Cationic dye-sensitized degradation of sodium hyaluronate through photoinduced electron transfer in the upper excited state

Photochemistry and Photobiology

Volumn 74, Issue 3, 2001, Pages 369-377

  Kojima, Masanobu ^a   Takahashi, Kazuya ^a   Nakamura, Kimitoshi ^a,b  

^a SHINSHU UNIVERSITY   (Japan)

^b Nakamura Eye Clinic   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHOXYETHANOL; ALGINIC ACID; ARGON; BETA CYCLODEXTRIN; CARBOXYL GROUP; CATION; DYE; GAMMA CYCLODEXTRIN; HYALURONIC ACID; HYDROXYL RADICAL; METHYLENE BLUE; OXYGEN; PARAQUAT; POLYGALACTURONIC ACID; POLYMER; POLYSACCHARIDE; PULLULAN; ROSE BENGAL; SINGLET OXYGEN; THIONINE; TITANIUM DIOXIDE;

ABSORPTION SPECTROSCOPY; AERATION; AQUEOUS SOLUTION; ARTICLE; CALIBRATION; CATALYST; COMPLEX FORMATION; ELECTROCHEMISTRY; ELECTRON TRANSPORT; FLUORESCENCE; LIGHT; PHOTODEGRADATION;

EID: 0035470637     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2001)074<0369:CDSDOS>2.0.CO;2     Document Type: Article

References (37)

