Effect of oxazolidine E on collagen fibril formation and stabilization of the collagen matrix

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 17, 2007, Pages 6813-6822

  Deb Choudhury, Santanu ^a   Haverkamp, Richard G ^a   DasGupta, Samir ^b   Norris, Gillian E ^a  

^a MASSEY UNIVERSITY   (New Zealand)

^b Leather & Shoe Research Association of New Zealand   (New Zealand)

Author keywords

AFM; Collagen; MS MS; Reconstituted collagen fibrils

Indexed keywords

COLLAGEN; CROSS LINKING REAGENT; OXAZOLE DERIVATIVE; OXAZOLIDINE; PEPTIDE; UNCLASSIFIED DRUG;

AMINO ACID SEQUENCE; ARTICLE; CHEMISTRY; DRUG STABILITY; MASS SPECTROMETRY; SCANNING ELECTRON MICROSCOPY;

AMINO ACID SEQUENCE; COLLAGEN; CROSS-LINKING REAGENTS; DRUG STABILITY; MICROSCOPY, ELECTRON, SCANNING; OXAZOLES; PEPTIDES; SPECTROMETRY, MASS, MATRIX-ASSISTED LASER DESORPTION-IONIZATION;

EID: 34548305124     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf070025i     Document Type: Article

References (47)

