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Synthesis and characterization of cryogels of p(HEMA-N-vinylformamide) and p(HEMA-N-Vinylpyrrolidone) for chemical release behaviour

Abstract

Macroporous polymeric gels has received great attention in many fields focused on biotechnological applications. In this study, two new HEMA-based cryogel columns were synthesized. To this end, poly(HEMA-VF) and poly(HEMA-NVP) cryogels were prepared by copolymerization of 2-Hydroxyethyl methacrylate (HEMA) with N-vinylformamide (VF) and N-vinylpyrrolidone (VP) in the presence of N,N-methylenebisacrylamide (as cross-linker), then polymerization initiated by ammonium persulfate (APS) and N,N,N′,N′-tetramethylenediamine (TEMED) with free-radical polymerizations method in cryogelation conditions, respectively. p(HEMA-VF) and p(HEMA-VP) cryogels contain a continuous polymeric matrix with interconnected pores of size 2–100 μm. Swelling behavior for these cryogels in various solvents was investigated, wherein the characterization of the cryogels is conducted via by surface area measurement (BET), Fourier transforms infrared spectroscopy (FT-IR), elemental analysis, scanning electron microscopy (SEM), Differential Scanning Calorimetry (DSC) and Thermogravimetric Analysis (TGA). As drug model compounds, Methyl Red (MR), methylene blue (MB) and methylene green (MG) were loaded into prepared cryogels and the controlled release properties of cryogel columns were examined comparatively each other. It has been shown that approximately 90% of its release from the cryogels occurred within about 2 h. In addition, MB release from p(HEMA-VF) and p(HEMA-VP) cryogels was found to be around 80% over a similar period. The proposed cryogels can be regarded as controlled release system on future biomedical applications.

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References

  1. 1.

    T. Zhang, Z. Xu, H. Gui, Q. Guo, J. Mater. Chem. A 5, 10161 (2017)

    CAS  Article  Google Scholar 

  2. 2.

    K.J. De France, F. Xu, T. Hoare, Adv. Healthc. Mater. 7, 1700927 (2018)

    Article  CAS  Google Scholar 

  3. 3.

    M.M. Elsayed, J. Polym. Environ. 27, 871 (2019)

    CAS  Article  Google Scholar 

  4. 4.

    L.L. Palmese, R.K. Thapa, M.O. Sullivan, K.L. Kiick, Curr. Opin. Chem. Eng. 24, 143 (2019)

    PubMed  PubMed Central  Article  Google Scholar 

  5. 5.

    V. Baudron, P. Gurikov, I. Smirnova, S. Whitehouse, Gels 5, 12 (2019)

    CAS  PubMed Central  Article  PubMed  Google Scholar 

  6. 6.

    T. Sedlačík, T. Nonoyama, H. Guo, R. Kiyama, T. Nakajima, Y. Takeda, T. Kurokawa, J.P. Gong, Chem. Mater. 32, 8576 (2020)

    Article  CAS  Google Scholar 

  7. 7.

    M. Zinggeler, J.N. Schönberg, P.L. Fosso, T. Brandstetter, J. Rühe, A.C.S. Appl, Mater. Interfaces 9, 12165 (2017)

    CAS  Article  Google Scholar 

  8. 8.

    E. Su, O. Okay, Polymer (Guildf). 178, 121603 (2019)

    CAS  Article  Google Scholar 

  9. 9.

    M. Razavi, Y. Qiao, A.S. Thakor, J. Biomed. Mater. Res. Part A 107, 2736 (2019)

    CAS  Article  Google Scholar 

  10. 10.

    V. Lozinsky, Gels 4, 77 (2018)

    CAS  PubMed Central  Article  PubMed  Google Scholar 

  11. 11.

    K. Şarkaya, M. Bakhshpour, A. Denizli, Sep. Sci. Technol. 1, 271 (2018)

    Google Scholar 

  12. 12.

    V.I. Lozinsky, Adv. Polym. Sci. (2014). https://doi.org/10.1007/978-3-319-05846-7

    Article  Google Scholar 

  13. 13.

