Abstract
Fluoroquinolones are defined as an important group of synthetic antibacterial compounds, having a fluorine atom at position 6 and a piperazine ring at position 7 of quinolone-3-carboxylic acid. It was proved that the activity of quinolones was decreased in the environment of certain metal ions by the formation of sparingly soluble metal complexes. The proposed reason for such maintenance might be the chelate bonding of the quinolone to the metal. Again, it was proposed that metal ions, especially magnesium ions, were engaged in the mode of action of quinolones. In this review article, selected structures of fluoroquinolones metal complexes were performed and discussed in terms of their therapeutic application. The nuclease activity and antibacterial activity tests were presented and the effects of metal complexes were compared to free fluoroquinolones. Finally, the results were introduced.
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Sarkozy, G., Vet.-Med. Czeh., 2001, vol. 46, no. 9–10, p. 257.
Scholar, E.M., Am. J. Pharm. Edic., 2002, vol. 66, no. 1, p. 164.
Huber, C.P., Sake Gowda, D.S., and Ravindra, A.K., Acta Crystallogr.: B., 1980, vol. 36, no. 2, p. 497.
Achari, A. and Neidle, S., Acta Crystallogr.: B., 1976, vol. 32, no. 3, p. 600.
Vincent, W.R., Schulman, S. G., Midgley, J. M., et al., Int. J. Pharm., 1981, vol. 9, no. 3, p. 191.
Behrens, N.B., Diaz, G.M., and Goodgame, D.M.L., Inorg. Chim. Acta, 1986, vol. 125, no. 1, p. 21.
Rosales, M.J., Toscano, R.A., Barba-Behrebs, N., and Garcia, J., Acta Crystallogr.: C., 1985, vol. 41, no. 12, p. 1825.
Reynolds, J.E.F., The Extra Pharmacopeia, 30th ed., London: Martindale, The Pharmaceutical Press, 1993, 145 p.
Woldson, J.S. and Hooper, D.C., Quinolone Antimicrodial Agents, Washington, DC: American Society for Microdiology, 1993, 55 p.
Sanchez, B.M., Cabarga, A.S., Navario, A.S., and Hule, A.D., Int. J. Pharm., 1994, vol. 106, no. 3, p. 229.
Koga, H., Iton, A., Murayama, S., et al., J. Med. Chem., 1980, vol. 23, no. 12, p. 1358.
Levine, C., Hiasa, H., and Mariabs, K.J., Biochim. Biophys. Acta, 1998, vol. 1400, no. 1, p. 29.
Zeiler, H.J., and Grohe, K., Eur. J. Clin. Microbiol., 1984, vol. 3, no. 4, p. 339.
Janiec, W. and Krupińska, J., Farmakodynamika, Warszawa: Wydawnictwo Lekarskie, 2005, 989 p.
Hooper, D., In: Mandell, G.L., Bennett, J.E., Dolin, R. et al., Principles and Practice of Infectious Disease, Philadelphia: Churchill Livingstone, 2000, p. 404.
Hooper, D.C., Drugs, 1999, vol. 58,suppl. 2, p. 6.
Anderson, V., Gootz, T., and Osheroff, N., J. Biol. Chem., 1998, vol. 273, no. 28, p. 17879.
Khobursky, A. and Cozzarelli, N., J. Biol. Chem., 1998, vol. 273, no. 41, p. 27668.
Marians, K. and Hiasa, H., J. Biol. Chem., 1997, vol. 272, no. 14, p. 9401.
Shen, L.L., Mischer, L.A., Sharma, P.N., et al., Biochemistry, 1989, vol. 28, no. 9, p. 3886.
Mischer, L.A., Chem. Rev., 2005, vol. 105, no. 2, p. 559.
Skauge, T., Turel, I., and Sletten, E., Inorg. Chim. Acta, 2002, vol. 339, p. 239.
Lorente, B., Leclerc, F., and Cedergen, R., Bioorg. Med. Chem., 1996, vol. 4. no. 1, p. 61.
Palú, G., Valisena, S., Ciarocchi, G., et al., Proc. Natl. Acad. Sci. USA, 1992, vol. 89, no. 20, p. 9671.
Takács-Novák, K., Noszál, B., Hermecz, I., et al., J. Pharm. Sci., 1990, vol. 79, no. 11, p. 1023.
