Hostname: page-component-cd9895bd7-hc48f Total loading time: 0 Render date: 2024-12-28T19:37:22.952Z Has data issue: false hasContentIssue false
  • English
  • Français

Engineering star-shaped lactic acid oligomers to develop novel functional adhesives

Published online by Cambridge University Press:  17 April 2018

João M.C. Santos ,
Diana R.S. Travassos ,
Paula Ferreira ,
Dina S. Marques ,
Maria H. Gil ,
Sónia P. Miguel ,
Maximiano P. Ribeiro ,
Ilidio J. Correia  and
Cristina M.S.G. Baptista Open the ORCID record for Cristina M.S.G. Baptista [Opens in a new window]
João M.C. Santos
Affiliation:
CIEPQPF, Department of Chemical Engineering, University of Coimbra, Coimbra P-3030 790, Portugal
Diana R.S. Travassos
Affiliation:
CIEPQPF, Department of Chemical Engineering, University of Coimbra, Coimbra P-3030 790, Portugal
Paula Ferreira
Affiliation:
CIEPQPF, Department of Chemical Engineering, University of Coimbra, Coimbra P-3030 790, Portugal
Dina S. Marques
Affiliation:
CIEPQPF, Department of Chemical Engineering, University of Coimbra, Coimbra P-3030 790, Portugal
Maria H. Gil
Affiliation:
CIEPQPF, Department of Chemical Engineering, University of Coimbra, Coimbra P-3030 790, Portugal
Sónia P. Miguel
Affiliation:
CICS-UBI, Health Sciences Research Center, University of Beira Interior, Covilhã P-6200 506, Portugal
Maximiano P. Ribeiro
Affiliation:
CICS-UBI, Health Sciences Research Center, University of Beira Interior, Covilhã P-6200 506, Portugal; and UDI-IPG-Research Unit for Inland Development, Polytechnic Institute of Guarda, Guarda P-6300 559, Portugal
Ilidio J. Correia
Affiliation:
CICS-UBI, Health Sciences Research Center, University of Beira Interior, Covilhã P-6200 506, Portugal
Cristina M.S.G. Baptista*
Affiliation:
CIEPQPF, Department of Chemical Engineering, University of Coimbra, Coimbra P-3030 790, Portugal
*
a)Address all correspondence to this author. e-mail: cristina@eq.uc.pt
Get access

Abstract

Direct polycondensation of L-lactic acid with a comonomer allows tailoring the properties of the product from the very first step. The viscous L-lactic acid co-oligomers with star-shaped architectures obtained were modified with three different acrylate monomers. Regardless the functionalization agent, UV curing was fast and all materials were cell compatible and promoted cell adhesion. The physical properties of the three star-shaped films exhibited a consistent trend as swelling capacity, hydrolytic instability, and gel content decreased simultaneously. A higher network density increased crosslinking degree and gel content among the films with an isocyanate group. The methacrylic end group functionalized material, lowest molecular weight, consistently exhibited the higher hydrolytic instability. Comparison of physical properties of these films with the corresponding linear materials reported previously confirmed the influence of precursor molecular architecture on the final material. The methodology developed herein is prone to scale-up and lead to the industrial production of new bioadhesives.

Keywords

L-lactic acidfunctional biomaterialbiocompatibility
Type
Article
Information
Journal of Materials Research , Volume 33 , Issue 10 , 28 May 2018 , pp. 1463 - 1474
Check for updates
Copyright
Copyright © Materials Research Society 2018 

Access options

Get access to the full version of this content by using one of the access options below. (Log in options will check for institutional or personal access. Content may require purchase if you do not have access.)