    I. Perçin, N. Idil, A. Denizli, Process Biochem. 80, 181 (2019)

    Article  CAS  Google Scholar 

  14. 14.

    M.D. Stanescu, A. Sanislav, R.V. Ivanov, A. Hirtopeanu, V.I. Lozinsky, Appl. Biochem. Biotechnol. 165, 1789 (2011)

    CAS  PubMed  Article  Google Scholar 

  15. 15.

    M. Zhai, F. Ma, J. Li, B. Wan, N. Yu, J. Biomater. Sci. Polym. Ed. 29, 1401 (2018)

    CAS  PubMed  Article  Google Scholar 

  16. 16.

    D.F.A. Loghin, G. Biliuta, S. Coseri, E.S. Dragan, Int. J. Biol. Macromol. 96, 589 (2017)

    Article  CAS  Google Scholar 

  17. 17.

    G. Uzunoğlu, D. Çimen, N. Bereli, K. Çetin, A. Denizli, J. Biomater. Sci. Polym. Ed. 30, 1276 (2019)

    PubMed  Article  CAS  Google Scholar 

  18. 18.

    G. Güven, S. Evli, M. Uygun, D.A. Uygun, J. Liq. Chromatogr. Relat. Technol. 42, 537 (2019)

    Article  CAS  Google Scholar 

  19. 19.

    M. Mavlan, L. Uzun, J.P. Youngblood, Cellulose 7, 1 (2020)

    Google Scholar 

  20. 20.

    K. Şarkaya, M. Bakhshpour, A. Denizli, Sep. Sci. Technol. 54, 2993 (2019)

    Article  CAS  Google Scholar 

  21. 21.

    K. Çetin, A. Denizli, Process Biochem. 79, 174 (2019)

    Article  CAS  Google Scholar 

  22. 22.

    B. Dmitriy, J. Clean. Prod. 247, 119089 (2020)

    CAS  Article  Google Scholar 

  23. 23.

    M. Çadırcı, K. Şarkaya, A. Allı, Mater. Sci. Semicond. Process. 119, 105269 (2020)

    Article  CAS  Google Scholar 

  24. 24.

    R. Jirakunakorn, S. Khumngern, J. Choosang, P. Thavarungkul, P. Kanatharana, A. Numnuam, Microchem. J. 154, 104624 (2020)

    CAS  Article  Google Scholar 

  25. 25.

    I. Guven, O. Gezici, M. Bayrakci, M. Morbidelli, J. Chromatogr. A 1558, 59 (2018)

    CAS  PubMed  Article  Google Scholar 

  26. 26.

    S.S. Suner, S. Demirci, B. Yetiskin, R. Fakhrullin, E. Naumenko, O. Okay, R.S. Ayyala, N. Sahiner, Int. J. Biol. Macromol. 130, 627 (2019)

    CAS  PubMed  Article  Google Scholar 

  27. 27.

    S.T. Koshy, D.K.Y. Zhang, J.M. Grolman, A.G. Stafford, D.J. Mooney, Acta Biomater. 65, 36 (2018)

    CAS  PubMed  Article  Google Scholar 

  28. 28.

    A.Z. Baimenov, D.A. Berillo, V.J. Inglezakis, J. Mol. Liq. 299, 112134 (2020)

    CAS  Article  Google Scholar 

  29. 29.

    R. Yao, Z. Yao, J. Zhou, Mater. Lett. 176, 199 (2016)

    CAS  Article  Google Scholar 

  30. 30.

    S. Pacelli, L. Di Muzio, P. Paolicelli, V. Fortunati, S. Petralito, J. Trilli, M.A. Casadei, Int (J. Biol, Macromol, 2020).

    Google Scholar 

  31. 31.

    K. Çetin, H. Alkan, N. Bereli, A. Denizli, J. Macromol. Sci. Part A 54, 502 (2017)

    Article  CAS  Google Scholar 

  32. 32.

