J Appl Biomed 12:161-169, 2014 | DOI: 10.1016/j.jab.2013.12.002

Interaction of free radicals of DOPA-melanin-streptomycin complexes with paramagnetic oxygen O2

Barbara K. Wierneka,*, Barbara Pilawaa, Magdalena Zdybela, Ewa Buszmanb, Dorota Wrześniokb
a Department of Biophysics, School of Pharmacy with the Division of Laboratory Medicine, Medical University of Silesia in Katowice, Poland
b Department of Pharmaceutical Chemistry, School of Pharmacy with the Division of Laboratory Medicine, Medical University of Silesia in Katowice, Poland

Oxygen plays an important role in the metabolism of all tissues. The level of oxygen in the environment of melanin biopolymer in human body may change toxic effects resulted from free radicals formation in melanin-drug complexes.
Using electron paramagnetic resonance (EPR) spectroscopy we measured the effect of molecular oxygen on concentration and properties of free radicals in 3,4-dihydroxyphenylalanine-melanin (DOPA-melanin) complexes with streptomycin. Studies have shown that free radical properties of melanin are heavily dependent on the presence of oxygen in the environment of the sample. Streptomycin increases the concentration of free radicals in DOPA-melanin but in the presence of oxygen this concentration is reduced.
The EPR studies confirmed the existence of stable o-semiquinone free radicals (∼1018-1019 spin/g) in DOPA-melanin-streptomycin complexes, both in air and in vacuum, and the formation of quasi-chemical bonds between the DOPA-melanin-streptomycin complexes and oxygen molecules, which are responsible for the decrease in the concentration of free radicals. Our study showed that oxygen exerts an influence on spin-spin and spin-lattice interactions in the investigated complexes. Such effects can also be expected in a living organism, because DOPA-melanin is a model eumelanin mainly present in human tissues.

Keywords: Oxygen; DOPA-melanin; Streptomycin; EPR spectroscopy; Free radicals; DOPA-melanin-drug complexes

Received: December 10, 2013; Accepted: December 12, 2013; Published: July 1, 2014  Show citation

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Wiernek BK, Pilawa B, Zdybel M, Buszman E, Wrześniok D. Interaction of free radicals of DOPA-melanin-streptomycin complexes with paramagnetic oxygen O2. J Appl Biomed. 2014;12(3):161-169. doi: 10.1016/j.jab.2013.12.002.
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    References

