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Poly(2-oxazoline) hydrogels by photoinduced thiol-ene “click” reaction using different dithiol crosslinkers

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Abstract

Fabrication of a library of biocompatible hydrogels by photoinduced thiol-ene “click” reaction is described. The hydrogels are based on two different statistical copolymers consisting of 2-butenyl-2-oxazoline (EnOx) with either 2-methyl-2-oxazoline (MeOx) or 2-ethyl-2-oxazoline (EtOx). Crosslinking is achieved via pendant vinyl groups of EnOx in the copolymers with selected dithiol crosslinkers, namely dithiothreitol, 1,3-propanedithiol, 1,6-hexanedithiol, and 1,9-nonanedithiol by thiol-ene photocoupling. On the basis of different polarity and flexibility of particular dithiols and three different molar ratios to double bonds, it is possible to control swelling and mechanical characteristics of resulting hydrogels. Biocompatibility of all hydrogel types is verified by determination of toxicity of hydrogel extracts and contact direct toxicity towards mice 3T3 fibroblast cell line. The resulting low toxicity of all prepared hydrogels predetermines its utilization in biomedicine.

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References

  1. Kade MJ, Burke DJ, Hawker CJ (2010) J Polym Sci Pt A Polym Chem 48:743–750

    Article  CAS  Google Scholar 

  2. Hoyle CE, Bowman CN (2010) Angew Chem Int Ed 49:1540–1573

    Article  CAS  Google Scholar 

  3. Gould ST, Darling NJ, Anseth KS (2012) Acta Biomater 8:3201–3209

    Article  CAS  Google Scholar 

  4. Tauhardt L, Pretzel D, Bode S, Czaplewska J, Kempe K, Gottschaldt M, Schubert US (2014) J Polym Sci Pt A Polym Chem 52:1–12

    Article  Google Scholar 

  5. Schmitz M, Kuhlmann M, Reimann O, Hackenberger CPR, Groll J (2015) Biomacromolecules 16:1088–1094

    Article  CAS  Google Scholar 

  6. Kharkar PM, Rehmann MS, Skeens KM, Maverakis E, Kloxin AM (2016) ACS Biomater Sci Eng 2:165–179

    Article  CAS  Google Scholar 

  7. Hoogenboom R (2009) Angew Chem - Int Ed 48:7978–7994

    Article  CAS  Google Scholar 

  8. Bauer M, Lautenschlaeger C, Kempe K, Tauhardt L, Schubert US, Fischer D (2012) Macromol Biosci 12:986–998

    Article  CAS  Google Scholar 

  9. Luxenhofer R, Han Y, Schulz A, Tong J, He Z, Kabanov AV, Jordan R (2012) Macromol Rapid Commun 33:1613–1631

    Article  CAS  Google Scholar 

  10. Kronek J, Kroneková Z, Lustoň J, Paulovičová E, Paulovičová L, Mendrek B (2011) J Mater Sci Mater Med 22:1725–1734

    Article  CAS  Google Scholar 

  11. Kronek J, Paulovičová E, Paulovičová L, Kroneková Z, Lustoň J (2012) J Mater Sci Mater Med 23:1457–1464

    Article  CAS  Google Scholar 

  12. Bauer M, Schroeder S, Tauhardt L, Kempe K, Schubert US, Fischer D (2013) J Polym Sci Pt A Polym Chem 51:1816–1821

    Article  CAS  Google Scholar 

  13. Goddard P, Hutchinson LE, Brown J, Brookman LJ (1989) J Control Release 10:5–16

    Article  CAS  Google Scholar 

  14. Gaertner FC, Luxenhofer R, Blechert B, Jordan R, Essler M (2007) J Control Release 119:291–300

    Article  CAS  Google Scholar 

  15. Wyffels L, Verbrugghen T, Monnery BD, Glassner M, Stroobants S, Hoogenboom R, Staelens S (2016) J Control Release 235:63–71

    Article  CAS  Google Scholar 

  16. Gress A, Völkel A, Schlaad H (2007) Macromolecules 40:7928–7933

    Article  CAS  Google Scholar 

  17. Diehl C, Schlaad H (2009) Macromol Biosci 9:157–161

    Article  CAS  Google Scholar 

  18. Tauhardt L, Pretzel D, Kempe K, Gottschaldt M, Schubert US (2014) Polym Chem 5:5751–5764

    Article  CAS  Google Scholar 

  19. Rinkenauer AC, Tauhardt L, Wendler F, Kempe K, Gottschaldt M, Traeger A, Schubert US (2015) Macromol Biosci 15:414–425

    Article  CAS  Google Scholar 

  20. Kempe K, Hoogenboom R, Schubert US (2011) Macromol Rapid Commun 32:1484–1489

    Article  CAS  Google Scholar 

  21. Kempe K, Hoogenboom R, Jaeger M, Schubert US (2011) Macromolecules 44:6424–6432

    Article  CAS  Google Scholar 

  22. Hartlieb M, Kempe K, Schubert US (2015) J Mater Chem B 3:526–538

    Article  CAS  Google Scholar 

  23. Hoffman AS (2012) Adv Drug Deliv Rev 64:18–23

    Article  Google Scholar 

  24. Lin CC, Ki CS, Shih H (2015) J Appl Polym Sci 132:1–11

    Article  Google Scholar 

  25. Hoare TR, Kohane DS (2008) Polymer 49:1993–2007

    Article  CAS  Google Scholar 

  26. Madaghiele M, Sannino A, Ambrosio L, Demitri C (2014) Burn Trauma 2:153–161

    Article  Google Scholar 

  27. Caló E, Khutoryanskiy VV (2015) Eur Polym J 65:252–267

    Article  Google Scholar 

  28. Dargaville TR, Forster R, Farrugia BL, Kempe K, Voorhaar L, Schubert US, Hoogenboom R (2012) Macromol Rapid Commun 33:1695–1700

