Identification of radicals from hyaluronan (hyaluronic acid) and crosslinked derivatives using electron paramagnetic resonance spectroscopy

Carbohydrate Polymers

Volumn 38, Issue 1, 1999, Pages 17-22

  Al Assaf, Saphwan ^a   Hawkins, Clare L ^b   Parsons, Barry J ^a   Davies, Michael J ^b   Phillips, Glyn O ^a  

^a GLYNDWR UNIVERSITY   (United Kingdom)

^b HEART RESEARCH INSTITUTE   (Australia)

Author keywords

EPR; Free radicals; Hyaluronan; Hydroxyl radicals; Hylan

Indexed keywords

CROSSLINKING; ELECTRON SPIN RESONANCE SPECTROSCOPY; FREE RADICAL REACTIONS; HYDROGEN PEROXIDE; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; MONOMERS; PH EFFECTS; REDOX REACTIONS; TITANIUM;

ACETYL GLUCOSAMINE; HYALURONIC ACID; HYDROGEN ABSTRACTION;

POLYSACCHARIDES;

EID: 0032715672     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0144-8617(98)00084-8     Document Type: Article

References (31)

1. Al-Assaf, S. (1997). Rheological properties and free radical stability of cross-linked hyaluronan (Hylan). Ph.D. thesis, University of Salford.
2. Al-Assaf, S., Phillips, G.O., Deeble, D.J., Parsons, B., Starnes, H., & von Sonntag, C. (1995). The enhanced stability of the cross-linked hylan structure to hydroxyl (OH) radical s compared with the uncross-linked hyaluronan. Radiat. Phys Chem., 46, 207-217.
3. Balazs, E.A., Davies, J.V., Phillips, G.O., & Young, M.D. (1967). Transient intermediates in the radiolysis of hyaluronic acid. Radiat. Res, 10, 243-255.
4. Balazs, E.A., & Leshchiner, E.A. (1989). Hyaluronan, its cross-linked derivative hylan and their medical application. In H. Inagaki & G.O. Phillips (Eds), Cellulosic utilization - research and rewards in cellulosic (pp. 233-241). Elsevier: New York.
5. Behrens, G., Koltzenburg, G., & Schulte-Frohlinde, D. (1982). Mode reactions for the degradation of DNA-4′ radicals in aqueous solution. Fast hydrolysis of α-alkoxyalkyl radicals with a leaving group in β-position followed by radical rearrangement and elimination reactions Z. Naturforsch., Teil C, 37, 1205-1227.
6. Buley, A.L., Norman, R.O.C., & Pritchett, R.J. (1966). Electron spin resonance studies of oxidation. Part VIII. Elimination reactions of some hydroxyalkyl radicals J. Chem. Soc. B, 849-852.
7. Deeble, D.J., Bothe, E., Schuchmann, H.-P., Parsons, B.J., Phillips, G.O., & von Sonntag, C. (1990). The kinetics of hydroxyl radical-induced strand breakage of hyaluronic acid: a pulse radiolysis study using conductometry and laser light scattering. Z. Naturforsch., Teil C, 45, 1031-1043.
8. Deeble, D.J., Phillips, G.O., Bothe, E., Schuchmann, H.-P., & von Sonntag, C. (1991). The radiation induced degradation of hyaluronic acid. Radiat. Phys Chem., 37, 115-118.
9. Gilbert, B.C., Larkin, J.P., & Norman, R.O.C. (1972). Electron spin resonance studies Part XXXIII. Evidence for heterolytic and homolytic transformations of radicals from 1,2-diols and related compounds J. Chem. Soc., Perkin Trans, 2, 794-802.
10. Gilbert, B.C., King, D.M., & Thomas, C.B. (1980). The selectivity of attack by OH radicals on myoinositol, and the importance of stereoelectronic factors upon radical rearrangement. An electron-spin-resonance study. J. Chem. Soc., Perkin Trans, 2, 1821-1827.
11. Gilbert, B.C., King, D.M., & Thomas, C.B. (1981). Radical reactions of carbohydrates Part 2. An electron spin resonance study of oxidation of D-glucose and related compounds with the hydroxyl radical. J. Chem. Soc., Perkin Trans, 2, 1186-1199.
