Portal de Periódicos da CAPES

A Photoactivated Diazopyruvoyl Cross-linking Agent for Bonding Tissue Containing Type-I Collagen¶

2003; Wiley; Volume: 78; Issue: 1 Linguagem: Inglês

10.1562/0031-8655(2003)078 2.0.co;2

1751-1097

Richard S. Givens, George T. Timberlake, Peter G. Conrad, Abraham L. Yousef, Jörg F. Weber, Sabine Amslinger,

Surgical Sutures and Adhesives

Photochemistry and PhotobiologyVolume 78, Issue 1 p. 23-29 A Photoactivated Diazopyruvoyl Cross-linking Agent for Bonding Tissue Containing Type-I Collagen¶ Richard S. Givens, Corresponding Author Richard S. Givens Department of Chemistry, University of Kansas, Lawrence, KS Department of Ophthalmology, University of Kansas Medical Center, Kansas City, KS *To whom correspondence should be addressed at: Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, 2010 Malott Hall, Lawrence, KS 66045-7582, USA. Fax: 785-864-5396; [email protected]Search for more papers by this authorGeorge T. Timberlake, George T. Timberlake Department of Chemistry, University of Kansas, Lawrence, KS Department of Ophthalmology, University of Kansas Medical Center, Kansas City, KSSearch for more papers by this authorPeter G. Conrad II, Peter G. Conrad II Department of Chemistry, University of Kansas, Lawrence, KSSearch for more papers by this authorAbraham L. Yousef, Abraham L. Yousef Department of Chemistry, University of Kansas, Lawrence, KSSearch for more papers by this authorJörg F. Weber, Jörg F. Weber Department of Chemistry, University of Kansas, Lawrence, KSSearch for more papers by this authorSabine Amslinger, Sabine Amslinger Department of Chemistry, University of Kansas, Lawrence, KSSearch for more papers by this author Richard S. Givens, Corresponding Author Richard S. Givens Department of Chemistry, University of Kansas, Lawrence, KS Department of Ophthalmology, University of Kansas Medical Center, Kansas City, KS *To whom correspondence should be addressed at: Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, 2010 Malott Hall, Lawrence, KS 66045-7582, USA. Fax: 785-864-5396; [email protected]Search for more papers by this authorGeorge T. Timberlake, George T. Timberlake Department of Chemistry, University of Kansas, Lawrence, KS Department of Ophthalmology, University of Kansas Medical Center, Kansas City, KSSearch for more papers by this authorPeter G. Conrad II, Peter G. Conrad II Department of Chemistry, University of Kansas, Lawrence, KSSearch for more papers by this authorAbraham L. Yousef, Abraham L. Yousef Department of Chemistry, University of Kansas, Lawrence, KSSearch for more papers by this authorJörg F. Weber, Jörg F. Weber Department of Chemistry, University of Kansas, Lawrence, KSSearch for more papers by this authorSabine Amslinger, Sabine Amslinger Department of Chemistry, University of Kansas, Lawrence, KSSearch for more papers by this author First published: 01 May 2007 https://doi.org/10.1562/0031-8655(2003)0780023APDCAF2.0.CO2Citations: 4 ¶ Posted on the website on 28 April 2003. Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onEmailFacebookTwitterLinkedInRedditWechat ABSTRACT 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-I 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 photoactivated cross-linking agent, N,N′-bis(3-diazopyruvoyl)-2,2′-(ethylenedioxy)bis(ethylamine) (DPD, 2), has been designed and synthesized specifically to "weld" collagenous tissues by cross-linking Type-I 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/cm2. 