Givens, R. S. and Timberlake, G. T. and Conrad, P. G. and Yousef, A. L. and Weber, J. F. and Amslinger, S. (2003) A photoactivated diazopyruvoyl cross-linking agent for bonding tissue containing type-I collagen. Photochem. Photobiol. 78 (1), pp. 23-29.
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On the basis of the earlier examples of diazopyruvoyl (DAP) groups reported by Lawton for covalent binding and cross-linking of proteins and oligopeptides and our recent demonstration that a coumaryl diazopyruvamide was used to label Type-l collagen, we have extended our investigations to the synthesis and cross-linking capabilities of a bis-DAP polyethylene glycol to cross-link Type-I collagen. The new photo-activated cross-linking agent, NN'-bis(3-diazopyruvoyl)-2,2'(ethylenedioxy)bis(ethylamine) (DPD, 2), has been designed and synthesized specifically to "weld" collagenous tissues by cross-linking Type-l collagen. A working model for the photochemical welding studies of collagenous; tissues was developed using gelatin strips (gel strips) composed of denatured Type-I collagen. Gel strips are transparent to near-UV and visible light, uniform in thickness, and have reproducible composition. Furthermore, the availability of nucleophilic amine sites in gel strips was demonstrated by reaction with o-phthalaldehyde, producing a fluorescent derivative of the protein. Gel strips were coated with a solution of DPD in chloroform 7 irradiated at 320-390 nm, and the resulting bonded gel strips were tested for the strength of the weld. The welds were generally brittle and had average tensile strengths that exceeded 100 N/cm(2). Welds were not formed in the absence of light or DPD. Scanning electron microscopy studies revealed a pockmarked surface from severed welds. Welds of rabbit Achilles tendon were also obtained using the tethered diazopyruvamide. These welds were much weaker, having an average tensile strength of 11.95 N/cm(2) for DPD-2,2'-ethylenedioxy(bis)ethylamine comonomers in the cross-linking reaction. In both studies the welds obtained by this method were significantly stronger than the controls.
|Additional information (public):||Times Cited: 3|
|Institutions:||Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Dr. Sabine Amslinger|
|Keywords:||1,8-naphthalimide dyes articular-cartilage tensile-strength photolysis protein family solder skin|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||No|
|Owner:||Dr. Sabine Amslinger|
|Deposited On:||13 Jan 2010 15:51|
|Last Modified:||12 Nov 2012 13:20|