DNA Strand-Breaking Activities of Quinolone Antimicrobial Agents under Visible Light Irradiation.

Iwamoto, Yoshihisa; Kurita, Akinobu; Shimizu, Tadayori; Masuzawa, Toshiyuki; Uno, Katsuji; Yagi, Motohiro; Kitagawa, Toshiro; Oku, Teruaki; Yanagihara, Yasutake

doi:10.1248/bpb.17.654

Cited by 27 publications

(22 citation statements)

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“…We have recently demonstrated that ENX andTFLX induce photodynamic single strand breaks in plasmid DNA, and that production of these breaks is extensively inhibited by NaN 3 but not by SOD or catalase. 16 On the other hand, we have also shown that euflavine's photobiological activity against yeast is inhibited by ethanol, which is known to be a hydroxy-radical scavenger. 17 Wagai and Tawara similarly suggested that hydroxyl radicals produced by UV-A irradiation might play a major role in the ear swelling of mice resulting from quinolone phototoxicity.…”

Section: Discussionmentioning

confidence: 93%

Phototoxicity of Quinolones: Measurement by UV-A Inhibition of Concanavalin A-Stimulated Lymphocyte Mitogenic Response

Shimizu

Imagawa

Asai

et al. 1995

Journal of Infection and Chemotherapy

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Section: Discussionmentioning

confidence: 93%

Phototoxicity of Quinolones: Measurement by UV-A Inhibition of Concanavalin A-Stimulated Lymphocyte Mitogenic Response

Shimizu

Imagawa

Asai

et al. 1995

Journal of Infection and Chemotherapy

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“…To determine the proper dose and observation intervals for screening of the phototoxic potentials of the FQs, the dose-response relationships and the time course of toxicity were examined with levofloxacin, tosufloxacin, and lomefloxacin, which are known from experimental and clinical studies (2,4,5,10,11,19) to be mildly, moderately, and seriously phototoxic FQs, respectively. These FQs were administered to ICR mice as an intravenous bolus to avoid the bias caused by the diversity of murine intestinal absorption of FQs.…”

Section: Resultsmentioning

confidence: 99%

New Findings on the Structure-Phototoxicity Relationship and Photostability of Fluoroquinolones with Various Substituents at Position 1

Hayashi

Nakata

Yazaki

2004

Antimicrob Agents Chemother

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The present study examined the phototoxicities of a series of 7-(3-aminopyrrolidinyl) quinolones containing various substituents at position 1 (in which the substituent at R8 is a hydrogen or a halogen) by use of a mouse model. For the 7-(3-aminopyrrolidinyl) quinolones with a halogen atom at position 8, well-known substituent groups such as a cyclopropyl, an ethyl, or a difluorophenyl at position 1 were found to be responsible for severe phototoxicity. However, when an aminodifluorophenyl or an isoxazolyl group was placed at position 1, even 8-halogeno quinolones were found to be mildly phototoxic. This is the first report of 8-halogeno quinolones that are not severely phototoxic. Two structurally similar 8-chloro quinolones (the 1-aminodifluorophenyl 8-chloro quinolone and the 1-difluorophenyl 8-chloro quinolone) were investigated further. The former was mildly phototoxic; the latter was severely phototoxic. We demonstrate that these two 8-chloro quinolones have practically the same areas under the concentration-time curves from 0 to 4 h in auricular tissue, suggesting that the mild phototoxicity is not due to pharmacokinetic instability. The rates of UV photodegradation of these compounds were also measured. We found that these two quinolones photodegrade at similar rates, suggesting that the mild phototoxicity is not attained through increased photostability. In conclusion, the phototoxic potentials of fluoroquinolones are influenced not only by the substituent at position 8 but also by that at position 1 (a new finding from this study). We also discovered a mildly phototoxic 8-chloro quinolone which did not have increased photostability.

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“…The mechanism of quinolone phototoxicity involves a transfer of energy from the photo-excited chromophore to molecular oxygen, generating reactive oxygen species, mainly hydroxyl radicals [24] . The in vitro induction of DNA strand-breaking activity was shown for small amounts of tosufloxacin, enoxacin [25] and sparfloxacin [23] (50, 2 and 10 µmol, respectively) in the assay system.…”

Section: Photosensitization By Quinolones and Fl Uoroquinolonesmentioning

confidence: 92%

“…For BALB/c mice, the estimated dose-related relative risk of phototoxicity was 1:3:17:19:21 for levofloxac in:ciprofloxacin:ofloxacin:enoxacin:lomefloxacin [27] . With lomefloxacin and sparfloxacin, relatively high frequencies of phototoxic reactions have been reported, although both compounds are about ten times less phototoxic than nalidixic acid [23,25] .…”

Section: Photosensitization By Quinolones and Fl Uoroquinolonesmentioning

confidence: 99%

Drug-induced phototoxicity evoked by inhibition of human ABC transporter ABCG2: development ofin vitrohigh-speed screening systems

Tamura

Hagiya

et al. 2008

Expert Opinion on Drug Metabolism & Toxicology

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Background : Photosensitivity depends on both genetic and environmental factors. Pheophorbide a, present in various plant-derived foods and food supplements, can be absorbed by the small intestine. Accumulation of pheophorbide a and porphyrins in the systemic blood circulation can result in phototoxic lesions on light-exposed skin. Objective : As the human ATP-binding cassette (ABC) transporter ABCG2 has been suggested to be critically involved in porphyrin-mediated photosensitivity, we aimed to develop in vitro screening systems for drug-induced phototoxicity. Conclusion : Functional impairment owing to inhibition of ABCG2 by drugs or its genetic polymorphisms can lead to the disruption of porphyrin homeostasis. This review article provides an overview on drug-induced photosensitivity, as well as our hypothesis on a potential role of ABCG2 in phototoxicity.

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DNA Strand-Breaking Activities of Quinolone Antimicrobial Agents under Visible Light Irradiation.

Cited by 27 publications

References 0 publications

Phototoxicity of Quinolones: Measurement by UV-A Inhibition of Concanavalin A-Stimulated Lymphocyte Mitogenic Response

Phototoxicity of Quinolones: Measurement by UV-A Inhibition of Concanavalin A-Stimulated Lymphocyte Mitogenic Response

New Findings on the Structure-Phototoxicity Relationship and Photostability of Fluoroquinolones with Various Substituents at Position 1

Drug-induced phototoxicity evoked by inhibition of human ABC transporter ABCG2: development ofin vitrohigh-speed screening systems

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