Competitive Binding of Novel Cyanine Dye AK3-5 and Europium Coordination Complexes to DNA

  • Olga Zhytniakivska Department of Physics and Technology, V.N. Karazin Kharkiv National University, Kharkiv, Ukraine https://orcid.org/0000-0001-9554-0090
  • Anna Zabrudska Department of Physics and Technology, V.N. Karazin Kharkiv National University, Kharkiv, Ukraine https://orcid.org/0000-0002-3611-8188
  • Uliana Tarabara Department of Physics and Technology, V.N. Karazin Kharkiv National University, Kharkiv, Ukraine https://orcid.org/0000-0002-7677-0779
  • Kateryna Vus Department of Physics and Technology, V.N. Karazin Kharkiv National University, Kharkiv, Ukraine http://orcid.org/0000-0003-4738-4016
  • Valeriya Trusova Department of Physics and Technology, V.N. Karazin Kharkiv National University, Kharkiv, Ukraine https://orcid.org/0000-0002-7087-071X
  • Galyna Gorbenko Department of Physics and Technology, V.N. Karazin Kharkiv National University, Kharkiv, Ukraine http://orcid.org/0000-0002-0954-5053
  • Atanas Kurutos Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, Sofia, Bulgaria https://orcid.org/0000-0002-6847-198X
  • Todor Deligeorgiev Faculty of Chemistry and Pharmacy, Sofia University ‘‘St. Kliment Ohridski’’, Sofia, Bulgaria
Keywords: trimethine cyanine dye, europium coordination complexes, antitumor drug, DNA

Abstract

The present study was undertaken to assess the applicability of the novel trimethine cyanine dye AK3-5 as a competitive ligand for the antitumor agents, Eu(III) coordination complexes (EC), in the DNA-containing systems, using the displacement assay as an analytical instrument. The analysis of fluorescence spectra revealed a strong association of AK3-5 with nucleic acids, with the strength of interaction being higher for the double stranded DNA, compared to the single-stranded RNA. The binding parameters of the cyanine dye have been determined in terms of the McGhee & von Hippel neighbouring site-exclusion model and a classical Langmuir model. The AK3-5 association constant in the presence of DNA was found to be equal to 5.1×104 M-1, which is consistent to those of the well-known DNA intercalators. In turn, the binding of the cyanine to the RNA was characterized by a significantly lower association constant ( ~ 3.4×103 M-1) indicating either the external or “partially intercalated” binding mode. The addition of the europium complexes to the AK3-5-DNA system was followed by the fluorescence intensity decrease, with a magnitude of this effect being dependent on the EC structure. The observed fluorescence decrease of AK3-5 in the presence of europium complexes V7 and V9 points to the competition between the cyanine dye and antitumor drugs for the DNA binding sites. The dependencies of the AK3-5-DNA fluorescence intensity decrease vs. europium complex concentration were analyzed in terms of the Langmuir adsorption model, giving the values of the drug association constant equal to 5.4×104 M-1and 3.9×105 M-1 for the europium complexes V7 and V9, respectively. A more pronounced decrease of the AK3-5 fluorescence in the presence of V5 and V10 was interpreted in terms of the drug-induced quenching of the dye fluorescence, accompanying the competition between AK3-5 and Eu(III) complexes for the DNA binding sites. Cumulatively, the results presented here strongly suggest that AK3-5 can be effectively used in the nucleic acid studies and in the dye-drug displacement assays.

Downloads

References

S.F. Cui, Y. Ren, S.L. Zhang, X.M. Peng, G.L. Damu, R.X. Geng and C.H. Zhou, Bioorg. Med. Chem. Lett. 23, 3267–3272 (2013). https://doi.org/10.1016/j.bmcl.2013.03.118

G. Momekov, T. Deligeorgiev, A. Vasilev, K. Peneva, S. Konstantinov and M. Karaivanova, Med. Chem. 2, 439–445 (2006).

A. Opar, Nat. Rev. Drug Discov., 8, 437–438 (2009). https://doi.org/10.1038/nrd2916

K. Qumaizi, R. Anwer, N. Ahmad and S. Alosaimi, J. Mol. Recognit. 31, 2735–2745 (2018). https://doi.org/10.1002/jmr.2735

M. Anjomshoa and M. Torkzadeh-Mahani, J. Fluoresc. 26, 1505–1510 (2016). https://doi.org/10.1007/s10895-016-1850-z

M. A. Husain, H. M. Ishqi, T. Sarwar, S.U. Rehman and M. Tabish, Med. Chem. Comm. 8, 1283–1296 (2017). https://doi.org/10.1039/C7MD00094D

W.S. Tse and D. Boger, Acc. Chem. Res. 37, 61–69 (2004). https://doi.org/10.1021/ar030113y

J. Szekely and K.S. Gates, Chem. Res. Toxicol. 19, 117–121 (2006). https://doi.org/10.1021/tx050197e

P. Cerutti, Science. 227, 375–381 (1985). https://doi.org/10.1126/science.2981433

K.E. Achyuthan and D.G. Whitten, Comb. Chem. High. Throughput Screen. 10, 399–412 (2007). https://doi.org/10.2174/138620707781996475

K.E. Achyuthan, D.G. Whitten and D.W. Branch, Anal. Sci. 26, 55–61 (2010). https://doi.org/10.2116/analsci.26.55