Hoffken, G., Borner, K., Glatzel, P.D., et al., Eur. J. Clin. Microbiol., 1985, vol. 4, no. 3, p. 345.
Ross, D.L. and Riley, C.M., Int. J. Pharm., 1993, vol. 93, no. 1–3, p. 121.
Gugler, R. and Allgayer, H., Clin. Pharmacokinet., 1990, vol. 18, no. 3, p. 210.
Hongtao, Y., Hurley, L.H., and Kerwin, S.M., J. Am. Chem. Soc., 1996, vol. 118, no. 1, p. 7040.
Polk, R.E., Am. J. Med., 1989, vol. 30, no. 87(5A), p. 76S.
Ma, H.H.M., Chiu, F.C.K., and Li, R.C., Pharm. Res., 1997, vol. 14, no. 3, p. 366.
Crumplin, G.C., In: The 4-Qiunolones: Antidacterial Agents in vitro, London: Springer-Verlag, 1990, 15 p.
Teixeira, M.H., Villas-Boas, L.F., and Gil, V.M., J. Chemother., 1995, vol. 7, no. 2, p. 126.
Mizuki, Y., Fujiwara, I., and Yamaguchi, T., J. Antimixrob. Chemother., 1996, vol. 37,suppl. A, p. 41.
Shen, L.L. and Perhet, A.G., Proc. Natl. Acad. Sci. USA, 1985, vol. 82, no. 2, p. 307.
Gellert, M., Mizuuchi, K., O’Dea, M.H., and Nash, H., Proc. Natl. Acad. Sci. USA, 1976, vol. 73, no. 11, p. 3872.
Valisena, S., Palumdo, M., Parolin, C., et al., Biochem. Pharmacol., 1990, vol. 40, no. 3, p. 431.
Belmont, P., Constant, J.F., and Demeunynck, M., Chem. Soc. Rev., 2001, vol. 30, no. 1, p. 70.
Castillo-Blaum, S.E., and Barba-Behrens, N., Coord. Chem. Rev., 2000, vol. 196, no. 1, p. 3.
Ming, L.J., Med. Res. Rev., 2003, vol. 23, no. 6, p. 697.
Froelich-Ammon, S.J., and Osheroff, N., J. Biol. Chem., 1995, vol. 270, no. 37, p. 21429.
Shea, M.E. and Hiasa, H., J. Boil. Chem., 2000, vol. 275, vol. 19, p. 14649.
Okhamafe, A.O., Akerele, J.O., and Chukuka, C.S., Int. J. Pharm., 1991, vol. 68, no. 1–3, p. 11.
Sheehan, G. and Chew, N.S.Y., In: Fluoroquinolone Antibiotics, Basel (Switzerland): Birkhauser, 2003, p. 1.
Robles, J., Polo, J.M., Valtierra, L.A., et al., Met.-Based Drugs, 2000, vol. 7, no. 6, p. 301.
Park, H.R., Oh, C.H., Lee, H.C., et al., Photochem. Photobiol., 2004, vol. 80, no. 3, p. 554.
Yukinori, K., Kyuichi, M., and Hideo, H., Chem. Pharm. Bull., 1996, vol. 44, no. 47, p. 1425.
Lee, D.S., Han, H.J., Kim, K., et al., J. Pharm. Biomed. Anal., 1994, vol. 12, no. 2, p. 157.
Turel, I. and Bukovec, N., Polyhedron., 1996, vol. 15, no. 2, p. 269.
Gao, F., Yang, P., Xie, J., and Wang, H., J. Inorg. Biochem., 1995, vol. 60, no. 1, p. 61.
Willmott, C.J. and Maxwell, A., Antimicrob. Agents Chemother., 1993, vol. 37, no. 1, p. 126.
Ross, D.L. and Riley, C.M., Int. J. Pharm., 1990, vol. 63, no. 3, p. 237.
Toffoli, P., Rodier, N., Ceolin, R., and Blain, Y., Acta Crystallogr.: C., 1987, vol. 43, no. 9, p. 1745.
Parvez, M., Arayne, M.S., Sultana, N., and Siddiqi, A.Z., Acta Crystallogr.: C., 2000, vol. 56, no. 7, p. 910.
