1010.1186/1477-3155-3-6 ↗
41. Harland RS, Peppas NA (1987) Solute diffusion in swollen membranes. Polym Bull 18:553–55610.1007/BF00255341 ↗
42. Wu CL, He H, Gao HJ, Liu G, Ma RJ, An YL, Shi LQ (2010) Synthesis of Fe3O4[SiO2]polymer nanoparticles for controlled drug release. Sci China Chem 53:514–51810.1007/s11426-010-0084-1 ↗
43. Higuchi T (1963) Mechanism of sustained-action medication: theoretical analysis of rate of release of solid drugs dispersed in soled matrices. J Pharm Sci 52:1145–114810.1002/jps.2600521210 ↗
44. Peppas NA, Sahlin JJ (1989) A simple equation for the description of solute release III. Coupling of diffusion and relaxation. Int J Pharm 57:169–17210.1016/0378-5173(89)90306-2 ↗
45. Yamoaka K, Nakagawa T, Uno T (1978) Application of the Akaike information criterion (AIC) in the evaluation of linear pharmacokinetics equations. J Pharmacokinet Biopharm 6:165–17510.1007/BF01117450 ↗
46. Tomić SLj, Dimitrijević SI, Marinković AD, Najman S, Filipović JM (2009) Synthesis and characterization of poly(2-hydroxyethyl methacrylate/itaconic acid) copolymeric hydrogels. Polym Bull 63:837–85110.1007/s00289-009-0123-2 ↗
47. Seda GS, Asli E (2010) Theoretical and vibrational studies of 4,5-diphenyl-2-2 oxazole propionic acid (oxaprozin). Spectrochim Acta A 75:1370–137610.1016/j.saa.2010.01.004 ↗
48. Wang XF, Sun XW, Liu WX, Gong BY, Gao NB (2008) Chitosan hydrogel beads for fulvic acid adsorption: behaviors and mechanisms. Chem Eng J 142:239–24710.1016/j.cej.2007.11.025 ↗
49. Pechenyuk SI (1999) The use of the pH at the point of zero charge for characterizing the properties of oxide hydroxides. Russ Chem B 48:1017–102310.1007/BF02495994 ↗
50. Asmarandei I, Fundueanu G, Cristea M, Harabagiu V, Constantin M (2013) Thermo- and pH.sensitive interpenetrating poly(N-isopropylacrylamide)/carboxymethyl pullulan network for drug delivery. J Polym Res 20:293–30610.1007/s10965-013-0293-3 ↗
51. Alvarez-Lorenzo C, Concheiro A (2002) Reversible adsorption by a pH- and temperature-sensitive acrylic hydrogel. J Control Release 80:247–25710.1016/S0168-3659(02)00032-9 ↗
52. Wang Y, Yuan ZC, Chen DJ (2012) Thermo- and pH-sensitive behavior of hydrogels based on oligo(ethylene glycol) methacrylates and acrylic acid. J Mater Sci 47:1280–1288. doi: 10.1007/s10853-011-5901-110.1007/s10853-011-5901-1 ↗
53. Ritger PL, Peppas NA (1987) A simple equation for description of solute release I. Fickian and non-Fickian release from non-swellable devices in the form of slabs, spheres, cylinders or discs. J Control Release 5:23–3610.1016/0168-3659(87)90034-4 ↗
54. Caykara T, Dogmus M, Kantoglu O (2004) Network structure and swelling-shrinking behaviors of pH-sensitive poly(acrylamide-co-itaconic acid) hydrogels. J Polym Sci Pol Phys 42:2586–259410.1002/polb.20129 ↗
55. Canal T, Peppas NA (1989) Correlation between mesh size and equilibrium degree of swelling of polymeric networks. J Biomed Mater Res 23:1183–119310.1002/jbm.820231007 ↗
56. Gudeman LF, Peppas NA (1995) pH-sensitive membranes from poly (vinyl alcohol)/poly (acrylic acid) interpenetrating networks. J Membr Sci 107:239–24810.1016/0376-7388(95)00120-7 ↗
57. Ruan G, Feng SS (2003) Preparation and characterization of poly(lactic-acid)-poly(ethylene glycol)-poly(lactic acid)(PLA-PEG-PLA) microspheres for controlled release of paclitaxel. Biomaterials 24:5037–504410.1016/S0142-9612(03)00419-8 ↗
58. Yu H, Xu X, Chen X, Lu T, Zhang P, Jing X (2007) Preparation and antibacterial effects of PVA–PVP hydrogels containing silver nanoparticles. J Appl Polym Sci 103:125–13310.1002/app.24835 ↗
59. Martineau L, Shek PN (2006) Evaluation of a bi-layer wound dressing for burn care: II In vitro and in vivo bactericidal properties. Burns 32:172–17910.1016/j.burns.2005.08.012 ↗
60. Kruszewska H, Zareba T, Tyski S (2002) Search of antimicrobial activity of selected non-antibiotic drugs. Acta Pol Pharm 59:463–469
61. Peppas NA, Buri PA (1985) Surface, intrerfacial and molecular aspects of polymer bioadhesion on soft tissues. J Control Release 2:257–27510.1016/0168-3659(85)90050-1 ↗