    1. Bartosz, G., 2006. Second Face of Oxygen. Free Radicals in Environment. PWN, Warszawa (in Polish).
    2. Beberok, A., Buszman, E., Zdybel, M., Pilawa, B., Wrześniok, D., 2010. EPR examination of free radical properties of DOPA- melanin complexes with ciprofloxacin, lomefloxacin, norfloxacin and sparfloxacin. Chem. Phys. Lett. 497, 115-122. Go to original source...
    3. Binns, F., Chapman, R.F., Robson, N.C., Swan, G.A., Waggott, A., 1970. Studies related to the chemistry of melanins. 8. The pyrrolecarboxylic acids formed by oxidation or hydrolysis of melanins derived from 3,4-dihydroxyphenethylamine or (plus or minus)-3,4-dihydroxyphenylalanine. J. Chem. Soc.: Perkin Trans. 8, 1128-1134. Go to original source... Go to PubMed...
    4. Buszman, E., Pilawa, B., Zdybel, M., Wrześniok, D., Grzegorczyk, A., Wilczok, T., 2005a. EPR examination of Zn2+ and Cu2+ effect on free radicals in DOPA-melanin-netilmicin complexes. Chem. Phys. Lett. 403, 22-28. Go to original source...
    5. Buszman, E., Pilawa, B., Zdybel, M., Wrześniok, D., Grzegorczyk, A., Wilczok, T., 2005b. Paramagnetic centers in DOPA- melanin-dihydrostreptomycin complexes. Acta Phys. Pol. A 108, 353-356. Go to original source...
    6. Chio, S.S., Hyde, J.S., Sealy, R.C., 1980. Temperature-dependent paramagnetism in melanin polymers. Arch. Biochem. Biophys. 199, 133-139. Go to original source... Go to PubMed...
    7. Chodurek, E., Zdybel, M., Pilawa, B., Dzierżewicz, Z., 2012. Examination by EPR spectroscopy of free radicals in melanins isolated from A-375 cells exposed on valproic acid and cisplatin. Acta Pol. Pharm. Drug Res. 69, 1334-1341. Go to PubMed...
    8. Chodurek, E., Zdybel, M., Pilawa, B., 2013. Application of EPR spectroscopy to examination of free radicals in melanins from A-375 and G-361 human melanoma malignum cells. J. Appl. Biomed. 11, 173-185. Go to original source...
    9. Eaton, G.R., Eaton, S.S., Salikhov, K.M., 1998. Foundations of Modern EPR. World Scientific, Singapore; River Edge, NJ. Go to original source...
    10. Enochs, W.S., Nilges, M.J., Swartz, H.M., 1993. A standardized test for the identification and characterization of melanins using electron paramagnetic resonance (EPR) spectroscopy. Pigment Cell Res. 6, 91-99. Go to original source... Go to PubMed...
    11. Hilding, D.A., Ginzberg, R.D., 1977. Pigmentation of the stria vascularis. The contribution of neural crest melanocytes. Acta Otolaryngol. 84, 24-37. Go to original source... Go to PubMed...
    12. Ibrahim, H., Aubry, A.F., 1995. Development of a melanin-based high-performance liquid chromatography stationary phase and its use in the study of drug-melanin binding interactions. Anal Biochem. 229, 272-277. Go to original source... Go to PubMed...
    13. Ilangovan, G., Zweier, J.L., Kuppusamy, P., 2004. Mechanism of oxygen-induced EPR line broadening in lithium phthalocyanine microcrystals. J. Magn. Reson. 170, 42-48. Go to original source... Go to PubMed...
    14. Kniep, B., Grisebach, H., 1980. Biosynthesis of streptomycin. Purification and properties of a dTDP-L-dihydrostreptose: streptidine-6-phosphate dihydrostreptosyltransferase from Streptomyces griseus. Eur. J. Biochem. 105, 139-144. Go to original source... Go to PubMed...
    15. Kościelniak-Ziemniak, M., Pilawa, B., 2012. Application of EPR spectroscopy for examination of free radical formation in thermally sterilized betamethasone, clobetasol, and dexamethasone. Appl. Magn. Reson. 42, 519-530. Go to original source...
    16. Latocha, M., Pilawa, B., Pietrzak, R., Nowicki, P., Wachowska, H., 2008. Conditions of photodynamic therapy of tumor cells examined by carbonized coal and EPR spectroscopy. Eng. Biomater. 73, 4-6.
    17. Leblanc, B., Jezequel, S., Davies, T., Hanton, G., Taradach, C., 1998. Binding of drugs to eye melanin is not predictive of ocular toxicity. Regul. Toxicol. Pharmacol. 28, 124-132. Go to original source... Go to PubMed...
    18. Marcotti, W., van Netten, S.M., Kros, C.J., 2005. The aminoglycoside antibiotic dihydrostreptomycin rapidly enters mouse outer hair cells through the mechanoelectrical transducer channels. J. Physiol. 567, 505-521. Go to original source... Go to PubMed...
    19. Marszall, M.P., Buciński, A., Goryński, K., Proszowska, A., Kaliszan, R., 2011. Magnetic beads method for determination of binding of drugs to melanin. J. Chromatogr. A 1218, 229-236. Go to original source... Go to PubMed...
    20. Mizoguchi, K., Kachi, N., Sakamoto, H., Yoshioka, K., Masubuchi, S., Kazama, S., 1998. The effect of oxygen on the ESR linewidth in polypyrrole doped by PF6À. Solid State Commun. 105, 81-84. Go to original source...
    21. Najder-Kozdrowska, L., Pilawa, B., Więckowski, A.B., Buszman, E., Wrześniok, D., 2009. Influence of copper(II) ions on radical in DOPA-melanin. Appl. Magn. Reson. 36, 81-88. Go to original source...
    22. Najder-Kozdrowska, L., Pilawa, B., Buszman, E., Więckowski, A.B., Świątkowska, L., Wrześniok, D., Wojtowicz, W., 2010. Triplet states in DOPA-melanin and in its complexes with kanamycin and copper Cu(II) ions. Acta Phys. Pol. A 118, 613-618. Go to original source...
    23. Okazaki, M., Kuwata, K., Miki, Y., Shiga, S., Shiga, T., 1985. Electron spin relaxation of synthetic melanin and melanincontaining human tissues as studied by electron spin echo and electron spin resonance. Arch. Biochem. Biophys. 242, 197-205. Go to original source... Go to PubMed...
