Skip to main content

Advertisement

Log in

In situ formation of adhesive hydrogels based on PL with laterally grafted catechol groups and their bonding efficacy to wet organic substrates

  • Biomaterials Synthesis and Characterization
  • Original Research
  • Published:
Journal of Materials Science: Materials in Medicine Aims and scope Submit manuscript

Abstract

Adhesives with catechol moieties have been widely investigated in recent years. However, actually how much catechol groups for these mussel bio-inspired adhesives, especially in their natural form under physiological condition, is appropriate to bond with organic substrates has not been studied intensively. This study blends ε-polylysine (PL), featuring laterally grafted catechols under physiological conditions (pH 7.4), with oxidized dextran to form a hydrogel in situ via the Schiff base without introducing small cytotoxic molecules as crosslinking agents. It finds that the amount of catechol groups imposes an obvious influence on gelation time, swelling behavior, and hydrogel morphology. Both the storage modulus and adhesion strength are found to increase first and decrease afterwards with an increase of pendent catechol content. Furthermore, catechol hydrogen interactions and the decrease in the crosslink density derived from the decrease of amino groups on PL are simultaneously found to affect the storage modulus. Meanwhile, multiple hydrogen-bonding interactions of catechol with amino, hydroxyl, and carboxyl groups, which are in abundance on the surface of tissue, are mainly found to provide an adhesive force. The study finds that with more catechol, there is a greater chance that the cohesive force will weaken, making the entire adhesion strength of the hydrogel decrease. Using a cytotoxicity test, the nontoxicity of the hydrogel towards the growth of L929 cells is proven, indicating that hydrogels have potential applications in soft tissue repair under natural physiological conditions.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Mehdizadeh M, Yang J. Design strategies and applications of tissue bioadhesives. Macromol Biosci. 2013;13:271–88.

    Article  Google Scholar 

  2. Duarte A, Coelho J, Bordado J, Cidade M, Gil M. Surgical adhesives: systematic review of the main types and development forecast. Prog Polym Sci. 2012;37:1031–50.

    Article  Google Scholar 

  3. Thetter O. Fibrin adhesive and its application in thoracic surgery. Thorac Cardiov Surg. 1981;29:290–2.

    Article  Google Scholar 

  4. Kim BJ, Oh DX, Kim S, Seo JH, Hwang DS, Masic A, et al. Mussel-mimetic protein-based adhesive hydrogel. Biomacromolecules. 2014;15:1579–85.

    Article  Google Scholar 

  5. Mehdizadeh M, Weng H, Gyawali D, Tang L, Yang J. Injectable citrate-based mussel-inspired tissue bioadhesives with high wet strength for sutureless wound closure. Biomaterials. 2012;33:7972–83.

    Article  Google Scholar 

  6. Bae KH, Wang L-S, Kurisawa M. Injectable biodegradable hydrogels: progress and challenges. J Mater Chem B. 2013;1:5371–88.

    Article  Google Scholar 

  7. Deming TJ. Synthetic polypeptides for biomedical applications. Prog Polym Sci. 2007;32:858–75.

    Article  Google Scholar 

  8. Ko DY, Shinde UP, Yeon B, Jeong B. Recent progress of in situ formed gels for biomedical applications. Prog Polym Sci. 2013;38:672–701.

    Article  Google Scholar 

  9. Hyon SH, Nakajima N, Sugai H, Matsumura K. Low cytotoxic tissue adhesive based on oxidized dextran and epsilon-poly-l-lysine. J Biomed Mater Res A. 2014;102:2511–20.

    Article  Google Scholar 

  10. Li Y, Liu C, Tan Y, Xu K, Lu C, Wang P. In situ hydrogel constructed by starch-based nanoparticles via a Schiff base reaction. Carbohyd Polym. 2014;110:87–94.

    Article  Google Scholar 

  11. Wang T, Nie J, Yang D. Dextran and gelatin based photocrosslinkable tissue adhesive. Carbohyd Polym. 2012;90:1428–36.

    Article  Google Scholar 

  12. Shukla SC, Singh A, Pandey AK, Mishra A. Review on production and medical applications of ɛ-polylysine. Biochem Eng J. 2012;65:70–81.

    Article  Google Scholar 

  13. Nakajima N, Sugai H, Tsutsumi S, Hyon SH. Self-degradable bioadhesive. Key Eng Mater. 2007;342:713–6.

    Article  Google Scholar 

  14. Takaoka M, Nakamura T, Sugai H, Bentley AJ, Nakajima N, Fullwood NJ, et al. Sutureless amniotic membrane transplantation for ocular surface reconstruction with a chemically defined bioadhesive. Biomaterials. 2008;29:2923–31.