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/cm2 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. REFERENCES 1 Mackenzie, D. (1973) The history of sutures. Med. Hist, 17, 158–168. 10.1017/S0025727300018469 CASPubMedGoogle Scholar 2 Snyder, C. C. (1976) On the history of the suture. Plast. Reconstr. Surg, 58, 401–405. 10.1097/00006534-197610000-00001 CASPubMedWeb of Science®Google Scholar 3 Black, J. J. 1982 A stitch in time—1: the history of sutures Nurs. Times 619–622. April 14th issue Google Scholar 4 Hamarneh, S. K., H. A. Awad (1977) Early surgical instruments excavated in old Cairo, Egypt. Int. Surg, 62, 520–524. PubMedWeb of Science®Google Scholar 5 Schober, R., F. Ulrich, T. Sander, H. Dürselen, S. Hessel (1986) Laser-induced alteration of collagen substructure allows microsurgical tissue welding. Science, 232, 1421–1422. 10.1126/science.3715454 CASPubMedWeb of Science®Google Scholar 6 Tang, J., G. Godlewski, S. Rouy, G. Delacrétaz (1997) Morphologic changes in collagen fibers after 830 nm diode laser welding. Lasers Surg. Med, 21, 438–443. 10.1002/(SICI)1096-9101(1997)21:5 3.0.CO;2-R CASPubMedWeb of Science®Google Scholar 7 Fried, N. M., J. T. Walsh (2000) Laser skin welding: in vivo tensile strength and wound healing results. Lasers Surg. Med, 27, 55–65. 10.1002/1096-9101(2000)27:1 3.0.CO;2-5 CASPubMedWeb of Science®Google Scholar 8 Bass, L. S., S. K. Libutti, A. M. Eaton 1993 New solders for laser welding and sealing Lasers Surg. Med. Suppl 5 63 Google Scholar 9 Phillips, A. B. M., B. Y. Ginsburg, S. J. Shin, R. Soslow, W. Ko, D. P. Poppas (1999) Laser welding for vascular anastomosis using albumin solder: an approach for MID-CAB. Lasers Surg. Med, 24, 264–268. 10.1002/(SICI)1096-9101(1999)24:4 3.0.CO;2-# CASPubMedWeb of Science®Google Scholar 10 McNally, K. M., B. S. Sorg, E. K. Chan, A. J. Welch, J. M. Dawes, E. R. Owen (1999) Optimal parameters for laser tissue soldering. Part I: tensile strength and scanning electron microscopy analysis. Lasers Surg. Med, 24, 319–331. 10.1002/(SICI)1096-9101(1999)24:5 3.0.CO;2-N CASPubMedWeb of Science®Google Scholar 11 Judy, M. M., J. L. Matthews, R. L. Boriack, A. Burlacu, D. E. Lewis, R. E. Utecht (1993) Photochemical cross-linking of proteins with visible-light-absorbing 1,8-naphthalimide dyes. SPIE, 1882, 305–308. 10.1117/12.147669 Web of Science®Google Scholar 12 Judy, M. M., H. Nosir, R. W. Jackson, J. L. Matthews, D. E. Lewis, R. E. Utecht, D. Yuan (1996) Bonding of human meniscal and articular cartilage with photoactive 1,8-naphthalimide dyes. SPIE, 2671, 251–255. 10.1117/12.240015 Web of Science®Google Scholar 13 Judy, M. M., H. Nosir, R. W. Jackson, J. L. Matthews, R. E. Utecht, D. E. Lewis, D. Yuan (1998) Photochemical bonding of skin with 1,8-naphthalimide dyes. SPIE, 3195, 21–24. 10.1117/12.297902 Web of Science®Google Scholar 14 Timberlake, G. T., P. V. Mitrev, M. M. Judy, H. Nosir, J. L. Matthews 1997 Corneal laser welding using a light-activated, protein-crosslinking dye Investig. Ophthalmol. Vis. Sci. (ARVO Suppl.) 38 S510 PubMedWeb of Science®Google Scholar 15 Judy, M. M., R. W. Jackson, H. R. Nosir, J. L. Matthews, J. D. Loyd, D. E. Lewis, R. E. Utecht, D. Yuan 1997 Healing results in meniscus and articular cartilage photochemically welded with 1,8-naphthalimide dyes SPIE 2970 257–260 10.1117/12.275051 Web of Science®Google Scholar 16 Stewart, R. B., C. B. Bleustein, P. B. Petratos, K. C. Chin, D. P. Poppas, R. T. V. Kung (2001) Concentrated autologous plasma protein: a biochemically neutral solder for tissue welding. Lasers Surg. Med, 29, 336–342. 