    24. Pilawa, B., Buszman, E., Wrześniok, D., Latocha, M., Wilczok, T., 2002. Application of EPR spectroscopy to examination of gentamicin and kanamycin binding to DOPA-melanin. Appl. Magn. Reson. 23, 181-192. Go to original source...
    25. Pilawa, B., Latocha, M., Buszman, E., Wilczok, T., 2003. Effect of oxygen on spin-spin and spin-lattice relaxation in DOPA- melanin. Complexes with chloroquine and metal ions. Appl. Magn. Reson. 25, 105-111. Go to original source...
    26. Pilawa, B., Latocha, M., Krzyminiewski, R., Kruczyński, Z., Buszman, E., Wilczok, T., 2004. Effect of temperature on melanin EPR spectra. Phys. Med. 20, 96-98.
    27. Pilawa, B., Latocha, M., Ramos, P., Kościelniak, M., Pietrzak, R., Wachowska, H., 2008. New paramagnetic probes and singlet oxygen formation in cells. Curr. Top. Biophys. 31, 10-15.
    28. Plonka, P.M., Michalczyk, D., Popik, M., Handjiski, B., Slominski, A., Paus, R., 2005. Splenic eumelanin differs from hair eumelanin in C57BL/6 mice. Acta Biochim. Pol. 52, 433-441. Go to original source... Go to PubMed...
    29. Plonka, P.M., Michalczyk, D., Popik, M., Handjiski, B., Paus, R., 2008. Electron paramagnetic resonance (EPR) spectroscopy for investigating murine telogen skin after spontaneous or depilation-induced hair growth. J. Dermatol. Sci. 49, 227-240. Go to original source... Go to PubMed...
    30. Priuska, E.M., Schacht, J., 1995. Formation of free radicals by gentamicin and iron and evidence for an iron/gentamicin complex. Biochem. Pharmacol. 50, 1749-1752. Go to original source... Go to PubMed...
    31. Ramos, P., Pilawa, B., 2010. The EPR examination of free radicals formation in thermally sterilized b-lactam antibiotics. Curr. Top. Biophys. 33, 183-187.
    32. Ramos, P., Pilawa, B., Biernaś, M., 2010. Effect of storage time on microwave saturation of EPR spectra of thermally sterilized streptomycyn and its practical applications. J. Med. Inform. Technol. 15, 185-191.
    33. Sarna, T., Sealy, R.C., 1984. Free radicals from eumelanins: quantum yields and wavelength dependence. Arch. Biochem. Biophys. 232, 574-578. Go to original source... Go to PubMed...
    34. Sarna, T., 1987. Photophysical properties of melanins and photoreactions of pigmented cells. Curr. Top. Biophys. 12, 119-132 (in Polish).
    35. Sealy, R.C., Hyde, J.S., Felix, C.C., Menon, I.A., Prota, G., 1982. Eumelanins and pheomelanins: characterization by electron spin resonance spectroscopy. Science 217, 545-547. Go to original source... Go to PubMed...
    36. Sentjurc, M., Cemazar, M., Sersa, G., 2004. EPR oximetry of tumors in vivo in cancer therapy. Spectrochim. Acta A: Mol. Biomol. Spectrosc. 60, 1379-1385. Go to original source... Go to PubMed...
    37. Singer, L.S., Mitchell, S., 1997. Diffusion of oxygen into pitch. Carbon 35, 599-604. Go to original source...
    38. Stolc, S., Valko, L., Valko, M., Lombardi, V., 1996. A technique for the fast sampling of biological tissues for electron paramagnetic resonance spectroscopy. Free Radic. Biol. Med. 20, 89-91. Go to original source... Go to PubMed...
    39. Tran, M.L., Powell, B.J., Meredith, P., 2006. Chemical and structural disorder in eumelanins: a possible explanation for broadband absorbance. Biophys. J. 90, 743-752. Go to original source... Go to PubMed...
    40. Wertz, J.E., Bolton, J.R., 1986. Electron spin Resonance: Elementary Theory and Practical Applications. Chapman and Hall, London. Go to original source...
    41. Wilczyński, S., Pilawa, B., Koprowski, R., Wróbel, Z., Ptaszkiewicz, M., Swakoń, J., Olko, P., 2012. EPR studies of free radicals decay and survival in gamma irradiated aminoglycoside antibiotics: sisomicin, tobramycin and paromomycin. Eur. J. Pharm. Sci. 24, 254-261. Go to original source... Go to PubMed...
    42. Wrześniok, D., Buszman, E., Trzcionka, J., Różańska, R., 1999. Streptomycin and dihydrostreptomycin binding to melanin in relation to aminoglycosides ototoxicity. Ann. Acad. Med. Siles 40-41, 63-76.
    43. Zdybel, M., Chodurek, E., Pilawa, B., 2011. EPR studies of DOPA- melanin complexes with Fe(III). Appl. Magn. Reson. 40, 113- 123. Go to original source...
    44. Zdybel, M., Pilawa, B., Buszman, E., Wrześniok, D., Krzyminiewski, R., Kruczyński, Z., 2012a. EPR studies of DOPA-melanin complexes with netilmicin and Cu(II) at temperatures in the range of 105-300 K. Appl. Magn. Reson. 43 (3) 341-351. Go to original source... Go to PubMed...
    45. Zdybel, M., Pilawa, B., Krzeszewska-Zaręba, A., 2012b. Lasers in ophthalmology. In: Rumelt, S. (Ed.), Advances in Ophthalmology. InTech, Rijeka, pp. 3-24. Go to original source...
    46. Zdybel, M., Pilawa, B., Buszman, E., Witoszyńska, T., 2013a. EPR studies of Cladosporium cladosporioides complexes with amphotericin B. Nukleonika 58, 401-405.
    47. Zdybel, M., Pilawa, B., Buszman, E., Wrześniok, D., 2013b. Effect of oxygen on free radicals in DOPA-melanin complexes with netilmicin, diamagnetic Zn(II), and paramagnetic Cu(II). Chem. Phys. Lett. 556, 278-286. Go to original source...
    48. Zembower, T.R., Noskin, G.A., Postelnick, M.J., Nguyen, C., Peterson, L.R., 1998. The utility of aminoglycosides in an era of emerging drug resistance. Int. J. Antimicrob. Agents 10, 95-105. Go to original source... Go to PubMed...

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