Biomechanical properties of carbodiimide crosslinked collagen: Influence of the formation of ester crosslinks

Journal of Biomedical Materials Research - Part A

Volumn 85, Issue 2, 2008, Pages 547-555

  Everaerts, Frank ^a   Torrianni, Mark ^b   Hendriks, Marc ^a   Feijen, Jan ^c  

^a MEDTRONIC BAKKEN RESEARCH CENTER   (Netherlands)

^b MEDTRONIC INC   (United States)

^c UNIVERSITY OF TWENTE   (Netherlands)

Author keywords

Carbodiimide crosslinking; Collagen; Hydrolysis; Jeffamine; Mechanical properties

Indexed keywords

CARBODIIMIDE CROSSLINKING; HYDROXYL GROUPS; JEFFAMINE;

BIOMECHANICS; CROSSLINKING; HYDROLYSIS;

COLLAGEN;

AMINE; CARBOXYL GROUP; COLLAGEN; CYANAMIDE; ESTER; HYDROXYL GROUP; N HYDROXYSUCCINIMIDE; N' (3 DIMETHYLAMINOPROPYL) N ETHYLCARBODIIMIDE; PROPIONALDEHYDE; UNCLASSIFIED DRUG;

ARTICLE; BIOMECHANICS; CHEMICAL BOND; COW; CROSS LINKING; DERMIS; HYDROLYSIS; NONHUMAN; PHYSICAL CHEMISTRY;

ANIMALS; BIOMECHANICS; CARBODIIMIDES; CATTLE; COLLAGEN; CROSS-LINKING REAGENTS; MATERIALS TESTING; TISSUE ENGINEERING;

EID: 42149190845     PISSN: 15493296     EISSN: 15524965     Source Type: Journal    
DOI: 10.1002/jbm.a.31524     Document Type: Article

References (29)

1. Hermansen GT. Bioconjugate Techniques. New York: Elsevier Science; 1996. p 144.
2. Hendriks M, Everaerts F, Verhoeven M. Alternative fixation of bioprosthesis. J Long Term Eff Med Implants 2001;11:163-183.
3. Olde Damink LH, Dijkstra PJ, van Luyn MJ, van Wachem PB, Nieuwenhuis P, Feijen J. Cross-linking of dermal sheep collagen using a water-soluble carbodiimide. Biomaterials 1996;17:765-773.
4. Olde Damink LH, Dijkstra PJ, van Luyn MJ, van Wachem PB, Nieuwenhuis P, Feijen J. In vitro degradation of dermal sheep collagen cross-linked using a water-soluble carbodiimide. Biomaterials 1996;17:679-684.
5. Rao KP. Recent developments of collagen-based materials for medical applications and drug delivery systems. J Biomater Sci Polym Ed 1995;7:623-645.
6. Olde Damink L. Structure and Properties of Crosslinked Dermal Sheep Collagen, PhD Thesis. Enschede, The Netherlands: University of Twente; 1993.
7. Eastoe JE. Composition of collagen and allied proteins. In: Davison P, editor. Treatise on Collagen, Vol. 1: Chemistry of Collagen. London: Academic Press; 1967. p 1-67.
8. Piez KA. Soluble collagen and the components resulting from its denaturation. In: Davison P, editor. Treatise on Collagen, Vol. 1: Chemistry of Collagen. London: Academis Press; 1967.
9. Koshland DE, Hoare DG. J Biol Chem 1967;242:2447-2453.
10. Sheehan JC. Carbodiimides in peptide chemistry. J Am Chem Soc 1955;77:1067.
11. Kurzer F, Douraghi-Zadeh K. Advances in the chemistry of carbodiimides. Chem Rev 1967;67:107-153.
12. Staros JV, Wright RW, Swingle DM. Enhancement by N-hydroxysulfosuccinimide of water-soluble carbodiimide-mediated coupling reactions. Anal Biochem 1986;156:220-222.
13. Powell HM, Boyce S. EDC cross-linking improves skin substitute strength and stability. Biomaterials 2006;27:5821-5827.
14. Hafemann B, Ghofrani K, Gattner HG, Stieve H, Pallua N. Cross-linking by 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC) of a collagen/elastin membrane meant to be used as a dermal substitute: Effects on physical, biochemical and biological features in vitro. J Mater Sci Mater Med 2001;12:437-446.
15. Buttafoco L, Kolkman NG, Engbers-Buijtenhuijs P, Poot AA, Dijkstra PJ, Vermes I, Feijen J. Electrospinning of collagen and elastin for tissue engineering applications. Biomaterials 2006;27:724-734.
16. Gratzer PF, Lee JM. Control of pH alters the type of crosslinking produced by 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (EDC) treatment of acellular matrix vascular grafts. J Biomed Mater Res 2001;58:172-179.
17. Hendriks M, Verhoeven M, Cahalan P, Torrianni M, Cahalan L, Fouache B. Process of making a bioprosthetic device. US Patent 6,166,184, December 26, 2000.
18. Hendriks M, Everaerts F, Gillissen M, Verhoeven M, Torrianni M. Methods of preparing crosslinked materials and bioprosthetic devices. US Patent 7,053,051 B2, May 30, 2006.
19. Everaerts FJL, Torrianni M, van Luyn M, Hendriks M, Feijen, J. Reduced calcification of bioprostheses, cross-linked via an improved carbodiimide based method. Biomaterials 2004;25:5523-5530.
20. Everaerts FJL, Gillissen M, Torrianni M, Zilla P, Human P, Feijen J. Reduction of calcification of carbodiimide-processed heart valve tissue by prior blocking of amine groups with monoaldehydes. J Heart Valve Dis 2006;15:269-277.
21. Girardot JM, Girardot MN. Amide cross-linking: An alternative to glutaraldehyde fixation. J Heart Valve Dis 1996;5:518-525.
22. Caruso A, Dunn M. Functional evaluation of collagen fiber scaffolds for ACL reconstruction: Cyclic loading in proteolytic enzyme solutions. J Biomed Mater Res A 2004;69:164-171.
23. Everaerts F, Torrianni, M, Hendriks M, Feijen J. Determination of carboxyl groups in carbodiimide cross-linked collagen sponges. J Biomed Mater Res A 2007 Jun 26; [Epub ahead of print].
24. Tomihata K, Ikada Y. Cross-linking of hyaluronic acid with water-soluble carbodiimide. J Biomed Mater Res 1997;37:243-251.
25. Zeeman R, Dijkstra PJ, van Wachem PB, van Luyn MJ, Hendriks M, Cahalan PT, Feijen J. Successive epoxy and carbodiimide cross-linking of dermal sheep collagen. Biomaterials 1999;20:921-931.
26. Zeeman R. Cross-linking and modification of porcine aortic heart valves. In: Cross-Linking of Collagen-Based Materials, PhD Thesis. Enschede, The Netherlands: University of Twente; 1998. p 125-148.
27. Morisson and Boyd. Organic Chemistry. Boston: Allyn and Bacon; 1981.
28. Girardot MN, Torrianni M, Girardot JM. Effect of AOA on glutaraldehyde-fixed bioprosthetic heart valve cusps and walls: Binding and calcification studies. Int J Artif Organs 1994;17:76-82.
29. Socrates, George. Infrared Characteristics Group Frequencies, 2nd ed. New York: Wiley; 1998.