    J. Li, Y. Wang, L. Zhang, Z. Xu, H. Dai, W. Wu, A.C.S. Sustain, Chem. Eng. 7, 6381 (2019)

    CAS  Google Scholar 

  33. 33.

    G.G. de Lima, F. Traon, E. Moal, M. Canillas, M.A. Rodriguez, H.O. McCarthy, N. Dunne, D.M. Devine, M.J.D. Nugent, Polym. Compos. 39, E210 (2018)

    Article  CAS  Google Scholar 

  34. 34.

    H. Zhao, J. Gao, R. Liu, S. Zhao, Carbohydr. Res. 428, 79 (2016)

    CAS  PubMed  Article  Google Scholar 

  35. 35.

    X. Zhou, J. Wang, J. Nie, B. Du, Polym. J. 48, 431 (2016)

    CAS  Article  Google Scholar 

  36. 36.

    H. Huang, L. Hou, F. Zhu, J. Li, M. Xu, RSC Adv. 8, 9334 (2018)

    CAS  Article  Google Scholar 

  37. 37.

    B.L. Abraham, E.S. Toriki, N.J. Tucker, B.L. Nilsson, J. Mater. Chem. B 8, 6366 (2020)

    CAS  PubMed  Article  Google Scholar 

  38. 38.

    N.I. Gorshkov, I.E. Alekseev, A.E. Miroslavov, A.Y. Murko, A.A. Lumpov, V.D. Krasikov, D.N. Suglobov, Int. J. Polym. Anal. Charact. 23, 290 (2018)

    CAS  Article  Google Scholar 

  39. 39.

    N.I. Gorshkov, A.E. Miroslavov, I.E. Alekseev, A.A. Lumpov, A.Y. Murko, I.I. Gavrilova, N.N. Saprykina, M.A. Bezrukova, A.I. Kipper, V.D. Krasikov, D.N. Suglobov, M.Y. Tyupina, E.F. Panarin, J. Label. Compd. Radiopharm. 60, 302 (2017)

    CAS  Article  Google Scholar 

  40. 40.

    H. Peng, X. Huang, A. Melle, M. Karperien, A. Pich, J. Colloid Interface Sci. 540, 612 (2019)

    CAS  PubMed  Article  Google Scholar 

  41. 41.

    M. Yue, K. Imai, Y. Miura, Y. Hoshino, Polym. J. 49, 601 (2017)

    CAS  Article  Google Scholar 

  42. 42.

    O.I. Timaeva, N.A. Arkharova, A.S. Orekhov, V.V. Klechkovskaya, S.P. Mulakov, G.M. Kuz’micheva, I.I. Pashkin, Polymer Guildf. 186, 122079 (2020)

    CAS  Article  Google Scholar 

  43. 43.

    P. Sheikholeslami, B. Muirhead, D.S.H. Baek, H. Wang, X. Zhao, D. Sivakumaran, S. Boyd, H. Sheardown, T. Hoare, Exp. Eye Res. 137, 18 (2015)

    CAS  PubMed  Article  Google Scholar 

  44. 44.

    H. Ajiro, K. Kan, M. Akashi, J. Nanosci. Nanotechnol. 17, 837 (2017)

    CAS  PubMed  Article  Google Scholar 

  45. 45.

    J. Long, B. Liang, S. Li, and zhenbin Chen. J. Sep. Sci. 40, 4847 (2017)

    CAS  PubMed  Article  Google Scholar 

  46. 46.

    K. Şarkaya, A. Demir, Polym. Bull. (2019). https://doi.org/10.1007/s00289-018-2657-7

    Article  Google Scholar 

  47. 47.

    L. Shan, Y. Gao, Y. Zhang, W. Yu, Y. Yang, S. Shen, S. Zhang, L. Zhu, L. Xu, B. Tian, J. Yun, Ind. Eng. Chem. Res. 55, 7655 (2016)

    CAS  Article  Google Scholar 

  48. 48.

    J. Siepmann, N.A. Peppas, Int. J. Pharm. 418, 6 (2011)

    CAS  PubMed  Article  Google Scholar 

  49. 49.

