Possible direct role of reactive oxygens in the cause of cutaneous phototoxicity induced by five quinolones in mice

Wagai, Nobuhiko; Tawara, Katsuhiko

doi:10.1007/bf02035128

Cited by 94 publications

(44 citation statements)

References 21 publications

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“…In this context, the membrane damage monitored by lipid peroxidation and protein cross-link seems to confirm this hypothesis. These data are in good agreement with the data reported by Wagai and Tawara [6] [7], who have demonstrated that the phototoxicity associated with quinolones in balb/c mice was initiated by the generation of ROS in the target tissue, which specifically involved hydroxyl radical, as well superoxide anion and hydrogen peroxide. Moreover, it has also been reported that the initial steps in the quinolone phototoxicity probably involve hydroxyl-radical attack on the cell membrane and mitochondria [32].…”

supporting

confidence: 94%

Photophysical and Phototoxic Properties of the Antibacterial Fluoroquinolones Levofloxacin and Moxifloxacin

Viola

Facciolo

Canton

et al. 2004

Chemistry & Biodiversity

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Two antibacterial fluoroquinolones, levofloxacin and moxifloxacin, were investigated to evaluate their photophysical properties and to explore the mechanism of their phototoxicity. Photophysical experiments were carried out in aqueous solution by stationary and time-resolved fluorimetry, and by laser flash photolysis, to obtain information on the various decay pathways of the excited states of the drugs and on transient species formed upon irradiation. The results obtained show that levofloxacin is able to photosensitize red blood cell lysis in an oxygen-independent way and induce a high decrease in cell viability after UVA irradiation, although to a lesser degree than the racemic mixture ofloxacin. Moxifloxacin, which is an 8-MeO-substituted fluoroquinolone, is less phototoxic than the other compounds. Cellular phototoxicity was inhibited by the addition of superoxide dismutase, catalase, and free radical and hydroxyl radical scavengers (BHA, GSH, mannitol, and DMTU), indicating the involvement of superoxide anion and/or a radical mechanism in their cytotoxicity. A good correlation was observed between lipid peroxidation, protein photodamage, and cellular phototoxicity, indicating that test compounds exert their toxic effects mainly in the cellular membrane. Experiments carried out on pBR322 DNA show that these derivatives do not significantly photocleave DNA directly, but single-strand breaks were evidenced after treatment of photosensitized DNA by two base-excision-repair enzymes, and Endo III.

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supporting

confidence: 94%

Photophysical and Phototoxic Properties of the Antibacterial Fluoroquinolones Levofloxacin and Moxifloxacin

Viola

Facciolo

Canton

et al. 2004

Chemistry & Biodiversity

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“…Furthermore, a-tocopherol acetate supplementation reduced enrofloxacin residues in turkey meat, which indicate a possible interaction between both molecules that reduces the amount of enrofloxacin in tissues [4,25]. Studies on phototoxic actions of fluoroquinolones revealed that these toxic effects are related to induction of reactive oxygen species [12,23,[27][28][29][30].…”

Section: Discussionmentioning

confidence: 95%

Ciprofloxacin-Induced Antibacterial Activity is Reversed by Vitamin E and Vitamin C

et al. 2012

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In the present study, we investigated the possible involvement of oxidative stress in ciprofloxacin-induced cytotoxicity against several reference bacteria including Pseudomonas aeruginosa ATCC 27853, Escherichia coli ATCC 25922, Staphylococcus aureus ATCC 29213, and clinical isolate of methicillin-resistant Staphylococcus aureus (MRSA). Oxidative stress was assessed by measurement of hydrogen peroxide generation using a FACScan flow cytometer. The antibacterial activity of ciprofloxacin was assessed using the disk diffusion method and by measuring the minimum inhibitory concentration (MIC). Ciprofloxacin induced a dose-dependent antibacterial activity against all bacteria where the highest tested concentration was 100 ug/ml. Results revealed that E. coli cells were highly sensitive to ciprofloxacin (MIC = 0.21 μg/mL ± 0.087), P. aeruginosa and S. aureus cells were intermediately sensitive (MIC = 5.40 μg/mL ± 0.14; MIC = 3.42 μg/mL ± 0.377, respectively), and MRSA cells were highly resistant (MIC = 16.76 μg/mL ± 2.1). Pretreatment of E. coli cells with either vitamin E or vitamin C has significantly protected cells against ciprofloxacin-induced cytotoxicity. These results indicate the possible antagonistic properties for vitamins C or E when they are used concurrently with ciprofloxacin.

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“…The action of these photosensitizers is dependent on the production of extremely reactive molecular species (reactive oxygen species, free radicals, photoproducts), able to modify the cell components, including lipids, proteins and nucleic acids, in combination with UVA; it has been suggested that the most phototoxic quinolones are those that induce the formation of reactive oxygen species (ROS), because these species cause severe tissue damages [6][7][8] . However, a correlation between the production of ROS and the phototoxic potency of fluoroquinolones cannot be drawn and other mechanisms, i.e.…”

Section: Introductionmentioning

confidence: 99%

Photoinduced modifications by fluoroquinolone drugs in bovine serum albumin (BSA) and ribonuclease A (RNAse) as model proteins

Dall’Acqua¹,

Viola²,

Vedaldi³

et al. 2007

Arkivoc

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Photosensitized protein oxidation by drugs, with the consequent modification of their structure is thought to be responsible for the occurrence of phototoxic phenomena such as photoallergy and loss of biological functions. In this paper we have investigated in detail the interaction of four fluoroquinolones namely ciprofloxacin, lomefloxacin, norfloxacin and ofloxacin with two proteins such as Bovine Serum Albumin (BSA) and Ribonuclease A (RNAse A) chosen as models. The interactions between the four drugs and the proteins, were studied by absorption and emission spectroscopy. Photophysical experiments were carried out in aqueous solutions by stationary and time-resolved fluorimetry and by laser flash photolysis, in the absence and in the presence of the proteins to obtain information on the various decay pathways of the excited states of the drugs and on transient species formed upon irradiation. In parallel we have investigated by a series of biochemical assays the photoinduced modifications exerted by the four drugs. The obtained results showed that the four drugs are able to photooxidize proteins with the formation of protein-protein cross-link. This effect was also confirmed in isolated erythrocyte membranes. Furthermore the effect of the fluoroquinolones was also evaluated on isolated aromatic aminoacids. In this context the four drugs are able to photodamage in particular tyrosine and histidine. These results are important in the light of the growing interest for the comprehension of the mechanism of phototoxicity induced by these antibacterial drugs.

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Possible direct role of reactive oxygens in the cause of cutaneous phototoxicity induced by five quinolones in mice

Cited by 94 publications

References 21 publications

Photophysical and Phototoxic Properties of the Antibacterial Fluoroquinolones Levofloxacin and Moxifloxacin

Photophysical and Phototoxic Properties of the Antibacterial Fluoroquinolones Levofloxacin and Moxifloxacin

Ciprofloxacin-Induced Antibacterial Activity is Reversed by Vitamin E and Vitamin C

Photoinduced modifications by fluoroquinolone drugs in bovine serum albumin (BSA) and ribonuclease A (RNAse) as model proteins

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