10.1002/lsm.1126 CASPubMedWeb of Science®Google Scholar 17 Goodfellow, V. S., M. Settineri, R. G. Lawton (1989) p-Nitrophenyl 3-diazopyruvate and diazopyruvamides, a new family of photoactivatable cross-linking bioprobes. Biochemistry, 28, 6346–6360. 10.1021/bi00441a030 CASPubMedWeb of Science®Google Scholar 18 Timberlake, G. T., G. K. Reddy, L. Stehno-Bittel, J. F. Weber, S. Amslinger, R. S. Givens (2002) Photoactivated coumaryl-diazopyruvate fluorescent label for amine functional groups of tissues containing type I collagen. Photochem. Photobiol, 76, 473–479. 10.1562/0031-8655(2002)0760473PCDFLF2.0.CO2 PubMedWeb of Science®Google Scholar 19 Meier, H., K. P. Zeller (1975) The Wolff rearrangement of α-diazo carbonyl compounds. Angew. Chem. Int. Ed. Engl, 14, 32–43. 10.1002/anie.197500321 Web of Science®Google Scholar 20 Wolff, L. (1902) Ueber diazoanhydride. Liebigs Annalen der Chemie, 325, 129–195. 10.1002/jlac.19023250202 Web of Science®Google Scholar 21 Wolff, L. (1913) Diazo anhydrides (1,2,3-oxydiazoles or diazo oxides) and diazo ketones. Liebigs Annalen der Chemie, 394, 23–59. 10.1002/jlac.19123940104 Google Scholar 22 Harrison, J. K., R. G. Lawton, M. E. Gnegy (1989) Development of a novel photoreactive calmodulin derivative: cross-linking of purified adenylate cyclase from bovine brain. Biochemistry, 28, 6023–6027. 10.1021/bi00440a045 PubMedWeb of Science®Google Scholar 23 Taylor, J. M., G. G. Jacob-Mosier, R. G. Lawton, R. R. Neubig (1994) Coupling an α2-adrenergic receptor peptide to G-protein: a new photolabeling agent. Peptides, 15, 829–834. 10.1016/0196-9781(94)90038-8 PubMedWeb of Science®Google Scholar 24 Jacob Mosier, G. G., R. G. Lawton (1995) Development of a new family of thiol specific photoactivatable cross-linking agents. J. Org. Chem, 60, 6953–6958. 10.1021/jo00126a055 Web of Science®Google Scholar 25 Woodhead-Galloway, J. 1980 Collagen: The Anatomy of a Protein, pp. 20–21 Edward Arnold (Publishers) Limited, London Google Scholar 26 Roth, M. (1971) Fluorescence reaction for amino acids. Anal. Chem, 43, 880–882. 10.1021/ac60302a020 CASPubMedWeb of Science®Google Scholar 27 Judy, M. M., J. L. Matthews, R. L. Boriack, A. Burlacu, D. E. Lewis, R. E. Utrecht (1993) Heat-free photochemical tissue welding with 1,8-naphthalimide dyes using visible (420 nm) light. SPIE, 1876, 175–179. 10.1117/12.147028 Web of Science®Google Scholar 28 Johns, P., A. Courts 1977 Relationship between collagen and gelatin In The Science and Technology of Gelatin (Edited by A. G. Ward and A. Courts). Academic Press, New York . pp 137–177 Google Scholar 29 Barton, D. H. R., G. Quinkert 1960 Photochemical transformations. VI. Photochemical cleavage of cyclohexadienones J. Chem. Soc. 1–9 Web of Science®Google Scholar 30 Chiang, Y., A. J. Kresge, V. V. Popik (1999) Scavenging of intermediates formed in photolysis of α-diazocarbonyl compounds and hydroxycyclopropenones. Implication on the mechanism of the photo-Wolff reaction. J. Am. Chem. Soc, 121, 5930–5932. 10.1021/ja9906406 CASWeb of Science®Google Scholar 31 Ortica, F., G. Pohlers, J. C. Scaiano, J. F. Cameron, A. Zampini (2000) Laser flash photolysis of 2-diazo-1,3-diphenyl-1,3-propanedione: an unusual long-lived triplet as a reaction intermediate. Org. Lett, 2, 1357–1360. 10.1021/ol005590k CASPubMedWeb of Science®Google Scholar Citing Literature Volume78, Issue1July 2003Pages 23-29 ReferencesRelatedInformation