References

REFERENCES

Donkerwolcke, M., Burny, F., and Muster, D.: Tissues and bone adhesives—Historical aspects. Biomaterials 19, 1461 (1998).Google Scholar
Duarte, A., Coelho, J., Bordado, J., Cidade, M., and Gil, M.: Surgical adhesives: Systematic review of the main types and development forecast. Prog. Polym. Sci. 37, 1031 (2012).Google Scholar
Mehdizadeh, M. and Yang, J.: Design strategies and applications of tissue bioadhesives. Macromol. Biosci. 13, 271 (2013).Google Scholar
Bouten, P.J., Zonjee, M., Bender, J., Yauw, S.T., van Goor, H., van Hest, J.C., and Hoogenboom, R.: The chemistry of tissue adhesive materials. Prog. Polym. Sci. 39, 1375 (2014).CrossRefGoogle Scholar
Mönkäre, J., Hakala, R., Vlasova, M., Huotari, A., Kilpeläinen, M., Kiviniemi, A., Meretoja, V., Herzig, K., Korhonen, H., and Seppälä, J.: Biocompatible photocrosslinked poly(ester anhydride) based on functionalized poly(ε-caprolactone) prepolymer shows surface erosion controlled drug release in vitro and in vivo. J. Controlled Release 146, 349 (2010).Google Scholar
Ifkovits, J.L. and Burdick, J.A.: Photopolymerizable and degradable biomaterials for tissue engineering applications. Tissue Eng. 13, 2369 (2007).CrossRefGoogle ScholarPubMed
Seppälä, J., Korhonen, H., Hakala, R., and Malin, M.: Photocrosslinkable polyesters and poly(ester anhydride)s for biomedical applications. Macromol. Biosci. 11, 1647 (2011).Google Scholar
Benson, R.S.: Use of radiation in biomaterials science. Nucl. Instrum. Methods Phys. Res., Sect. B 191, 752 (2002).Google Scholar
Decker, C.: Kinetic study and new applications of UV radiation curing. Macromol. Rapid Commun. 23, 1067 (2002).Google Scholar
Balakrishnan, B., Mohanty, M., Umashankar, P., and Jayakrishnan, A.: Evaluation of an in situ forming hydrogel wound dressing based on oxidized alginate and gelatin. Biomaterials 26, 6335 (2005).CrossRefGoogle Scholar
Dong-An, W., Varghese, S., Sharma, B., Strehin, I., Fermanian, S., Gorham, J., Fairbrother, D.H., Cascio, B., and Elisseeff, J.H.: Multifunctional chondroitin sulphate for cartilage tissue-biomaterial integration. Nat. Mater. 6, 385 (2007).Google Scholar
Serrero, A., Trombotto, S., Bayon, Y., Gravagna, P., Montanari, S., and David, L.: Polysaccharide-based adhesive for biomedical applications: Correlation between rheological behavior and adhesion. Biomacromolecules 12, 1556 (2011).Google Scholar
Ferreira, P., Coelho, J., and Gil, M.: Development of a new photocrosslinkable biodegradable bioadhesive. Int. J. Pharm. 352, 172 (2008).CrossRefGoogle ScholarPubMed
Brubaker, C.E. and Messersmith, P.B.: Enzymatically degradable mussel-inspired adhesive hydrogel. Biomacromolecules 12, 4326 (2011).CrossRefGoogle ScholarPubMed
Kord Forooshani, P. and Lee, B.P.: Recent approaches in designing bioadhesive materials inspired by mussel adhesive protein. J. Polym. Sci., Part A: Polym. Chem. 55, 9 (2017).Google Scholar
Xiao, L., Wang, B., Yang, G., and Gauthier, M.: Poly(lactic acid)-based biomaterials: Synthesis, modification and applications. In Biomedical Science, Engineering and Technology, Ghista, D.N., ed. (InTech, Rijeka, Croatia, 2012); p. 248.Google Scholar
Zheng, X., Wang, Y., Lan, Z., Lyu, Y., Feng, G., Zhang, Y., Tagusari, S., Kislauskis, E., Robich, M.P., and McCarthy, S.: Improved biocompatibility of poly(lactic-co-glycolic acid) and poly-L-lactic acid blended with nanoparticulate amorphous calcium phosphate in vascular stent applications. J. Biomed. Nanotechnol. 10, 900 (2014).Google Scholar
Marques, D., Santos, J., Ferreira, P., Correia, T., Correia, I., Gil, M., and Baptista, C.: Photocurable bioadhesive based on lactic acid. Mater. Sci. Eng. C 58, 601 (2016).Google Scholar
Marques, D.S., Santos, J.M., Ferreira, P., Correia, T.R., Correia, I.J., Gil, M.H., and Baptista, C.M.: Functionalization and photocuring of an L-lactic acid macromer for biomedical applications. Int. J. Polym. Mater. Polym. Biomater. 65, 497 (2016).Google Scholar
Santos, J., Marques, D., Alves, P., Correia, T., Correia, I., Baptista, C.M., and Ferreira, P.: Synthesis, functionalization and characterization of UV-curable lactic acid based oligomers to be used as surgical adhesives. React. Funct. Polym. 94, 43 (2015).Google Scholar
