Coumarin-3-carboxylic acid as a detector for hydroxyl radicals generated chemically and by gamma radiation

Radiation Research

Volumn 148, Issue 6, 1997, Pages 580-591

  Manevich, Yefim ^a   Held, Kathryn D ^b   Biaglow, John E ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

^b MASSACHUSETTS GENERAL HOSPITAL   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

7 HYDROXYCOUMARIN 3 CARBOXYLIC ACID; ASCORBIC ACID; CARBOXYLIC ACID DERIVATIVE; COPPER; COUMARIN 3 CARBOXYLIC ACID; COUMARIN DERIVATIVE; HYDROXYL RADICAL; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; FLUORESCENCE; GAMMA IRRADIATION; HYDROXYLATION; KINETICS; PRIORITY JOURNAL; SCAVENGING SYSTEM;

SIGMOIDEA;

EID: 0030680226     PISSN: 00337587     EISSN: None     Source Type: Journal    
DOI: 10.2307/3579734     Document Type: Article

References (37)

1. H. Schuessler and K. Schilling, Oxygen effect in the radiolysis of proteins. Part 2. Bovine serum albumin. Int. J. Radiat. Biol. 45, 267-281 (1984).
2. L. K. Mee and S. J. Adelstein, Radiation damage to histone H2A by the primary aqueous radicals. Radiat. Res. 110, 155-160 (1987).
3. M. Dizdaroglu and E. Gajewski, Structure and mechanism of hydroxyl radical induced formation of a DNA-protein crosslink involving thymine and lysine in nucleohistone. Cancer Res. 49, 3463-3467 (1989).
4. R. E. Krisch, M. B. Flick and C. N. Trumbore, Radiation chemical mechanisms of single- and double-strand break formation in irradiated SV40 DNA. Radiat. Res. 126, 251-259 (1991).
5. S. Shubutani, M. Takeshita and L. L. Grollman, Insertion of specific bases during DNA synthesis past the oxidation-damaged base 8-oxodG. Nature 349, 431-434 (1991).
6. M. Tien and S. D. Aust, Comparative aspects of several model lipid peroxidation systems. In Lipid Peroxides in Biology and Medicine (K. Yagi, Ed.), pp. 23-41. Academic Press, San Diego, 1982.
7. Y. Mamone, R. Datta, N. Taneja, T. Shafman, E. Bump, R. Haas, R. Weichselbaum and D. Kufe, Coinduction of c-jun gene expression and internucleosomal DNA fragmentation by ionizing radiation. Biochemistry 32, 10607-10613 (1993).
8. M. B. Grisham, Reactive Metabolites of Oxygen and Nitrogen in Biology and Medicine. R. G. Landes Company, Austin, TX, 1994.
9. K. L. Hopcia, Y. L. McCarey, F. C. Sylvester and K. D. Held, Radiation-induced apoptosis in HL60 cells: Oxygen effect, relationship between apoptosis and loss of clonogenicity, and dependence of time to apoptosis on radiation dose. Radiat. Res. 145, 315-323 (1996).
10. J. R. Lakowicz, Principles of Fluorescence Spectroscopy. Plenum Press, New York, 1986.
11. H. Kaur and B. Halliwell, Detection of hydroxyl radicals by aromatic hydroxylation. Meth. Enzymol. 233, 67-82 (1994).
12. J. E. Biaglow, Y. Manevich, F. Uckun and K. D. Held, Quantitation of hydroxyl radicals produced by radiation and copper-linked oxidation by 2-deoxy-D-ribose method. Free Radical Biol. Med. 27, 1129-1134 (1997).
13. O. I. Auroma, Deoxyribose assay for detecting hydroxyl radicals. Meth. Enzymol. 233, 57-66 (1994).
14. S. C. Ashawa, U. R. Kini and U. Madhvanath, The aqueous coumarin system as a low range chemical dosimeter. Int. J. Appl. Radiat. Isot. 30, 7-10 (1979).
15. A. K. Collins, G. M. Makrigiorgos and G. K. Svensson, Coumarin chemical dosimeter for radiation therapy. Med. Phys. 21, 1741-1747 (1994).
16. S. H. Kennedy, Y. Manevich and J. E. Biaglow, Benzoyl peroxide acts as promoter of radiation induced malignant transformation in vivo. Biochem. Biophys. Res. Commun. 212, 118-125 (1995).
