Abstract
1H-NMR spectroscopy (500 MHz) was used to study the complexation of the antibacterial agent norfloxacin (NOR) with DNA tetramers 5′-d(TpGpCpA) and 5′-d(CpGpCpG) in aqueous solution. For the first time, the equilibrium parameters (equilibrium constants, enthalpy, and entropy) were obtained for NOR binding with single-stranded and duplex DNA tetramers. By analyzing the complexation parameters and the induced proton chemical shifts in NOR in various complexes, the character of NOR binding was identified as intercalation in the case of the duplex tetramers and as intercalation with external binding in the case of single-stranded tetramers. NOR proved to preferentially bind to GC sites in DNA duplexes.
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References
Appelbaum P.C., Hunter P.A. 2000. The fluoroquinolone antibacterials: Past, present, and future perspectives. Int. J. Antimicrob. Agents. 16, 5–15.
Christian J.S. 1996. The quinolone antibiotics. Obstetr. Gynecol. 3, 87–92.
Hooper D.C. 1999. Mode of action of fluoroquinolones. Drugs. 58, 6–10.
Shen L.L. 1994. Molecular mechanisms of DNA gyrase inhibition by quinolone antibacterials. Adv. Pharmacol. 29A, 285–304.
Drlica K., Zhao X. 1997. DNA gyrase, topoisomerase IV, and the 4-quinolones. Microbiol. Mol. Biol. Rev. 61, 377–392.
Shen L.L., Pernet A.G. 1985. Mechanism of inhibition of DNA gyrase by analogues of nalidixic acid: The target of the drugs is DNA. Proc. Natl. Acad. Sci. USA. 82, 307–311.
Shen L.L., Kohlbrenner W.E., Weigl D., Baranowski J. 1989. Mechanism of quinolone inhibition of DNA gyrase. J. Biol. Chem. 264, 2973–2978.
Bourguignon G.J., Levitt M., Sternglanz R. 1973. Studies on the mechanism of action of nucleic acid. Antimicrob. Agents Chemother. 4, 479–486.
Le Goffic F. 1985. Les quinolones, mecanisme d’action. In: Les Nouvelles Quinolones. Paris: Editiones Arnette, pp. 15–23.
Dreyfuss J.M., Midgley J.M. 1983. Structure-activity relationships in aromatic ring fused 4-pyridones substituted at position 3. J. Pharm. Pharmacol. 83, 75.
Tornaletti S., Pedrini A.M. 1988. Studies on the interaction of 4-quinolones with DNA by DNA unwinding experiments. Biochim. Biophys. Acta. 949, 279–287.
Son G.-S., Yeo J.-A., Kim J.-M., Kim S.K., Moon H.R., Nam W. 1998. Base specific complex formation of norfloxacin with DNA. Biophys. Chem. 74, 225–236.
Bailly C., Colson P., Houssier C. 1998. The orientation of Norfloxacin bound to double-stranded DNA. Biochem. Biophys. Res. Commun. 243, 844–848.
Sandstrom K., Warmlander S., Leijon M., Groslund A. 2003. 1H NMR studies of selective interactions of norfloxacin with double-stranded DNA. Biochem. Biophys. Res. Commun. 304, 55–59.
Son G.S., Yeo J.-A., Kim M.-S., Kim S.K., Holmen A., Akerman B. 1998. Binding mode of norfloxacin to calf thymus DNA. J. Am. Chem. Soc. 120, 6451–6457.
Davies D.B., Veselkov A.N. 1996. Structural and thermodynamical analysis of molecular complexation by 1H NMR spectroscopy. Intercalation of ethidium bromide with the isomeric deoxytetranucleoside triphosphates 5′-d(GpCpGpC) and 5′-d(CpGpCpG) in aqueous solution. J. Chem. Soc. Faraday Trans. 92, 3545–3557.
Davies D.B., Eaton R.J., Baranovsky S.F., Veselkov A.N. 2000. NMR investigation of the complexation of daunomycin with deoxytetranucleotides of different base sequence in aqueous solution. J. Biomol. Struct. Dyn. 17, 887–901.
Eaton R.J., Veselkov D.A., Pakhomov V.I., Baranovsky S.F., Bolotin P.A., Osetrov S.G., Dymant L.N., Davies D.B., Veselkov A.N. 1999. NMR study of the sequence specificity of complex formation of the antibiotic daunomycin with isomeric tetradeoxynucleotides 5′-d(ACGT), 5′-d(AGCT), and 5′-d(TGCA). Mol. Biol. 33, 803–813.
Veselkov A.N., Dymant L.N., Kodintsev V.V., Lisyutin V.A., Parkes H., Davies D.B. 1995. 1H NMR analysis of self-association of deoxytetraribonucleoside triphosphate molecules d(TpGpCpA) in aqueous solution. Biofizika. 40, 283–292.
Evstigneev M.P., Rybakova K.A., Davies D.B. 2006. Complexation of Norfloxacin with DNA in the presence of caffeine. Biophys. Chem. 121, 84–95.
Ross R.D., Subramanian S. 1981. Thermodynamics of protein association reactions: Forces contributing to stability. Biochemistry. 20, 3096–3102.
Feigon J., Denny W.A., Leupin W., Kearns D.R. 1984. Interactions of antitumor drugs with natural DNA: 1H NMR study of binding mode and kinetics. J. Med. Chem. 27, 450–465.
Lee E.-J., Yeo J.-A., Cho C.-B., Lee G.-J., Han S.W., Kim S.K. 2000. Amine group of guanine enhances the binding of norfloxacin antibiotics to DNA. Eur. J. Biochem. 267, 6018–6024.
Lee H.M., Kim J.-K., Kim S.K. 2002. Molecular modeling study of the Norfloxacin-DNA complex. J. Biomol. Struct. Dyn. 19, 1083–1091.
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Original Russian Text © M.P. Evstigneev, S.F. Baranovsky, K.A. Rybakova, D.B. Davies, 2006, published in Molekulyarnaya Biologiya, 2006, Vol. 40, No. 5, pp. 894–899.
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Evstigneev, M.P., Baranovsky, S.F., Rybakova, K.A. et al. Complexation of the quinolone antibiotic norfloxacin with DNA. Mol Biol 40, 805–810 (2006). https://doi.org/10.1134/S0026893306050165
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DOI: https://doi.org/10.1134/S0026893306050165