    Article  CAS  Google Scholar 

  29. Farrugia BL, Kempe K, Schubert US, Hoogenboom R, Dargaville TR (2013) Biomacromolecules 14:2724–2732

    Article  CAS  Google Scholar 

  30. Kalaoglu-Altan OI, Verbraeken B, Lava K, Gevrek TN, Sanyal R, Dargaville TR, De Clerck K, Hoogenboom R, Sanyal A (2016) ACS Macro Lett 5:676–681

    Article  CAS  Google Scholar 

  31. Englert C, Tauhardt L, Hartlieb M, Kempe K, Gottschaldt M, Schubert US (2014) Biomacromolecules 15:1124–1131

    Article  CAS  Google Scholar 

  32. Fimberger M, Behrendt A, Jakopic G, Stelzer F, Kumbaraci V, Wiesbrock F (2016) Macromol Rapid Commun 37:233–238

    Article  CAS  Google Scholar 

  33. Schenk V, Ellmaier L, Rossegger E, Edler M, Griesser T, Weidinger G, Wiesbrock F (2012) Macromol Rapid Commun 33:396–400

    Article  CAS  Google Scholar 

  34. Dargaville TR, Lava K, Verbraeken B, Hoogenboom R (2016) Macromolecules 49:4774–4783

    Article  CAS  Google Scholar 

  35. Luef KP, Petit C, Ottersböck G, Ehrenfeld F, Grassl B, Reynaud S, Wiesbrock F (2016) Eur Polym J. 88:701-712

  36. Zahoranová A, Kroneková Z, Zahoran M, Chorvát D, Janigová I, Kronek J (2016) J Polym Sci Pt A Polym Chem 54:1548–1559

    Article  Google Scholar 

  37. Néry L, Lefebvre H, Fradet A (2003) Macromol Chem Phys 204:1755–1764

    Article  Google Scholar 

  38. Kasák P, Kroneková Z, Krupa I, Lacík I (2011) Polymer 52:3011–3020

    Article  Google Scholar 

  39. Luxenhofer R, Bezen M, Jordan R (2008) Macromol Rapid Commun 29:1509–1513

    Article  CAS  Google Scholar 

  40. Glassner M, D’Hooge DR, Young Park J, Van Steenberge PHM, Monnery BD, Reyniers MF, Hoogenboom R (2015) Eur Polym J 65:298–304

    Article  CAS  Google Scholar 

  41. Cramer NB, Scott JP, Bowman CN (2002) Macromolecules 35:5361–5365

    Article  CAS  Google Scholar 

  42. Peppas NA, Hilt JZ, Khademhosseini A, Langer R (2006) Adv Mater 18:1345–1360

    Article  CAS  Google Scholar 

  43. Discher DE, Janmey P, Wang YL (2005) Science 310:1139–1143

    Article  CAS  Google Scholar 

  44. Anseth KS, Bowman CN, Brannon-Peppas L (1996) Biomaterials 17:1647–1657

    Article  CAS  Google Scholar 

  45. Kyburz KA, Anseth KS (2013) Acta Biomater 9:6381–6392

    Article  CAS  Google Scholar 

  46. Kroneková Z, Mikulec M, Petrenčíková N, Paulovičová E, Paulovičová L, Jančinová V, Nosál’ R, Reddy PS, Shimoga GD, Chorvát D, Kronek J (2016) Macromol Biosci 16:1200–1211

    Article  Google Scholar 

  47. Pu X, Kamendulis LM, Klaunig JE (2006) Environ Mol Mutagen 47:631–638

    Article  CAS  Google Scholar 

  48. Banerjee S, Segal A (1986) Cancer Lett 32:293–304

    Article  CAS  Google Scholar 

  49. Kronek J, Lustoň J, Kroneková Z, Paulovičová E, Farkaš P, Petrenčíková N, Paulovičová L, Janigová I (2010) J Mater Sci Mater Med 21:879–886

    Article  CAS  Google Scholar 

  50. Luxenhofer R, Sahay G, Schulz A, Alakhova D, Bronich TK, Jordan R, Kabanov AV (2011) J Control Release 153:73–82

    Article  CAS  Google Scholar 

  51. Williams CG, Malik AN, Kim TK, Manson PN, Elisseeff JH (2005) Biomaterials 26:1211–1218

    Article  CAS  Google Scholar 

  52. Bryant SJ, Nuttelman CR, Anseth KS (2000) J Biomater Sci Polym Ed 11:439–457

    Article  CAS  Google Scholar 

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Acknowledgements

The authors acknowledge the Slovak Grant Agency VEGA for the financial support in the project No. 2/0163/15 and the Slovak Research and Development Agency for financial support in the project No. APVV-15-0485. This work was also supported by the M-ERA.NET Transantional Call 2013 with the acronym M2Neural. The authors are thankful to Angela Kleinová for FTIR measurements and Ondrej Slučiak for his practical advice and comments.

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Correspondence to Juraj Kronek.

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Šrámková, P., Zahoranová, A., Kroneková, Z. et al. Poly(2-oxazoline) hydrogels by photoinduced thiol-ene “click” reaction using different dithiol crosslinkers. J Polym Res 24, 82 (2017). https://doi.org/10.1007/s10965-017-1237-0

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