1. Lapčík Jr., Ľ., L. Lapčík, S. De Smedt, J. Demeester and P. Chabreček (1998) Hyaluronan: preparation, structure, properties, and applications. Chem. Rev. 98, 2663-2682.
2. Balazs, E. A. and J. L. Denlinger (1982) Aging changes in the vitreus. In Aging and Human Visual Function, Vol. 2 (Edited by R. Sekuler, D. Kline and K. Dismukes), pp. 45-57. Alan R. Liss, New York.
3. Lapčík Jr., Ľ., L. Omelka, K. Kuběna, A. Glatík and V. Kellö (1990) Photodegradation of hyaluronic acid and of the vitreous body. Gen. Physiol. Biophys. 9, 419-429.
4. Ueno, N. (1995) Changes in vitreous structure caused by oxygen free radicals. J. Jpn. Opthalmol. Soc. 99, 1342-1360.
5. Schepens, C. L. (1983) Retinal Detachment and Allied Diseases, pp. 36-67. Saunders, Philadelphia. [See also pp. 599-638]
6. Chaine, C., J. Sebag and C. Coscas (1983) The induction of retinal detachment. Trans. Ophthalmol. Soc. UK 103, 480-485.
7. Schwartz, E. (1988) Connective tissue alterations in the skin of ultraviolet irradiation hairless mice. J. Invest. Dermatol. 91, 158-161.
8. Takahashi, Y., O. Ishikawa, K. Okada, Y. Kojima, Y. Igarashi and Y. Miyachi (1996) Disaccharide analysis of human skin glycosaminoglycans in sun-exposed and sun-protected skin of aged people. J. Dermatol. Sci. 11, 129-133.
9. Wong, S. F., B. Halliwell, R. Richmond and W. R. Skowroneck (1981) The role of superoxide and hydroxyl radicals in the degradation of hyaluronic acid induced by metal ions and by ascorbic acid. J. Inorg. Biochem. 14, 127-134.
10. Myint, P., D. J. Deeble, P. C. Beaumont, S. M. Blake and G. O. Phillips (1987) The reactivity of various free radicals with hyaluronic acid: steady-state and pulse radiolysis studies. Biochem. Biophys Acta 925, 194-202.
11. Akiba, J., N. Ueno and B. Chakrabarti (1994) Mechanisms of photo-induced vitreous liquefaction. Curr. Eye Res. 13, 505-512.
12. Hikichi, T., J. Akiba, N. Ueno, A. Yoshida and B. Chakrabarti (1997) Cross-linking of vitreous collagen and degradation of hyaluronic acid induced by bilirubin-sensitized photochemical reaction. Jpn. J. Ophthalmol. 41, 154-159.
13. Frati, E., A.-M. Khative, P. Front, A. Panasyuk, F. Aprile and D. R. Mitrovic (1997) Degradation of hyaluronic acid by photosensitized riboflavin in vitro. Modulation of the effect by transition metals, radical quenchers, and metal chelators. Free Radic. Biol. Med. 22, 1139-1144.
14. McCord, J. M. (1974) Free radicals and inflammation: protection of synovial fluid by superoxide dismutase. Science 185, 529-531.
15. Greenwald, R. A. and W. W. Moy (1980) Effect of oxygen-derived free radicals on hyaluronic acid. Arthritis Rheum. 23, 455-463.
16. Andley, U. P. and B. Chakrabarti (1983) Role of singlet oxygen in the degradation of hyaluronic acid. Biochem. Biophys. Res. Commun. 115, 894-901.
17. Lapčík Jr., Ľ. and J. Schurz (1991) Photochemical degradation of hyaluronic acid by singlet oxygen. Colloid Polym. Sci. 269, 633-635.
18. Wasserman, H. H. and R. W. Murray (1979) Singlet Oxygen. Academic Press, New York.
19. Kojima, M., T. Takagi, C. Matsubara and K. Nakamura (2000) Methylene blue sensitized degradation of sodium hyaluronate through photoinduced electron transfer. Chem. Lett. 354-355. [Our previous paper]
20. De Smedt, S. C., P. Dekeyser, V. Ribitsch, A. Lauwers and J. Demeester (1993) Viscoelastic and transient network properties of hyaluronic acid as a function of the concentration. Biorheology 30, 31-41.
21. Stramel, R. D. and J. K. Thomas (1986) Photochemistry of methyl viologen in aqueous solution containing polymeric carboxylic acids. J. Chem. Soc., Faraday Trans. 2 82, 799-809.
22. 2 and cyclodextrins on the aggregation of dyes in aqueous solutions. J. Chem. Soc., Perkin Trans. 2, 455-459.
23. Koizumi, M., S. Kato, N. Mataga, T. Matsuura and Y. Usui (1978) Photosensitized Reactions. Kagakudojin, Kyoto.
24. Kojima, M., Y. Kuriyama, H. Sakuragi and K. Tokumaru (1991) Dye-sensitized oxygenation and dimerization of 4-methoxystyrene through electron transfer. Bull. Chem. Soc. Jpn. 64, 2724-2729.
25. Sherrington, D. C. (1990) Reaction of polymers. In Concise Encyclopedia of Polymer Science and Technology (Edited by J. I. Kroshwitz), pp. 964-969. Wiley, New York.
26. Sawyer, D. T. and E. T. Seo (1977) One-electron mechanism for the electrochemical reduction of molecular oxygen. Inorg. Chem. 16, 499-501.
27. Grela, M. A., M. E. J. Coronel and A. J. Colussi (1996) Quantitative spin-trapping studies of weakly illuminated titanium dioxide sols. Implications for the mechanism of photocatalysis. J. Phys. Chem. 100, 16 940-16 946.
28. 2 suspensions. J. Phys. Chem. B 101, 7127-7134.
29. Dunford, R., A. Salinaro, L. Cai, N. Serpone, S. Horikoshi, H. Hidaka and J. Knowland (1997) Chemical oxidation and DNA damage catalysed by inorganic sunscreen ingredients. FEBS Lett. 418, 87-90.
30. 2 photocatalysis. Photochemistory 29, 2-5.
31. Scotto, J. E. and M. J. Tigewell (1973) Periodate-induced viscosity decreases in aqueous solution of acetal- and ether-linked polymers. Carbohyd. Res. 28, 53-59.
32. Gilbert, B. C., D. M. King and C. B. Thomas (1984) The oxidation of some polysaccharides by the hydroxyl radical: an E.S.R investigation. Carbohydr. Res. 125, 217-235.
33. Murata, S., C. Iwanaga, T. Toda and H. Kokubun (1972) Fluorescence and radiationless transitions from the second excited states of azulene derivatives. Ber. Bunsen-Ges. Phys. Chem. 76, 1176-1183.
34. Turro, N. J., V. Ramamurthy, W. Cherry and W. Farneth (1978) The effect of wavelength on organic photoreactions in solution. Reactions from upper excited states. Chem. Rev. 78, 125-145.
35. Lapčík Jr., Ľ., P. Chabreček and A. Staško (1991) Photodegradation of hyaluronic acid: EPR and size exclusion chromatography study. Biopolymers 31, 1429-1435.
36. Balazs, E. A., Laurent T. C., Howe A. P. and Varga L. (1959) Irradiation of mucopolysaccharides with ultraviolet light and electrons. Radiat. Res. 11, 149-164.
37. Rehm, D. and A. Weller (1970) Kinetics of fluorescence quenching by electron and H-atom transfer. Isr. J. Chem. 8, 259-271.