Porphyrin-induced photooxidation of conjugated bilirubin

Free Radical Research

Volumn 37, Issue 10, 2003, Pages 1061-1067

  Shishido, Naomi ^a   Nakayama, Kenji ^b   Nakamura, Masao ^a  

^a ASAHIKAWA MEDICAL COLLEGE   (Japan)

^b HOKKAIDO INSTITUTE OF PUBLIC HEALTH   (Japan)

Author keywords

Bilirubin; Conjugated bilirubin; Hyperbilirubinaemia; Phototherapy; Singlet oxygen; Uroporphyrin

Indexed keywords

BILIRUBIN; BILIRUBIN DERIVATIVE; BILIRUBIN GLUCURONIDE; BILIVERDIN; COPPER COMPLEX; COPROPORPHYRIN; PIPERIDINE DERIVATIVE; PORPHYRIN; PYRROLE DERIVATIVE; SCAVENGER; SINGLET OXYGEN; SODIUM AZIDE; UROPORPHYRIN;

ARTICLE; BLEACHING; CHEMICAL REACTION; CONCENTRATION RESPONSE; CONTROLLED STUDY; ELECTRON SPIN RESONANCE; LIGHT ABSORPTION; LIGHT IRRADIANCE; PH; PHOTOOXIDATION; ULTRAVIOLET RADIATION;

ANTIOXIDANTS; AZIDES; BILIRUBIN; COPPER; CYCLIC N-OXIDES; ELECTRON SPIN RESONANCE SPECTROSCOPY; HUMANS; LIGHT; OXYGEN; PHOTOTHERAPY; PORPHYRINS; SODIUM AZIDE; SPECTROPHOTOMETRY; TIME FACTORS; UROPORPHYRINS;

EID: 0142094029     PISSN: 10715762     EISSN: None     Source Type: Journal    
DOI: 10.1080/10715760310001600381     Document Type: Article

References (33)