    I.Y. Wu, S. Bala, N. Škalko-Basnet, M.P. di Cagno, Eur. J. Pharm. Sci. 138, 105026 (2019)

    CAS  PubMed  Article  Google Scholar 

  50. 50.

    N. Sahiner, Polym. Adv. Technol. 29, 2184 (2018)

    CAS  Article  Google Scholar 

  51. 51.

    E. Jain, A. Damania, A.K. Shakya, A. Kumar, S.K. Sarin, A. Kumar, Colloids Surfaces B Biointerfaces 136, 761 (2015)

    CAS  PubMed  Article  Google Scholar 

  52. 52.

    D. Pamfil, C. Schick, C. Vasile, Ind. Eng. Chem. Res. 53, 11239 (2014)

    CAS  Article  Google Scholar 

  53. 53.

    B.D. Fecchio, S.R. Valandro, M.G. Neumann, C.C.S. Cavalheiro, J. Braz. Chem. Soc. 27, 278 (2016)

    CAS  Google Scholar 

  54. 54.

    I.E. Raschip, N. Fifere, C.D. Varganici, M.V. Dinu, Int. J. Biol. Macromol. 156, 608 (2020)

    CAS  PubMed  Article  Google Scholar 

  55. 55.

    S.S. Liu, X.P. Li, P.J. Qi, Z.J. Song, Z. Zhang, K. Wang, G.X. Qiu, G.Y. Liu, Polym. Test. 81, 106170 (2020)

    CAS  Article  Google Scholar 

  56. 56.

    M.V. Martinez, M. Molina, C.A. Barbero, J. Phys. Chem. B 122, 9038 (2018)

    CAS  PubMed  Article  Google Scholar 

  57. 57.

    M.V. Martinez, M.A. Molina, S.B. Abel, C.A. Barbero, MRS Adv. 3, 3735–3740 (2018)

    CAS  Article  Google Scholar 

  58. 58.

    J. Sameni, S. Krigstin, M. Sain, Acetylation & Lignin Solubility 12, 1548 (2017)

    CAS  Google Scholar 

  59. 59.

    İ Şener, K. Şarkaya, Süleyman Demirel Üniversitesi Fen Edeb. Fakültesi Fen Derg. 8, 175 (2013)

    Google Scholar 

  60. 60.

    K. Çetin, A. Denizli, Colloids Surfaces B Biointerfaces 126, 401 (2015)

    PubMed  Article  CAS  Google Scholar 

  61. 61.

    P. Öncel, K. Çetin, A.A. Topçu, H. Yavuz, A. Denizli, J. Biomater. Sci. Polym. Ed. 28, 519 (2017)

    PubMed  Article  CAS  Google Scholar 

  62. 62.

    M. Bakhshpour, H. Yavuz, A. Denizli, Artif Cells Nanomedicine Biotechnol. 46, 946 (2018)

    CAS  Article  Google Scholar 

  63. 63.

    P. Sharma, B.K. Saikia, M.R. Das, Colloids Surfaces A Physicochem. Eng. Asp. 457, 125 (2014)

    CAS  Article  Google Scholar 

  64. 64.

    M.V. Konovalova, P.A. Markov, E.A. Durnev, D.V. Kurek, S.V. Popov, V.P. Varlamov, J. Biomed. Mater. Res. Part A 105, 547 (2017)

    CAS  Article  Google Scholar 

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Acknowledgements

This work was supported financially by the Düzce University Research Fund (Grant Number 2019.05.03.1024).

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Correspondence to Koray Şarkaya.

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Şarkaya, K., Allı, A. Synthesis and characterization of cryogels of p(HEMA-N-vinylformamide) and p(HEMA-N-Vinylpyrrolidone) for chemical release behaviour. J Porous Mater 28, 853–865 (2021). https://doi.org/10.1007/s10934-021-01037-9

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Keywords

  • Drug delivery systems
  • N-vinylformamide (VF)
  • N-vinylpyrrolidone (VP)
  • Supermacroporous cryogel