Turel, I., Bukovec, P., and Quirós, M., Int. J. Pharm., 1997, vol. 152, no. 1, p. 59.
Prasanna, M.D. and Row, T.N.G., J. Mol. Struct., 2001, vol. 559, no. 1–3, p. 255.
Drakopoulos, A.I. and Ioannou, P.C., Anal. Chim. Acta, 1997, vol. 354, no. 1, 1974.
Turel, I., Leban, I., Klintschar, G., et al., J. Inorg. Biochim., 1997, vol. 66, no. 2, p. 77.
Chen, Z.F., Xiong, R.G., Zuo, J.L., et al., Dalton Trans., 2000, no. 22, p. 4013.
Florence, J.A., Kennedy, A.R., Shankland N., et al., Acta Crystallogr.: C., 2000, vol. 56, no. 11, p. 1372.
European Pharmacopoeia, 5th ed., 15 June 2004.
Metz, P., Kohlhepp, S.J., and Gilbert, D.N., J. Chromatogr.: B, 2002, vol. 773, no. 2, p. 159.
Lu, Z. and Feng, Y., Chin. J. Anal. Chem., 2005, vol. 33, no. 7, p. 999.
El-Kommos, M.E., Saleh, G.A., El-Gizawi, S.M., and Abou-Elwafa, M.A., Talanta, 2003, vol. 60, no. 5, p. 1033.
Ovakovik, J., Nesmerak, K., Nova, H., and Filka, K., J. Pharm. Bioved. Anal., 2001, vol. 25, no. 5–6, p. 957.
Mostafa, S., El-Sadek, M., and Alla, E.A., J. Pharm. Biomed. Anal., 2002, vol. 27, no. 1–2, p. 133.
Sakai, M., Hara, A., Anjo, S., and Nakamura, M., J. Pharm. Biomed. Anal., 1999, vol. 18, no. 6, p. 1057.
Eng-Lin, Z., Bian-Zhen, X., Zhi-Quan, Z., and Shen-Yang, T., J. Pharm. Biomed. Anal., 1999, vol. 21, no. 2, p. 355.
Gonzalez, J.A.O., and Mochon, M.C., Talanta, 2000, vol. 52, no. 6, p. 1149.
Gong, Q.J., Qiao, J.L., Du, L.M., et al., Talanta, 2000, vol. 53, no. 2, p. 359.
Rizk, M., Belal, F., Aly, F.A., and El-Enany, N.M., Talanta, 1998, vol. 46, no. 1, p. 83.
Vichez, J.L., Araujo, L., Prieto, A., and Navalon, A., J. Pharm. Biomed. Anal., 2001, vol. 26, no. 1, p. 23.
Hernandez, M., Borrull, F., and Calull, M., J. Choromatogr.: B., 2000, vol. 742, no. 2, p. 255.
Falagas, M.E., Matthaiou, D.K., and Bliziotis, I.A., Alim. Pharmacol. Therap., 2007, vol. 25, no. 2, p. 123.
Cole, A., Goodfield, J., Williams, D.R., and Midgley, J.M., Inorg. Chim. Acta, 1984, vol. 92, no. 2, p. 91.
Turel, I. and Bukovec, P., Thermochim. Acta, 1996, vol. 287, no. 2, p. 311.
Furet, Y.X., Deshusses, J., and Pechère, J.C., Antimicrob. Agents Chemother., 1992, vol. 36, no. 11, p. 2506.
Harbi, D.J., Hanson, C.W., Hensey, D.M., et al., J. Antimicrob. Chemother., 1988, vol. 22, no. 5, p. 631.
Diemer, R. and Keppler, B.K., J. Inorg. Biochem., 1993, vol. 51, no. 1–2, p. 436.
Stone, J.W., Wise, R., Donovan, I.A., and Gearty, J., J. Antimicrod. Chemother., 1988, vol. 22, no. 1, p. 92.
Turel, I., Leban, I., and Bukovec, N., J. Inorg. Biohem., 1997, vol. 66, no. 4, p. 241.
Rehder, D., Costa Pessoa, J., Geraldes, C.F.G.C., et al., J. Biol. Inorg. Chem., 2002, vol. 7, no. 4–5, p. 384.
Zupancic, M., Arcon, I., Bukovec, P., and Kodre, A., Croatica Chemica Acta, 2002, vol. 75, no. 1, p. 1.