B. Armitage, Topp. Curr. Chem. 253, 55-76 (2005). https://doi.org/10.1007/b100442

H. Rye, S. Yue, D. Wemmer, M. Quesada, P. Haugland, R. Mathies and A. Glazer, Nucleic Acid Res. 20, 2803-2812 (1992). https://doi.org/10.1093/nar/20.11.2803

X. Yan, W. Grace, T. Yoshida, R. Habbersett, N. Velappan, J. Jett, R. Keller and B. Marrone, Anal. Chem. 71, 5470-5480 (1999). https://doi.org/10.1021/ac990780y

S. Gurrieri, K. Wells, I. Johnson and C. Bustamente, Anal. Biochem. 249, 44-53 (1997). https://doi.org/10.1006/abio.1997.2102

T. Biver, A. Boggioni, F, Secco, E. Turriani, S. Venturini and S. Yarmoluk, Arch. Biochem. Biophys. 465, 90-100 (2007). https://doi.org/10.1016/j.abb.2007.04.034

S. Kaloyanova, V. Trusova, G. Gorbenko and T. Deligeorgiev, J. Photochem. Photobiol. A. 217, 147-156 (2011). https://doi.org/10.1016/j.jphotochem.2010.10.002

L. Glavas-Obrovac, I. Piantanida, S. Marczi, L. Masic, I. Timcheva and T. Deligeorgiev, Bioorg. Med. Chem. 17, 4747-4755 (2009). https://doi.org/10.1016/j.bmc.2009.04.070

A. Kurutos, O. Ryzhova, V. Trusova, U. Tarabara, G. Gorbenko, N. Gadjev and T. Deligeorgiev, Dyes and Pigments. 130, 122-128 (2016). https://doi.org/10.1016/j.dyepig.2016.03.021

A. Kurutos, O. Ryzhova, V. Trusova, G. Gorbenko, N. Gadjev and T. Deligeorgiev. J. Fluoresc. 26, 177-187 (2015). https://doi.org/10.1007/s10895-015-1700-4

A. Kurutos, I. Crnolatac, I. Orehovec, N. Gadjev, I. Piantanida and T. Deligeorgiev, J. Liminescence. 174, 70-76 (2016). https://doi.org/10.1016/j.jlumin.2016.01.035

J. Petty and M. Bordelon, J. Phys. Chem. B. 1041, 7221-7227 (2000). https://doi.org/10.1021/jp000916s

H. LeVine, Protein Sci. 2, 404-410 (1993), https://doi.org/10.1002/pro.5560020312.

K.D. Volkova, V.B. Kovalska, A.O. Balanda, M.Y. Losytskyy, A.G. Golub, R.J. Vermeij, V. Subramaniam, O.I. Tolmachev and S.M. Yarmoluk, Bioorg. Med. Chem. 16, 1452-1459 (2008), https://doi.org/10.1016/j.bmc.2007.10.051.

I.I. Timcheva, V.A. Maximova, T.G. Deligeorgiev, N.I. Gadjev, R.W. Sabnis and I.G. Ivanov, FEBS Lett. 405, 141-141 (1997), https://doi.org/10.1016/S0014-5793(97)00171-3.

J. Nygren, N. Svanvik and M. Kubista, Biopolymers. 46, 39-51 (1998), https://doi.org/10.1002/(SICI)1097-0282(199807)46:1%3C39::AID-BIP4%3E3.0.CO;2-Z.

K.M. Sovenyhazy, J.A. Bordelon and J.T. Petty, Nucleic Acids Res. 31, 2561-2569 (2003), https://doi.org/10.1093/nar/gkg363.

J. Kapuscinski, Z. Darzynkiewicz and M. Melamed, Biochem. Pharmacol. 32, 3679-3694 (1983), https://doi.org/10.1016/0006-2952(83)90136-3.

H. Rye, M. Quesada, K. Peck, R. Mathies and A. Glazer, Nucleic Acid Res. 19, 327-333 (1991), https://doi.org/10.1093/nar/19.2.327.

L.C.T. Shoute and G.R. Loppnow, Phys. Chem. Chem. Phys. 20, 4772-4780 (2018), https://doi.org/10.1039/C7CP06058K.

M.M. Islam, P. Pandya, S.R. Chowdhury, S. Kumar and G.S. Kumar, J. Mol. Struct. 891, 498-507 (2008), https://doi.org/10.1016/j.molstruc.2008.04.043.

H.K. Liu and P.J. Sadler, Acc. Chem. Res. 44, 349-359 (2011), https://doi.org/10.1021/ar100140e.

V. Trusova, A. Yudintsev, L. Limanskaya, G. Gorbenko and T. Deligeorgiev, J. Fluoresc. 23, 193-202 (2013), https://doi.org/10.1007/s10895-012-1134-1.

Citations

Novel cyanine dye as competitive ligand for probing the drug–nucleic acid interactions
(2020) Biophysical Bulletin
Crossref

Published
2019-10-01
Cited
How to Cite
Zhytniakivska, O., Zabrudska, A., Tarabara, U., Vus, K., Trusova, V., Gorbenko, G., Kurutos, A., & Deligeorgiev, T. (2019). Competitive Binding of Novel Cyanine Dye AK3-5 and Europium Coordination Complexes to DNA. East European Journal of Physics, (3), 63-70. https://doi.org/10.26565/2312-4334-2019-3-08