Abstract
A number of new p-tert-butylthiacalix[4]arenes containing one triethoxysilyl fragment and tertiary amino groups in the cone and 1,3-alternate conformations have been synthesized. New hybrid organic−inorganic silicon dioxide nanoparticles with p-tert-butylthiacalix[4]arene fragments have been obtained. It has been shown that nanoparticles formed from p-tert-butylthiacalix[4]arenes in the cone conformation and SiO2 selectively bind salmon milt DNA. Silico dioxide/p-tert-butylthiacalix[4]arene nanoparticles in the 1,3-alternate conformation containing N,N-diethylaminopropyl fragments can bind the model calf thymus DNA. The resulting hybrid materials can be used in medicine as nucleic acid carriers.
Similar content being viewed by others
REFERENCES
Bagwe, R.P., Hilliard, L.R., and Tan, W., Langmuir, 2006, vol. 22, p. 4357. https://doi.org/10.1021/la052797j
Santra, S., Zhang, P., Wang, K., Tapec, R., and Tan, W., Anal. Chem., 2001, vol. 73, p. 4988. https://doi.org/10.1021/ac010406+
Kuzin, Y., Kappo, D., Porfireva, A., Shurpik, D., Stoikov, I., Evtugyn, G., and Hianik, T., Sensors, 2018, vol. 18, p. 3489. https://doi.org/10.3390/s18103489
Stoikova, E.E., Sorvin, M.I., Shurpik, D.N., Budnikov, H.C., Stoikov, I.I., and Evtugyn, G.A., Electroanalysis, 2015, vol. 27, p. 440. https://doi.org/10.1002/elan.201400494
Monger, B.C. and Landry, M.R., Appl. Environ. Microbiol., 1993, vol. 59, p. 905. https://doi.org/10.1128/aem.59.3.905-911.1993
Zhang, Y., Tu, J., Wang, D., Zhu, H., Maity, S.K., Qu, X., Bogaert, B., Pei, H., and Zhang, H., Adv. Mater., 2018, vol. 30, p. 1703658. https://doi.org/10.1002/adma.201703658
Pjura, P.E., Grzeskowiak, K., and Dickerson, R.E., J. Mol. Biol., 1987, vol. 197, p. 257. https://doi.org/10.1016/0022-2836(87)90123-9
Wilson, W.D., Tanious, F.A., Barton, H.J., Jones, R.L., Fox, K., Wydra, R.L., and Strekowski, L., Biochemistry, 1990, vol. 29, p. 8452. https://doi.org/10.1021/bi00488a036
Martin, R.F. and Denison, L., Int. J. Radiat. Oncol. Biol. Phys., 1992, vol. 23, p. 579. https://doi.org/10.1016/0360-3016(92)90014-9
Hasanzadeh, M., Pournaghi-Azar, M.H., Shadjou, N., and Jouyban, A., J. Anal. Chem., 2016, vol. 71, p. 386. https://doi.org/10.1134/S106193481602009X
Sivasankarapillai, V.S., Pillai, A.M., Rahdar, A., Sobha, A.P., Das, S.S., Mitropoulos, A.C., Mokarra, M.H., and Kyzas, G.Z., Nanomaterials, 2020, vol. 10, p. 852. https://doi.org/10.3390/nano10050852
Wang, Y., Sun, S., Zhang, Z., and Shi, D., Adv. Mater., 2018, vol. 30, p. 1705660. https://doi.org/10.1002/adma.201705660
Xu, S., Lu, H., Zheng, X., and Chen, L., J. Mater. Chem. C, 2013, vol. 1, p. 4406. https://doi.org/10.1039/C3TC30496E
Rosenholm, J.M., Sahlgren, C., and Lindén, M., Nanoscale, 2010, vol. 2, p. 1870. https://doi.org/10.1039/C0NR00156B
Larsericsdotter, H., Oscarsson, S., and Buijs, J., J. Colloid Interface Sci., 2001, vol. 237, p. 98. https://doi.org/10.1006/jcis.2001.7485
Kesse, S., Boakye-Yiadom, K.O., Ochete, B.O., Opoku-Damoah, Y., Akhtar, F., Filli, M.S., Farooq, M.A., Aquib, M., Mily, B.J.M., Murtaza, G., and Wang, B., Pharmaceutics, 2019, vol. 11, p. 77. https://doi.org/10.3390/pharmaceutics11020077
