Effects of bio-compatible metal ions on rufloxacin photochemistry, photophysics and photosensitization: Copper(II)

Journal of Photochemistry and Photobiology B: Biology

Volumn 101, Issue 3, 2010, Pages 295-303

  Cuquerella, Maria Consuelo ^a   Belvedere, Alessandra ^b   Catalfo, Alfio ^b   Miranda, Miguel Angel ^a   Scaiano, J C ^c   Guidi, Guido de ^b  

^a UNIVERSITAT POLITÈCNICA DE VALÈNCIA   (Spain)

^b UNIVERSITY OF CATANIA   (Italy)

^c UNIVERSITY OF OTTAWA   (Canada)

Author keywords

Copper; DNA; Fluoroquinolone; Photochemistry; Phototoxicity

Indexed keywords

CUPRIC ION; DEOXYGUANOSINE; RUFLOXACIN; SINGLET OXYGEN;

ARTICLE; BIOCOMPATIBILITY; CONCENTRATION (PARAMETERS); DRUG BIOAVAILABILITY; PHOTOCHEMISTRY; PHOTODEGRADATION; PHOTOSENSITIZATION; PRIORITY JOURNAL;

AIR; ANTI-BACTERIAL AGENTS; COPPER; DEOXYGUANOSINE; FLUOROQUINOLONES; NITROGEN; PHOTOCHEMICAL PROCESSES; PHOTOLYSIS; PHOTOSENSITIZING AGENTS; SINGLET OXYGEN; WATER;

EID: 77958152207     PISSN: 10111344     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jphotobiol.2010.07.015     Document Type: Article

References (60)