Jimenez-Garrido, N., Perello, L., Ortiz, R., et al., J. Inorg. Biochem., 2005, vol. 99, no. 3, p. 677.
Chiou, S.H., Ohtsu, N., and Bensch, K.G., In: Biological and Inorganic Copper Chemistry, New York: Adenine Press, 1985, 119 p.
Himphreys, K.J., Johnson, A.E., Karlin, K.D., and Rokita, S.E., J. Biol. Inorg. Chem., 2002, vol. 7, no. 7–8, p. 835.
Addison, A.W., Hendriks, H.M.L., Reedijk, J., and Thompson, L.K., Inorg. Chem., 1981, vol. 20, no. 1, p. 103.
Turel, I., Komrlj, J., Andersen, B., and Slettenm E., Metal-Based Drugs, 1999, vol. 6, no. 1, p. 1.
Wallis, S.C., Gahan, L.R., Charles, B.G., et al., J. Inorg. Biohem., 1996, vol. 62, no. 1, p. 1.
Turel, I., Leban, I., and Bukovec, N., J. Inorg. Biohem., 1994, vol. 56, no. 4, p. 273.
Turel, I., Golic, L., Leonel, O., and Ramirez, R., Acta Chim. Slov., 1999, vol. 46, no. 2, p. 203.
Drevensk, P., Zupancic, T., Pihlar, B., et al., J. Inorg. Biohem., 2005, vol. 99, no. 2, p. 432.
Requena, J.R., Groth, D., Legname, G., et al., Proc. Natl. Acad. Sci. USA, 2001, vol. 98, no. 13, p. 7170.
Breeze, S.R. and Wang, S., Inorg. Chem., 1996, vol. 35, no. 11, p. 3404.
Kuzelka, J., Mukhopadhyay, S., Spingler, B., and Lippard, S.J., Inorg. Chem., 2004, vol. 43, no. 5, p. 1751.
Wallis, S.C., Gahan, L.R., Charles, B.G., and Hambley, T.W., Polyhedron, 1995, vol. 14, no. 20–21, p. 2835.
Turel, I., Golobica, A., Klavzara, A., et al., J. Inorg. Biohem., 2003, vol. 95, no. 2–3, p. 199.
Zupancic, M., Turel, I., Bukovec, P., et al., Croatia Chemica Acta, 2001, vol. 74, no. 1, p. 61.
Son, G.S., Yeo, J.A., Kim, M.S., et al., J. Am. Chem. Soc., 1998, vol. 120, no. 26, p. 6451.
Mokrushina, G.A., Kotovskaya, S.K., Baskakova, Z.M., et al., Pharm. Chem. J., 1996, vol. 30, no. 8, p. 540.
Alkaysi, H.N., Abdel-Hay, M.H., Sheikh Salem, M., et al., Int. J. Pharm., 1992, vol. 87, no. 1–3, p. 73.
Chen, Z.F., Xiong, R.G., Zuo, J.L., et al., Dalton Trans., 2000, vol. 22, p. 4013.
Al-Mustafa, J., Acta Chim. Slov., 2002, vol. 49, no. 3, p. 457.
Zupančič, M., Cerc Korošec, R., and Bukovec, P., J. Therm. Anal., 2001, vol. 63, no. 3, p. 787.
Chen, Z.F., Li B.Q., Xie, Y.R., et al., Inorg. Chem. Commun., 2001, vol. 4, no. 7, p. 346.
Turel, I., Leban, I., Klintschar, G., et al., J. Inorg. Biohem., 1997, vol. 61, no. 1, p. 77.
Gao, F., Yang, P., Xie, J., and Wang, H., J. Inorg. Biohem., 1995, vol. 60, no. 1, p. 61.
Pojanagaroon, T., Watanesk, S., Rattanaphani, V., and Liawrungrath, S., Talanta, 2002, vol. 58, no. 6, p. 1293.
Issopoulos, P.B., Ana1yst, 1989, vol. 114, no. 5, p. 627.
Wallis, S.C., Charles, B.G., Gahan, L.R., et al., J. Pharm. Sci., 1996, vol. 85, no. 8, p. 803.
Sadeek, S.A., J. Mol. Struct., 2005, vol. 753, no. 1, p. 1.