12. Gilbert, B.C., King, D.M., & Thomas, C.B. (1982). Radical reactions of carbohydrates Part 3. ESR investigation of base catalysed rearrangements of radicals derived from D-glucose and related compounds J. Chem. Soc., Perkin Trans, 2, 169-179.
13. Gilbert, B.C., King, D.M., & Thomas, B. (1984). The oxidation of some polysaccharides by the hydroxyl radical: an ESR investigation. Carbohydr. Res, 125, 217-235.
14. Greenwald, R.A. (1991). Oxygen radicals, inflammation, and arthritis - pathophysiological considerations and implications for treatment. Semin. Arthritis Rheum., 20, 219-240.
15. Gutteridge, J.M.C. (1987). Bleomycin-detectable iron in knee-joint synovial-fluid from arthritic patients and its relationship to the extracellular antioxidant activities of ceruloplasmin, transferrin and lactoferrin. Biochem. J., 245, 415-421.
16. Gunning, A.P., Morris, V.J., Al-Assaf, S., & Phillips, G.O. (1996). Atomic force microscopic studies of hylan and hyaluronan. Carbohydr. Polym., 30, 1-8.
17. Halliwell, B. (1985). Metal ions and oxygen radical reactions in human inflammatory joint disease. Philos Trans R. Soc. London, Series B, 311, 659-671.
18. Halliwell, B. (1987). Oxidants, inflammation and anti-inflammatory drugs. FASEB J., 2, 2867-2873.
19. Hawkins, C.L., & Davies, M.J. (1996). Direct detection and identification of radical s generated during the hydroxyl radical-induced degradation of hyaluronic acid and related materials Free Radical Biol. Med., 21, 275-290.
20. Livingston, R., & Zeldes, H. (1966). Paramagnetic resonance study of liquids during photolysis. III. Aqueous solutions of alcohols with hydrogen peroxide. J. Am. Chem. Soc., 88, 4333-4336.
21. Moore, J.S., Phillips, G.O., Davies, J.V., & Dodgson, K.S. (1970). Reactions of the connective and related polyanions with hydrated electrons and hydroxyl radicals Carbohydr. Res, 12, 253-260.
22. Myint, P., Deeble, D.J., Beaumont, P.C., Blake, S.M., & Phillips, G.O. (1987). The reactivity of various free radicals with hyaluronic acid: steady state and pulse radiolysis studies Biochim. Biophys Acta, 925, 194-202.
23. Nakamura, Y., Ogiwara, Y., & Phillips, G.O. (1985). Freeradical formation and degradation of cellulose by ionising radiation. Polym. Photochem., 6, 135-159.
24. Parsons, B.J. (1994). Chemical aspects of free radical reactions in connective tissue. In C.A. Rice-Evans & R.H. Burdon (Eds), Free radical damage and its control (pp. 281-300). Amsterdam: Elsevier.
25. Phillips, G.O. (1992). Molecular transformations in connective tissue hyaluronic acid. In W.G. Glasser & H. Hatakayma (Eds), Am. Chem. Soc. Symposium Series 489 (pp. 168-183).
26. Steenken, S., Davies, M.J., & Gilbert, B.C. (1986). Pulse radiolysis and electron spin resonance studies of the dehydration of radicals from 1,2-diols and related compounds J. Chem. Soc., Perkin Trans, 2, 1003-1014.
27. 2O-saturated aqueous solution. Part II. Quantitative measurement. Mechanisms of the radical-induced scission of the glycosidic linkage. Z. Naturforsch., Teil B, 31, 857-864.
28. von Sonntag, C. (1980). Free radical reactions of carbohydrates as studied by radiation chemistry techniques Adv. Carbohydr. Chem. Biochem., 37, 7-77.
29. von Sonntag, C. (1987). The chemical basis of radiation biology. London: Taylor & Francis
30. Wedlock, D.J., Phillips, G.O., Davies, A., Gormally, J., & Wyn-Jones, E. (1983). Depolymerisation of sodium hyaluronate during freeze drying. Int. J. Biol. Macromol., 5, 186-188.
31. Weissman, B., & Meyer, K. (1954). The structure of hyalubiuronic acid and hyaluronic acid from umbilical cord. J. Am. Chem. Soc., 76, 1753-1757.