1. Aleixandre V., Herrera G., Urios A., Blanco M. Effects of ciprofloxacin on plasmid DNA supercoiling of Escherichia coli topoisomerase I and gyrase mutants. Antimicrob. Agents Chemother. 1991, 35:20-23.
2. Lhiaubet-Vallet V., Cuquerella M.C., Castell J.V., Bosca F., Miranda M.A. Triplet excited fluoroquinolones as mediators for thymine cyclobutane dimer formation in DNA. J. Phys. Chem. B 2007, 111:7409-7414.
3. Fernandez E., Sanchez G. Structure-photostability and phototoxicity relations in fluoroquinolones. Anal. Real Acad. Nac. Farm. 2005, 71:835-848.
4. Agrawal N., Ray R.S., Farooq M., Pant A.B., Hans R.K. Photosensitizing potential of ciprofloxacin at ambient level of UV radiation. Photochem. Photobiol. 2007, 83:1226-1236.
5. Ray R.S., Agrawal N., Misra R.B., Farooq M., Hans R.K. Radiation-induced in vitro phototoxic potential of some fluoroquinolones. Drug Chem. Toxicol. 2006, 29:25-38.
6. Dawe R.S., Ibbotson S.H., Sanderson J.B., Thomson E.M., Ferguson J. A randomized controlled trial (volunteer study) of sitafloxacin, enoxacin, levofloxacin and sparfloxacin phototoxicity. Brit. J. Dermatol. 2003, 149:1232-1241.
7. Kang J.S., Kim T.H., Park K.B., Chung B.H., Youn J.I. Enoxacin photosensitivity. Photodermatol. Photoimmunol. Photomed. 1993, 9:159-161.
8. Shelley E.D., Shelley W.B. The subcorneal pustural drug eruption, an example induced by norfloxacin. Cutis 1988, 42:24-27.
9. Granowitz E.V. Photosensitivity rash in a patient being treated with ciprofloxacin. J. Infect. Dis. 1989, 160:910-911.
10. Kurimaji Y., Shono M. Scarified photopatch testing in lomefloxacin photosensivity. Contact Dermatitis 1992, 26:5-10.
11. Ferguson J. Fluoroquinolone photosensitization: a review of clinical and laboratory studies. Photochem. Photobiol. 1995, 62:954-958.
12. Johnson B.E., Gibbs N.K., Ferguson J. Quinolone antibiotic with potential to photosensitize skin tumorigenesis. J. Photochem. Photobiol. B: Biol. 1997, 37:171-173.
13. Klecak G., Urbach F., Urwyler H. Fluoroquinolone antibacterials enhance UVA induced skin tumours. J. Photochem. Photobiol. B: Biol. 1997, 37:174-181.
14. Makinen M., Forbes P.D., Stenback F. Quinolone antibacterials: a new class of photochemical carcinogens. J. Photochem. Photobiol. B: Biol. 1997, 37:182-187.
15. Brendler-Schwaab S.Y., von Kautz E., Schlüter G., Herbold B.A. A new approach to screen for photomutagenicity with the HPRT assay. Toxicologist 1995, 14:323.
16. Martinez L.J., Sik R.H., Chignell C.F. Fluoroquinolone antimicrobials: singlet oxygen, superoxide and phototoxicity. Photochem. Photobiol. 1998, 67:399-403.
17. Vargas F., Zoltan T., Ramirez A.H., Cordero T., Chavez V., Izzo C., Lopez V., Cardenas Y.M., Fernandez A., Hincapie L., Fuentes A. Studies of the photooxidant properties of antibacterial fluoroquinolones and their naphthalene derivatives. Pharmazie 2009, 64:116-122.
18. E Spratt T., Schultz S.S., Levy D.E., Chen D., Schluter G., Williams G.M. Different mechanisms for the photoinduced production of oxidative DNA damage by fluoroquinolones differing in photostability. Chem. Res. Toxicol. 1999, 12:809-815.
19. Sauviago S., Douki T., Odin F., Caillat S., Ravanat J.L., Cadet J. Analysis of fluoroquinolone-mediated photosensitization of 2'-deoyguanosine, calf thymus and cellular DNA: determination of type-I, type-II and triplet-triplet energy transfer mechanism contribution. Photochem. Photobiol. 2001, 73:230-237.
20. Ames B.N., Gold L.S., Willett W.C. The causes and prevention of cancer. Proc. Natl. Acad. Sci. USA 1995, 92:5258-5265.
21. Halicka H.D., Smart D.J., Traganos F., Williams G.M., Darzynkiewicz Z. Fluoroquinolones lower constitutive H2AX and ATM phosphorylation in TK6 lymphoblastoid cells via modulation of the intracellular redox status. Pharmacol. Rep. 2009, 61:711-718.
22. Izzotti A., Cartiglia C., Taningher M., De Flora S., Balansky R. Age-related increases of 8-hydroxy-2'-deoxyguanosine and DNA-protein crosslinks in mouse organs. Mutat. Res. 1999, 446:215-223.
