EPR examination of free radical properties of DOPA–melanin complexes with ciprofloxacin, lomefloxacin, norfloxacin and sparfloxacin

Beberok, Artur; Buszman, Ewa; Zdybel, Magdalena; Pilawa, Barbara; Wrześniok, Dorota

doi:10.1016/j.cplett.2010.07.079

Cited by 29 publications

(22 citation statements)

References 41 publications

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“…The authors indicate that such relations among drugs, melanin and metal ions may occur similarly in a living body. Moreover, one has to take into consideration that, as we previously demonstrated, free radicals play also an important role in fluoroquinolones (ciprofloxacin, lomefloxacin, norfloxacin and sparfloxacin) binding to melanin [3].…”

Section: Discussionmentioning

confidence: 99%

Cytotoxic effect of lomefloxacin in culture of human epidermal melanocytes

Beberok

Otręba

Wrześniok

et al. 2013

Pharmacological Reports

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Abstract:Backround: Lomefloxacin is a potent bactericidal antibiotic. The use of this drug in treatment of various infections is accompanied by serious adverse effects on pigmented tissues. The exact mechanisms of lomefloxacin side effects have not been well established yet. The aim of this study was to characterize the interaction between lomefloxacin and melanin, and to examine how this interaction affects the cell viability and melanization in melanocytes. Methods: Normal human epidermal melanocytes and the model DOPA-melanin were used. The binding parameters of lomefloxacin-melanin complexes as well as the antibiotic effect on cell viability and melanization in pigmented cells were investigated using a spectrophotometric method. Results: Our results indicate that lomefloxacin forms stable complexes with melanin. The analysis of drug binding to melanin has shown that at least two classes of independent binding sites are involved in formation of these complexes. The WST-1 assay was used to detect the antibiotic cytotoxic effect. The value of ED 50 for lomefloxacin was about 0.75 mmol/l. It has been shown that lomefloxacin causes inhibition of tyrosinase activity, and reduces melanin content in human skin melanocytes in a dose-dependent manner. Conclusion:The ability of the analyzed fluoroquinolone to form complexes with melanin, and the demonstrated inhibitory effect on a melanization process in melanocytes in vitro may explain a potential role of melanin biopolymer in the mechanisms of undesirable side effects of lomefloxacin in vivo resulting from its accumulation in pigmented tissues.

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Section: Discussionmentioning

confidence: 99%

Cytotoxic effect of lomefloxacin in culture of human epidermal melanocytes

Beberok

Otręba

Wrześniok

et al. 2013

Pharmacological Reports

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“…Electron paramagnetic resonance (EPR) studies indicated that o-semiquinone free radicals exist in melanins (Sarna, 1981;Sealy et al, 1982;Shima et al, 1997;Ito and Wakamatsu, 2003;Latocha et al, 2004b;Beberok et al, 2010). EPR spectra of euand pheomelanins differ in shape, and it is used to determine the type of natural melanin in the biological samples and biomaterials (Sarna, 1981;Sealy et al, 1982;Shima et al, 1997;Ito and Wakamatsu, 2003;Latocha et al, 2004aLatocha et al, , 2004bMatuszczyk et al, 2004;Buszman et al, 2006).…”

Section: Introductionmentioning

confidence: 97%

“…It is known that both eu-and pheomelanins are paramagnetic (Sarna, 1981;Sealy et al, 1982;Pasenkiewicz-Gierula and Sealy, 1986;Pilawa et al, 2002;Beberok et al, 2010). Electron paramagnetic resonance (EPR) studies indicated that o-semiquinone free radicals exist in melanins (Sarna, 1981;Sealy et al, 1982;Shima et al, 1997;Ito and Wakamatsu, 2003;Latocha et al, 2004b;Beberok et al, 2010).…”

Section: Introductionmentioning

confidence: 97%

Free radicals in ultraviolet irradiated melanins and melanin complexes with Cd(II) and Cu(II) - EPR examination

2015

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“…The EPR method was used to examine the free radical formation in other sterilized drugs [10][11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27]. Both heating and gamma irradiation caused the free radicals formation in aminoglycoside antibiotics [13].…”

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confidence: 99%

Application of EPR Spectroscopy for Examination of Free Radical Formation in Thermally Sterilized Betamethasone, Clobetasol, and Dexamethasone

Kościelniak-Ziemniak

Pilawa

2012

Appl Magn Reson

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Paramagnetic centers in the three glucocorticosteroid drugs, such as betamethasone, clobetasol, and dexamethasone, were examined by the use of X-band (9.3 GHz) electron paramagnetic resonance (EPR) spectroscopy. Glucocorticosteroid drugs were sterilized according to the norms at 160°C (120 min), 170°C (60 min), and 180°C (30 min). Free radical properties, types, and concentrations in the individual glucocorticosteroids were compared. The lineshape and parameters of EPR curves recorded in the range of the microwave power of 0.7-70 mW were tested. The non-heated drugs were diamagnetic. Free radicals were formed in clobetasol and dexamethasone drugs during process of their thermal sterilization, while free radicals were not detected in thermally sterilized betamethasone. Fast spin-lattice relaxation processes existed in heated clobetasol and dexamethasone. Their EPR lines were homogeneously broadened. A complex free radical system characterized these two drugs. Optimal conditions of sterilization of glucocorticosteroids were obtained. Betamethasone may be sterilized at 160, 170, and 180°C. Clobetasol may be sterilized at 160 and 170°C. Dexamethasone may be sterilized at 170 and 180°C.

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EPR examination of free radical properties of DOPA–melanin complexes with ciprofloxacin, lomefloxacin, norfloxacin and sparfloxacin

Cited by 29 publications

References 41 publications

Cytotoxic effect of lomefloxacin in culture of human epidermal melanocytes

Cytotoxic effect of lomefloxacin in culture of human epidermal melanocytes

Free radicals in ultraviolet irradiated melanins and melanin complexes with Cd(II) and Cu(II) - EPR examination

Application of EPR Spectroscopy for Examination of Free Radical Formation in Thermally Sterilized Betamethasone, Clobetasol, and Dexamethasone

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