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Crosslinking of poly(N-vinyl pyrrolidone-co-n-butyl methacrylate) copolymers for controlled drug delivery

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Abstract

Poly(N-vinyl pyrrolidone-co-n-butyl methacrylate) P(NVP-co-nBMA) copolymers containing high N-vinyl pyrrolidone content were crosslinked to increase their hydro-stable nature for controlled drug delivery. Diethylene glycol dimethacrylate (DEGDMA) and trimethylolpropane trimethacrylate (TMPTMA) were used as crosslinkers. The effect of crosslinker concentration and functionality on gel content, thermal stability and water uptake at 37 °C was investigated. The gel contents and thermal stability increased while water uptake decreased with increasing concentration and functionality of crosslinker. The copolymer crosslinked by TMPTMA showed good mechanical properties. The porous network structure of the copolymers was confirmed by scanning electron microscopic studies. Dexamethasone was selected as a model drug and its controlled release was observed for 22 days from TMPTMA crosslinked copolymer (NB91-T2) film, whereas 96 % drug was released in 35 days for DEGDMA crosslinked copolymer (NB91-D2) film. The kinetics of 10 h drug release identified first-order drug release for NB91-D2 and Higuchi kinetics for NB91-T2. The initial 60 % drug release followed non-Fickian diffusion mechanism. These results indicate the future application of NB91-D2 and NB91-T2 copolymer films as a drug carrier for implant coatings.

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References

  1. Yeh JT, Chen CL, Huang KS, Nien YH, Chen JL, Huang PZ (2006) Synthesis, characterization and application of PVP/chitosan blended polymers. J Appl Polym Sci 101:885–891

    Article  CAS  Google Scholar 

  2. Brar AS, Kumar R (2002) Sequencing of N-vinyl-2-pyrrolidone/glycidyl methacrylate copolymers by one-dimensional and two-dimensional nuclear magnetic resonance spectroscopy. J Appl Polym Sci 84:50–60

    Article  CAS  Google Scholar 

  3. Ahmad B, Bashir S, Nisa S, Huglin MB (2004) Chemically crosslinked N-vinyl-2-pyrrolidone/2-hydroxyethyl methacrylate (VP/HEMA) copolymer for the controlled release of cyclic oligopeptide. Turk J Chem 28:279–285

    CAS  Google Scholar 

  4. Sadeghi M, Soleimani F, Shahsavari H, Ghasemi N (2012) Optimization of effective parameters onto synthesis and swelling behavior of macromolecules hydrogels based on carboxymethylcellulose. J Basic Appl Sci Res 2:769–776

    Google Scholar 

  5. Hanssen HHL, Wetzels GMR et al (1999) Metallic wires with an adherent lubricious and blood-compatible coating and their use in the manufacture of novel slippery-when-wet guidewires: possible applications related to controlled local drug delivery. J Biomed Mater Res 48:820–828

    Article  CAS  Google Scholar 

  6. Leon MB, Abizaid A, Mosses JW (2003) The CYPHER™ stent: a new gold standard in the treatment of coronary artery disease. The Cardiovascular Research Foundation, New York, p 90

  7. Patel MP, Pearson GJ, Braden M, Mirza MA (1998) Fluoride ion release from two methacrylate polymer systems. Biomaterials 19:1911–1917

    Article  CAS  Google Scholar 

  8. Islam A, Yasin T (2012) Controlled delivery of drug from pH sensitive chitosan/poly(vinyl alcohol) blend. Carbohydr Polym 88:1055–1060

    Article  CAS  Google Scholar 

  9. Fratoddi I, Venditti I, Cametti C, Palocci C, Chronopoulou L, Marino M, Acconcia F, Russo MV (2012) Functional polymeric nanoparticles for dexamethasone loading and release. Colloids Surf B Biointerfaces 93:59–66

    Article  CAS  Google Scholar 

  10. Kim J, Chauhan A (2008) Dexamethasone transport and ocular delivery from poly(hydroxyethyl methacrylate gels. Int J Pharm 353:205–222

    CAS  Google Scholar 

  11. Song CX, Labhasetwar V, Murphy H, Qu X, Humphrey WR, Shebuski RJ, Levy RJ (1997) Formulation and characterization of biodegradable nanoparticles for intravascular local drug delivery. J Control Release 43:197–212

    Article  Google Scholar 

  12. Kenyon CJ, Nardi RV, Wong D, Hooper G, Wilding IR, Friend DR (1997) Colonic delivery of dexamethasone: a pharmacoscintigraphic evaluation. Aliment Pharmacol Ther 11:205–213

    Article  CAS  Google Scholar 

  13. Mukherjee B, Mahapatra S, Gupta R, Patra B, Tiwari A, Arora P (2005) A comparison between povidone–ethylcellulose and povidone–eudragit transdermal dexamethasone matrix patches based on in vitro skin permeation. Eur J Pharm Biopharm 59:475–483

    Article  CAS  Google Scholar 

  14. Jin L, Lu P, You H, Chen Q, Dong J (2009) Vitamin B12 diffusion and binding in crosslinked poly(acrylic acid)s and poly(acrylic acid-co-N-vinyl pyrrolidinone)s. Int J Pharm 371:82–88

    Article  CAS  Google Scholar 

  15. Broido A (1969) A simple, sensitive graphical method of treating thermogravimetric analysis data. J Polym Sci A-2 Polym Phys 7:1761–73

