Abstract
A water-soluble thiacalix[4]arene derivative containing four diethylenetriamine fragments in 1,3-alternate stereoisomeric form has been obtained for the first time. Using ethidium bromide, it has been found that the macrocycle can interact with calf thymus DNA. The macrocycle has been found to interact with DNA via groove binding. The presence of four diethylenetriamine fragments on the calixarene platform leads to multivalent interactions with DNA, resulting in an increase in the binding constant by two orders of magnitude compared to individual diethylenetriamine.
Similar content being viewed by others
References
Hannon, M.J., Chem. Soc. Rev., 2007, vol. 36, p. 280. https://doi.org/10.1039/b606046n
Casnati, A. and Sansone, F., Reference Module in Chemistry, Molecular Sciences and Chemical Engineering, 2015, p. 1. https://doi.org/10.1016/B978-0-12-409547-2.10827-3
Giuliani, M., Morbioli, I., Sansone, F., and Casnati, A., Chem. Commun., 2015, vol. 51, p. 14140. https://doi.org/10.1016/j.cis.2019.04.004
Solovieva, S.E., Burilov, V.A., and Antipin, I.S., Macroheterocycles, 2017, vol. 10, p. 134. https://doi.org/10.6060/mhc170512a
Ibragimova, R.R., Burilov, V.A., Aimetdinov, A.R., Mironova, D.A., Evtugyn, V.G., Osin, Yu.N., Solovieva, S.E., and Antipin, I.S., Macroheterocycles, 2016, vol. 9, p. 433. https://doi.org/10.6060/mhc161180b
Bitter, I. and Csokai, V., Tetrahedron Lett., 2003, vol. 44, p. 2261. doihttps://doi.org/10.1016/S0040-4039(03)00285-5
Ovsyannikov A. Noamane, M., Abidi, R., Ferlay, S., Solovieva, S., Antipin, I., Konovalov, A., Kyritsakas, N., and Hosseini, M., Cryst. Eng. Comm., 2016, vol. 18, p. 691. https://doi.org/10.1039/c5ce02310f
Taouai, M., Abidi, R., Garcia, J., Siriwardena, A., and Benazza, M., J. Org. Chem., 2014, vol. 79, p. 10743. https://doi.org/10.1021/jo5015504
Puplampu, J.B. Yakimova, L.S., Vavilova, A.A., Rizvanov, I.K., and Stoikov, I.I., Macroheterocycles, 2015, vol. 8, p. 75. https://doi.org/10.6060/mhc140722s
Valiyakhmetova, A.M., Sultanova, E.D., Burilov, V.A., Solovieva, S.E., and Antipin, I.S., Russ. Chem. Bull., 2019, vol. 68, p. 1067. https://doi.org/10.1007/s11172-019-2521-4
Guo, Q., Lu, M., Marky, L.A., and Kallenbach, N.R., Biochemistry, 1992, vol. 31, p. 2451. https://doi.org/10.1021/bi00124a002
Satyanarayana, S., Dabrowiak, J.C., and Chaires, J.B., Biochemistry, 1992, vol. 31, p. 9319. https://doi.org/10.1021/bi00154a001
Kabir, A. and Kumar, S., PLOS ONE, 2013, vol. 8, p. e70510. https://doi.org/10.1371/journal.pone.0070510
Fan, P., Wan, L., Shang, Y., Wang, J., Liu, Y., Sun, X., and Chen, C., Bioorg. Chem., 2014, vol. 58, p. 88. https://doi.org/10.1016/j.bioorg.2014.12.002
Pyle, A.M., Rehmann, J.P., Meshoyrer, R., Kumar, C.V., Turro, N.J., and Barton, J.K., J. Am. Chem. Soc., 1989, vol. 111, p. 3051. https://doi.org/10.1021/ja00190a046
Armarego, W.L.F. and Chai, C.L., Purification of Laboratory Chemicals, New York: Elsevier, 2009, p. 743.
Iki, N., Kabuto, C., Fukushima, T., Kumagai, H., Takeya, H., Miyanari, S., Miyashi, T., and Miyano, S., Tetrahedron, 2000, vol. 56, p. 1437. https://doi.org/10.1016/S0040-4020(00)00030-2
Brown, N.G., VanderLinden, R., Watson, E.R., Qiao, R., Grace, C.R.R., Yamaguchi, M., Weissmann, F., Frye, J.J., Dube, P., Ei Cho, S., Actis, M.L., Rodrigues, P., Fujii, N., Peters, J.M., Stark, H., and Schulman, B.A., Proc. Nat. Acad. Sci., 2015, vol. 112, p. 5272. https://doi.org/10.1073/pnas.1504161112
Funding
This study was financially supported by the subsidy allocated to Kazan Federal University in the scope of the State Task in the field of research activity (4.1493.2017/4.6, 4.5151.2017/6.7).
Author information
Authors and Affiliations
Corresponding author
Additional information
To the 80th Anniversary of R.A. Cherkasov
Conflict of Interest
No conflict of interest was declared by the authors.
Russian Text © The Author(s), 2020, published in Zhurnal Obshchei Khimii, 2020, Vol. 90, No. 1, pp. 129–135.
Rights and permissions
About this article
Cite this article
Burilov, V.A., Mironova, D.A., Grygoriev, I.A. et al. Synthesis of Water-Soluble Polyammonium Thiacalix[4]arene Derivative and Its Interaction with Calf Thymus DNA. Russ J Gen Chem 90, 99–104 (2020). https://doi.org/10.1134/S1070363220010156
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070363220010156