Comparison of DNA damage photoinduced by ketoprofen, fenofibric acid and benzophenone via electron and energy transfer

Photochemistry and Photobiology

Volumn 74, Issue 5, 2001, Pages 670-678

  Lhiaubet, Virginie ^a   Paillous, Nicole ^a   Chouini Lalanne, Nadia ^a,b  

^a UNIVERSITÉ PAUL SABATIER   (France)

^b UMR 5623 CNRS UPS)   (France)

Author keywords

[No Author keywords available]

Indexed keywords

5,5 DIMETHYL 1 PYRROLINE 1 OXIDE; BENZOPHENONE; CYCLOBUTANE DERIVATIVE; CYTOSINE; DIMER; DNA; ENDONUCLEASE; FENOFIBRATE; FENOFIBRIC ACID; HYDROXYL RADICAL; KETOPROFEN; MANNITOL; OLIGONUCLEOTIDE; PHOSPHORUS 32; PIPERIDINE; THYMINE DERIVATIVE;

ARTICLE; COMPARATIVE STUDY; DNA DAMAGE; DNA STRAND BREAKAGE; ELECTRON SPIN RESONANCE; ELECTRON TRANSPORT; ENERGY TRANSFER; IONIZATION; IRRADIATION; ISOTOPE LABELING; NUCLEOTIDE SEQUENCE; PHOTODEGRADATION; PHOTOSENSITIZATION;

ANTICHOLESTEREMIC AGENTS; BENZOPHENONES; CYTOCHROME C GROUP; DNA; DNA DAMAGE; ELECTRON SPIN RESONANCE SPECTROSCOPY; KETOPROFEN; OLIGODEOXYRIBONUCLEOTIDES; PHOTOSENSITIZING AGENTS; POLAROGRAPHY; PROCETOFEN;

EID: 0035526604     PISSN: 00318655     EISSN: None     Source Type: Journal    
DOI: 10.1562/0031-8655(2001)074<0670:CODDPB>2.0.CO;2     Document Type: Article

References (50)