17. J. E. Biaglow, K. D. Held, Y. Manevich, A. Kachur, S. Tuttle and F. Uckun, Role of guanosine triphosphate in ferric ion-linked Fenton chemistry. Radiat. Res. 145, 554-562 (1996).
18. G. M. Makrigiorgos, J. Baranowska-Kortylewicz, E. Bump, S. K. Sahu, R. M. Berman and A. I. Kassis, A method for detection of hydroxyl radicals in the vicinity of biomolecules using radiation-induced fluorescence of coumarin. Int. J. Radiat. Biol. 63, 445-458 (1993).
19. G. M. Makrigiorgos, M. Folkard, C. Huang, E. Bump, J. Baranowska-Kortylewicz, S. K. Sahu, B. D. Michael and A. I. Kassis, Quantification of radiation-induced hydroxyl radicals within nucleohistones using a molecular fluorescent probe. Radiat. Res. 138, 177-185 (1994).
20. R. D. H. Murray, J. Mendez and S. A. Brown, The Natural Coumarins. Occurrence, Chemistry and Biochemistry. Wiley, Chichester, 1982.
21. J. A. R. Mead, J. N. Smith and R. T. Williams, The metabolism of coumarin and of o-coumaric acid. Biochem. J. 68, 67-74 (1958).
22. P. Fromherz and B. Masters, Interfacial pH at electrically charged lipid monolayers investigated by the lipid pH-indicator method. Biochim. Biophys. Acta 356, 270-275 (1974).
23. P. Fromherz, Lipid coumarin dye as a probe of interfacial electrical potential in biomembranes. Meth. Enzymol. 171, 376-394 (1989).
24. D. G. Crosby and R. V. Bertold, Fluorescence spectra of some simple coumarins. Anal Chem. 34, 349-357 (1962).
25. W. R. Sherman and E. Robins, Fluorescence of substituted 7-hydroxy-coumarins. Anal. Chem. 40, 803-805 (1968).
26. R. H. Goodwin and F. Kavanagh, The fluorescence of coumarin derivatives as a function of pH. II. Arch. Biochem. 36, 442-445 (1952).
27. B. B. Brodie, J. Axelrod, P. A. Shore and S. Udenfriend, Ascorbic acid in aromatic hydroxylation. II. Products formed by reaction of substrates with ascorbic acid, ferrous ion, and oxygen. J. Biol. Chem. 208, 741-749 (1954).
28. J. T. Edsall and J. Wyman, Biophysical Chemistry, Vol. 1. Academic Press, New York, 1958.
29. J. M. C. Gutteridge and S. Wilkins, Copper salt-dependent hydroxyl radical formation. Damage to proteins acting as antioxidants. Biochim. Biophys. Acta 759, 38-41 (1983).
30. S. D. Varma, X. Shen and W. Lohman, Copper catalyzed oxidation of ascorbate: Chemical and ESR studies. Lens Eye Toxic. Res. 7, 49-66 (1990).
31. M. M. T. Khan and A. E. Martell, Metal ion and metal chelate catalyzed oxidation of ascorbic acid by molecular oxygen. I. Cupric and ferric ion catalyzed oxidation. J. Am. Chem. Soc. 89, 4176-4189 (1967).
32. A. Weissberger and J. E. LuValle, Oxidation processes. XVII. The autooxidation of ascorbic acid in the presence of copper. J. Am. Chem. Soc. 66, 700-705 (1944).
33. R. R. Grinstead, The oxidation of ascorbic acid by hydrogen peroxide. Catalysis by ethylenediaminetetraacetato-iron(III). J. Am. Chem. Soc. 82, 3464-3471 (1960).
34. E. J. Nanni, M. D. Stallings and D. T. Sawyer, Does superoxide ion oxidize catechol, α-tocopherol, and ascorbic acid by direct electron transfer? J. Am. Chem. Soc. 102, 4481-4485 (1980).
35. M. Paya, B. Halliwell and J. R. S. Hoult, Interaction of a series of coumarins with reactive oxygen species scavanging of superoxide, hypochlorous acid and hydroxyl radical. Biochem. Pharmacol. 44, 205-214 (1992).
36. C. von Sonntag, The Chemical Basis of Radiation Biology. Taylor & Francis, London, 1987.
37. J. E. Biaglow, J. B. Mitchell and K. D. Held, The importance of peroxide and superoxide in the x-ray response. Int. J. Radiat. Oncol. Biol. Phys. 22, 665-669 (1992).