Molecular Mechanism of Photosensitization XI. Membrane Damage and DNA Cleavage Photoinduced by Enoxacin

Sortino, Salvatore; Condorelli, G.; Guidi, Guido De; Giuffrida, Salvatore

doi:10.1111/j.1751-1097.1998.tb02525.x

Cited by 37 publications

(49 citation statements)

References 30 publications

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“…of phosphorylated sugars, radical processes of the type discussed above may be initiated. Thus, it may be that the reported DNA photocleavage caused by fluoroquinolones, [23] a phenomenon that is related to the remarkable phototoxicity of these molecules, widely used as bactericidal drugs, involves a reaction with the phosphorylated deoxyribose units. Clearly, more work is needed in this field.…”

Section: Resultsmentioning

confidence: 99%

Unexpected Photoreactions of Some 7-Amino-6-fluoroquinolones in Phosphate Buffer

et al. 2001

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The products of irradiation of some 6‐fluoro‐7‐piperazino‐4‐quinolone‐3‐carboxylic acids in phosphate buffer arise from a combination of reductive defluorination of the heteroaryl ring and oxidative fragmentation of the piperazine side chain. This unusual reaction contrasts with the fluorine atom substitution observed in neat water. The results of steady‐state and time‐resolved experiments are consistent with initiation of the process by electron‐transfer quenching of the triplet state of these heterocycles by the phosphate anion. For one of the compounds, a transient band (λmax = 670 nm), previously attributed to the defluorinated cation, must now be reassigned to the radical anion. This intermediate undergoes inefficient reductive defluorination of the ring. In the process, a phosphate radical anion is expected to be formed and to abstract a hydrogen atom from the piperazine group, leading to degradation of the latter.

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Section: Resultsmentioning

confidence: 99%

Unexpected Photoreactions of Some 7-Amino-6-fluoroquinolones in Phosphate Buffer

et al. 2001

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“…UVA irradiation of PAHs in the presence of a free radical scavenger or enhancer was used to determine the involvement of free radical intermediates in the peroxidation [170]. The free radical scavengers dithiothreitol (DTT) and NaN 3 [171][172][173], and the superoxide free radical scavenger superoxide dismutase (SOD) [172,174] were used. Besides as a free radical scavenger, NaN 3 also effectively reacts with singlet oxygen ( 1 O 2 ) (173) and hydroxyl radical [173,174].…”

Section: Formation Of 8-oxo-2 -Deoxyguanine (8-oxodg) Adductmentioning

confidence: 99%

Phototoxicity and Environmental Transformation of Polycyclic Aromatic Hydrocarbons (PAHs)—Light-Induced Reactive Oxygen Species, Lipid Peroxidation, and DNA Damage

Xia

Sun

et al. 2012

Journal of Environmental Science and Health, Part C

196

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Polycyclic aromatic hydrocarbons (PAHs) are a class of mutagenic and tumorigenic environmental contaminants. Although the mechanisms by which PAHs induce cancer in experimental animals have been extensively studied and the metabolic activation pathways have been determined, the environmental fate of PAHs and the phototoxicity exerted by PAHs, as well as their photoreaction products formed in the environment, have received much less attention. In this review, the formation of oxygenated PAHs, PAH quinones, nitro-PAHs, and halogenated PAHs from photoreaction of environmental PAHs are addressed. Upon light irradiation, PAHs and all PAH photoreaction products can absorb light energy to reach photo-excited states, which react with molecular oxygen, medium, and coexisting chemicals to produce reactive oxygen species (ROS) and other reactive intermediates, such as oxygenated PAHs and free radicals. These intermediates, including ROS, induce lipid peroxidation, and DNA damage including DNA strand breakage, oxidation to 8-oxo-2'-deoxyguanosine, and DNA-adducts. Since these toxicological endpoints are associated with age-related diseases, including cancer, environmental PAHs concomitantly exposed to sunlight may potentially promote human skin damage, leading to ageing and skin cancers. Thus, we suggest that (i) in addition to the widely recognized metabolic pathways, more attention must be paid to photoreaction as an important activation pathway for PAHs, (ii) risk assessment of environmental PAHs should take into consideration the complex photochemical reactions leading to mixtures of products that are also phototoxic; and (iii) the study of structure-toxicity relationships should be expanded to cover the complex photoreactions and extrinsic factors that affect phototoxicity endpoints.

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“…Its spectrum of activity includes aerobeic gram-positive and gram-negative organisms as well as anaerobic pathogens [12,13]. The photosensitizing activity of enoxacin which belongs to the family of naphthyridine analogs has been studied extensively [14].…”

Section: Introductionmentioning

confidence: 99%

Crystal structure analysis of 5‐amino‐7‐(pyrrolidin‐1‐yl)‐2,4,4‐trimethyl‐1,4‐dihydro‐1,6‐naphthyridine‐8‐carbonitrile

Selvanayagam¹,

Rajakannan²,

Rao³

et al. 2004

Cryst. Res. Technol.

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Molecular Mechanism of Photosensitization XI. Membrane Damage and DNA Cleavage Photoinduced by Enoxacin

Cited by 37 publications

References 30 publications

Unexpected Photoreactions of Some 7-Amino-6-fluoroquinolones in Phosphate Buffer

Unexpected Photoreactions of Some 7-Amino-6-fluoroquinolones in Phosphate Buffer

Phototoxicity and Environmental Transformation of Polycyclic Aromatic Hydrocarbons (PAHs)—Light-Induced Reactive Oxygen Species, Lipid Peroxidation, and DNA Damage

Crystal structure analysis of 5‐amino‐7‐(pyrrolidin‐1‐yl)‐2,4,4‐trimethyl‐1,4‐dihydro‐1,6‐naphthyridine‐8‐carbonitrile

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