    Article  Google Scholar 

  15. Lee BP, Messersmith PB, Israelachvili JN, Waite JH. Mussel-inspired adhesives and coatings. Annu Rev Mater Res. 2011;41:99.

    Article  Google Scholar 

  16. Sedó J, Saiz-Poseu J, Busqué F, Ruiz-Molina D. Catechol-based biomimetic functional materials. Adv Mater. 2013;25:653–701.

    Article  Google Scholar 

  17. Bouten PJ, Zonjee M, Bender J, Yauw ST, van Goor H, van Hest J, et al. The chemistry of tissue adhesive materials. Prog Polym Sci. 2014;39:1375–405.

    Article  Google Scholar 

  18. Burke SA, Ritter-Jones M, Lee BP, Messersmith PB. Thermal gelation and tissue adhesion of biomimetic hydrogels. Biomed Mater. 2007;2:203.

    Article  Google Scholar 

  19. Choi YC, Choi JS, Jung YJ, Cho YW. Human gelatin tissue-adhesive hydrogels prepared by enzyme-mediated biosynthesis of DOPA and Fe3+ ion crosslinking. J Mater Chem B. 2014;2:201–9.

    Article  Google Scholar 

  20. Oh DX, Hwang DS. A biomimetic chitosan composite with improved mechanical properties in wet conditions. Biotechnol Progr. 2013;29:505–12.

    Article  Google Scholar 

  21. Zhang H, Bré LP, Zhao T, Zheng Y, Newland B, Wang W. Mussel-inspired hyperbranched poly (amino ester) polymer as strong wet tissue adhesive. Biomaterials. 2014;35:711–9.

    Article  Google Scholar 

  22. Huang K, Lee BP, Ingram DR, Messersmith PB. Synthesis and characterization of self-assembling block copolymers containing bioadhesive end groups. Biomacromolecules. 2002;3:397–406.

    Article  Google Scholar 

  23. Yavvari PS, Srivastava A. Robust, self-healing hydrogels from catechol rich polymers. J Mater Chem B. 2015;3:899–910.

    Article  Google Scholar 

  24. Xu J, Zhou Z, Wu B, He B. Enzymatic formation of a novel cell-adhesive hydrogel based on small peptides with a laterally grafted l-3,4-dihydroxyphenylalanine group. Nanoscale. 2014;6:1277–80.

    Article  Google Scholar 

  25. Yu M, Hwang J, Deming TJ. Role of l-3,4-dihydroxyphenylalanine in mussel adhesive proteins. J Am Chem Soc. 1999;121:5825–6.

    Article  Google Scholar 

  26. Jenkins CL, Meredith HJ, Wilker JJ. Molecular weight effects upon the adhesive bonding of a mussel mimetic polymer. ACS Appl Mater Int. 2013;5:5091–6.

    Article  Google Scholar 

  27. Matos-Pérez CR, White JD, Wilker JJ. Polymer composition and substrate influences on the adhesive bonding of a biomimetic, cross-linking polymer. J Am Chem Soc. 2012;134:9498–505.

    Article  Google Scholar 

  28. Meredith HJ, Jenkins CL, Wilker JJ. Enhancing the adhesion of a biomimetic polymer yields performance rivaling commercial glues. Adv Funct Mater. 2014;24:3259–67.

    Article  Google Scholar 

  29. Maia J, Ferreira L, Carvalho R, Ramos MA, Gil MH. Synthesis and characterization of new injectable and degradable dextran-based hydrogels. Polymer. 2005;46:9604–14.

    Article  Google Scholar 

  30. Hoffmann B, Volkmer E, Kokott A, Augat P, Ohnmacht M, Sedlmayr N, et al. Characterisation of a new bioadhesive system based on polysaccharides with the potential to be used as bone glue. J Mater Sci Mater Med. 2009;20:2001–9.

    Article  Google Scholar 

  31. Saxer S, Portmann C, Tosatti S, Gademann K, Zürcher S, Textor M. Surface assembly of catechol-functionalized poly(l-lysine)-graft-poly (ethylene glycol) copolymer on titanium exploiting combined electrostatically driven self-organization and biomimetic strong adhesion. Macromolecules. 2009;43:1050–60.

    Article  Google Scholar 

  32. Jin R, Hiemstra C, Zhong Z, Feijen J. Enzyme-mediated fast in situ formation of hydrogels from dextran-tyramine conjugates. Biomaterials. 2007;28:2791–800.

    Article  Google Scholar 

  33. JungáChung H, GwanáPark T. Thermo-sensitive, injectable, and tissue adhesive sol-gel transition hyaluronic acid/pluronic composite hydrogels prepared from bio-inspired catechol-thiol reaction. Soft Matter. 2010;6:977–83.