Karikari, A.S., Mather, B.D., and Long, T.E.: Association of star-shaped poly(D,L-lactide)s containing nucleobase multiple hydrogen bonding. Biomacromolecules 8, 302 (2007).CrossRefGoogle ScholarPubMed
Hakala, R.A., Korhonen, H., and Seppälä, J.V.: Hydrolysis behaviour of crosslinked poly(ester anhydride) networks prepared from functionalised poly(ε-caprolactone) precursors. React. Funct. Polym. 73, 11 (2013).Google Scholar
Helminen, A.O., Korhonen, H., and Seppälä, J.V.: Structure modification and crosslinking of methacrylated polylactide oligomers. J. Appl. Polym. Sci. 86, 3616 (2002).Google Scholar
Marrian, S.: The chemical reactions of pentaerythritol and its derivatives. Chem. Rev. 43, 149 (1948).Google Scholar
Åkesson, D., Skrifvars, M., Seppälä, J., Turunen, M., Martinelli, A., and Matic, A.: Synthesis and characterization of a lactic acid-based thermoset resin suitable for structural composites and coatings. J. Appl. Polym. Sci. 115, 480 (2010).Google Scholar
Karikari, A.S., Edwards, W.F., Mecham, J.B., and Long, T.E.: Influence of peripheral hydrogen bonding on the mechanical properties of photo-cross-linked star-shaped poly(D,L-lactide) networks. Biomacromolecules 6, 2866 (2005).Google Scholar
Vieira, A., Ferreira, P., Coelho, J., and Gil, M.: Photocrosslinkable starch-based polymers for ophthalmologic drug delivery. Int. J. Biol. Macromol. 43, 325 (2008).Google Scholar
Almeida, J., Ferreira, P., Lopes, A., and Gil, M.: Photocrosslinkable biodegradable responsive hydrogels as drug delivery systems. Int. J. Biol. Macromol. 49, 948 (2011).Google Scholar
Dinescu, S., Galateanu, B., Albu, M., Cimpean, A., Dinischiotu, A., and Costache, M.: Sericin enhances the bioperformance of collagen-based matrices preseeded with human-adipose derived stem cells (hADSCs). Int. J. Mol. Sci. 14, 1870 (2013).Google Scholar
Miguel, S.P., Ribeiro, M.P., Brancal, H., Coutinho, P., and Correia, I.J.: Thermoresponsive chitosan–agarose hydrogel for skin regeneration. Carbohydr. Polym. 111, 366 (2014).Google Scholar
Makadia, H.K. and Siegel, S.J.: Poly lactic-co-glycolic acid (PLGA) as biodegradable controlled drug delivery carrier. Polymers 3, 1377 (2011).Google Scholar
Ma, X., Oyamada, S., Wu, T., Robich, M.P., Wu, H., Wang, X., Buchholz, B., McCarthy, S., Bianchi, C.F., and Sellke, F.W.: In vitro and in vivo degradation of poly(D,L-lactide-co-glycolide)/amorphous calcium phosphate copolymer coated on metal stents. J. Biomed. Mater. Res., Part A 96, 632 (2011).Google Scholar
Mason, N., Miles, C., and Sparks, R.: Hydrolytic degradation of poly DL-(Lactide). In Biomedical and Dental Applications of Polymers, Vol. 14, Gebelein, C.G. and Koblitz, F.F., eds. (Polymer Science and Technology, Plenum, New York, 1981); p. 279.CrossRefGoogle Scholar
Vidovic, E.: The development of bioabsorbable hydrogels on the basis of polyester grafted poly(vinyl alcohol). Ph.D. thesis, Rheinisch-Westfälischen Technischen Hochschule Aachen, Aachen, Germany, 2006.Google Scholar
Fraley, S.I., Feng, Y., Krishnamurthy, R., Kim, D-H., Celedon, A., Longmore, G.D., and Wirtz, D.: A distinctive role for focal adhesion proteins in three-dimensional cell motility. Nat. Cell Biol. 12, 598 (2010).Google Scholar
Supplementary material: Image

Santos et al. supplementary material

Santos et al. supplementary material 1

Download Santos et al. supplementary material(Image)
Image 2.8 MB
Supplementary material: Image

Santos et al. supplementary material

Santos et al. supplementary material 2

Download Santos et al. supplementary material(Image)
Image 186.6 KB
Supplementary material: Image

Santos et al. supplementary material

Santos et al. supplementary material 3

Download Santos et al. supplementary material(Image)
Image 17.2 MB
Supplementary material: Image

Santos et al. supplementary material

Santos et al. supplementary material 4

Download Santos et al. supplementary material(Image)
Image 3 MB
Supplementary material: Image

Santos et al. supplementary material

Santos et al. supplementary material 5

Download Santos et al. supplementary material(Image)
Image 1.7 MB