Abstract
New copolymers of methyl acrylate with 1-vinylimidazole, 1-vinyl-1,2,4-triazole, and 4-vinyl-1,2,3-triazole are synthesized by radical copolymerization. It is shown that the reactivity ratios for methyl acrylate and 1-vinylimidazole are 0.83 ± 0.09 and 0.25 ± 0.02, for methyl acrylate and 1-vinyl-1,2,4-triazole are 1.0 ± 0.04 and 0.27 ± 0.01, and for methyl acrylate and (4-vinyl-1Н-1,2,3-triazolyl)-methyl pivalate are 0.56 ± 0.03 and 2.90 ± 0.20, respectively. The behavior of the copolymers in aqueous media and their thermoresponsive properties are studied by potentiometric titration and dynamic light scattering. Copolymer macromolecules occur in aqueous solutions in the form of large associates the fraction of which increases upon heating; in some cases, an insoluble phase is formed. It is found that the copolymers with the grafted oligopropylamine moieties containing N-vinylazole units can interact with the DNA oligonucleotide, stimulating their research as agents for the delivery of nucleic acids to living cells.
Similar content being viewed by others
REFERENCES
S. Tan, K. Saito, and M. T. Hearn, Curr. Opin. Biotechnol. 53, 209 (2018).
C. Lu and M. W. Urban, Prog. Polym. Sci. 78, 24 (2018).
J. Xu, P. Zhu, Y. Wang, and K.-L. Zhang, Inorg. Chim. Acta 503, (2019). https://doi.org/10.1016/j.ica.2019.119376
Y. Xian, Y. Shui, M. Li, C. Pei, Q. Zhang, and Y. Yao, J. Appl. Polym. Sci. 137, (2020). https://doi.org/10.1002/app.49032
X. Fu, L. Hosta-Rigau, R. Chandrawati, and J. Cui, Chem – Cell Press 4, 2084 (2018).
M. Sponchioni, U. C. Palmiero, and D. Moscatelli, Mater. Sci. Eng., C 102, 589 (2019).
A. Koochaki, M. R. Moghbeli, S. J. Nikkhah, A. Ianiro, and R. Tuinier, RSC Adv. 10, 3233 (2020).
M. V. Shirmanova, I. N. Druzhkova, M. M. Lukina, M. E. Matlashov, V. V. Belousov, L. B. Snopova, N. Prodanetz, V. V. Dudenkova, S. A. Lukyanov, and E. V. Zagaynova, Biochim. Biophys. Acta 1850, 1905 (2015).
O. Boussif, F. Lezoualc, M. A. Zanta, M. D. Mergny, D. Scherman, B. Demeneix, and J.-P. Behr, Proc. Natl. Acad. Sci. U. S. A. 92, 7297 (1995).
M. Chen, Y. Tang, T. Wang, Q. Long, Z. Zeng, H. Chen, and X. Feng, Mater. Sci. Eng., C 69, 1367 (2016).
X. Wang, D. Niu, C. Hu, and P. Li, Curr. Pharm. Des. 21, 6140 (2015).
A. Katchalsky, J. Mazur, and P. Spitnik, J. Polym. Sci. 23 (104), 513 (1957).
D. Fischer, Y. Li, B. Ahlemeyer, J. Krieglstein, and T. Kissel, Biomaterials 24, 1121 (2003).
T. G. Ermakova, N. P. Kuznetsova, and K. A. Maksimov, Russ. J. Appl. Chem. 76, 1971 (2003).
V. N. Kizhnyaev, F. A. Pokatilov, and L. I. Vereshchagin, Polym. Sci., Ser. C 50, 1 (2008).
M. V. Kurik, G. F. Myachina, and T. G. Ermakova, Mol. Cryst. Liq. Cryst. 468, 669 (2007).
V. N. Kizhnyaev, T. L. Petrova, F. A. Pokatilov, R. G. Zhitov, and O. A. Edel’shtein, Polym. Sci., Ser. B 56, 490 (2014).
N. L. Mazyar, V. V. Annenkov, V. A. Kruglova, S. M. Ananiev, E. N. Danilotseva, A. V. Rokhin, and S. V. Zinchenko, Russ. Chem. Bull. 49, 2013 (2000).
N. P. Bayramgil, Colloids Surf., B 97, 182 (2012).
G. Kandasamy, E. N. Danilovtseva, V. V. Annenkov, and U. M. Krishnan, Beilstein J. Nanotechnol. 11, 354 (2020).
V. V. Annenkov, U. M. Krishnan, V. A. Pal’shin, S. N. Zelinskiy, G. Kandasamy, and E. N. Danilovtseva, Chin. J. Polym. Sci. 36, 1114 (2018).