    Article  Google Scholar 

  34. Kull S, Martinelli I, Briganti E, Losi P, Spiller D, Tonlorenzi S, et al. Glubran2 surgical glue. In vitro evaluation of adhesive and mechanical properties. J Surg Res. 2009;157:e15–21.

    Article  Google Scholar 

  35. Ninan L, Monahan J, Stroshine RL, Wilker JJ, Shi R. Adhesive strength of marine mussel extracts on porcine skin. Biomaterials. 2003;24:4091–9.

    Article  Google Scholar 

  36. Chung H, Grubbs RH. Rapidly cross-linkable dopa containing terpolymer adhesives and PEG-based cross-linkers for biomedical applications. Macromolecules. 2012;45:9666–73.

    Article  Google Scholar 

  37. Weng L, Chen X, Chen W. Rheological characterization of in situ crosslinkable hydrogels formulated from oxidized dextran and N-carboxyethyl chitosan. Biomacromolecules. 2007;8:1109–15.

    Article  Google Scholar 

  38. Zhou Y, Nie W, Zhao J, Yuan X. Rapidly in situ forming adhesive hydrogel based on a PEG-maleimide modified polypeptide through Michael addition. J Mater Sci Mater Med. 2013;24:2277–86.

    Article  Google Scholar 

  39. Peak CW, Wilker JJ, Schmidt G. A review on tough and sticky hydrogels. Colloid Polym Sci. 2013;291:2031–47.

    Article  Google Scholar 

  40. Zhang F, Liu S, Zhang Y, Wei Y, Xu J. Underwater bonding strength of marine mussel-inspired polymers containing DOPA-like units with amino groups. RSC Adv. 2012;2:8919–21.

    Article  Google Scholar 

  41. Weng L, Romanov A, Rooney J, Chen W. Non-cytotoxic, in situ gelable hydrogels composed of N-carboxyethyl chitosan and oxidized dextran. Biomaterials. 2008;29:3905–13.

    Article  Google Scholar 

  42. Zhang H, Qadeer A, Chen W. In situ gelable interpenetrating double network hydrogel formulated from binary components: thiolated chitosan and oxidized dextran. Biomacromolecules. 2011;12:1428–37.

    Article  Google Scholar 

  43. Sparks BJ, Hoff EF, Hayes LP, Patton DL. Mussel-inspired thiolene polymer networks: influencing network properties and adhesion with catechol functionality. Chem Mater. 2012;24:3633–42.

    Article  Google Scholar 

  44. Tung CYM, Dynes PJ. Relationship between viscoelastic properties and gelation in thermosetting systems. J Appl Polym Sci. 1982;27:569–74.

    Article  Google Scholar 

  45. Winter HH, Chambon F. Analysis of linear viscoelasticity of a crosslinking polymer at the gel point. J Rheol (1978–present). 1986;30:367–82.

    Article  Google Scholar 

  46. Hong S, Yang K, Kang B, Lee C, Song IT, Byun E, et al. Hyaluronic acid catechol: a biopolymer exhibiting a pH-dependent adhesive or cohesive property for human neural stem cell engineering. Adv Funct Mater. 2013;23:1774–80.

    Article  Google Scholar 

  47. Lih E, Lee JS, Park KM, Park KD. Rapidly curable chitosan–PEG hydrogels as tissue adhesives for hemostasis and wound healing. Acta Biomater. 2012;8:3261–9.

    Article  Google Scholar 

  48. Serrero A, Trombotto S, Bayon Y, Gravagna P, Montanari S, David L. Polysaccharide-based adhesive for biomedical applications: correlation between rheological behavior and adhesion. Biomacromolecules. 2011;12:1556–66.

    Article  Google Scholar 

  49. Wang J, Liu C, Lu X, Yin M. Co-polypeptides of 3,4-dihydroxyphenylalanine and l-lysine to mimic marine adhesive protein. Biomaterials. 2007;28:3456–68.

    Article  Google Scholar 

Download references

Acknowledgments

The authors respectively acknowledge the support of this research from the National Natural Science Foundation of China. (Grant 51103095).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Jin Zhao.

Additional information

Mingming Ye and Rui Jiang have contributed equally to this article.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ye, M., Jiang, R., Zhao, J. et al. In situ formation of adhesive hydrogels based on PL with laterally grafted catechol groups and their bonding efficacy to wet organic substrates. J Mater Sci: Mater Med 26, 273 (2015). https://doi.org/10.1007/s10856-015-5608-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10856-015-5608-y

Keywords

Navigation