23. Rosen J.E., Prahalad A.K., Chen D., Williams G.M. Quinolone antibiotic photodynamic production of 8-oxo-7,8-dihydro-2'-deoxyguanosine in cultured liver epithelial cells. Photochem. Photobiol. 1997, 65:990-996.
24. Rosen J.E., Chen D., Prahalad A.K., Spratt T.E., Schluter G., Williams G.M. A fluoroquinolone antibiotic with a methoxy group at the 8-position yields reduced generation of 8-oxo-7,8-dihydro-2'-deoxyguanosine after UVA irradiation. Toxicol. Appl. Pharmacol. 1997, 145:381-387.
25. Verna L.K., Chen D., Schluter G., Williams G.M. Inhibition by singlet oxygen quenchers of oxidative damage to DNA produced in cultured cells by exposure to a quinolone antibiotic and ultraviolet A irradiation. Cell. Biol. Toxicol. 1997, 14:237-242.
26. Belvedere A., Bosca F., Catalfo A., Cuquerella M.C., De Guidi G., Miranda M.A. Type II guanine oxidation photoinduced by the antibacterial fluoroquinolone rufloxacin in isolated DNA and in 2'-deoxyguanosine. Chem. Res. Toxicol. 2002, 15:1142-1149.
27. Cuquerella M.C., Bosca F., Miranda M.A., Belvedere A., Catalfo A., De Guidi G. Photochemical properties of ofloxacin involved in oxidative DNA damage: a comparison with rufloxacin. Chem. Res. Toxicol. 2003, 16:562-570.
28. Catalfo A., Calandra M.L., Renis M., Serrentino M.E., De Guidi G. Rufloxacin-induced photosensitization in yeast. Photochem. Photobiol. Sci. 2007, 6:181-189.
29. Martinez L.J., Li G., Chignell C.F. Photogeneration of fluoride by fluoroquinolone antimicrobial agents lomefloxacin and fleroxacin. Photochem. Photobiol. 1997, 65:599-602.
30. Condorelli G., De Guidi G., Giuffrida S., Sortino S., Chillemi R., Sciuto S. Molecular mechanism of photosensitization induced by drugs. XII. Photochemistry and photosensitization of Rufloxacin: an unusual photodegradation path for the antibacterials containing a fluoroquinolones like chromophore. Photochem. Photobiol. 1999, 70:280-286.
31. Aratane N.UmezawaK., Ruy A., Mashiko S., Hirobe M., Nagano T. Participation of reactive oxygen species in phototoxicity induced by quinolone antibacterial agents. Arch. Biochem. Biophys. 1997, 342:275-281.
32. Martinez L.J., Chignell C.F. Photocleavage of DNA by the fluoroquinolone antibacterials. J. Photochem. Photobiol. B: Biol. 1998, 45:51-59.
33. Belvedere A., Bosca F., Cuquerella M.C., De Guidi G., Miranda M.A. Photoinduced N-demethylation of rufloxacin and its methyl ester under aerobic conditions. Photochem. Photobiol. 2002, 76:252-258.
34. Costanzo L.L., De Guidi G., Giuffrida S., Sortino S., Condorelli G. Antioxidant effect of inorganic ions on UVC and UVB induced lipid peroxidation. J. Inorg. Biochem. 1995, 59:1-13.
35. Giuffrida S., De Guidi G., Miano P., Sortino S., Condorelli G., Costanzo L.L., Effect of inorganic ions on membrane damage photosensitized by naproxen Molecular mechanism of drug photosensitization: VIII. J. Inorg. Biochem. 1996, 63:253-263.
36. De Guidi G., Giuffrida S., Condorelli G., Costanzo L.L., Miano P., Sortino S. Molecular mechanism of drug photosensitization. IX. Effects of inorganic ions on DNA cleavage photosensitized by naproxen. Photochem. Photobiol. 1996, 63:455-462.
37. Bonomo R.P., Conte E., De Guidi G., Maccarrone G., Rizzarelli E., Vecchio G. Characterization and superoxide dismutase activity of copper(II) complexes of 6A,6X-difunctionalized β-cyclodextrins. J. Chem. Soc., Dalton Trans. 1996, 63:4351-4355.
38. Sortino S., De Guidi G., Costanzo L.L., Scaiano J.C. Copper(II), in the parts per million range, modulates photochemical and photosensitizing properties of tolmetin via electron transfer with a triplet carbanion. Chem. Commun. 1999, 19:2003-2004.
39. Turel I. The interactions of metal ions with quinolone antibacterial agents. Coord. Chem. Rev. 2002, 232:27-47.
40. Gao F., Yang P., Xie J., Wang H. Synthesis, characterization and antibacterial activity of novel Fe(III), Co(II), and Zn(II) complexes with norfloxacin. J. Inorg. Biochem. 1995, 60:61-67.
41. Zak B. Simple procedure for the single sample determination of serum copper and iron. Clin. Chim. Acta 1958, 3:328-334.