Al-Mustafa, J. and Tashtoush, B., J. Coord. Chem., 2003, vol. 56, no. 2, p. 113.
Permana, P.A., Snapka, R.M., Shen, L.L., et al., Biochemistry, 1994, vol. 33, no. 37, p. 11333.
Chen, Z.F., Liang, H., Hu, H.M., et al., Inorg. Chem. Commun., 2003, vol. 6, no. 3, p. 241.
Li, Y.X., Chen, Z.F., Xiong, R.G., et al., Inorg. Chem. Commun., 2003, vol. 6, no. 7, p. 819.
Chen, Z.F., Xiong, R.G., Zhang, J., et al., Inorg. Chem., 2001, vol. 40, no. 16, p. 4075.
Hayakawa, I., Atarashi, S., Jokohama, S., et al., Antimicrob. Agents Chemother., 1986, vol. 29, no. 1, p. 163.
Hwangbo, H.J., Yun, B.H., Cha, J.S., et al., Eur. Pharm. Sci., 2003, vol. 18, no. 2, p. 197.
Kapettanovic, V., Milovanovic, L., and Erce, M., Talanta, 1996, vol. 43, no. 12, p. 2123.
Morrisey, I., Hoshino, K., Sato, K., et al., Antimicrob. Agents Chemother., 1996, vol. 40, no. 8, p. 1775.
Irving, H., and Williams, R.J.P., Nature, 1948, vol. 162, no. 4125, p. 746.
Drevensek, P., Kosmrlj, J., Giester, G., et al., J. Inorg. Biohem., 2006, vol. 100, no. 11, p. 1755.
Kawai, Y.K. and Matsubayashi, H., Chem. Pharm. Bull., 1996, vol. 44, no. 8, p. 1425.
Navon, G. and Valensin, G., In: Metal Ions in Biological Systems, New York: M. Dekker, 1987, vol. 21, 1447 p.
Sagdinc, S. and Bayari, S., J. Mol. Struct., 2004, vol. 691, no. 1–3, p. 107.
Macias, B., Villa, M.V., Sastre, M., et al., J. Pharm. Sci., 2002, vol. 91, no. 11, p. 2416.
Macias, B., Villa, M.V., Rubio, I., et al., J. Inorg. Biohem., 2001, vol. 84, no. 3, p. 163.
Lecomte, S., Baron, M.H., Chenon, M.T., et al., Antimicrob. Agents. Chemother., 1994, vol. 38, no. 12, p. 2810.
Lecomte, S. and Chenon, M.T., Int. J. Pharm., 1996, vol. 139, no. 1–2, p. 105.
Baenziger, N.C., Fox, C.L., and Modak, S.L., Acta Crystallogr.: C, 1986, vol. 42, no. 11, p. 1505.
Turel, I., Coord. Chem. Rev., 2002, vol. 232, no. 1–2, p. 27.
Nakamoto, K., Infrared and Raman Spectra of Inorganic and Coordination Comprounds, New York: John Wiley and Sons, 1986, p. 230.
Silverstein, R.M., Bassler, G.C., and Morril, T.C., Spectroscopic Identification of Organic Comprounds, New York: John Wiley and Sons, 1991.
López-Gresa, M.P., Ortiz, R., Perelló, L., et al., J. Inorg. Biochem., 2002, vol. 92, no. 1, p. 65.
Koppenhöfer, A., Hartmann, U., and Vahrenkamp, H., Chem. Ber., 1995, vol. 128, no. 8, p. 779.
Conry, R.R. and Karlin, K.D., In: Encyclopedia of Inorganic Chemistry, vol. 2, Chichester: John Wiley and Sons, 1994, p. 9.
Akriff, Y., Server-Carrió, J., Sancho, A., et al., Inorg. Chem., 1999, vol. 38, no. 6, p. 1174.
Kivelson, D. and Neiman, R., J. Chem. Phys., 1961, vol. 35, no. 1, p. 149.
Deacon, G.B. and Phillips, R.J., Coord. Chem. Rev., 1980, vol. 33, no. 3, p. 227.
Ruiz, M., Ortiz, R., Perelló, L., et al., Inorg. Chim. Acta, 1994, vol. 217, no. 1, p. 149.
Palu, G., Valisena, S., Ciarrocchi, G., et al., Proc. Natl. Acad. Sci. USA, 1992, vol. 89, no. 20, p. 9671.