    Google Scholar 

  16. Huma F, Akhter Z, Zafar-Uz-Zaman M, Yasin T (2013) Release of dexamethasone from poly(N-vinyl pyrrolidone-co-n-hexyl methacrylate copolymers of controlled hydrophilicity. J Appl Polym Sci 128:444–450

    Article  CAS  Google Scholar 

  17. Honary S, Hoseinzadeh B, Shalchian P (2010) The effect of polymer molecular weight on citrate crosslinked chitosan films for site-specific delivery of a non polar drug. Trop J Pharm Res 9:525–531

    CAS  Google Scholar 

  18. Geever LM, Devine DM, Nugent MJD, Kennedy JE, Lyons JG, Higginbotham CL (2006) The synthesis, characterization, phase behavior and swelling of temperature sensitive, physically crosslinked poly(1-vinyl-2-pyrrolidone)/poly(N-isopropylacrylamide) hydrogels. Eur Polym J 42:69–80

    Article  CAS  Google Scholar 

  19. Wu YH, Freeman BD (2009) Structure, water sorption, and transport properties of crosslinked N-vinyl-2-pyrrolidone/N, N′-bismethacrylamide films. J Membr Sci 344:182–189

    Article  CAS  Google Scholar 

  20. Száraz I, Forsling W (2000) A spectroscopic study of the salvation of 1-vinyl-2-pyrrolidone and poly(1-vinyl-2-pyrrolidone) in different solvents. Polymer 41:4831–4839

    Article  Google Scholar 

  21. Dutta K, Brar AS (1999) Poly(vinylpyrrolidone): configurational assignments by one- and two-dimensional NMR spectroscopy. J Polym Sci Part A Polym Chem 37:3922–3928

    Article  CAS  Google Scholar 

  22. Ibrahim K, Löfgren B, Seppälä J (2003) Towards more controlled poly(n-butyl methacrylate) by atom transfer radical polymerization. Eur Polym J 39:939–944

    Article  CAS  Google Scholar 

  23. Bianco G, Soldi MS, Pinheiro EA, Pires ATN, Gehlen MH, Soldi V (2003) Thermal stability of poly(N-vinyl-2-pyrrolidone-co-methacrylic acid) copolymers in inert atmosphere. Polym Degrad Stab 80:567–574

    Article  CAS  Google Scholar 

  24. Jones DS, Djokic J, McCoy CP, Gorman SP (2002) Poly(ε-caprolactone) and poly(ε-caprolactone)–polyvinylpyrrolidone–iodine blends as ureteral biomaterials: characterization of mechanical and surface properties, degradation and resistance to encrustation in vitro. Biomaterials 23:4449–4458

    Article  CAS  Google Scholar 

  25. Mano JF, Vaz CM, Mendes SC, Reis RL, Cunha AM (1999) Dynamic mechanical properties of hydroxyapatite-reinforced and porous starch-based biodegradable biomaterials. J Mater Sci Mater Med 10:857–862

    Article  CAS  Google Scholar 

  26. Adhyapak A, Desai BG (2011) Preparation and in vitro characterization of the transdermal drug delivery system containing tamoxifen citrate for breast cancer. Asian J Pharm 5:41–45

    Article  CAS  Google Scholar 

  27. Hong Y, Chirila TV, Cuypers MJ, Constable IJ (1996) Polymers of 1-vinyl-2-pyrrolidinone as potential vitreous substitutes: physical selection. J Biomater Appl 11:135–181

    CAS  Google Scholar 

  28. Davis TP, Huglin MB (1991) Effect of crosslinking on the properties of poly(2-hydroxyethyl methacrylate) hydrogels. Angew Makromol Chem 189:195–205

    Article  CAS  Google Scholar 

  29. Jansook P, Ritthidej GC, Ueda H, Stefánsson E, Loftsson T (2010) γCD/HPγCD mixtures as solubilizer: solid-state characterization and sample dexamethasone eye drop suspension. J Pharm Pharm Sci 13:336–350

    CAS  Google Scholar 

  30. Tickler WJ, Nagvekar AA, Dash AK (2008) A novel nanoparticle formulation for sustained paclitaxel delivery. AAPS Pharm Sci Tech 9:486–493

    Article  Google Scholar 

  31. Fan LT, Singh SK (1989) Controlled release: a quantitative treatment. Springer, Berlin

    Book  Google Scholar 

  32. Mathew ST, Devi SG, Sandhya KV (2007) Formulation and evaluation of ketorolac tromethamine-loaded albumin microspheres for potential intramuscular administration. AAPS Pharm Sci Tech 8:E100–E108

    Article  Google Scholar 

  33. Korsmeyer RW, Gurny R, Doelker E, Buri P, Peppas NA (1983) Mechanisms of solute release from porous hydrophilic polymers. Int J Pharm 15:25–35

    Article  CAS  Google Scholar 

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Correspondence to Zareen Akhter.

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Huma, F., Akhter, Z., Yasin, T. et al. Crosslinking of poly(N-vinyl pyrrolidone-co-n-butyl methacrylate) copolymers for controlled drug delivery. Polym. Bull. 71, 433–451 (2014). https://doi.org/10.1007/s00289-013-1069-y

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  • DOI: https://doi.org/10.1007/s00289-013-1069-y

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