E. N. Danilovtseva, U. M. Krishnan, V. A. Pal’shin, and V. V. Annenkov, Chin. J. Polym. Sci. 37, 637 (2019).
V. Aseyev, H. Tenhu, and F. M. Winnik, Adv. Polym. Sci. 242, 29 (2011).
T. Mori, Y. Fukuda, H. Okamura, K. Minagawa, S. Masuda, and M. Tanaka, J. Polym. Sci., Part A: Polym. Chem. 42, 2651 (2004).
X. Peng, Y. Zhang, W. Fehg, L.-M. Ai, and F. Zhang, J. Mol. Struct. 1041, 139 (2013).
G. A. Mun, P. I. Urkimbaeva, M. B. Primbetova, R. B. Bakytbekov, A. Shaikhutdinova, and G. Zh. Eligbaeva, Izv. Nauch.-Tekh. O-va “KAKhAK”, No. 2, 36 (2012).
H. Okamura, S. Masuda, K. Minagawa, T. Mori, M. Tanaka, Eur. Polym. J. 38, 639 (2008).
G. A. Mun, RF Patent No. 19953 (2008).
E. N. Danilovtseva, M. A. Chafeev, and V. V. Annenkov, J. Polym. Sci., Part A: Polym. Chem. 50, 1539 (2012).
H. Hopff and M. Lippay, Macromol. Chem. 66, 157 (1963).
V. V. Annenkov, S. N. Zelinskiy, E. N. Danilovtseva, and C. C. Perry, ARKIVOC 13, 116 (2009).
B. Keil, Laboratory Technique of Organic Chemistry, Ed. by L. D. Bergel’sona (Mir, Moscow, 1966) [in Russian].
A. Kubotera and R. Saito, Polym. J. 48, 611 (2016).
H. Mori, K. Ishikawa, Y. Abiko, K. Nakabayashi, A. Onuma, and M. Morishima, Polymer 54, 2001 (2013).
M. Talu, E. U. Demiroğlu, Ş. Yurdakul, and S. Badoğlu, Spectrochim. Acta, Part A 134, 267 (2015).
Q. Liu and M. Zhu, Polym. Test. 56, 174 (2016).
V. V. Annenkov, O. V. Lebedeva, E. N. Danilovtseva, and A. I. Mikhaleva, Polym. Sci., Ser. B 43, 247 (2001).
J-F. Kuo and C. -Y. Chen, J. Appl. Polym. Sci. 26, 1117 (1980).
A. I. Ezrielev, E. L. Brokhina, and E. S. Roskin, Vysokomol. Soedin., Ser. A 11, 1670 (1969).
M. B. Lachinov and E. V. Chernikova, Manuals to Practice on Polymer Synthesis, Ed. by V. P. Shibaeva (MGU, Moscow, 2002) [in Russian].
V. A. Kruglova, V. N. Kizhnyaev, N. A. Ivanova, and L. I. Vereshchagin, Vysokomol. Soedin., Ser. B 29, 416 (1987).
J. L. Lippert, J. A. Robertson, J. R. Havens, and J. S. Tan, Macromolecules 18, 63 (1985).
V. A. Kruglova, V. V. Annenkov, G. V. Ratovskii, and O. A. Shivernovskaya, Vysokomol. Soedin., Ser. B 30, 233 (1988).
E. N. Zil’berman, Vysokomol. Soedin., Ser. B 21, 33 (1979).
U. P. Strauss, U. P. Barbieri, and G. Wong, J. Phys. Chem. 83, 2840 (1979).
K. A. Hasselbalch, Biochem. Z. 78, 112 (1917).
E. F. Vainshtein, A. A. Berlin, and S. G. Entelis, Vysokomol. Soedin., Ser. B 17, 835 (1975).
V. V. Annenkov, V. A. Kruglova, and N. L. Mazyar, J. Polym Sci., Part B: Polym. Phys. 36, 931 (1998).
ACKNOWLEDGMENTS
We are grateful to the Shared Research Center Ultramicroanalysis for providing us with the equipment.
Funding
This work was supported by the Ministry of Science and Higher Education of the Russian Federation and the Russian Academy of Sciences (project no. АААА-А19-119100490016-4).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated by T. Soboleva
Rights and permissions
About this article
Cite this article
Strelova, M.S., Danilovtseva, E.N. & Annenkov, V.V. Copolymers of Methyl Acrylate and Vinylazoles: Synthesis, Thermolabile Properties, and Grafting of Polyamine Chains. Polym. Sci. Ser. B 63, 41–51 (2021). https://doi.org/10.1134/S1560090421010061
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1560090421010061