1. Cusano, F., R. Rafenelli, R. Bacchilega and G. Errico (1987) Photo-contact dermatitis from ketoprofen. Contact Dermatis 17, 108-109.
2. Mozzanica, N. and P. D. Piggatto (1990) Contact and photocontact allergy to ketoprofen, clinical and experimental study. Contact Dermatitis 23, 336-340.
3. Serrano, G., J. M. Fortea, J. M. Latasa, F. Millan, C. James, F. Bosca and M. A. Miranda (1992) Photosensitivity induced by fibric acid and derivatives and its relation to photocontact dermatitis to ketoprofen. J. Am. Acad. Dermatol. 27, 204-208.
4. Leroy, D., A. Dompmartin, E. Lorler, Y. Leport and C. Audebert (1990) Photosensitivity induced by fenofibrate. Photodermatol. Photoimmunol. Photomed. 7, 136-138.
5. Jeanmougin, M., A. Petit, J. R. Manciet, M. Sigal and L. Dubertret (1996) Eczéma photoallergique de contact au kétoprofène. Ann. Dermatol. Venerol. 123, 251-255.
6. Ljunggren, B. (1985) Propionic acid-derivated nonsteroidal antiinflammatory drugs are phototoxic in vitro. Photodermatology 2, 3-9.
7. Kochevar, I. E. (1989) Phototoxicity of non steroidal antiinflammatory drugs: coincidence or specific mechanism? Arch. Dermatol. 125, 824-826.
8. Lhiaubet, V., F. Gutierrez, F. Penaud-Berruyer, E. Amouyal, J. P. Daudey, R. Poteau, N. Chouini-Lalanne and N. Paillous (2000) Spectroscopic and theoretical studies of the excited states of fenofibric acid and ketoprofen in relation with their photosensitizing properties. New J. Chem. 24, 403-410.
9. Monti, S., S. Sortino, G. De Guidi and G. Marconi (1997) Photochemistry of 2-(3-benzoylphenyl)propionic acid (ketoprofen). Part 1. A picosecond and nanosecond time resolved study in aqueous solution. J. Chem. Soc., Faraday Trans. 93, 2269-2275.
10. Marguery, M. C., N. Chouini-Lalanne, J. C. Ader and N. Paillous (1998) Comparison of the DNA damage photoinduced by fenofibrate and ketoprofen, two phototoxic drugs of parent structure. Photochem. Photobiol. 68, 679-684.
11. Boscà, F. and M. A. Miranda (1998) Photosensitizing drugs containing the benzophenone chromophore. J. Photochem. Photobiol. B: Biol. 43, 1-26.
12. Boscà, F., M. A. Miranda, G. Carganico and D. Mauleon (1994) Photochemical and photobiological properties of ketoprofen associated with the benzophenone chromophore. Photochem. Photobiol. 60, 96-101.
13. Martinez, L. J. and J. C. Scaiano (1997) Transient intermediates in the laser flash photolysis of ketoprofen in aqueous solutions: unusual photochemistry for the benzophenone chromophore. J. Am. Chem. Soc. 119, 11 066-11 079.
14. Miranda, M. A., F. Boscà, F. Vargas and N. Canudas (1994) Photosensitization by fenofibrate. II. In vitro phototoxicity of the major metabolites. Photochem. Photobiol. 59, 171-174.
15. Costanzo, L. L., G. De Guidi, C. Condorelli, A. Cambria and M. Fama (1989) Molecular mechanism of drug photosensitization-II. Photohemolysis sensitized by ketoprofen. Photochem. Photobiol. 50, 359-365.
16. Boscà, F., G. Carganico, J. V. Castell, M. J. Gomez-Lechon, D. Hernandez, D. Mauleon, L. A. Martinez and M. A. Miranda (1995) Evaluation of ketoprofen (R,S and R/S) phototoxicity by a battery of in vitro assays. J. Photochem. Photobiol. B: Biol. 31, 133-138.
17. Artuso, T., J. Bernadou, B. Meunier, J. Piette and N. Paillous (1991) Mechanism of DNA cleavage mediated by photoexcited non-steroidal antiinflammatory drugs. Photochem. Photobiol. 54, 205-213.
18. Chouini-Lalanne, N., M. Defais and N. Paillous (1998) Nonsteroidal antiinflammatory drug-photosensitized formation of pyrimidine dimer in DNA. Biochem. Pharmacol. 55, 441-446.
19. Charlier, M., C. Helene and W. L. Carrier (1972) Photochemical reactions of aromatic ketones with nucleic acids and their components-III. Chain breakage and thymine dimerization in benzophenone photosensitized DNA. Photochem. Photobiol. 15, 527-536.
20. Greenstock, C. L. and H. E. Johns (1968) Photosensitized dimerization of pyrimidines. Bioch. Biophys. Res. Commun. 30, 21-27.
21. Wood, P. D. and R. W. Redmond (1996) Triplet state interactions between nucleic acid bases in solution at room temperature: intermolecular energy and electron transfer. J. Am. Chem. Soc. 118, 4256-4263.
22. Gut, I. G., P. D. Wood and R. W. Redmond (1996) Interaction of triplet photosensitizers with nucleotides and DNA in aqueous solution at room temperature. J. Am. Chem. Soc. 118, 2366-2373.
23. Delatour, T., T. Douki, C. D'Ham and J. Cadet (1998) Photosensitization of thymine nucleobase by benzophenone through energy transfer, hydrogen abstraction and one-electron oxidation. J. Photochem. Photobiol. B: Biol. 44, 191-198.
24. Maxam, A. M. and W. Gilbert (1980) Sequencing end-labeled DNA with base-specific chemical cleavages. Methods Enzymol. 65, 499-559.
25. Rubin, C. M. and C. W. Schmid (1980) Pyrimidine-specific chemical reactions useful for DNA sequencing. Nucleic Acids Res. 8, 4613-4619.