Sissi, C., Perdonà, E., Domenici, E., et al., J. Mol. Biol., 2001, vol. 311, no. 1, p. 195.
Brighty, K.E. and Gootz, T.D., In: The Quinolones, San Diego: Academic Press, 2000, 33 p.
Sissi, C., Andreolli, M., Cecchetti, V., et al., Bioorg. Med. Chem., 1998, vol. 6, no. 9, p. 1555.
Mitscher, L.A., Chem. Rev., 2005, vol. 105, no. 2, p. 559.
Hou, M.H., Robinson, H., Gao, Y.G., and Wang, A.H.J., Nucl. Actids Res., 2004, vol. 32, no. 7, p. 2214.
Turel, I., Golic, L., Bukovec, P., and Gubina, M., J. Inorg. Biochem., 1998, vol. 71, no. 1–2, p. 53.
Drevenšek, P., Golobič, A., Turel, I., et al., Acta Chim. Slov., 2002, vol. 49, no. 4, p. 857.
Ball, P., In: The Quinolones, San Diego: Academic Press, 2000, 1 p.
The Quinolones, Stahlmann, R., Lode, H., Andriole, V.T., Eds, San Diego: Academic Press, 2000, 397 p.
Turel, I., Sonc, A., Zupancic, M., et al., Met.-Based Drugs, 2000, vol. 7, p. 101.
Annear, D.I., J. Antimicrob. Chemother., 1982, vol. 10, no. 4, p. 260.
Finney, L.A. and O’Halloran, T.V., Sceince, 2003, vol. 5621, p. 931.
Ramirez-Ramirez, N., Mendoza-Diaz, G., Gutierrez-Corona, F., and Pedraza-Reyes, M., J. Biol. Inorg. Chem., 1998, vol. 3, no. 2, p. 188.
Pope, L.E. and Sigman, D.S., Proc. Natl. Acad. Sci. USA, 1984, vol. 81, no. 1, p. 3.
Drevenšek, P., Turel, I., and Ulrich, N.P., J. Inorg. Biochem., 2003, vol. 96, no. 2–3, p. 407.
Tak, A., Arjmand, F., and Tabassum, S., Transition Met. Chem., 2003, vol. 28, no. 7, p. 741.
Lopez-Gresa, M.P., Ortiz, R., Perello, L., et al., J. Inorg. Biocgem., 2002, vol. 92, no. 1, p. 65.
Thomas, A.M., Nethaji, M., Mahadevan, S., and Chakravarty, A., J. Inorg. Biochem., 2003, vol. 94, no. 1–2, p. 171.
Saglam, N., Colak, A., Serbest, K., et al., Biometals, 2002, vol. 15, no. 4, p. 357.
Garcia-Raso, A., Fiol, J.J., Adrover, B., et al., J. Inorg. Biochem., 2003, vol. 95, no. 2–3, p. 77.
Reddy, P.A.N., Santra, B.K., Nethaji, M., and Chakravarty, A.R., J. Inorg. Biochem., 2004, vol. 98, no. 2, p. 377.
Oyoshi, T. and Sugiyama, H., J. Am. Chem. Soc., 2000, vol. 122, no. 26, p. 6313.
Thederahn, T.B., Kuwadara, M.D., Larsen, T.A., and Sigman, D.S., J. Am. Chem. Soc., 1989, vol. 111, no. 13, p. 4941.
Yamamoto, K. and Kawanishi, S., J. Biol. Chem., 1989, vol. 264, no. 26, p. 15435.
Leżowska-Bojczuk, M., Szczepaniak, W., Leśniak, W., et al., Eur. J. Biochem., 2002, vol. 269, no. 22, p. 5547.
Lecomte, S., Moreau, N.J., and Chinon, M.T., Int. J. Pharm., 1998, vol. 164, no. 1–2, p. 57.
Turel, I., Golobic, A., Klavzar, A., et al., J. Inorg. Biochem., 2003, vol. 95, no. 2–3, p. 199.
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Serafin, A., Stańczak, A. The complexes of metal ions with fluoroquinolones. Russ J Coord Chem 35, 81–95 (2009). https://doi.org/10.1134/S1070328409020018
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DOI: https://doi.org/10.1134/S1070328409020018