42. Ravanat J.L., Cadet J., Araki K., Toma H.E., Medeiros M.H.G., Di Mascio P. Supramolecular cationic tetraruthenated porphyrin and light-induced decomposition of 2'-deoxyguanosine predominantly via a singlet oxygen-mediated mechanism. Photochem. Photobiol. 1998, 68:698-702.
43. Sortino S., Marconi G., Giuffrida S., De Guidi G., Monti S. Photophysical properties of rufloxacin in neutral aqueous solution. Photochem. Photobiol. 1999, 70:731-736.
44. Buxton G.V., Greenstock C.L., Helman W.P., Ross A.B. Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals in aqueous solution. J. Phys. Chem. Ref. Data 1988, 17:513-886.
45. Wallis S.C., Gahan L.R., Charles B.G., Hambley T.W., Duckworth P.A. Copper(II) complexes of the fluoroquinolone antimicrobial ciprofloxacin. Synthesis, x-ray structural characterization, and potentiometric study. J. Inorg. Biochem. 1996, 62:1-16.
46. Turel I., Leban I., Bukovec N. Synthesis, characterization, and crystal structure of a copper(II) complex with quinolone family member (ciprofloxacin): bis(1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylate)copper(II) chloride hexahydrate. J. Inorg. Biochem. 1994, 56:273-282.
47. Macias B., Villa M.V., Rubio I., Castineiras A., Borras J. Complexes of Ni(II) and Cu(II) with ofloxacin. Crystal structure of a new Cu(II) ofloxacin complex. J. Inorg. Biochem. 2001, 84:163-170.
48. Gan H., Zhao X., Whitten D.G. Amine photoredox reactions: a photoinduced methylene shuttle initiated via two-electron oxidation of a tertiary amine by anthraquinone. J. Am. Chem. Soc. 1991, 113:9409-9411.
49. Ravanat J.L., Saint-Pierre C., Cadet J. One-electron oxidation of the guanine moiety of 2'-deoxyguanosine: influence of 8-oxo-7,8-dihydro-2'-deoxyguanosine. J. Am. Chem. Soc. 2003, 125:2030-2031.
50. Niles J.C., Wishnok J.S., Tannenbaum R.S. Spiroiminodihydantoin is the major product of the 8-oxo-7,8-dihydroguanosine reaction with peroxynitrite in the presence of thiols and guanosine photooxidation by methylene blue. Org. Lett. 2000, 3:963-966.
51. Adam W., Arnold M.A., Grune M., Werner M.N., Pischel U., Chantu R.S. Spiroiminodihydantoin is a major product in the photooxidation of 2'-deoxyguanosine by the triplet states and oxyl radicals generated from hydroxyacetophenone photolysis and dioxetane thermolysis. Org. Lett. 2002, 4:537-540.
52. Martinez G.R., Ravanat J.-L., Cadet ; J., Gennari de Medeiros M.H., Di Mascio P. Spiroiminodihydantoin nucleoside formation from 2'-deoxyguanosine oxidation by [18O-labeled] singlet molecular oxygen in aqueous solution. J. Mass Spectrom. 2007, 42:1326-1332.
53. Ravanat J.L., Douki T., Cadet J. Direct and indirect effect of UV radiation on DNA and its components. J. Photochem. Photobiol. B: Biol. 2001, 63:88-102.
54. Chu X., Shen G.L., Jiang J.H., Kang T.F., Xiong B., Yu R.Q. Voltammetric studies of the interaction of daunomycin anticancer drug with DNA and analytical applications. Anal. Chim. Acta 1998, 373:29-33.
55. Zhang N., Zhang X. Voltammetric study of the interaction of the ofloxacin-copper complex with DNA. Microchim. Acta 2007, 159:65-70.
56. Gameiro P., Rodrigues C., Baptista T., Sousa I., de Castro B. Solution studies on binary and ternary complexes of copper(II) with some fluoroquinolones and 1,10-phenanthroline: antimicrobial activity of ternary metalloantibiotics. Int. J. Pharm. 2007, 334:129-136.
57. Katsarou M.E., Efthimiadou E.K., Psomas G., Karaliota A., Vourloumis D. Novel copper (II) complex of N-propyl-norfloxacin and 1,10-phenanthroline with enhanced antileukemic and DNA nuclease activities. J. Med. Chem. 2008, 51:470-478.
58. Americo, L., Catalfo, A., Miranda, M.A., Renis, M., Sage, E., Scajano, T., Serrentino, M.E., de Guidi, G., 2007. Bio-compatible oligoelement effect on photosensitization of antibacterial drugs in membrane metal protein and DNA. In: Proc. 7th Workshop "Pharmaco-Bio-Metallics" Palermo, Italy.
59. Chen R., Avotinsh Y., Freeman G.R. Solvent effects on the reactivity of solvated electrons with ions in isobutanol/water mixed solvents. Can. J. Chem. 1994, 72:1083-1093.
60. Fox Marye Anne, Chanon Michel Photoinduced Electron Transfer: Part B, Experimental Techniques and Medium Effects 1998, Elsevier.