26. Saito, I., M. Takayama, H. Sugiyama and T. Nakamura (1996) Design of photoactivable DNA-cleaving amino-acids with high sequence selectivity, In DNA and RNA Cleavers and Chemotherapy of Cancer and Viral Diseases (Edited by B. Meunier), pp. 163-176. Kluwer Academic, Netherlands.
27. Sugiyama, H. and I. Saito (1996) Theorical studies of -GG-specific photocleavage of DNA via electron transfer: significant lowering of ionization potential and 5′-localization of HOMO of stacked GG bases in B-form DNA. J. Am. Chem. Soc. 118, 7063-7068.
28. Lommel, L. and P. C. Hanawalt (1991) Preparation and determination of T4 endonuclease V activity. Mutat. Res. 255, 183-191.
29. Amankwa, L. and L. G. Chatten (1984) Electrochemical reduction of ketoprofen and its determination in pharmaceutical dosage forms by differential-pulse polarography. Analyst 109, 57-60.
30. Nadjo, L. and J. M. Savéant (1971) Electrochemical reduction of substituted benzophenones and fluorenones in media of low proton availability. Mechanisms of the reductive cleavage of bromo and chlorobenzophenone. J. Electroanal. Chem. 30, 41-57.
31. Rehm, D. and A. Weller (1970) Kinetics of fluorescence quenching by electron and H-atom transfer. Isr. J. Chem. 8, 259-271.
32. Steenken, S. and S. V. Jovanovic (1997) How easily oxidizable is DNA? One electron reduction potentials of adenosine and guanosine radicals in aqueous solution. J. Am. Chem. Soc. 119, 617-618.
33. De la Peña, D., C. Marti, S. Nonell, L. A. Martinez and M. A. Martinez (1997) Time resolved near infrared studies on singlet oxygen production by the photosensitizing 2-aryl-propionic acids. Photochem. Photobiol. 65, 828-832.
34. Darmanyan, A. P. and C. S. Foote (1993) Solvent effects on singlet oxygen yield from nπ* and ππ* triplet carbonyl compounds. J. Phys. Chem. 97, 5032-5035.
35. Castelli, F., G. De Guidi, S. Guiffrida, P. Miano and S. Sortino (1999) Molecular mechanism of photosensitization XIII: a combined differential scanning calorimetry and DNA photosensitization study in non steroidal antiinflammatory drugs-DNA interaction. Int. J. Pharmaceutics 184, 21-33.
36. Saito, I., M. Takayama, H. Sugiyama and K. Nakatani (1995) Photoinduced DNA cleavage via electron transfer: demonstration that guanine residues located 5′ to guanine are the most electron donating sites. J. Am. Chem. Soc. 117, 6406-6407.
37. Starrs, S. M. and R. J. H. Davies (2000) Sequence specificity of alkali-labile DNA damage photosensitized by suprofen. Photochem. Photobiol. 72, 291-297.
38. Nakatani, K., K. Fujisawa, C. Dohno, T. Nakamura and I. Saito (1998) p-Cyano substituted 5-benzoyldeoxyuridine as a novel electron accepting nucleobase for one electron oxidation of DNA. Tetrahedron Lett. 39, 5995-5998.
39. Adam, W., C. R. Saha-Moller and A. Schonberger (1997) Type I and type II photosensitized oxidative modification of 2′-deoxyguanosine (dGuo) by triplet excited ketones generated thermally from the 1,2-dioxetane HTMD. J. Am. Chem. Soc. 119, 719-723.
40. Douki, T. and J. Cadet (1999) Modification of DNA bases by photosensitized one-electron oxidation. Int. J. Radiat. Biol. 75, 571-581.
41. Burrows, C. J. and J. G. Muller (1998) Oxidative nucleobase modification leading to strand scission. Chem. Rev. 98, 1109-1151.
42. Radschuweit, A., H. H. Rüttinger, P. Nuhn, W. Wohlrab and C. Huschka (2001) UV-induces formation of hydrogen peroxide based on the photochemistry of ketoprofen. Photochem. Photobiol. 73, 119-127.
43. Charlier, M. and C. Helene (1972) Photochemical reactions of aromatic ketones with nucleic acids and their components-I. Purine and pyrimidine bases and nucleosides. Photochem. Photobiol. 15, 71-87.
44. Roth, H. D. and A. A. Lamola (1974) Chemically induced dynamic nuclear polarization and exchange broadening in an electron-transfer reaction. J. Am. Chem. Soc. 96, 6270-6275.
45. Peters, K. S. and J. Lee (1993) Picosecond dynamics of the photoreduction of benzophenone by DABCO. J. Phys. Chem. 97, 3761-3764.
46. Devadoss, C. and R. W. Fessenden (1990) Picosecond and nanosecond studies of the photoreduction of benzophenone by 1,4-diazabicyclo[2.2.2]octane: characterization of the transient. J. Phys. Chem. 94, 4540-4549.
47. Gentil, A., F. Le Page and A. Sarasin (1997) The consequence of translesional replication of unique UV-induced photoproducts. Biol. Chem. 378, 1287-1292.
48. Bourre, F., G. Renault, P. C. Seawell and A. Sarasin (1985) Distribution of ultraviolet-induced lesions in Simian Virus 40 DNA. Biochimie 67, 293-299.
49. Rahn, R. O. (1979) Triplet sensitization of DNA. Acta Biol. Med. Germ. 38, 1225-1231.
50. Kochevar, I. E. and D. A. Dunn (1990) Photosensitized reactions of DNA: cleavage and addition, In Bioorganic Photochemistry, Photochemistry and the Nucleic Acids, Vol. 1 (Edited by H. Morrison), pp. 273-316. John Wiley and Sons, New York.