1. Chapman, J. A.; Tzaphlidou, M.; Meek, K. M.; Kadler, K. E. The collagen fibril-a model system for studying the staining and fixation of a protein. Electron Microsc. Rev. 1990, 3, 143-182.
2. Kadler, K. E. Extracellular matrix 1: Fibril-forming collagens. Protein Profile 1995, 2, 491-619.
3. Sato, K.; Ebihara, T.; Adachi, E.; Kawashima, S.; Hattori, S.; Irie, S. Possible involvement of aminotelopeptide in self-assembly and thermal stability of collagen I as revealed by its removal with proteases. J. Biol. Chem. 2000, 275, 25870-25875.
4. Kadler, K. E.; Holmes, D. F.; Trotter, J. A.; Chapman, J. A. Collagen fibril formation. Biochem. J. 1996, 316 (1), 1-11.
5. Veis, A.; George, A. In Fundamentals of interstitial collagen self-assembly. In Extracellular Matrix assembly and structure; Yurchenco, P. D., Birk, D. E., Mecham, R. P., Eds; Academic press: San Diego, CA, 1994; pp 15-45.
6. Gayatri, R.; Sharma. A. K.; Rajaram. R.; Ramasami, T. Chromium(III)-induced structural changes and self-assembly of collagen. Biochem. Biophys. Res. Commun. 2001, 283 (1), 229-235.
7. Wold, F. The reaction of bovine serum albumin with the bifunctional reagent p,p′-difluoro-m,m′-dinitro-diphenyl-sulfone. J. Biol. Chem. 1961, 236, 106-111.
8. Marfey, P. S.; Nowak, H.; Uziel, M.; Yphantis, D. A. Reaction of bovine pancreatic ribonuclease A with 1,5-difluoro-2,4-dinitrobenzene. I. Preparation of monomelic intramolecularly bridged derivatives. J. Biol. Chem. 1965, 240, 3264-3269.
9. Ramirez, D. M.; Leppla, S. H.; Schneerson, R.; Shiloach, J. Production, recovery and immunogenicity of the protective antigen from a recombinant strain of Bacillus anthracis. J. Ind. Microbiol. Biotechnol. 2002, 28 (4), 232-238.
10. Leppla, S. H.; Robbins, J. B.; Schneerson, R.; Shiloach, J. Development of an improved vaccine for anthrax. J. Clin. Invest. 2002, 110 (2), 141-144.
11. Murdin, A. D.; Barreto, L.; Plotkin, S. Inactivated poliovirus vaccine: past and present experience. Vaccine 1996, 14 (8), 735-746.
12. Kambic, H.; Picha, G.; Kiraly, R.; Koshino, L.; Nose, Y. Application of aldehyde treatments to cardiovascular devices. Trans. Am. Soc. Artif. Intern. Organs 1976, 22, 664-672.
13. Veis, A.; Drake, M. P. The introduction of intramolecular covalent cross linkages into ichthyocol tropocollagen with monofunctional aldehydes. J. Biol. Chem. 1963, 238, 2003-2011.
14. Scott, J. E.; Thomlinson, A. M. The structure and interfibrillar proteoglycan bridges ('shape modules') in extracellular matrix of fibrous connective tissues and their stability in various chemical environments. J. Anat. 1998, 192, 391-405.
15. Haverkamp, R. G.; Williams, M. A. K.; Scott, J. E. Stretching Single Molecules of Connective Tissue Glycans to Characterize Their Shape-Maintaining Elasticity Biomacromolecules 2005, 6, 1816-1818.
16. Greenwald, R. A.; Schwartz, C. E.; Cantor, J. O. Interaction of cartilage proteoglycans with collagen-substituted agarose gels. Biochem. J. 1975, 145, 601-605.
17. Gilbert, D. L.; Okano, T.; Miyata, T.; Sung Wan Kim. Wan. Macromolecular diffusion through collagen membranes. Int. J. Pharm. 1988, 47 (1-3), 79-88.
18. Vasantha, R.; Sehgal, P. K.; Panduranga Rao, K. Collagen ophthalmic inserts for pilocarpine drug delivery system. Int. J. Pharm. 1988, 47 (1-3), 95-102.
19. D'Aquino, A.; Barbani, N.; D'Elia, G.; Lupinacci, D.; Naviglio, B.; Seggiani, M.; Tomaselli, M.; Vitolo, S. Combining Organic tanning Based On Mimosa And Oxazolidine: Development Of A Semi-Industrial Scale Process For High-Quality Bovine Upper Leather. J. Soc. Leather Technol. Chem. 2003, 88, 47-55.
20. Lu, Z.; Liao, X.; Shi, B. The reaction of vegetable tannin-aldehyde- collagen: a further understanding of vegetable tannin-aldehyde combination tannage. J. Soc. Leather Technol. Chem. 2003, 87 (5), 173-178.
21. Covington, A. D.; Shi, B. High stability organic tanning using plant polyphenols. Part 1. The interactions between vegetable tannins and aldehydic crosslinkers. J. Soc. Leather Technol. Chem. 1998, 82 (2), 64-71.
22. Okitani, A.; Kaneko, S.; Tashiro, Y.; Hayase, F.; Kato, H. Polymerization of proteins and impairment of their amino acid residues due to vaporized hexanal. Dev. Food Sci. 1986, 13 (Amino-Carbonyl React. Food Biol. Syst.), 125-134.
23. Fraenkel-Conrat, H.; Olcott, H. S. Reaction of formaldehyde with proteins. V. Cross-linking between amino and primary amide or guanidyl groups. J. Am. Chem. Soc. 1948, 70, 2673-2684.