1. Kopelman, A.E., Brown, R.S. and Odel, G.B. (1972) "The bronze baby syndrome: a complication of phototherapy", J. Pediatr. 81, 466-472.
2. Lucey, J., Ferreiro, M. and Hewitt, J. (1968) "Prevention of hyperbilirubinemia of prematurity by phototherapy" Pediatrics 41, 1047-1054.
3. Bonnett, R., Davies, J.E. and Hursthouse, M.B. (1976) "Structure of bilirubin" Natur̄e 262, 326-328.
4. McDonagh, A.F. and Ramonas, L.M. (1978) "Jaundice phototherapy: micro flow-cell photometry reveals rapid biliary response of Gunn rats to light" Science 201, 829-831.
5. McDonagh, A.F., Palma, L.A., Trull, F.R. and Lightner, D.A. (1982) "Phototherapy for neonatal jaundice. Configurational isomers of bilirubin" J. Am. Chem. Soc. 104, 6865 - 6867.
6. McDonagh, A.F., Palma, L.A. and Lightner, D.A. (1982) "Phototherapy for neonatal jaundice. Stereospecific and regioselective photoisomerization of bilirubin bound to human serum albumin and NMR characterization of intramolecularly cyclized photoproducts" J. Am. Chem. Soc. 104, 6867-6869.
7. Onishi, S., Itoh, S., Isobe, K., Togari, H., Kitoh, H. and Nishimura, Y (1982) "Mechanism of development of bronze baby syndrome in neonates treated with phototherapy" Pediatrics 69, 273-276.
8. Onishi, S., Miura, I., Isobe, K., Itoh, S., Ogino, T., Yokoyama, T. and Yamakawa, T. (1984) "Structure and thermal interconversion of cyclobilirubin IXα", Biochem. J. 218, 667-676.
9. Ostrow, J.D. and Branham, R.V (1970) "Photodecomposition of bilirubin and biliverdin in vitro" Gastroenterology 58, 15-25.
10. McDonagh, A.F. (1971) "The role of singlet oxygen in bilirubin photo-oxidation", Biochem. Biophys. Res. Commun. 44,1306-1311.
11. McDonagh, A.F. (1972) "Evidence for singlet oxygen quenching by biliverdin IXα dimethyl ester and its relevance to bilirubin photo-oxidation", Biochem. Biophys. Res. Commun. 48, 408-415.
12. Foote, C.S. and Ching, T-Y. (1975) "Chemistry of singlet oxygen. XXI. Kinetics of bilirubin photooxygenation", J. Am. Chem. Soc. 97,6209-6214.
13. Stocker, R. and Peterhans, E. (1989) "Antioxidant properties of conjugated bilirubin and biliverdin: biologically relevant scavenging of hypochlorous acid", Free Radic. Res. Commun. 6, 57-66.
14. Jirsa, M., Jr, Sip, M. and Jirsa, M. (1990) "Influence of hyperbaric oxygenation on bilirubin and ditaurobilirubin auto-oxidation and porphyrin-sensitized photo-oxidation", J. Photochem. Photobiol. B: Biol. 5, 295-302.
15. Stocker, R., Yamamoto, Y, McDonagh, A.F., Glazer, A.N. and Ames, B.N. (1987) "Bilirubin is an antioxidant of possible physiological importance", Science 235, 1043-1046.
16. Stocker, R., Glazer, A.N. and Ames, B.N. (1987) "Antioxidant activity of albumin-bound bilirubin", Proc. Natl Acad. Sci. USA 84,5918-5922.
17. Stocker, R. and Ames, B.N. (1987) "Potential role of conjugated bilirubin and copper in the metabolism of lipid peroxides in bile", Proc. Natl Acad. Sci. USA 84, 8130-8134.
18. Rubaltelli, F.F., Jori, G. and Reddi, E. (1983) "Bronze baby syndrome: a new porphyrin-related disorder", Pediatr. Res. 17, 327-330.
19. Jori, G., Reddi, E. and Rubaltelli, F.F (1990) "Bronze baby syndrome: an animal model", Pediatr. Res. 27,22-25.
20. Pedersen, A.O., Schonheyder, E and Brodersen, R. (1977) "Photooxidation of human serum albumin and its complex with bilirubin", Eur. J. Biochem. 72, 213-221.
21. Yamaguchi, T., Horio, F., Hashizume, T., Tanaka, M., Ikeda, S., Kakinuma, A. and Nakajima, H. (1995) "Bilirubin is oxidized in rats treated with endotoxin and acts as physiological antioxidant synergistically with ascorbic acid in vivo", Biochem. Biophys. Res. Commun. 214,11-19.
22. Yamaguchi, T., Terakado, M., Horio, F, Aoki, K., Tanaka, M. and Nakajima, H. (1996) "Role of bilirubin as an antioxidant in an ischemia-reperfusion of rat liver and induction of heme oxygenase", Biochem. Biophys. Res. Commun. 223,129-135.
23. Izumi, Y., Yamazaki, M., Shimizu, S., Shimizu, K., Yamaguchi, T. and Nakajima, H. (1988) "Anti-bilirubin monoclonal antibody II. Enzyme-linked immunosorbent assay for bilirubin fractions by combination of two monoclonal antibodies" Biochim. Biophys. Acta 967, 261-266.
24. Yamaguchi, T., Shioji, I., Sugimoto, A., Komoda, Y. and Nakajima, H. (1996) "Epitope of 24G7 anti-bilirubin monoclonal antibody" Biochim. Biophys. Acta 1289,110-114.
25. Rimington, C. (1960) "Spectral-absorption coefficients of some porphyrins in the Soret-band region", Biochem. J. 75, 620-623.
26. Blum, A. and Grossweiner, L.I. (1985) "Singlet oxygen generation by hematoporphyrin IX, uroporphyrin I and hematoporphyrin derivative at 546nm in phosphate buffer and in the presence of egg phosphatidylcholine liposomes", Photochem. Photobiol. 41, 27-32.
27. Lion, Y., Delmelle, M. and van de Vorst, A. (1976) "New method of detecting singlet oxygen production", Nature 263, 442-443.
28. Lamola, A.A., Eisinger, J., Blumberg, W.E., Patel, S.C. and Flores, J. (1979) "Fluorometric study of the partition of bilirubin among blood components: basis for rapid microassays of bilirubin and bilirubin binding capacity in whole blood", Anal. Biochem. 100, 25-42.
29. Stevens, B. and Small, R.D., Jr. (1976) "The photoperoxidation of unsaturated organic molecules-XV. O2 quenching by bilirubin and biliverdin", Photochem. Photobiol. 23, 33-36.
30. Ando, T., Yoshikawa, T., Tanigawa, T., Kohno, M., Yoshida, N. and Kondo, M. (1997) "Quantification of singlet oxygen from hematoporphyrin derivative by electron spin resonance", Life Sci. 61, 1953-1959.
31. Brodersen, R. and Bartels, P. (1969) "Enzymatic oxidation of bilirubin", Eur. J. Biochem. 10, 468-473.
32. Meisel, P., Jahrig, D. and Meisel, M. (1987) "Detection of photobilirubin in urine of jaundiced infants supporting the diagonosis of 'bronze baby syndrome'", Clin. Chim. Acta 166, 61-65.
33. Morehouse, K.M., Moreno, S.N. and Mason, R.P. (1987) "The one-electron reduction of uroporphyrin I by rat hepatic microsomes", Arch. Biochem. Biophys. 257, 276-284.