Amirkhanov, R.N., Zarytova, V.F., and Zenkova, M.A., Russ. Chem. Rev., 2017, vol. 86, p. 113. https://doi.org/10.1070/RCR4604/meta
Li, J., Wang, Y., Zhu, Y., and Oupický, D., J. Control. Release, 2013, vol. 172, p. 589. https://doi.org/10.1016/j.jconrel.2013.04.010
Järver, P., O’Donovan, L., and Gait, M.J., Nucleic. Acid. Ther., 2014, vol. 24, p. 37. https://doi.org/10.1089/nat.2013.0454
Lebleu, B., Moulton, H.M., Abes, R., Ivanova, G.D., Abes, S., Stein, D.A., Iversen, P.L., Arzumanov, A.A., and Gait, M.J., Adv. Drug Deliv. Rev., 2008, vol. 60, p. 517. https://doi.org/10.1016/j.addr.2007.09.002
Torres, A.G., Threlfall, R.N., and Gait, M.J., Artif. DNA PNA XNA, 2011, vol. 2, p. 71. https://doi.org/10.4161/adna.17731
Han, L., Zhao, J., Zhang, X., Cao, W., Hu, X., Zou, G., Duan, X., and Liang, X.J., ACS Nano, 2012, vol. 6, p. 7340. https://doi.org/10.1021/nn3024688
Tarahovsky, Y.S. Biochemistry. 2009, 74, p. 1293. https://doi.org/10.1134/S0006297909120013
Saito, Y., Kawakami, S., Yabe, Y., Yamashita, F., and Hashida, M., Biol. Pharm. Bull., 2006, vol. 29, p. 1986. https://doi.org/10.1248/bpb.29.1986
Pelisek, J., Gaedtke, L., DeRouchey, J., Walker, G.F., Nikol, S., and Wagner, E., J. Gene Med., 2006, vol. 8, p. 186. https://doi.org/10.1002/jgm.836
Yakimova, L.S., Ziatdinova, R.V., Evtugyn, V.G., Rizvanov, I.K., and Stoikov, I.I., Russ. Chem. Bull., 2016, vol. 65, p. 1053. https://doi.org/10.1007/s11172-016-1412-1
Stoikov, I.I., Galukhin, A.V., Zaikov, E.N., and Antipin, I.S., Mendeleev Commun., 2009, vol. 19, p. 193. https://doi.org/10.1016/j.mencom.2009.07.006
Kubasov, A.S., Turishev, E.S., Golubev, A.V., Bykov, A.Y., Zhizhin, K.Y., and Kuznetsov, N.T., Inorganica Chim. Acta, 2020, vol. 507, p. 119589. https://doi.org/10.1016/j.ica.2020.119589
Luo, D., Han, E., Belcheva, N., and Saltzman, W.M., J. Control. Release, 2004, vol. 95, p. 333. https://doi.org/10.1016/j.jconrel.2003.11.019
Ukhatskaya, E.V., Kurkov, S.V., Matthews, S.E., and Loftsson, T., J. Pharm. Sci., 2013, vol. 102, p. 3485. https://doi.org/10.1002/jps.23681
Hu, W., Blecking, C., Kralj, M., Šuman, L., Piantanida, I., and Schrader, T., Chem. Eur. J., 2012, vol. 18, p. 3589. https://doi.org/10.1002/chem.201100634
Cleaves, II H.J., Crapster-Pregont, E., Jonsson, C.M., Jonsson, C.L., Sverjensky, D.A., and Hazen, R.A., Chemosphere, 2011, vol. 83, p. 1560. https://doi.org/10.1016/j.chemosphere.2011.01.023
Funding
The work was financially supported by the Priority-2030 Strategic Academic Leadership Program, Kazan (Volga Region) Federal University.
Author information
Authors and Affiliations
Corresponding authors
Ethics declarations
The authors declare no conflict of interest.
Additional information
Translated from Zhurnal Organicheskoi Khimii, 2022, Vol. 58, No. 8, pp. 862–877 https://doi.org/10.31857/S0514749222080109.
In memory of Academician A.I. Konovalov
Rights and permissions
About this article
Cite this article
Shurpik, R.V., Shurpik, D.N., Gerasimov, A.V. et al. Modification of Silicon Dioxide with Variously Substituted minothiacalix[4]arenes: Organic−Inorganic Nanoparticles or Nucleic Acid Binding. Russ J Org Chem 58, 1141–1153 (2022). https://doi.org/10.1134/S1070428022080103
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428022080103