24. Shi, B.; He, Y.; Fan, H.; Zeng, S.; Covington, A. D.; Attenburrow, G. E. High stability organic tanning using plant polyphenols. Part 2.: The mechanism of the vegetable tannin-oxazolidine tannage. J. Soc. Leather Technol. Chem. 1999, 83 (1), 8-13.
25. Hansma, H. G.; Hoh, J. H. Biomolecular imaging with the atomic force microscope. Annu. Rev. Biophys. Biomol. Struct. 1994, 23, 115-39.
26. Paige, M. F.; Rainey, J. K.; Goh, M. C. Fibrous long spacing collagen ultrastructure elucidated by atomic force microscopy. Biophys. J. 1998, 74, 3211-3216.
27. Wallace, D. The role of hydrophobic bonding in collagen fibril formation: a quantitative model. Biopolymers 1985, 24, 1705-1720.
28. Trelstad, R. L.; Hayashi, K.; Gross, J. Collagen Fibrillogenesis: Intermediate Aggregates and Suprafibrillar Order. PNAS 1976, 73, 4027-4031.
29. Prockop, D. J.; Fertala, A. Inhibition of the self-assembly of collagen I into fibrils with synthetic peptides. Demonstration that assembly is driven by specific binding sites on the monomers. J. Biol. Chem. 1998, 273, 15598-15604.
30. Williams, B. R.; Gelman, R. A.; Poppke, D. C.; Piez, K. A. Collagen fibril formation. Optimal in vitro conditions and preliminary kinetic results. J. Biol. Chem. 1978, 253, 6578-6585.
31. Kadler, K. E.; Hojima, Y.; Prockop, D. J. Assembly of type I collagen fibrils de novo. Between 37 and 41°C the process is limited by micro-unfolding of monomers. J. Biol. Chem. 1988, 263, 10517-10523.
32. Holmes, D. F.; Watson, R. B.; Chapman, J. A.; Kadler, K. E. Enzymic control of collagen fibril shape. J. Mol. Biol. 1996, 261, 93-97.
33. Hulmes, D. J. S.; Miller, A.; Parry, D. A. D.; Piez, K. A.; Woodhead-Galloway, J. Analysis of the primary structure of collagen for the origins of molecular packing. J. Mol. Biol. 1973, 79, 137-148.
34. Suarez, G.; Veliz, M.; Nagel, R. L. Role of hydrophobic interactions in collagen fibril formation: effect of alkylureas in vitro. Arch. Biochem. Biophys. 1980, 205, 422-427.
35. Kuznetsova, N.; Chi, S. L.; Leikin, S. Sugars and polyols inhibit fibrillogenesis of type I collagen by disrupting hydrogen-bonded water bridges between the helices. Biochemistry 1998, 37, 11888-11895.
36. Adachi, E.; Hopkinson, I.; Hayashi, T. Basement-membrane stromal relationships: interactions between collagen fibrils and the lamina densa. Int. Rev. Cytol. 1997, 173, 73-225.
37. Metz, B.; Kersten, G. F. A.; Hoogerhout, P.; Brugghe, H. F.; Timmermans, H. A. M.; deJong, A.; Meiring, H.; Ken, H. J.; Henninks, W. E.; Crommelin, D. J. A.; Jiskoot, W. Identification of formaldehyde-induced modifications in proteins. J. Biol. Chem. 2004, 279, 6235-6243.
38. Shevchenko, A.; Wilm, M.; Vorm, O.; Mann, M. Mass Spectrometric Sequencing of Proteins from Silver-Stained Polyacrylamide Gels. Anal. Chem. 1996, 68, 850-858.
39. Aubert-Foucher, E.; Font, B.; Eichenberger, D.; Goldschmidt, D.; Lethias, C.; van der Rest, M. Purification and characterization of native type XIV collagen. J. Biol. Chem. 1992, 267, 15759-15764.
40. Chandrakasan, G.; Torchia, D. A.; Piez, K. A. Preparation of intact monomelic collagen from rat tail tendon and skin and the structure of the nonhelical ends in solution. J. Biol. Chem. 1976, 251 (19), 6062-6067.
41. Suzuki, Y.; Someki, I.; Adachi, E.; Me, S.; Hattori, S. Interaction of collagen molecules from the aspect of fibril formation: acid-soluble, alkali-treated, and MMP1-digested fragments of type I collagen. J. Biochem. (Tokyo) 1999, 126, 54-67.
42. Fu, Q.; Li, L. Fragmentation of Peptides with N-terminal Dimethylation and Imine/Methylol Adduction at the Tryptophan Side-Chain. J. Am. Soc. Mass Spectrom. 2006, 17, 859-866.
43. Deb Choudhury, S.; DasGupta, S.; Norris, G. E. Unravelling the mechanism of the interactions of oxazolidine A and E with collagens in ovine skin. Int. J. Biol. Macromol. 2006 (doi:10.1016/j.ijbiomac.2006.09.003).
44. The Journal of Experimental Medicine; The Rockefeller Institute for Medical Research: New York, 1948; Vol. 88, pp 555-568.
45. Gutsman, T.; Fantner, G. E.; Venturoni, M.; Ekani-Nkodo, A.; Thompson, J. B.; Kindt, J. H.; Morse, D. E.; Fygenson, D. K.; Hansma, P. K. Evidence that collagen fibrils in tendons are inhomogenously structured in a tubelike manner. Biophys. J. 2003, 84, 2593-2598.
46. Watanabe, K.; Nakagawa, J.; Ebihara, T.; Okamoto, Y. Structural effects of cross-linking reagents on triple-helix reformation of intramolecularly cross-linked collagen. Polymer 1996, 37, 1285-1288.
47. Gelman, R. A.; Williams, B. R.; Piez, K. A. Collagen fibril formation. Evidence for a multistep process. J. Biol. Chem. 1979, 254, 180-186.